1394 Rentals: Anna Maria Island & Holmes Beach

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Get help finding your rental: 941.900.4552

North End Lux Anna Maria Rental Home Private Heated Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 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

Anna Maria Eight Bedroom Luxury Vacation Home With Pool

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

Anna Maria Island Luxury Vacation Home Ocean Front Property

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

Luxury Anna Maria Island Three Bedroom Home Private Pool

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

Luxury Villa Anna Maria Island 100 Steps to the Beach

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

Luxury Anna Maria Island Vacation Rental with Boat Dock

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

Luxury Anna Maria Island Vacation Rental On North End

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 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

Canal front beauty on Anna Maria Rental with Pool

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

Luxury Vacation Rental Home on Anna Maria - Pool and Spa

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

Anna Maria Island 4 Bedroom Luxury Vacation Rental Sleeps 8

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

Bayfront Vacation Home in Anna Maria with Pool & Spa

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

Luxury Anna Maria Eight Bedroom Beachfront Home with Pool

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

Anna Maria Luxury Vacation Home One Minute Walk to Beach

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

West of Gulf Drive Luxury home Rental

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

Three Bedroom Luxury Vacation Rental in Anna Maria Island

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

Anna Maria Island 5 Bedroom Gulf Front Property Sleeps 10

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

One of the Best Beach Vacation Rentals On Anna Maria Island.

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

One of the Best Anna Maria Island Vacation Rental Homes

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

Epitome of Luxury for a Dream Vacation Home in Anna Maria!

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

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

Anna Maria 4 Bedroom 4 Bathroom Vacation Home Sleeps 8

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

3 Bedroom Vacation Home with Private Access to the Bay

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

Luxury Five Bedroom Anna Maria Island Rental - Sleeps 12

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

A Stunning Anna Maria Island Vacation Home Sleeps 8

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

One of the Most Stunning Rentals on Anna Maria Island 5 Star

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 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

Stunning 4 Bedroom Canal Front Home with Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 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 11

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  • Platinum
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 11
  • 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

Four Bedroom Island Home Steps from Sugar White Sandy Beach

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

Luxury Anna Maria North End Beach Cottage with Private Pool

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

Anna Maria Luxury Four Bedroom Vacation Rental Sleeps 12

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

Luxury Holmes Beach Rental on Anna Maria Island Sleeps 8

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 6 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

Luxury Anna Maria Island Vacation Home with Private Pool

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

Stunning Luxury Anna Maria Beachfront Pool Home 8 Bedrooms

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

Anna Maria Island Vacation Home Sleeps Sixteen Guests

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

Bradenton Beach Vacation Pool Home with Gulf Views Sleeps 18

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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

Beachfront Anna Maria Beach House

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  • Platinum
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Stunning Luxury Vacation Home Private Pool & Spa

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

Anna Maria Island Home On the Beach Bloc!

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

Spectacular Rental Anna Maria Island Vacation Pool Home

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

Luxury Holmes Beach Vacation Home Sleeps 8 Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 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

Bradenton Vacation Rental Home Three Bedrooms

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

The Ultimate Anna Maria Vacation Residence Private Pool

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

Luxury Anna Maria Island Vacation Home Sleeps 8 Private Pool

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

Breathtaking Brand new Luxury Home in Bradenton Beach

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

Luxe Rental Located between City Pier and Rod N Reel Pier

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

Lovely 4 Bedroom Home w/Pool & Spa Sleeps 10 Walk to Beach

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

Beautiful Waterfront Anna Maria Home with Private Bay Beach

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  • Platinum
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury Vacation Pool Home on Anna Maria Sleeps Eight

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

Anna Maria Island Vacation Pool Home Sleeps 8 Guests

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

Holmes Beach Vacation Home Sleeps 8 Guests

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

Luxury Five Bedroom Home Bay & Gulf Views with Boat Dock

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

Anna Maria Four Bedroom Vacation Home Walk To Beach

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

Anna Maria Island Luxury 9 Bedroom Vacation Home

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

Luxury 5 Bedroom Anna Maria Vacation Pool Home Walk To Beach

  Save Rental
  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 5 Bedrooms
  • 3 Bathrooms

Four Bedroom Holmes Beach Vacation Home Sleeps 8 Guests

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  • Platinum
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Anna Maria Luxury Canal Front Home Sleeps 8 With Pool & SPA

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

Beautiful 4 Bedroom Canal Front Home in Anna Maria Island

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

On Beach Anna Maria Island Vacation Home With Private Pool

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

Anna Maria Island Vacation Pool Home Just Steps To Beach

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

Steps to Beach Anna Maria Island Vacation Home Four Bedrooms

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

1/2 Block to Beach Anna Maria Island Vacation Pool Home

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

Luxury Four Bedroom Canal Front home on Anna Maria Island

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

Luxury Vacation Home 1.5 Blocks Walk to Beach in Anna Maria

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

Anna Maria Island Luxury Vacation Rental 4 Plus Loft

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

Anna Maria Island Beach Family Vacation Rental Pool Home

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 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: 12
  • 6 Bedrooms
  • 6 Bathrooms

Short Walk to Beach Vacation Home Private Pool

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

Beautiful Anna Maria Luxury Vacation Pool Home Sleeps 8

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

Eight Bedroom Posh Vacation Home in Bradenton Beach

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

Anna Maria 4 Bedroom Vacation Home Walk to Beach Sleeps 8

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

Luxury Anna Maria Villa Sleeps 8 Short Walk To Beach

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

Luxury Anna Maria Island Vacation Pool Home

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

Luxury Anna Maria 4 Bedroom Home with Private Pool & Spa

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

Holmes Beach Luxury 3 Bedroom Rental Private Outdoor Pool

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

Three Bedroom Rental Two Blocks from Bean Point

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

Anna Maria Vacation Rental Walk To Beach With Boat Dock

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

Anna Maria Island Luxury Vacation Rental Home 8 Guests

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

The Ultimate Bayside Vacation Retreat Boat Dock

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

Anna Maria 5 Bedroom Pool Home Walk To Beach Sleeps Eight

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

Anna Maria Island & Holmes Beach Home 878132

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

3 Bedroom Canal View Home Anna Maria

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

Holmes Beach Vacation Pool Home With Three Great Bedrooms

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

Luxury Bradenton Beach 3 Bedroom Vacation Duplex Rental

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

Bradenton Beach Rental Home with Pool Sleeps 10

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

Anna Maria Vacation Rental Bayfront 4 Bedroom Home Plus Den

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

Stunning Anna Maria Vacation Home With Large Pool Sleeps 8

  Save Rental
  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 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: 10
  • 5 Bedrooms
  • 3 Bathrooms

Anna Maria Island Vacation Rental Duplex - Sleeps 8

  Save Rental
  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Holmes Beach Vacation Rental Home West of Gulf Drive

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

Anna Maria Three Bedroom Rental Home Great Interior Decor

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

Anna Maria Island Five Bedroom Vacation Rental Pool Home

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

Three Bedroom Luxury Anna Maria Rental Close To The Beach

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

Holmes Beach 3 Bedroom Home With Amazing Outdoor Escape

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

Anna Maria Luxury Vacation Home 5 houses to beach

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

Anna Maria Island 4 Bedroom Canal Front Rental Private Pool

  Save Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury Anna Maria Island 2 Bedroom Rental with Private Pool

  Save Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 3 Bathrooms

Holmes Beach Luxury Vacation Home Sleeps 10 Stroll To Beach

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

Island 3 Bedroom Vacation Rental with Pool Peeks of Gulf

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

Holmes Beach Three bedroom Vacation Condo Full Gulf View

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

Holmes Beach One Block to Beach Vacation Home Sleeps Six

  Save Rental
  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 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

Gulf Front Vacation Home On Anna Maria Island

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 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

Luxury Anna Maria Vacation Home Sleeps 8 Private Pool

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

Anna Maria Luxury 6 Bedroom Rental - Best Rental Home Award

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

Holmes Beach Four Bedroom Vacation Pool Home Sleeps 8

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

Four Bedroom 3 Bath Rental A Few Homes Back from Gulf

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

Great Anna Maria Vacation Beach Home with Pool - Sleeps 10

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

Anna Maria Island Vacation Beach Villa 4 Bedrooms Sleeps 8

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

Anna Maria Beach House for Rent Best On The Island with Pool

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

Anna Maria 7 Bedroom Vacation Rental Sleeps 14 Private Pool

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

Luxury Anna Maria Vacation Rental 4 Bedrooms Plus Den

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

Beachfront Luxury Vacation Home On Holmes Beach Sleeps 6

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Coastal Anna Maria Island Vacation Pool Home Walk to Beach

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

Luxury Beachfront Anna Maria Island 3 Bedroom Cottage

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

What An Amazing Anna Maria Island Vacation Home Available

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

Walk to Beach Vacation Duplex on Holmes Beach PRIVATE Pool

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

Four Bedroom Rental on Anna Maria Island Sleeps Eight

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

Luxury Holmes Beach Vacation Home with Private Pool Sleeps 8

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

Four Bedroom Luxury Island Vacation Rental Home Sleeps 8

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

Three Great Bedroom Rental has Boat Dock Anna Maria Island

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

Located on the Much Coveted North End Of Anna Maria Island

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

New 4 bedroom Anna Maria rental WHOLE DUPLEX

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 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

Three Bedroom Anna Maria Vacation Home with Pool

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

Anna Maria Luxury Six Bedroom Home Walk To Beach

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

Anna Maria Island Right on Sand Rental

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Luxurious 5 Bedroom North Anna Maria Island Vacation Rental

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

Private Luxury Home Anna Maria Island Home for Rent

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

One House Back from the Beach A 30 Second Walk to Sand!

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Renovated Anna Maria Island Pool Home Walk To Beach

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

Holmes Beach 3 Bedroom Rental Only One Block to Beach Access

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

Great Four Bedroom Pool Home in Holmes Beach Sleeps Eight

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

Two Bedroom Anna Maria Town Home will Accommodate Four.

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 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

Anna Maria 2 Bedroom Vacation Home - Five Houses from Beach

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 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

Anna Maria Private Pool Vacation Home Close to Beaches

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

Anna Maria 4 Bedroom Pool Home Close to the Beach

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

Anna Maria Four Bedroom Vacation Home Sleeps 8 Private Pool

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

Anna Maria Islands Most Amazing Vacation Rental Waterfront

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

Charming Vacation Rental in Holmes Beach 2 Bedrooms Sleeps 6

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

A Rare Anna Maria Island Three Bedroom Villa on the Beach

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

True Island Beauty Anna Maria Vacation Pool Home 3 Bedrooms

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

Four Bedroom Rental Sleeps 8 Guests On Anna Maria Island

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 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

Holmes Beach 4 Bedroom Beachfront Luxury Vacation Pool Home

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

2 Bedroom Vacation Home Rental- Views of Gulf 2.5 Bathrooms

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 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

Holmes Beach Victorian Style Large Heated Pool 3 Bedrooms

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

3 Bedroom Holmes Beach Vacation Rental Sleeps 6 Walk to Beaches

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 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

Three Bedroom Vacation Rental Luxury Pool Home Holmes Beach

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

Anna Maria Island Luxury Vacation Home 2 Bedrooms Sleeps 4

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 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 Lovely Vacation Home with Pool

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

Beach House for Rent- Sleeps 6 Guests on Beach

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

Almost Beachfront Home with Pool

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

Anna Maria Island Cottage with Pool Sleeps Nine

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

Casa Bella. Luxury 4 Bedroom House

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

Anna Maria 3 Bedroom Vacation Rental Cottage With Pool

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

Three Bedroom Rental Home on Anna Maria with Pool

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

Anna Maria Six Bedroom Luxury Vacation Rental - Private Pool

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

Anna Maria Island Vacation Home Sleeps 8 BEACHFRONT

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Luxury 4 Bedroom Home Private Pool Great Family Rental

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 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 Four Bedroom Vacation Home with Dock

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

One of the top Four Bedroom Rentals in Anna Maria Sleeps 10

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

Charming Pool Home for Rent on Anna Maria Sleeps 8 Guests

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

Anna Maria Private Villa with Pool Sleeps 12 With Gulf Views

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

Anna Maria Four Bedrooms Vacation Home Sunshine Skyway Views

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

Anna Maria Sleep 10 Vacation Rental Steps from Beaches

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 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 Rental Pool Home

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

4 Bedroom Home with Dock and Short Walk to Beach

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

Anna Maria Island Rental Home with 4 Bedrooms 3.5 Bathrooms

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

Four Min Walk to Anna Maria Beaches.

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

Holmes Beach Canal Front Home With Pool Sleeps 10 Guests

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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

Anna Maria Island 4 Bedroom Vacation Rental Sleeps 8 Pool

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

Tropical Grounds 3 Bedroom Vacation Rental Duplex with Pool!

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

Luxury Five Bedroom Vacation Rental Anna Maria Island

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

Anna Maria Island Luxury Pool Vacation Home Walk To Beach

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

Luxury 4 Bedroom Plus 2 Lofts Anna Maria Cottage Sleeps 14

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

Holmes Beach 3 Bedroom Vacation Rental Home - Sleeps 8

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 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