210 Rentals: Anna Maria Island & Holmes Beach 5+ Bedrooms

Get help finding your rental: 941.900.4552

Anna Maria Luxury Vacation Home 5 houses to beach

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

5 Star Luxury Rental on Anna Maria Sleeps 16 With Gulf Views

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

Beautiful Pool Home on Anna Maria Island Sleeps 16

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

Anna Maria Direct Bay Front Luxury Vacation Home - Boat Dock

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

Anna Maria Island Luxury 5 Bedroom Beach 1 Minute Walk

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 15
  • 5 Bedrooms
  • 3 Bathrooms

Stunning Gulf and Bay Views Bradenton Rental Roof Top Views

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

Six Bedroom Luxury Vacation Rental Anna Maria With Pool

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

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens! Top Rentals

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 20
  • 7 Bedrooms
  • 5 Bathrooms

Almost Beachfront - Luxury Anna Maria Island Vacation Home

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

Luxury Anna Maria 9 Bedroom Beach Vacation Rental with Pool

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

Luxury Anna Maria Eight Bedroom Beach Rental Home with Pool

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

Anna Maria Vacation Home Just One Minute Walk to Beach

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

Anna Maria Island Six Bedrooms Walk to Beach Home Sleeps 14

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

Five Bedroom Luxury Beachfront Home with Private Pool & Spa

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

Luxury Five Bedroom Luxury Anna Maria Island Rental Home

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

Epitome of Luxury for a Dream Vacation in Anna Maria!

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

Rent Anna Maria Beachfront 7 Bedroom Vacation Pool Home

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

Luxury Anna Maria 7 Bedroom Rental Private Beach Sleeps 16

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

Stunning 10 Bedroom Estate on the Beach with Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 20
  • 10 Bedrooms
  • 7 Bathrooms

Luxury Five Bedroom Anna Maria Vacation Home Sleeps 12

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

Luxury Anna Maria Six Bedroom Bayfront Vacation Rental Home

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  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 18
  • 6 Bedrooms
  • 5 Bathrooms

Luxury Anna Maria Vacation Home Short Walk to Beach Sleep 14

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  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms

Newly Constructed Home 2 Blocks from Beach!

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

Large & Luxurious Anna Maria Island 7 Bedroom Rental

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

Luxury Bradenton Beach Top Rental Home Luxury All the Way!

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 10 Bedrooms
  • 8 Bathrooms

Wow Luxury Anna Maria Beachfront Pool Home Sleeps 18

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

Bradenton Beach Vacation Pool Home with Gulf Views

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

Anna Maria Vacation Home Rental Sleeps 12 Guests

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

Anna Maria Island Home Sleeps Twelve Guests

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

Spectacular Rental Anna Maria Island Vacation Pool Home

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

Luxurious 7 Bedroom Home Featuring a Tropical Outdoor Oasis

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

Breathtaking Brand new Luxury Home in Bradenton Beach

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

Anna Maria Island Luxury 9 Bedroom Vacation Home

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • 9 Bedrooms
  • 8 Bathrooms

Luxury 5 Bedroom Anna Maria Vacation Pool Home

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

Luxury Anna Maria Vacation Pool Home Four Bedrooms Sleeps 10

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

Water Views Anna Maria Island Vacation Home Private Pool

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

Private Pool Holmes Beach Vacation Home + Guest House

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

Short Walk to Beach Anna Maria Island Vacation Pool Home

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

The Ultimate Bayside Vacation Retreat Boat Dock

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 19
  • 5 Bedrooms
  • 3 Bathrooms

Super Short Walk to Beach One Minute Walk!

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

Anna Maria 5 Bedroom Vacation Rental Private Pool WOW Rental

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

Anna Maria 7 Bedroom Private Pool Vacation Beach Home

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

Large Anna Maria Vacation Rental Home with Six Bedrooms

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

Anna Maria Luxury 6 Bedroom Rental - Best Rental Home Award

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

Anna Maria 7 Bedroom Vacation Rental Sleeps 16 Private Pool

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

Anna Maria 5 Bedroom Rental Sleeps 12 Guests - Gulf Views

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

Anna Maria Six Bedroom Villa Just 100ft to Sandy Beach

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

Luxury Vacation Home 6 Bedrooms Anna Maria Island Sleeps 12

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

Luxurious 5 Bedroom North Anna Maria Island Vacation Rental

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 11
  • 5 Bedrooms
  • 3 Bathrooms

Beachfront 5 Bedroom Vacation Pool Home Anna Maria Island

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

Canal front 5 Bedroom Vacation Rental Ground One Level Home

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

Beachfront Anna Maria Island Beach House Vacation Rental

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 13
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island 5 Bedroom Vacation Rental Incredible Pool

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

Anna Maria Luxury 6 Bedroom Vacation Home 450ft to beach

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

Luxury Anna Maria Island Private Pool Rental Available Now

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

Anna Maria Six Bedroom Luxury Vacation Rental - Private Pool

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

Luxury 6 Bedroom Anna Maria Home with Pool

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

Anna Maria Private Villa with Pool Sleeps 12 Gulf Views

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

6 Bedroom No Roads to Cross to Beach Anna Maria Rental

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

50 STEPS TO BEACH Anna Maria 6 Bedroom Pool Rental Home

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

Eight Bedroom Luxury Vacation Home with Pool on Anna Maria

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

Stunning Anna Maria 5 Bedroom 4 Bathroom Home Close to Beach

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

Anna Maria Bedroom Luxury Home - Boat Dock & Pool Sleeps 14

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

Five Bedroom Rental with Boat Dock and One Block to Beach

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

Lovely Five Bedroom Beach Vacation Rental on Holmes Beach

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

Luxury Five Bedroom Vacation Rental Anna Maria Island

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

Six Bedroom Anna Maria Rental - Peeks of The Gulf of Mexico

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

Anna Maria West of Gulf Drive Five Bedroom Pool Home

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

One of the Best 5 Bedroom Homes on Anna Maria with Boat Dock

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

Waterfront Anna Maria Rental 3 Minute Walk to Beaches

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

Anna Maria Bayfront Luxury Home Sleeps 17 - Six Bedrooms

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

Anna Maria Vacation Rental 5 Bedrooms Sleeps 10 Private Pool

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

Anna Maria Five Bedroom Rental -Stunning

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

Holmes Beach Luxury Vacation Pool Home Sleeps 14

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

Five Bedroom Anna Maria Home with Water Slide Pool & Views

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

Anna Maria Island Five Bedroom Rental Home - SLEEPS 12

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

Anna Maria 6 Bedroom Luxury Vacation Rental Home - Sleeps 12

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

Anna Maria Six Bedroom Vacation Weekly Rental Sleeps 12

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

Anna Maria Island Luxury Vacation Rental with Pool

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

Six Bedroom Vacation Rentals on Anna Maria Island Sleeps 12

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

The Ultimate Anna Maria Luxury Beach House Sleeps 21

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

5 Bedroom Vacation Rental on Anna Maria Island Sleeps 10

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

Anna Maria Rental You Can Almost Throw Frizbee to the Beach

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

Luxury Anna Maria Island Rental Home 6 Bedrooms with Pool

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

Anna Maria Vacation Home 100 Steps to the Beach - Sleeps 12

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

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

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

Anna Maria Luxury Five Bedroom Rental Sleeps Eight

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

Anna Maria 5 Bedroom Vacation Rental with Pool & Boat Dock

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

Anna Maria Private Pool Vacation Home Two Houses Back Beach

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

Luxury 8 Bedroom Rental Home Anna Maria Island with Pool

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

Luxury Anna Maria Vacation Home Five Bedrooms - Sleeps 10

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

Fabulous Anna Maria Island 8 Bedroom Luxury Home Sleeps 16

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

Anna Maria Main House & Guest House with Pool Sleeps 20

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

North End Anna Maria 5 Bedroom Home Steps To The Beach

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

Anna Maria Island Pool Home 5 bedrooms

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

One of the Few Five Bedroom Rentals on Anna Maria Island

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

Anna Maria Island Vacation Home on the North End of Island

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

Five Bedroom Rental on the North End of Anna Maria Island

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

Anna Maria Island 5 Bedroom Rental Pool Close to Bean Point

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

Rent Luxury Vacation Home on Anna Maria - Pool and Spa

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

Anna Maria Island Beach House for Rent with POOL

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

Steps to Beach with Views 5 Bedroom Sleeps 10 Holmes Beach

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

Anna Maria Beach House, 6 Bdrm with Private Pool

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

Eight Bedroom Deluxe Anna Maria Rental With Private Pool

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

Luxury Anna Maria Island Eight Bedroom Rental Pool Home

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

Anna Maria Island Rental with Pool

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

Luxury Five Bedroom Vacation Pool Home in Anna Maria

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

Anna Maria Island Five Bedroom Vacation Rental Pool & Spa

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

Steps to the beach with luxury 5 bedroom Anna Maria rental

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

Anna Maria Island Five Bedroom Luxury Vacation Rental

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

North End Anna Maria Rental No Streets to Cross to Beach!

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

Fabulous Rental Steps to the Beach

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

Anna Maria 5 Bedroom Villa Luxury Interior & Private Pool

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

One of Anna Maria Islands Most Luxurious Vacation Rentals

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

Anna Maria Island Rental 6 Bedroom Short Walk to Beach

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

Luxury Anna Maria Island 7 Bedroom Vacation Rental Sleeps 19

  Save Rental
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 19
  • 7 Bedrooms
  • 7 Bathrooms

Five Bedroom Luxury Vacation Home on Anna Maria Island

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

Luxury Anna Maria Island Five Bedroom Beach Home Sleeps 10

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

Anna Maria Island Rentals Stunning Vacation Rentals!

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

Luxury Anna Maria Island Six Bedroom Luxury Pool Rental

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

Anna Maria Island 5 Bedroom Two Houses Away Beach Access

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

Anna Maria Posh Five Bedroom Vacation Rental Close to Beach

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

Luxury 5 Bedroom Anna Maria Island Rental 2 Blocks to Beach

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

Anna Maria Vacation Property Six Bedrooms Sleeps 14 Guests

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

Five Bedroom Anna Maria Island Rental Pool Home Sleeps 10!

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

Anna Maria Island 6 Bedroom Vacation Rental Pool Home

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

Anna Maria Island 5 Bedroom Gulf Front Property Sleeps 10

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

Anna Maria 5 Bedroom Vacation Home -2 Houses From Gulf

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

5 Bedroom North End Anna Maria Rental Home with Private Pool

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

Luxury Six Bedroom Private Pool Rental on Anna Maria Island

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

Anna Maria Island Holmes Beach Rental Home 6 Bedrooms

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

Anna Maria Luxury Vacation Rental - Sleeps 30 Guests

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

Bradenton Beach Pool Vacation Rental Home Sleeps 22

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

Anna Maria Vacation Home 5 Bedrooms Sleeps 12 North End

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

Luxury Five Bedroom Anna Maria Island Rental - Sleeps 12

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

Anna Maria 6 Bedroom Private Pool 3 Moin Walk Beach

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

Luxury Anna Maria Vacation Rental Home with Five Bedrooms

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

Anna Maria Five Bedroom Vacation Home Private Pool Sleeps 14

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

Spacious Anna Maria Vacation Rental 5 Bedrooms Sleeps 10

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

Holmes Beach 6 Bedroom Vacation Rental Sleeps 14

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

Holmes Beach Five Bedroom Vacation Home Private Pool

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

Private Pool at this Five Bedroom Anna Maria Vacation Rental

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

Three Level Six Bedroom Anna Maria Island Pool Home

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

Anna Maria Island Vacation Home Sleeps Fourteen.

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

Anna Maria Island Luxury Vacation Home Six Bedrooms

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

Anna Maria Island Six Bedroom Luxury Home with Pool

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

Homes Beach Vacation Rental Home Pool & Bar

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

Anna Maria Vacation Rental Home 5 Bedrooms Sleeps 12

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

Bradenton Beach Beauty Best Ever Rental Six Bedrooms - Views

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

Anna Maria Island Rent the Entire Resort!

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  • Gold
  • Condo
  • Pool
  • Max Occupancy: 22
  • 8 Bedrooms
  • 4 Bathrooms

Anna Maria Vacation Rentals 6 Bedrooms Private Pool

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

Luxury 6 Bedroom Anna Maria Vacation Rental - Pets Welcome

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

Anna Maria Island Five Bedrooms Sleeps 12 Private Pool

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

Vacation Villa Short Walk to Bean Point on Anna Maria Island

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

Luxury Seven Bedroom Bradenton Beach Rental Home Canal Views

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

Anna Maria Island Vacation Home Sleeps Sixteen Guests

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

Holmes Beach Vacation Home Rental Sleeps Fourteen

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

Bradenton Beach Vacation Pool Rental Home Sleeps 18

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

Holmes Beach Rental Home Sleeps 10 Guests Partial Gulf View

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

Holmes Beach Vacation Rental 5 Bedrooms Sleeps Ten Guests

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

Anna Maria Island 7 Bedroom Villa Luxury 5 Min Walk to Beach

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

World Class Bradenton Beach Vacation Pool Home

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

Luxury Holmes Beach Vacation Rental Six Bedrooms with Pool

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

Anna Maria Island Vacation Home Sleeps Twelve Guests

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

Anna Maria Stunning Luxury Vacation Home Private Pool & Spa

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

Anna Maria Island 5 Bedroom Luxury Pool Vacation Home

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

Holmes Beach Luxury Vacation Rental Home Six Bedrooms

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

Five Bedroom Villa with Private Pool and Lush Yard

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

Bay View 5 Bedroom Vacation Pool Home in Anna Maria

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

Anna Maria Island & Holmes Beach Home 922232

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

Anna Maria Amazing 7 Bedroom Home with a Beautiful Pool

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

Holmes Beach Vacation Rental Pool Home Five Bedrooms

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

Anna Maria Island Vacation Home

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

Anna Maria Island Luxury Vacation Rental Home Five Bedrooms

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

Bradenton Beach Luxury Vacation Rental Home

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

Bradenton Beach Luxury Vacation Rental Pool Home 7 Bedrooms

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

Anna Maria Walk to Beach Five Bedroom Vacation Home

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

Luxury Five Bedroom Home Bay & Gulf Views with Boat Dock

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

Beachfront Holmes Beach Vacation Home Sleeps 14 Guests

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

Gulf Views Bradenton Beach Vacation Home Six Bedroom

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  • Gold
  • Condo
  • Hot Tub / No Pool
  • Max Occupancy: 18
  • 6 Bedrooms
  • 4 Bathrooms

Short Walk to Beach Anna Maria Island Vacation Pool Home

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

Luxury Holmes Beach 5 Bedroom Rental with Private Pool

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

Bradenton Beach Vacation Pool & Spa Home Walk to Beach

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

Bayfront Five Bedroom Pool Home in Bradenton Sleeps 12

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

Short Walk to Beach Anna Maria Island Vacation Pool Home

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

Private Caged Pool Bradenton Vacation Home with Guest House

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 19
  • 8 Bedrooms
  • 5 Bathrooms

Eight Bedrooms Posh Vacation Home in Bradenton Beach

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

Anna Maria Island Five Bedroom Vacation Rental Cottage

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

5 Bedroom Anna Maria Island Rental with Pool

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

Spectacular Vacation Home with Boat Dock on Anna Maria

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

Six Bedroom Rental Canal Home Boat Dock Bay

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

Vacation Homes for Rent Anna Maria Island Florida

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

Anna Maria Stunning 6 Bedroom Impressive Home Close to Beach

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

Six Bedroom Anna Maria Vacation Rental Steps from Beach

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 14
  • 6 Bedrooms
  • 4 Bathrooms

Posh Vacation Rental Home with Four Bedrooms and Private Pool

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

Swimming Pool View from this Luxury Private Vacation Rental

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

Beachside Anna Maria Vacation Six Bedrooms Sleeps 12

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

Anna Maria Island Rent All 3 Units - Sleeps 10 - Pool Gulf

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

Anna Maria Island Vacation Rental Sleeps 16

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

Anna Maria 5 Bedroom Vacation Home Close to Beach Sleeps 10

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

Five Bedroom Rental That Sleeps 12 Anna Maria Island

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

Anna Maria Island 5 Bedroom Home Approx 30 Seconds to Beach

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

Holmes Beach Vacation Rental

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

Holmes Beach Home with Pool Five Bedrooms Sleeps Twelve

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

Bradenton Beach Vacation Duplex - Short Stroll to Beach

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

Anna Maria Island Holmes Beach Rentals Beach Across Street

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

Holmes Beach Vacation Home Sleeps Sixteen Guests

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  • Silver
  • Home/Villa
  • Max Occupancy: 16
  • 5 Bedrooms
  • 3 Bathrooms

Palmetto Vacation Rental Home Five Bedrooms

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

Holmes Beach Vacation Pool Home Sleeps 10 Guests

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

Anna Maria Island Vacation Pool Home With 5 Bedrooms

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