57 Rentals: Anna Maria IslandPlatinum 5+ Bedrooms

All Pool Options   |   Walk to Beach

Get help finding your rental: 941.900.4552

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

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • 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

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

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

Just a Block to the Beach Vacation Home On Anna Maria Island

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 6 Bedrooms
  • 4 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: 14
  • 7 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

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

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 Island Six Bedroom Bayfront Vacation 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 Only 2 Blocks from the Beach!

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

Luxury Walk to Beach Home with Private Pool in Anna Maria Island

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

Luxury Seven Bedroom Bradenton Beach Rental Home Canal Views

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

Gorgeous 5 Bedroom Vacation Pool Home in Anna Maria Island

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

Stunning Vacation Pool Home in Anna Maria Sleeps 8 Guests

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

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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

Anna Maria Amazing 7 Bedroom Home with a Beautiful Pool

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

Anna Maria Island Luxury Vacation Rental Home Five Bedrooms

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

Bradenton Beach Luxury Vacation Rental Home

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

Breathtaking Bradenton Beach Luxury Pool Home Walk To Beach

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

Luxury 5 Bedroom Home with Bay & Gulf Views

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

Anna Maria Island Luxury 9 Bedroom Vacation Pool Home

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

Eight Bedroom Posh Vacation Home in Bradenton Beach

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

Beach to Bay Seven Bedrooms Vacation Rental Beach

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

Holmes Beach Luxury Six Bedroom Villa

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

The Ultimate Anna Maria lIsland Luxury Villa Six Bedrooms

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

Gorgeous Brand New Build! Sleeps 18 Guests

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

Nine Bedroom Luxury Vacation Villa in Bradenton Beach

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

Bradenton Beach Vacation Pool Home Seven Bedroom

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

Nine Bedroom Luxury Vacation Rental Home Anna Maria Two Properties From Gulf Beach

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

An Island Paradise with Rooftop Views of Bay & Gulf

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

Gorgeous Home in Bradenton with Pool and Close to Beach

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

Stunning Luxurious Pool Home For Anna Maria Vacation

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

Luxury Vacation Home Roof Top Deck, Pool, Spa Steps to Beach

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

Waterside Vacation Home One Block to The Beach

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

Bradenton Vacation Home Six Bedroom

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

Anna Maria Coastal Luxury Home with Private Pool & Close to Beach

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

Bradenton Beach Vacation Home Ten Bedroom Walk to Beach

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 23
  • 10 Bedrooms
  • 10+ Bathrooms

Anna Maria Island Vacation Home Nine Bedroom Walk to Beach

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

Bradenton Beach Luxury Vacation Home Seven Bedroom Walk to Beach

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

Exquisite Holmes Beach Bayfront Luxurious Vacation Pool Home

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

Canalfront Luxury Vacation Pool Home in Anna Maria Sleeps 8

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

Luxurious Villa by the Beach in Bradenton Beach

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

Luxury Anna Maria Island Vacation Pool Home Six Bedroom

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

Anna Maria Island Vacation Home Five Bedrooms Bay Views

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

Bradenton Beach Luxury 7 Bedroom Walk to Beach Home with Pool

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

2 min to Beach Vacation Home in Bradenton Beach

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

Anna Maria Six Bedroom Walk to the Beach Vacation Rental

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