167 Vacation Rentals Found: 5+ Bedroom Anna Maria Island & Holmes Beach

Get help finding your rental: (866) 922.0572

Vacation Rental on Anna Maria island with Pool and Boat Dock

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

Luxury Island Rental Home- Six Bedrooms Mediterranean Style

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

Eight Bedroom - Sleep 16 North Holmes Beach One Min to Beach

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 8 Bedrooms
  • 5 Bathrooms

No Roads to Cross Sleeps 10! Pool/Hot Tub Anna Maria Rental

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

Anna Maria Five Bedroom Rental - Rarely Look This Great!

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

Six Bedroom Luxury Vacation Rental Home - Sleeps 12

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

Six Bedroom 5 Bathroom Vacation Rentals - Available Weekly

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

Beautiful Beach Pool Home on Anna Maria Island. Sleeps 16

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

Largest Anna Maria Beach House Estate Sleeps 21

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

Direct Bay Front Luxury Vacation Rental with Boat Dock

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

Anna Maria Island Luxury Beach Vacation Rental Sleeps 12

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

Luxury Anna Maria Island Rental

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

Anna Maria Island Luxury 5 Bedroom Vacation Rental with Pool

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

Six Bedroom Family Vacation Rental, Sleeps 16 Guests

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

Luxury Anna Maria Estate in Cortez Main and Guest Home

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

Fabulous Anna Maria Island Luxury Home Sleeps 16- Eight Bdrm

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

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens!

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

Beachfront private pool Anna Maria Rental sleeps 18

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 4 Bathrooms

8 bedroom deluxe pool sleep 16 rental on Anna Maria

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

Anna Maria Island Five Bedroom Vacation Rental Pool & Spa

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

Almost Beachfront Luxury Anna Maria Island Vacation Home

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 18
  • 7 Bedrooms
  • 5 Bathrooms

Gulf Views from Holmes Beach 5 Bed Pool Rental on Anna Maria

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

Anna Maria 9 Bedroom Beach Vacation Rental with Pool

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 9 Bedrooms
  • 6 Bathrooms

Five Bedroom Villa Luxury Interior & Large Private Pool

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

Six Bedroom Luxury Vacation Rental on Anna Maria Sleeps 14

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

Luxury Anna Maria Eight Bedroom Beach Rental Home with Pool

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 8 Bedrooms
  • 6 Bathrooms

One of Anna Maria Islands Most Luxurious Vacation Rental

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 15
  • 6 Bedrooms
  • 4 Bathrooms

Luxury 7 bedroom sleep 21 on Anna Maria Island

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

Luxury Anna Maria Island Five Bedroom Beach Home Sleeps 10

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

Anna Maria Island 5 Bedroom Luxury Vacation Home- Gulf Views

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

Anna Maria Island 5 Bedroom Luxury Beachfront Vacation Home

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

6 Bedroom with Private Pool Rental on Anna Maria Island

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

Luxury Five Bedroom Luxury Anna Maria Island Vacation Home

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

Luxury Vacation Rental - Sleeps Maximum of 30 Guests

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 30
  • 11 Bedrooms
  • 8 Bathrooms

Beachfront Nine Bedroom Sleeps 28 Anna Maria Rental W/Pool

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 28
  • 9 Bedrooms
  • 9 Bathrooms

Rent Beachfront 7 Bedroom 6 Bathroom Vacation House Pool

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

Nine Bedroom Vacation Home Sleeps 22 Anna Maria island

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 22
  • 9 Bedrooms
  • 6 Bathrooms

Luxury Five Bedroom Vacation Home Sleeps 12 Guests

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

Luxury Anna Maria Vacation Rental Home with Five Bedrooms

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

Anna Maria Luxury Five Bedroom Vacation Home Sleeps Eight

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

Bradenton Beaches Top Rental Home Luxury All the Way

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 26
  • 10 Bedrooms
  • 9 Bathrooms

Bayfront 5 Bedroom Sleeps 12 with Boat Dock

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Beach House- Short Walk to Beach North End

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

Five Bedroom Vacation Rental Private Pool WOW Rental

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island Five Bedroom Vacation Rental Homes.

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Gulf Views Sleeps 12 Guests Take a Look Great Home

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

5 Bedroom Value Priced Anna Maria Island Rental with Pool

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Five Bedroom Rental- Home Pool at Door Oasis!

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Luxury Pool Rental Island- Canal- North End

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

Huge Anna Maria Vacation Rental Home with Six Bedrooms

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

Luxury 6 Bedroom Rental Best Rental Home Award Anna Maria

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 17
  • 6 Bedrooms
  • 4 Bathrooms

Seven bedroom Vacation Rental - Sleeps 16 - Private Pool.

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 4 Bathrooms

Six Bedroom Rental Canal Home Boat Dock

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Stunning Six Bedroom Super Impressive Home Close to Beach

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

Rental Sleeps 12 Guests Gulf Views 1 Min Walk to Sand

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Six Bedroom Custom Built Luxury Pool Home

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

5 bedroom North Anna Maria Rental

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Luxury six bedroom 5 bath Rental- Breathtaking views

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 6 Bedrooms
  • 5 Bathrooms

5 Bedroom pool Vacation Rental North Anna Maria Island

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Beachfront pool home on North Anna Maria Island- Sleeps 14

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 4 Bathrooms

Canal front 5 Bedroom Vacation Rental Ground One Level Home

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island 5 Bedroom Vacation Rental Incerdible Pool

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Luxury 6 Bedroom Vacation Home Sleeps 16 Guests

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

Luxury Anna Maria Island private pool rental

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Six Bedroom Luxury Vacation Rental Private Pool Anna Maria

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

West of Gulf Drive 6 bedroom pool Anna Maria rental

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

Anna Maria Private Villa with Pool Sleeps 12 Gulf Views

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

One of the Largest Vacation Rental 8 Bedroom Luxury 7 Bath

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 8 Bedrooms
  • 7 Bathrooms

6 Bedroom no roads to cross to beach Anna Maria rental

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

Six Bedroom Bayfront Luxury Home with Pool and Boat Dock.

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

50 STEPS TO BEACH Anna Maria 6 bedroom pool rental

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

Eight Bedroom Luxury Vacation Home with Pool.

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 8 Bedrooms
  • 5 Bathrooms

Stunning Anna Maria 5 Bedroom 4 Bathroom Home Close to Beach

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

6 Bedroom w/ Boat Dock and pool sleeps 14 Anna Maria Rental

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

Five Bedroom Rentals with Boat Dock and One Block to Beach

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

Lovely Five Bdrm Beach Rental on Holmes Beach- Tropical Pool

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Luxury Five Bedroom Vacation Rental One of the Islands Best

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Luxury 6 Bedroom Anna Maria Cottage Sleeps 16 Steps to Beach

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

Six Bedroom Ultimate with Peeks of the View of The Gulf of Mexico

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

Fabulous Five Bedroom Villa & Private Pool in Holmes Beach

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

West of Gulf Drive 5 bedroom pool Home with 4.5. Bathrooms

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

One of the Best Five Bedroom Homes on the Island Boat Dock

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

Bradenton Waterfront Luxury Rental 3 min Walk to Beaches.

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 18
  • 6 Bedrooms
  • 4 Bathrooms

Bayfront Luxury Sleep 15 Six Well Appointed Bedrooms

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 17
  • 6 Bedrooms
  • 4 Bathrooms

Holmes Beach Luxury Vacation Pool Home

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

Great Canal Front Home with Water Slide Pool and Views

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island Five Bedroom Rental Home - SLEEPS 12

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

Luxury Vacation Homes with Pool Anna Maria Island

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Six Bedroom Vacation Rentals on Anna Maria Island Sleeps 12

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

5 Bedroom Vacation Rental on Anna Maria Island Sleeps 10

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Value Priced Vacation Rental Home Anna Maria Island & Pool

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

Swimming Pool View from this Luxury Private Vacation Rental

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

Beachside Anna Maria Vacation Six Bedrooms Sleeps 12

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

100 Steps to the Beach- Walk to Bridge Street Shops

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

Anna Maria Vacation Home with Bay View & Short Walk to Beach

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

Anna Maria 5 bedroom Vacation Rentals on Water Boat Dock

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Stunning Gulf and Bay Views Bradenton Rental Roof Top Views

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 17
  • 6 Bedrooms
  • 4 Bathrooms

Anna Maria 2 houses off the beach with private pool home

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

Five Bedroom Luxury Vacation Rental Anna Maria- With Pool

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

Luxury 8 Bedroom Rental Home Anna Maria Island Pool

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

Best Anna Maria Vacation Rental Five Bedrooms- Sleeps 10

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island Five Bedroom Vacation Rentals

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

Main House & Guest House with Tropical Pool Sleeps 20

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

North end Anna Maria sleeps 8 within steps of the beach

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 5 Bedrooms
  • 2 Bathrooms

One of the Few Five Bedroom Rentals on Anna Maria Island

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

Anna Maria Island Vacation Home on the North End of Island.

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

Five bedroom No Streets to Cross Steps to Beach Sleeps 12

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

NEW 5 bedroom rental on the North end of Anna Maria Island.

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 11
  • 5 Bedrooms
  • 4 Bathrooms

Island Five Bedroom Rental with a Pool Close to Bean Point

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

Large Anna Maria Home, Sleeps 20

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 20
  • 8 Bedrooms
  • 8 Bathrooms

Rent Luxury on Anna Maria- Pool Hot tub

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 13
  • 5 Bedrooms
  • 4 Bathrooms

Anna Maria Island Beach House for Rent with POOL

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

Steps to Beach with Views 5 Bedroom Sleeps 10 Anna Maria

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

Big Family Anna Maria Beach House

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Five Bedroom Home for Rent with a Pool on Anna Maria Island

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

Luxury Anna Maria Island 8 Bedroom Rental Home

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

Anna Maria Island Rental with Pool

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

Rental Home on Anna Maria Island- 5 bedrooms

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

Steps to the beach with luxury 5 bedroom Anna Maria rental

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

Anna Maria Island Large Vacation Rentals

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

Anna Maria Island Five Bedroom Luxury Vacation Rental

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

North end Anna Maria Rental w/ no streets to cross sleep 12

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

New Anna Maria Island Rental 6 bedroom 1 min walk to beach

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

7 BEDROOM SLEEP 15 W/ 1 MIN WALK TO ANNA MARIA BEACH

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 15
  • 7 Bedrooms
  • 6 Bathrooms

Five Bedroom Luxury Vacation Home on Anna Maria Island

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 3 Bathrooms

Luxury Anna Maria Island Six Bedroom Luxury Rental

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

Anna Maria Island 6 bedroom vacation Rentals

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

Posh Five Bedroom Vacation Rental One Min Walk to Beaches!!!

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

Anna Maria Island Sleeps 14 Six Bedrooms Five King Beds

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

Luxury 5 Bedroom Anna Maria Island Rental Walk to Beach

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

Sleep 14 with this NEW Anna Maria Property with 6 Bedrooms

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

Five Bedroom Anna Maria Island Rental Pool Home Sleeps 10!!

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island Six Bedroom Vacation Home with a Pool

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

Anna Maria 5 Bedroom Vacation Home - Sleeps 10

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

SIX Bedroom Anna Maria Rental Private Home with Pool

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

Luxury Seven Bedroom Rental Sleeps 18 with Stunning Views

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 18
  • 7 Bedrooms
  • 7 Bathrooms

Anna Maria Island 5 Bedroom Home Approx 30 Seconds Beach

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

Gulf and Bay View 9 bedroom sleeps 24 Anna Maria Pool Rental

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 22
  • 9 Bedrooms
  • 6 Bathrooms

WOW Great Family Rental Sleeps 11 Guests with Private Pool

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

Seven Bedroom Rental Sleeps 18 Guests with Private Pool

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 7 Bedrooms
  • 6 Bathrooms

Vacation Home Sleeps 14 on Anna Maria - 4 Houses from Beach

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

Luxury Five Bedroom Anna Maria Island Rental - Sleeps 12

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

Six Bedroom Vacation Homes with Private Pool Sleep 12

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

Luxury Six Bedroom Vacation Home Sleeps 12 Private Pool

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Anna Maria Six Bedroom Bayfront Vacation Rental Home

  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 5 Bathrooms

Anna Maria Island Luxury Across from Beach

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 15
  • 5 Bedrooms
  • 4 Bathrooms

Five Bedroom Vacation Home Short Walk to Beach Sleeps 12

  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 5 Bathrooms

Five Bedroom Vacation Home with Private Pool Sleeps 16

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Vacation Rental

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Five Bedroom Vacation Home Private Pool Walk to Beach

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

Private Pool at this Five Bedroom Anna Maria Vacation Rental

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 13
  • 5 Bedrooms
  • 4 Bathrooms

Anna Maria Island & Holmes Beach Home 908020

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

Bradenton Beach Beauty Best Ever Rental Six bedrooms Views

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

Anna Maria Vacation Rentals

  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 17
  • 7 Bedrooms
  • 7 Bathrooms

Anna Maria Vacation Rentals 6 Bedrooms Private Pool

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

Anna Maria Five Bedroom Rental

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

Beachfront Anna Maria Island Beach House Vacation Rental

  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 3 Bathrooms

Six bedroom Anna Maria Vacation Rental Steps from Beach

  • Silver
  • Condo
  • Pool
  • Max Occupancy: 18
  • 6 Bedrooms
  • 5 Bathrooms

Six Bedroom Rentals on Anna Maria with Pools!

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

Anna Maria Island Vacation Rental Sleeps 16

  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

North Anna Maria 9 bedroom resort SLEEP 26

  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 26
  • 9 Bedrooms
  • 6 Bathrooms

DIRECTLY ACROSS ST FROM BEACH SLEEP 24 WITH POOL

  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 8 Bathrooms

Five Bedroom Home For Rent Cortez Village

  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 3 Bathrooms

STEPS TO BEACH WHOLE RESORT SLEEP 18 ANNA MARIA RENTAL

  • Silver
  • Condo
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 5 Bathrooms

Five Bedroom Rental That Sleeps 12 Anna Maria Island

  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island & Holmes Beach Home 908021

  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 3 Bathrooms

New Duplex Short Stroll to Beach Bradenton Beach

  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms