Siesta Key Home & Villa Rentals

All Pool Options

192 matching vacation rentals found.

We receive new listings daily. Call your agent at 888.478.2796 for an up to date list of available rental options.

Four Bedroom Home with Private Pool and Hot Tub Sleeps 12

Four Poster BedPool
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4389/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Four Bedroom Vacation Rental Estate

Luxury Four Bedroom Vacation Rental EstateLuxury Four Bedroom Vacation Rental Estate
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4,995-10,195/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Vacation House for Rent with Private Pool.

Three Bedroom Vacation House for Rent with Private Pool.Siesta key Beach
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2394-5495/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Three Bedroom Home With Pool and Games Room

Luxury Three Bedroom Home With  Pool and Games RoomLuxury Three Bedroom Home With  Pool and Games Room
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $4995/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Luxury Rental Home - 3,000 sq ft - Canal View

Three Bedroom Luxury Rental Home - 3,000 sq ft - Canal ViewThree Bedroom Luxury Rental Home - 3,000 sq ft - Canal View
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2624/Week plus taxes and fees

Available: YesMap888-478-2796

Five bedroom Vacation Home Great Pool and Canal View

Five bedroom Vacation Home Great Pool and Canal ViewFive bedroom Vacation Home Great Pool and Canal View
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 13
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $4325-8283/Week plus taxes and fees

Available: YesMap888-478-2796

Welcome to Paradise! Four Bedroom Home with Private Pool

Sandy BeachPool and Patio
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $3000-4750/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely Private Vacation Home 4 Bedr Pool and Outdoor Kitchen

Lovely Private Vacation Home 4 Bedr Pool and Outdoor KitchenLovely Private Vacation Home 4 Bedr Pool and Outdoor Kitchen
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $6700/Month plus taxes and fees

Available: YesMap888-478-2796

A Great Residence Updated Decor and Furnishings - Pool

A Great Residence Updated Decor and Furnishings - PoolA Great Residence Updated Decor and Furnishings - Pool
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3600/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Duplex Town Home with Communal Pool

Exterior View of Vacation Rental Duplex HomeCommunal Pool with Outdoor Furniture
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,795-2995/Week plus taxes and fees

Available: YesMap888-478-2796

The Most Amazing Luxury Vacation Rental with Pool Sleeps 11

Siesta Key Sandy BeachDining Area Table Seats 8
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $4795-9990/Week plus taxes and fees

Available: YesMap888-478-2796

Gulf Views from the this stunning 3 bedroom plus BONUS ROOM

Gulf Views from the this stunning 3 bedroom plus  BONUS ROOMGulf Views from the this stunning 3 bedroom plus  BONUS ROOM
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2632-4988/Week plus taxes and fees

Available: YesMap888-478-2796

Newly Renovated three bedroom on Siesta Key

Newly Renovated three bedroom on Siesta KeyNewly Renovated three bedroom on Siesta Key
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $15000/Month plus taxes and fees

Available: YesMap888-478-2796

Vacation Rental Home 4 Bedroom Sleeps 12 Modern Upscale !

Vacation Rental Home 4 Bedroom Sleeps 12  Modern Upscale !Vacation Rental Home 4 Bedroom Sleeps 12  Modern Upscale !
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Comfortable Large Four Bedroom Vacation Home Pool Sleeps 12

Comfortable Large Four Bedroom Vacation Home Pool Sleeps 12Comfortable Large Four Bedroom Vacation Home Pool Sleeps 12
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $4056/Week plus taxes and fees

Available: YesMap888-478-2796

Eight Bedroom Luxury Vacation Rental on Beach

Living RoomLiving Room
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 8 Bedrooms
  • 9 Bathrooms

Starting at $9,595/Week plus taxes and fees

Available: YesMap888-478-2796

One of The Best Vacation Rentals- New Rental!

One of The Best Vacation Rentals- New Rental!One of The Best Vacation Rentals- New Rental!
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4495/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Home with Private Pool and Canal Front Sleeps 12

Siesta Key Home with Private Pool and Canal Front Sleeps 12Siesta Key Home with Private Pool and Canal Front Sleeps 12
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $12000-15000/Month plus taxes and fees

Available: YesMap888-478-2796

Sarasota 3 Bedroom Vacation Rental -Pool Seasonal Rental

Sarasota 3 Bedroom Vacation Rental -Pool Seasonal RentalWalk to Beach Home with Caged Pool in Siesta Key, Florida
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $7995/Month plus taxes and fees

Available: YesMap888-478-2796

Perfectly Located on North side of Siesta Key! Three Bedrms

Perfectly Located on North side of Siesta Key! Three BedrmsClose to Beach Home for Rent with Pool in Siesta Key, Florida
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3500/Week plus taxes and fees

Available: YesMap888-478-2796

Posh Three bedroom Vacation rental with Pool Stickney Point

Posh Three bedroom Vacation rental with Pool Stickney PointHome with Pool
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3059-5126/Week plus taxes and fees

Available: YesMap888-478-2796

The largest Luxury Siesta Key Vacation Rental Sleeps 20+

The largest Luxury Siesta Key Vacation Rental Sleeps 20+The largest Luxury Siesta Key Vacation Rental Sleeps 20+
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 25
  • 8 Bedrooms
  • 5 Bathrooms

Starting at $7995-19595/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Villa Luxury Inside and Out

Three Bedroom Villa Luxury Inside and OutThree Bedroom Villa Luxury Inside and Out
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3495-4453/Week plus taxes and fees

Available: YesMap888-478-2796

Elegant Four Bedroom Rental Views of the Gulf of Mexico

Sandy BeachSandy Beach
  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 9
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2495-4495/Week plus taxes and fees

Available: YesMap888-478-2796

4 bedroom Pool Vacation Rental Home With Classy Interior.

Siesta Key beachBed
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4500/Week plus taxes and fees

Available: YesMap888-478-2796

Upscale Home with Outdoor Pool Great for Family Vacation

Upscale Home with Outdoor Pool Great for Family VacationUpscale Home with Outdoor Pool Great for Family Vacation
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3,495-4,395/Week plus taxes and fees

Available: YesMap888-478-2796

Stunning inside and Out Quite Simply the Best! Upscale Home

Stunning inside and Out Quite Simply the Best! Upscale HomeStunning inside and Out Quite Simply the Best! Upscale Home
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $3995-5995/Week plus taxes and fees

Available: YesMap888-478-2796

Rare Eight Bedroom Luxury Vacation Rental Gulf View Sleep 22

Rare Eight Bedroom Luxury Vacation Rental Gulf View Sleep 22Rare Eight Bedroom Luxury Vacation Rental Gulf View Sleep 22
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 22
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $5000-20,000/Week plus taxes and fees

Available: YesMap888-478-2796

The Largest Vacation Rental Home Sleeps 26 !

Pool and PatioSandy Beach at Siesta Key
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 26
  • 8 Bedrooms
  • 7 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Eight Bedroom Rental Sleep 24 What a Rare Find!

Aerial View of PoolPool
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 8 Bathrooms

Starting at $4,195/Week plus taxes and fees

Available: YesMap888-478-2796

Fantastic 5 Bedroom Vacation Home that Sleeps 12 Guests.

Fantastic 5 Bedroom Vacation Home that Sleeps 12 Guests.Fantastic 5 Bedroom Vacation Home that Sleeps 12 Guests.
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $4795/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Private Home with Heated Pool & Cabana

PoolLiving Area
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4850-8450/Week plus taxes and fees

Available: YesMap888-478-2796

Fantastic Three Bedroom with a GREAT Pool

Outdoor Furniture on Deck Overlooking PoolSpacious Living Area with Wall Mounted TV
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3,795-4,995/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key The Ultimate Vacation Home- Beach Rental

Siesta Key The Ultimate Vacation Home- Beach RentalSiesta Key The Ultimate Vacation Home- Beach Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 6 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Stunning Six Bedroom Siesta Key Vacation Rental

Outdoor dining areaLiving room
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 6 Bathrooms

Starting at $6500-17500/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Siesta Key Vacation Rental Canal Front Close to Beach

BalconyLiving room
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 17
  • 6 Bedrooms
  • 5 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Beautiful 4 bedroom Home Short Walk to the Beach and Village

External View of Rental with Ample ParkingSpacious Living Area with Doors to Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $7200-12000/Month plus taxes and fees

Available: YesMap888-478-2796

Posh 4 bedroom Home For Rent Boat Dock, Pool Great Rental!

Private PoolCaged Pool
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3495-6520/Week plus taxes and fees

Available: YesMap888-478-2796

6 Bedroom Vacation Rental with Pool - Near Beach

6 Bedroom Vacation Rental with Pool - Near Beach6 Bedroom Vacation Rental with Pool - Near Beach
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 6 Bedrooms
  • 5 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Luxury Vacation Home - Three Bedrooms - Close to Beaches

Vacation VillaLiving Area with Comfy Chairs
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,795-2,995/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely Four Bedroom Home with Pool on Siesta Key

Private PoolLiving Area
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $6,295-12,495/Month plus taxes and fees

Available: YesMap888-478-2796

Pool Home Casual Beachy Vacation Rental with Three Bedrooms

Large outdoor poolSwimming pool outdoor
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4000-9375/Month plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Pool Home Sleeps 11 Guests

Pool and Patio AreaSiesta Key Sandy Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 11
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3059/Week plus taxes and fees

Available: YesMap888-478-2796

3 Bedroom Vacation Rental Private Pool Sleeps 6

Siesta Key Three Bedroom Vacation Home PoolMaster Bedroom King Bed
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $7195/Month plus taxes and fees

Available: YesMap888-478-2796

Luxury Rental Three Bedrooms Gulf Views & Pool

Exterior View of PropertyPartial Gulf View
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 4 Bathrooms

Starting at $2,095-3,795/Week plus taxes and fees

Available: YesMap888-478-2796

Sleeps Eight Three Bedrooms Private Pool

Sleeps Eight Three Bedrooms Private PoolSleeps Eight Three Bedrooms Private Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2465-3795/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Three Bedroom 2.5 Bath Luxury

Siesta Key luxury vacation home with poolmodern interior open living dining area
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $6,295-11,895/Month plus taxes and fees

Available: YesMap888-478-2796

Lovely Three Bedroom Two Bathroom Vacation Rental

Vacation Rental in Siesta KeyCovered lanai
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2095-3940/Week plus taxes and fees

Available: YesMap888-478-2796

Two Bedroom Rental Cottage/Rent Both Sleep 12!

Two Bedroom Rental Cottage/Rent Both Sleep 12!Two Bedroom Rental Cottage/Rent Both Sleep 12!
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Starting at $1895/Week plus taxes and fees

Available: YesMap888-478-2796

3 Bed 3 Ba Home on Siesta Just a half block to the Beach

3 Bed 3 Ba Home on Siesta Just a half block to the Beach3 Bed 3 Ba Home on Siesta Just a half block to the Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2,595-4995/Week plus taxes and fees

Available: YesMap888-478-2796

Hacienda Style Luxury Estate Home Sleeps 14

Siesta Key Rental - Exterior View at NightHacienda Style Luxury Estate Home Sleeps 14
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 14
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $14995/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Home Short Walk to the Beach

Exterior viewDining Table & Chairs
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 20
  • 7 Bedrooms
  • 5 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Amazing Five Bedroom Vacation home with Pool - Sleeps 14

Amazing Five Bedroom Vacation home with Pool - Sleeps 14Contemporary Siesta Key Vacation Home
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 4 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Four Bedroom Rental Home with Pool 3 Blocks Beach

Canal Front Home with Pool in Siesta Key, FloridaSiesta Key Four Bedroom Rental Home with Pool 3 Blocks Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $2992/Week plus taxes and fees

Available: YesMap888-478-2796

4 Bedroom Rental 4 min Walk to Worlds Best Beach

4 Bedroom Rental 4 min Walk to Worlds Best Beach4 Bedroom Rental 4 min Walk to Worlds Best Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $2,295/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Home 4 Bedroom Sleeps 12

Siesta Key Vacation Rental Home 4 Bedroom Sleeps 12Sandy Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $3695-6320/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Siesta Key Vacation Rental

Four Bedroom Siesta Key Vacation RentalFour Bedroom Siesta Key Vacation Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $3795/Week plus taxes and fees

Available: YesMap888-478-2796

Stunning Luxury Vacation Home with 5 Bedroom Pools

Two blocks to beachStunning Luxury Vacation Home with 5 Bedroom Pools
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Luxury Bay front home with Boat Dock and Private pool

Luxury Bay front home with Boat Dock and Private poolLuxury Bay front home with Boat Dock and Private pool
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 4 Bathrooms

Starting at $3990/Week plus taxes and fees

Available: YesMap888-478-2796

Beaches 2 Min Walk Away Three Bedroom Town Home

Beaches 2 Min Walk Away Three Bedroom Town HomeBeaches 2 Min Walk Away Three Bedroom Town Home
  • Gold
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2,895-6,095/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Home with Private Pool 3 Min to Beaches.

Luxury Home with Private Pool 3 Min to Beaches.Luxury Home with Private Pool 3 Min to Beaches.
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3795-4541/Week plus taxes and fees

Available: YesMap888-478-2796

Two Bedroom Plus Den Luxury Vacation home Private Pool !

Two Bedroom Plus Den Luxury Vacation  home Private Pool !Two Bedroom Plus Den Luxury Vacation  home Private Pool !
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,595-2,995/Week plus taxes and fees

Available: YesMap888-478-2796

Beach House at Siesta Key with Shared Pool and Garden Patio

Beach House at Siesta Key with Shared Pool and Garden PatioBeach House at Siesta Key with Shared Pool and Garden Patio
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3595-5395/Week plus taxes and fees

Available: YesMap888-478-2796

A Beautiful Spacious Four Bedroom Vacation Home

Siesta Key BeachHammock on Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2,495/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Two Bedroom Upscale Home Private Pool Village Nearby

Siesta Key Vacation HomePool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $1,995-2,995/Week plus taxes and fees

Available: YesMap888-478-2796

Close to Siesta Key Village A great Town House

Close to Siesta Key Village A great Town HouseClose to Siesta Key Village A great Town House
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

3 Bedroom Vacation Rental Home with Private Pool

3 Bedroom Vacation Rental Home with Private Pool3 Bedroom Vacation Rental Home with Private Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $1,495-2,495/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Siesta Key Four Bedroom Vacation Home - Large Pool

Luxury Siesta Key Four Bedroom Vacation Home -  Large PoolLuxury Siesta Key Four Bedroom Vacation Home -  Large Pool
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $3,795-8,695/Month plus taxes and fees

Available: YesMap888-478-2796

Classy Three Bedroom For Rent- Simply the Best Large Home

Classy Three Bedroom For Rent- Simply the Best Large HomeClassy Three Bedroom For Rent- Simply the Best Large Home
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4795/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Vacation Home Sleeps 10 Short Walk to Beach

Private PoolLiving Room
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2,495/Week plus taxes and fees

Available: YesMap888-478-2796

Ideally Situated Between the 2 Best Beaches on Siesta

Ideally  Situated Between the 2 Best Beaches on SiestaIdeally  Situated Between the 2 Best Beaches on Siesta
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4795/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom- Luxury Siesta Key Home with Pool on the Water

Entrance HallPool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Rent One or Both Units 4 Min Walk to Siesta Key Beaches

Rent One or Both Units 4 Min Walk to Siesta Key BeachesRent One or Both Units 4 Min Walk to Siesta Key Beaches
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,795/Week plus taxes and fees

Available: YesMap888-478-2796

Large Pool Home Rent One or Multiple Units

Large Pool Home Rent One or Multiple UnitsLarge Pool Home Rent One or Multiple Units
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Rent One or All units and Sleep up to 12 Guests

Rent One or All units and Sleep up to 12 GuestsRent One or All units and Sleep up to 12 Guests
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental with two Bedrooms Walk to Beach

Siesta Key Vacation Rental with two Bedrooms Walk to BeachSiesta Key Vacation Rental with two Bedrooms Walk to Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Vacation Rental Home with Two Bedrooms

Siesta Key Vacation Rental Home with Two BedroomsSiesta Key Vacation Rental Home with Two Bedrooms
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Two Bedroom Vacation Rentals Siesta Key Walk to Beach

Two Bedroom  Vacation Rentals Siesta Key Walk to  BeachTwo Bedroom  Vacation Rentals Siesta Key Walk to  Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Vacation Home with Pool Sleeps 10

Sandy BeachAerial view
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2,495-6995/Week plus taxes and fees

Available: YesMap888-478-2796

Rent 1 Villa or Both Villas on Siesta Key Combined Sleeps 12

Rent 1 Villa or Both Villas on Siesta Key Combined Sleeps 12Rent 1 Villa or Both Villas on Siesta Key Combined Sleeps 12
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Rent One or Both Units at Siesta Key Accommodations

Rent One or Both Units at Siesta Key AccommodationsRent One or Both Units at Siesta Key Accommodations
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Luxury Rental Accommodation One Block Beach

Three  Bedroom Luxury Rental Accommodation One Block BeachThree  Bedroom Luxury Rental Accommodation One Block Beach
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3059/Week plus taxes and fees

Available: YesMap888-478-2796

Charming 2 Bedroom Cottage Siesta Key Walk to Beach

Charming 2 Bedroom Cottage Siesta Key Walk to BeachCharming 2 Bedroom Cottage Siesta Key Walk to Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Siesta Key Sleeps 10 Two Bathroom

Four Bedroom  Siesta Key Sleeps 10 Two BathroomFour Bedroom  Siesta Key Sleeps 10 Two Bathroom
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Luxury Vacation Rental Home Pool

Siesta Key Luxury Vacation Rental Home PoolSiesta Key Luxury Vacation Rental Home Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Large Rental Rent Both Sides! & Sleeps 16 Guests

Large Rental Rent Both Sides! & Sleeps 16 GuestsLarge Rental Rent Both Sides! & Sleeps 16 Guests
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3059/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Home sleeps 12 Short Walk to Beach

Siesta Key Vacation Home sleeps 12  Short Walk to BeachSiesta Key Vacation Home sleeps 12  Short Walk to Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4056-6240/Week plus taxes and fees

Available: YesMap888-478-2796

A Fabulous Walk to Beach Rental Property

A Fabulous Walk to Beach Rental PropertyShared Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

One Bedroom Home Rent Separately or Together Pool

Walk to Siesta Key BeachSiesta Key Vacation Home Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

Starting at $1064/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Four Bedroom Beach Home for Rent

walk to crescent beach 1/4 mile awayKitchen with Breakfast Area
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $4999/Week plus taxes and fees

Available: YesMap888-478-2796

One of The Largest Rentals Sleeps 24 A Huge Home

One of The Largest Rentals Sleeps 24 A Huge HomeOne of The Largest Rentals Sleeps 24 A Huge Home
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 25
  • 8 Bedrooms
  • 5 Bathrooms

Starting at $5,595/Week plus taxes and fees

Available: YesMap888-478-2796

Stunning Siesta Key Village Rental Home - Four Bedrooms

Exterior View of Vacation RentalSpacious Living Area with Wall Mounted TV
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Six Bedroom Family Vacation Rental Sleeps 16

Swimming Pool WowMaster Bedroom Matrimonial Bed
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $6051/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedrooms Professionally Decorated

Luxury KitchenSiesta Key Luxury Rental Home
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $8495/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Vacation Home Siesta Key Florida Pool on Water

Three Bedroom Vacation Home Siesta Key Florida Pool on WaterThree Bedroom Vacation Home Siesta Key Florida Pool on Water
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2660/Week plus taxes and fees

Available: YesMap888-478-2796

Sleeps 10 Siesta Luxury Rental Home

Sleeps 10 Siesta Luxury Rental HomeSleeps 10 Siesta Luxury Rental Home
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2992/Week plus taxes and fees

Available: YesMap888-478-2796

3 Bedroom Siesta Key Rental Home. For your next Vacation.

Siesta Key beachsiesta key beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,795/Week plus taxes and fees

Available: YesMap888-478-2796

A Rares Siesta Key Four Bedroom Vacation Rental WOW

A Rares Siesta Key Four Bedroom Vacation Rental WOWSiesta Key Cottage
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $4056/Week plus taxes and fees

Available: YesMap888-478-2796

Imagine The Largest Beach Rental Sleeps up to 24 8 Bedroom

Luxury Siesta Key Eight Bedroom Vacation rentalCustom Out Door Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 8 Bathrooms

Starting at $6995/Week plus taxes and fees

Available: YesMap888-478-2796

WOW posh Home 2 bedrooms and Classy Interiors

WOW posh Home 2 bedrooms and Classy InteriorsWOW posh Home 2 bedrooms and Classy Interiors
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Cottage with Four Bedrooms

Siesta Key Vacation Rental  Cottage with Four BedroomsSiesta Key Vacation Rental  Cottage with Four Bedrooms
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $4056/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Four Bedroom luxury Rental Sleeps 12

Siesta Key Four Bedroom luxury Rental Sleeps 12Siesta Key Four Bedroom luxury Rental Sleeps 12
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Rental Home Pool Entertaining Area Contemporary in Design

Pool with Chairs and LoungersSandy Beach at Siesta Key
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2100-3720/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Four Bedroom Rental Home with Pool Walk Beach

Siest Key Sandy BeachExterior View of Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4375-8750/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Value Priced Four Bedroom Vacation Home

Siesta Key Value Priced Four Bedroom Vacation HomeSiesta Key Value Priced Four Bedroom Vacation Home
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $4395-8795/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Village home with pool

Siesta Key Village home with poolSiesta Key Village home with pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3,995-6,595/Week plus taxes and fees

Available: YesMap888-478-2796

2 Bedroom 2 Bath home step to Beach and Village Area

2 Bedroom 2 Bath home step to Beach and Village AreaFully Equipped Kitchen with Seating
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2995-5995/Week plus taxes and fees

Available: YesMap888-478-2796

Spacious Luxury Vacation Rental Home - Sleeps 12 Guests

Spacious Luxury Vacation Rental Home - Sleeps 12 GuestsOutdoor seating area at this Siesta Key Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 13
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2095-5995/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Plus Loft Pool Home Sleeps 15

Siesta Key Pool Vacation HomeAerial View of Pool
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 15
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $6995-17995/Week plus taxes and fees

Available: YesMap888-478-2796

Eight Bedroom Luxury Huge Outdoor Pool Area Call Agent Views

Eight Bedroom Luxury Huge Outdoor Pool Area Call Agent ViewsEight Bedroom Luxury Huge Outdoor Pool Area Call Agent Views
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $4,795/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Two Bedroom Vacation Villa with Community Pool

Exterior View of Siesta Key RentalModern Kitchen
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $3458/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Townhouse Directly Across From Beach

Siesta Key Townhouse Directly Across From BeachSiesta Key Townhouse Directly Across From Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

3 Bedroom 3 Bath Home Coastal Decor

Pool with Sun Loungers3 Bedroom 3 Bath Home Coastal Decor
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2995-5500/Week plus taxes and fees

Available: YesMap888-478-2796

Brand New 7 Bedroom Vacation Rental Private Pool Sleeps 23

Brand New 7 Bedroom Vacation Rental Private Pool Sleeps 23Outdoor Seating Area
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 7 Bedrooms
  • 6 Bathrooms

Starting at $6995-17995/Week plus taxes and fees

Available: YesMap888-478-2796

Stunning 4 bedroom screened pool canalfront home

Stunning 4 bedroom screened pool canalfront homeStunning 4 bedroom screened pool canalfront home
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $5000/Month plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Vacation Rental Sleeps 12 Guests Private Pool

Outdoor Entertaining AreaSun Loungers By Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3395 - 5600/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Townhome steps to beach

Private poolPool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2495-5300/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Home 896223

Siesta Key Home 896223Siesta Key Home 896223
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 20
  • 6 Bedrooms
  • 6 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Luxury Siesta Key Vacation Cottage Sleeps 12 Guests

Large Bedroom with King BedWall Mounted TV in Bedroom
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2850/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Luxury Accommodations with Four Bedrooms

Siesta Key Luxury Accommodations with Four BedroomsSiesta Key Luxury Accommodations with Four Bedrooms
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3895-8395/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Siesta Key Cottage Sleeps 12 Private Pool

Open Plan LivingLarge Dining Room Table and Chairs
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $4850-8450/Week plus taxes and fees

Available: YesMap888-478-2796

The Ultimate Vacation Accommodation on Siesta Key

Breakfast Counter with SeatingKitchen
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3,895-7652/Week plus taxes and fees

Available: YesMap888-478-2796

The Ultimate in Siesta Key vacationing

The Ultimate in Siesta Key vacationingThe Ultimate in Siesta Key vacationing
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $3695/Week plus taxes and fees

Available: YesMap888-478-2796

Luxury Vacation Home Comprising of Two Units Sleeps Up To 24

Balcony With Pool ViewSpacious Living Area
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $5565/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Keys Most Spectacular Vacation Rental Homes - Pool

Luxury vacation rental home with pool iesta Key Villagekitchen modern white
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $5,595/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Luxury 8 bed home - 2 minute walk to the beach

Siesta Key Luxury 8 bed home - 2 minute walk to the beachSiesta Key Luxury 8 bed home - 2 minute walk to the beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $6895-12955/Week plus taxes and fees

Available: YesMap888-478-2796

Large Home - Eight Bedroom Luxury Residence Sleeps 24 Guests

Breakfast Counter with SeatingOpen Plan Living
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $6895-12780/Week plus taxes and fees

Available: YesMap888-478-2796

Updated Flat Short Walk to Beach in Siesta Key Village

Siesta Key BeachKing Bed
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Starting at $3495-6230/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Pool Home Sleeps 10 Guests View Updated Rental

Four Bedroom Pool Home Sleeps 10 Guests View Updated RentalPool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $4750-10000/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Vacation Rental with Private Pool Sleeps 6

Sandy Beach at Siesta KeyPool with Sun Loungers
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2500-5100/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely 2 Bedroom 2 Bathroom Condo - Siesta Key

Spacious Living AreaPool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Two Bedroom Rentals Sleeps 6 with Pool in Siesta Key

Pool & PatioLarge Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Newly Renovated-Lovely 2 Bed 2 Bath Private Home with Pool.

Siesta Key Vacation Pool HomeSiesta Key Beach
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $3500-7500/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedrooms Sleeps Six Canal View Short Walk to Beach

Large Patio Around PoolPrivate Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

This Fabulous Siesta Key Rental Sleeps Ten Guests

This Fabulous Siesta Key Rental Sleeps Ten GuestsThis Fabulous Siesta Key Rental Sleeps Ten Guests
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $2,495-6,595/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Luxury Vacation Rental Home Available Today

Aerial ViewOutdoor Entertaining Area
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3500- 6785/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Three Bedroom Home Sleeps 8 Bay View

Siesta Key Vacation Rental HomePrivate Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $6,895-12,395/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Beachfront Unit Sleeps 6 Short Walk to Beach

Living AreaFlat Screen TV in Living Area
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2,195/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Home Short Walk to Beach 3 Bedrooms

Front View of PropertyBeach Views
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Short Walk to Beach from the Ground Level Siesta Key Home

Pool and Patio AreaPool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 22
  • 6 Bedrooms
  • 6 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Luxury Four Bedroom Sleeps 9 Private Pool Close to Beach

Open Plan Living SpacePrivate Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

One of Siesta Keys (Palm Island) Finest Vacation Rentals

One of Siesta Keys (Palm Island)  Finest Vacation RentalsVacation Rental Home in Siesta Key
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 3 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Vacation Condo Two Bedrooms Sleeps 6

Living RoomDining Room
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Starting at $4,395/Week plus taxes and fees

Available: YesMap888-478-2796

Two Bedrooms Two Bathrooms Sleeps Four Guests

Siesta Key BeachFront View of Property
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $1,995/Week plus taxes and fees

Available: YesMap888-478-2796

Five Bedroom Vacation Home Sleeps 11 Guests

Rear View of PropertyPrivate Pool
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 11
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $5795-7895/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Three Bedroom Rental Sleeps 8 Guests

Siesta Key Three Bedroom Rental Sleeps 8 GuestsSandy Beach at Siesta Key
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Accommodation Sleeps 8

Sandy BeachSiesta Key Accommodation Sleeps 8
  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $6500-8200/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key home located in the Village

Siesta Key home located in the VillageSiesta Key home located in the Village
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2900/Week plus taxes and fees

Available: YesMap888-478-2796

Vacation Rental with Three Bedrooms

Vacation Rental with Three BedroomsPrivate pool
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $4995/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Home 884948

Bay front home in Siesta Key, FloridaExterior view
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3850/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Three Bedroom Vacation Home Rentals

Spacious Living AreaFlat Screen TV in Living Area
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2,395-5995/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Home 876600

Siesta Key Home 876600Siesta Key Home 876600
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2200.00/Week plus taxes and fees

Available: YesMap888-478-2796

Four Bedroom Value Priced Pool Vacation Home For RentMonthly

Four Bedroom Value Priced Pool Vacation Home For RentMonthlyFour Bedroom Value Priced Pool Vacation Home For RentMonthly
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Starting at $3400/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Home 877171

Siesta Key Home 877171Siesta Key Home 877171
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $5495/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Townhome by the Village Beach Beauty

Deck with Outdoor FurnitureSpacious Living Area
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2,495-3,795/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely 2 Bedroom 2 Bathroom Siesta Key Townhouse

Lovely 2 Bedroom 2 Bathroom Siesta Key TownhouseLovely 2 Bedroom 2 Bathroom Siesta Key Townhouse
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Value Priced Siesta Key Vacation Rental

Siesta Key BeachLarge Living Area with Wooden Floor
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2295/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely 2 bed 2 ba Siesta Key Villa

Lovely 2 bed 2 ba Siesta Key VillaLovely 2 bed 2 ba Siesta Key Villa
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2,295-5,595/Month plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Siesta Key Pool Rental Home

Queen BedroomPrivate Caged Pool
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2,095-3,795/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Village Vacation Rental with Three Bedrooms

Siesta Key Village Vacation Rental with Three BedroomsSiesta Key Village Vacation Rental with Three Bedrooms
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2,095-3795/Week plus taxes and fees

Available: YesMap888-478-2796

Charming 3 bed Siesta Key home

Charming 3 bed Siesta Key homeCharming 3 bed Siesta Key home
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2295/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Sleeps 10

Siesta Key Vacation Rental Sleeps 10Siesta Key Vacation Rental Sleeps 10
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3495/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Value Vacation Rental with Pool

Siesta Key Value Vacation Rental with PoolSiesta Key Value Vacation Rental with Pool
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2195-3380/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation home with pool on water

Siesta Key Vacation home with pool on waterThree min walk from Siesta Key rental to beach
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $6995/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key 1 bedroom vacation rental sleeps 4 pool

Siesta Key 1 bedroom vacation rental sleeps 4 poolPorch with table set
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

Starting at $950.00/Week plus taxes and fees

Available: YesMap888-478-2796

A Rare Value Priced 2 Bedroom Vacation Rental Together

A Rare Value Priced 2 Bedroom Vacation Rental TogetherMaster Bedroom with Queen Bed
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Beachside, Pool and Great Amenities Nearby Villa Style

Beachside, Pool and Great Amenities Nearby Villa StyleBeachside, Pool and Great Amenities Nearby Villa Style
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $1325/Week plus taxes and fees

Available: YesMap888-478-2796

Shabby Chic, newly updated Siesta Keys beach house.

Vacation rental home in Siesta Key, FloridaDining area
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4995/Month plus taxes and fees

Available: YesMap888-478-2796

Private Beach access and Chairs Set Up for Guests use.

Private Beach access and Chairs Set Up for Guests use.Equipped Kitchen with Stainless Steel Appliances
  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Single Level Home A Flip Flop Walk to the Beach

Single Level Home A Flip Flop Walk to the BeachSingle Level Home A Flip Flop Walk to the Beach
  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

2 Bedroom Villa - Shared Pool - Walk to Village for Dining

Sandy Beach at Siesta KeyPool Area
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Starting at $850/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Value Rental Villa in Beach Community

Siesta Key Value Rental Villa in Beach CommunitySiesta Key Value Rental Villa in Beach Community
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 5
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2195/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Property with Two Bedrooms

Siesta Key Vacation Rental Property with Two BedroomsSiesta Key Vacation Rental Property with Two Bedrooms
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

Walk to Village no Roads to Cross to Beaches from this Villa

Walk to Village no Roads to Cross to Beaches from this VillaWalk to Village no Roads to Cross to Beaches from this Villa
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Call 888-478-2796 for Rates

Available: YesMap888-478-2796

Siesta Key Home 889124

Siesta Key Home 889124Siesta Key Home 889124
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Starting at $1195/Week plus taxes and fees

Available: YesMap888-478-2796

Private home with Pool steps to Siesta Key Beach

Private home with Pool steps to Siesta Key BeachPrivate home with Pool steps to Siesta Key Beach
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2375-2625/Week plus taxes and fees

Available: YesMap888-478-2796

Rent One or Both Units Sleeps 8- 16 Guests HUGE Rental

Rent One or Both Units Sleeps 8- 16 Guests HUGE RentalRent One or Both Units Sleeps 8- 16 Guests HUGE Rental
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3059/Week plus taxes and fees

Available: YesMap888-478-2796

Value Priced Vacation Rental Cottage with Three Bedrooms

Value Priced  Vacation Rental  Cottage with Three BedroomsValue Priced  Vacation Rental  Cottage with Three Bedrooms
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1596/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Condo Sleeps Six

Siesta Key Condo Sleeps SixSiesta Key Condo Sleeps Six
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $995-2300/Week plus taxes and fees

Available: YesMap888-478-2796

Rent one unit Sleep Six or Both and Sleep 12! Large Rentals

Rent one unit Sleep Six or Both and Sleep 12! Large RentalsRent one unit Sleep Six or Both and Sleep 12! Large Rentals
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2061/Week plus taxes and fees

Available: YesMap888-478-2796

A Rare Three Bedroom Vacation Town Home Beach Across Street

A Rare Three Bedroom Vacation Town Home  Beach Across StreetA Rare Three Bedroom Vacation Town Home  Beach Across Street
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2981/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental Sleeps 12 Guests

Siesta Key Vacation Rental Sleeps 12 GuestsSiesta Key Vacation Rental Sleeps 12 Guests
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $2495/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Vacation Rental that Sleeps 14!

Siesta Key Vacation Rental that Sleeps 14!Siesta Key Vacation Rental that Sleeps 14!
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $2995-4256/Week plus taxes and fees

Available: YesMap888-478-2796

Three Bedroom Siesta Key Cottage for Rent Sleeps 10

Siesta Key beachAerial View of Siesta Key Beach
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3,795-8,395/Month plus taxes and fees

Available: YesMap888-478-2796

Stunning views from this one bedroom Townhome

Stunning views from this one bedroom TownhomeStunning views from this one bedroom Townhome
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 3
  • 1 Bedroom
  • 1 Bathroom

Starting at $2328/Week plus taxes and fees

Available: YesMap888-478-2796

Lovely 2 bed 2 bath Canal front home

Lovely 2 bed 2 bath Canal front homeLovely 2 bed 2 bath Canal front home
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $5500/Month plus taxes and fees

Available: YesMap888-478-2796

Villa Style Accommodation in Resort Community

Villa Style Accommodation in Resort CommunityVilla Style Accommodation in Resort Community
  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 5
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2200.00/Week plus taxes and fees

Available: YesMap888-478-2796

Small Complex - Three Bedroom Rental - Sleeps 8 - Pool

Wide sandy beachLiving area
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $1,295-3,495/Week plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Value Vacation Rentals Monthly Min 1 Block Beach

Siesta Key Value Vacation Rentals  Monthly Min 1 Block BeachSiesta Key Value Vacation Rentals  Monthly Min 1 Block Beach
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4,395-11,295/Month plus taxes and fees

Available: YesMap888-478-2796

Siesta Key Amazing Beach Condo

Sandy BeachVacation Rentals
  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $1,895-2,395/Week plus taxes and fees

Available: YesMap888-478-2796

Private Pool at this Three Bedroom Vacation Rental

Vacation Rental Home in Siesta KeyPool
  • Value
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3,495-7,495/Month plus taxes and fees

Available: YesMap888-478-2796

Two Bedroom Two Bathroom Siesta Key Rental - Sleeps 4

Exterior View of RentalCommunal Pool
  • Value
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $895-1,595/Night plus taxes and fees

Available: YesMap888-478-2796