Platinum Anna Maria Island & Holmes Beach Vacation Rentals

All Pool Options

80 matching vacation rentals found.

We receive new listings daily. Call your agent at 844.826.5260 for an up to date list of available rental options.

Three Bedroom Vacation Rentals Anna Maria island. Gulf Front

Heated Pool with Hot Tub
  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $6507/Week

Available: Yes844-826-5260

Three Bedroom Luxury Condo on the Beach on Anna Maria Island

Vacation condo in Holmes Beach, Florida
  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3295/Week

Available: Yes844-826-5260

Anna Maria Island 3 Bedroom Vacation Condos On Beach


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3995/Week

Available: Yes844-826-5260

Four Bedroom Anna Maria Island Vacation Rentals

Rental home with private pool & hot tub in Holmes Beach, Florida
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $2395/Week

Available: Yes844-826-5260

Anna Maria Gulf front Vacation Rental with Three Bedroom


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3295/Week

Available: Yes844-826-5260

Three Bedroom Vacation Rental Luxury on Anna Maria Island


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3295/Week

Available: Yes844-826-5260

Gulf Front Anna Maria Vacation Condo sleeps 6


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $4595/Week

Available: Yes844-826-5260

Four Bedroom Luxury Beachfront Rental on Anna Maria Island


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $6377/Week

Available: Yes844-826-5260

Luxury Anna Maria Rental with Three Bedrooms, Walk to Beach!


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3995/Week

Available: Yes844-826-5260

7 Bedroom Luxury Anna Maria Beach Rental with Pool

Private pool & spa
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 7 Bedrooms
  • 4 Bathrooms

Starting at $8495/Week

Available: Yes844-826-5260

Anna Maria Luxury 2 bedroom Vacation Rental Pools


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $2795/Week

Available: Yes844-826-5260

Anna Maria Vacation Condos

Master bedroom with flat screen TV
  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3495/Week

Available: Yes844-826-5260

Anna Maria Luxury Rental Home with Five Bedrooms

Canalside pool
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $6495/Week

Available: Yes844-826-5260

Vacation Home Anna Maria Island Pool 4 Bedrooms!

One minute walk to beachOutdoor Area
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Call for Rates

Available: Yes844-826-5260

Six bedroom Luxury Vacation Rental on Anna Maria with Pool


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 3 Bathrooms

Starting at $5995/Week

Available: Yes844-826-5260

Eight Bedroom vacation rental on Anna Maria Island- Sleep 18

Holmes Beach rental home sleeps 18!
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 8 Bedrooms
  • 5 Bathrooms

Starting at $14495/Week

Available: Yes844-826-5260

Anna Maria Island Luxury 3 Bedroom Vacation Rental Views


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $6973/Week

Available: Yes844-826-5260

Six Bedroom Rental Anna Maria Island with Views.


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $0.00/Week

Available: Yes844-826-5260

Gulf View Luxury Three Bedroom Beach Rentals Anna Maria


  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4465/Week

Available: Yes844-826-5260

Seven Bedroom Anna Maria Rental with Six King Bedrooms


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 7 Bedrooms
  • 5 Bathrooms

Starting at $9795/Week

Available: Yes844-826-5260

Gulf front Condo on Anna Maria in Gated Tropical Community.


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3495/Week

Available: Yes844-826-5260

Anna Maria 5 Bedroom Rentals- Rarely this Great!


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $5586/Week

Available: Yes844-826-5260

Anna Marias Most Beautiful Vacation Rental Homes

Front ViewEntrance
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $5120/Week

Available: Yes844-826-5260

Anna Maria Luxury Beach Condo with Two Bedrooms

Dining Room with Panoramic Gulf ViewOpen Plan Living Space
  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $8083/Month

Available: Yes844-826-5260

Great Canal front home with water slide pool on Anna Maria


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy:
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $5995/Week

Available: Yes844-826-5260

Anna Maria Six bedroom Luxury Vacation Rental with Pool


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $8495/Week

Available: Yes844-826-5260

Six Bedroom Vacation Rental Home Anna Maria Island.Sleeps 16

Front view of property
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $6495/Week

Available: Yes844-826-5260

Posh Anna Maria vacation rental home with four bedrooms


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $4795/Week

Available: Yes844-826-5260

Six Bedroom 5 bathroom Vacation Rentals on Anna Maria Island


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $4000/Week

Available: Yes844-826-5260

Beautiful Beach Home on Anna Maria Island.Sleep 16


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 6 Bedrooms
  • 3 Bathrooms

Starting at $6095/Week

Available: Yes844-826-5260

Anna Maria Beach House Rental - Nine Bedrooms Sleeps 21!


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 21
  • 9 Bedrooms
  • 6 Bathrooms

Starting at $8495/Week

Available: Yes844-826-5260

Direct Bay front Luxury on Anna Maria Island - Boat Dock

Rear view of propertyPool & bay view from balcony
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $0.00/Week

Available: Yes844-826-5260

Value Priced Luxury Three bedroom Plus Den Anna Maria Rental

Holmes Beach rental villaHolmes Beach rental with Bay view
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $2695/Week

Available: Yes844-826-5260

Three Bedroom Vacation Condo for Rent Anna Maria Island


  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $4200/Week

Available: Yes844-826-5260

Anna Maria Island & Holmes Beach Home 878624


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $00/Month

Available: Yes844-826-5260

Five Bedroom Luxury Rentals on Anna Maria Island- All Pools

Anna Maria Island
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $5795/Week

Available: Yes844-826-5260

Anna Maria Island Luxury Beach Vacation Rental Sleeps 16

Anna Maria 6 bedroomoPrivate pool
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $8495/Week

Available: Yes844-826-5260

Spectacular Anna Maria Island Vacation Rental 12 bedrooms

Exterior view
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $5795/Week

Available: Yes844-826-5260

Anna Maria Island & Holmes Beach Home 880516


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $5187/Week

Available: Yes844-826-5260

Luxury Anna Maria Vacation Home Rental- Boat Lift 4 bedrooms

Private hot tubFully equipped kitchen
  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $12995/Month

Available: Yes844-826-5260

Three Bedroom Beachfront Condo for Rent on Anna Maria Beach

Gulf view balcony with outdoor furnitureLiving room
  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $13495/Month

Available: Yes844-826-5260

Anna Maria Six Bedroom Vacation Rental - Sleeps 16


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Starting at $6538/Week

Available: Yes844-826-5260

Anna Maria Island Most Prestigious Vacation Rental


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $4000/Week

Available: Yes844-826-5260

Luxury Anna Maria Estate for Rent- Guest House & Main House

Large Heated Swimming PoolBay front vacation home in Cortez, Florida
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $7495/Week

Available: Yes844-826-5260

Five Bedrm Luxury Vacation Rental Anna Maria- With Pool

Swim up table
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $5995/Week

Available: Yes844-826-5260

Super Updated Three Bedroom on Anna Maria Island- Ranch


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $2495/Week

Available: Yes844-826-5260

Fabulous Anna Maria Island Luxury Home Sleeps 20- Eight Bdrm


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $14495/Week

Available: Yes844-826-5260

Main House & Guest House with Tropical Pool Sleeps 22


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 20
  • 8 Bedrooms
  • 6 Bathrooms

Starting at $11969/Week

Available: Yes844-826-5260

Anna Maria Island Pool Home 5 bedrooms


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $5995/Week

Available: Yes844-826-5260

Anna Maria Island Vacation Rental on North End


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 9
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $5195/Week

Available: Yes844-826-5260

Luxury Four Bedroom Rentals in Anna Maria

Luxurious home for rent in Anna Maria Island, Florida
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $6495/Week

Available: Yes844-826-5260

Luxury Anna Maria Rentals with Six Bedrooms


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $5795/Week

Available: Yes844-826-5260

Anna Maria Island 4 Bedroom Vacation Rental Sleeps 12

Beautiful vacation home in Anna Maria, Florida
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $5100/Week

Available: Yes844-826-5260

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens!


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 6 Bathrooms

Starting at $14995/Week

Available: Yes844-826-5260

Anna Maria Island Home for Rent on Beach

Bay Front Rental Home in Anna Maria, Florida
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Starting at $6495/Week

Available: Yes844-826-5260

Luxury Vacation Rental Home sleeps Eight / Anna Maria Island


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $3995/Week

Available: Yes844-826-5260

Beach House on Anna Maria Island- 6 Bedrooms

Chairs on the BalconyPrivate Pool is Beachside
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $11995/Week

Available: Yes844-826-5260

Anna Maria Rental Sleeps 20- Eight Bedrooms


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 8 Bedrooms
  • 7 Bathrooms

Starting at $8495/Week

Available: Yes844-826-5260

North Anna Maria Island Rentals

Gulf View from Property
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $6995/Week

Available: Yes844-826-5260

Anna Maria Island Luxury Beach House- Sits on Sand


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $7500/Week

Available: Yes844-826-5260

Anna Maria 9 Bedroom Beach Vacation Rental with Pool


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 24
  • 9 Bedrooms
  • 6 Bathrooms

Starting at $18,500/Week

Available: Yes844-826-5260

Five Bedroom Villa Luxury Interior & Large Private Pool

New Villa Painted in Ocean Blue TonesWood Floors Modern Kitchen
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Starting at $6495/Week

Available: Yes844-826-5260

Stunning 3 Bedroom Anna Maria Villa Rental with Private Pool

Canal Front Home with Pool  in Anna Maria, FloridaOpen Plan Living Space
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $3458/Week

Available: Yes844-826-5260

Six Bedroom Luxury Vacation Rental on Anna Maria Sleeps 14


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 6 Bedrooms
  • 3 Bathrooms

Starting at $5680/Week

Available: Yes844-826-5260

Anna Maria Island 8 Bedroom Beach House with Pool SLEEPS 17


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

Starting at $12950/Week

Available: Yes844-826-5260

A Tropical Hideaway on Anna Maria Island

Open Kitchen & Living AreaWall Mounted TV in Living Area
  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 7 Bathrooms

Starting at $8995/Week

Available: Yes844-826-5260

Anna Maria Island Luxury Home with Pool


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 4 Bathrooms

Starting at $4995/Week

Available: Yes844-826-5260

Luxury Homes Beach 4 Bedroom Rental Walk to Beach with Pools

Stunning Interior KitchenLuxury Anna Maria Home
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $3195/Week

Available: Yes844-826-5260

Luxury Anna Maria Five Bedroom Beach Home


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $7495/Week

Available: Yes844-826-5260

Luxury Anna Maria Island Six Bedroom Luxury Rental


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 4 Bathrooms

Starting at $0.00/Week

Available: Yes844-826-5260

Anna Maria Island 5 Bedroom Luxury Vacation Home- Gulf Views


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $0.00/Week

Available: Yes844-826-5260

Exceptional Anna Maria Island Club Rental


  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Starting at $3095/Week

Available: Yes844-826-5260

Three Bedroom Luxury Vacation Rental Anna Maria Island


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $3026/Week

Available: Yes844-826-5260

Anna Maria Island 5 Bedroom Luxury Beach Front


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 5 Bathrooms

Starting at $8985/Week

Available: Yes844-826-5260

Luxury Three Bedroom Plus Loft Vacation Home on the Water


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Starting at $5621/Week

Available: Yes844-826-5260

One of the Best Vacation Rentals On Anna Maria Island.


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $7000/Week

Available: Yes844-826-5260

Anna Maria Island & Holmes Beach Home 894195


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Starting at $4459/Week

Available: Yes844-826-5260

Anna Maria Island & Holmes Beach Home 894529


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Starting at $8379/Week

Available: Yes844-826-5260

Anna Maria Island Four Bedroom Luxury Pool Vacation Rental


  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 Bathrooms

Starting at $5319/Week

Available: Yes844-826-5260

Bradenton Beach Vacation Home


  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Starting at $7182/Week

Available: Yes844-826-5260