72 Rentals: Anna Maria Island & Holmes BeachPlatinum

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Get help finding your rental: 941.900.4552

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

Bay View Luxury Three bedroom Vacation Rental Plus Den

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

Anna Maria Island Luxury 5 Bedroom Vacation Rental

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 5 Bedrooms
  • 3 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 4 Bedroom - 2 Living Areas - Pool - North Anna Maria

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 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: 16
  • 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

Five Bedroom Rental on the North End of Anna Maria Island

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

Anna Maria Luxury Four Bedroom Rental with Gulf Views

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 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

Stunning 3 Bedroom Anna Maria Villa Rental with Private Pool

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

A stunning Beach House on Anna Maria with Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 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 Luxury Home with Pool Two Blocks to Beach

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

West of Gulf Drive Luxury home Rental

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

Three Bedroom Luxury Vacation Rental Anna Maria Island

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

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

Steps from Beach at this 4 Bedroom Anna Maria Vacation

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

Epitome of Luxury for a Dream Vacation in Anna Maria!

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 28
  • 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: 14
  • 7 Bedrooms
  • 7 Bathrooms

Anna Maria 7 Bedroom Rental Sleeps 18 Guests- Private Pool

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

Anna Maria 4 Bedroom 4 Bathroom Vacation Home Sleeps 12

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

Luxury Four Bedroom Home on the Beach

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

A Stunning an 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 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

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

Anna Maria 4 Bedroom Vacation Home Canal View and Pool

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

Holmes Beach Anna Maria Island Luxury Pool Vacation Home

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 4 Bedrooms
  • 4 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 Luxury Vacation Home Sleeps Eight Guests

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

The Most Beautiful Luxury Beach Home on Anna Maria Island

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 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

Private 3 Bedroom 2 Bathroom only 75 Yards to the Beach!

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

Bradenton Beach 7 Bedroom Vacation Home Sleeps 18

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

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 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 Vacation Home Sleeps 8 Guests

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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

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

Luxury Beach House Best On Anna Maria Island

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

Holmes Beach Vacation Home Sleeps 12 Guests

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

Anna Maria Island Luxury 9 Bedroom Vacation Home

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

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

Holmes Beach Luxury Vacation Rental Sleeps Eight Guests

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  • Platinum
  • Home/Villa
  • Pool
  • 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: 10
  • 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