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Anna Maria Island & Holmes Beach Vacation Rentals with Private Pools

Browse professionally managed Anna Maria Island and Holmes Beach vacation rentals with a recorded fenced, unfenced or indoor private pool. Showing 25–48 of 1,169 matching vacation rentals, page 2 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Platinum Gulf Front Upscale Four Bedroom Vacation Home in Holmes Beach
Anna Maria Island & Holmes Beach

Gulf Front Upscale Four Bedroom Vacation Home in Holmes Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
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Platinum Walk to Beach Anna Maria Island Vacation Home
Anna Maria Island & Holmes Beach

Walk to Beach Anna Maria Island Vacation Home

5 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,326 / night
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Platinum Anna Maria Island Beachfront Home With Private Pool Island Delight
Anna Maria Island & Holmes Beach

Anna Maria Island Beachfront Home With Private Pool Island Delight

4 Bedrooms · 5 Bathrooms · Sleeps 8
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Platinum Luxurious Gulf Front Anna Maria Island Vacation Estate
Anna Maria Island & Holmes Beach

Luxurious Gulf Front Anna Maria Island Vacation Estate

5 Bedrooms · 5 Bathrooms · Sleeps 8
From $4,999 / night
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Platinum One Of The Best Beach Homes in All Anna Maria Island!!
Anna Maria Island & Holmes Beach

One Of The Best Beach Homes in All Anna Maria Island!!

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,769 / night
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Platinum Gorgeous House with 4 Bedroom, Pool & Spa
Anna Maria Island & Holmes Beach

Gorgeous House with 4 Bedroom, Pool & Spa

4 Bedrooms · 4 Bathrooms · Sleeps 8
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Platinum Luxury Holmes Beach Rental Walk to Beach & Rooftop Views
Anna Maria Island & Holmes Beach

Luxury Holmes Beach Rental Walk to Beach & Rooftop Views

4 Bedrooms · 5 Bathrooms · Sleeps 8
From $2,464 / night
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Platinum Luxury Canal Front Three Bedroom Rental in Bradenton
Anna Maria Island & Holmes Beach

Luxury Canal Front Three Bedroom Rental in Bradenton

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $931 / night
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Platinum Bradenton 5 Bedroom Vacation Rental Great Views
Anna Maria Island & Holmes Beach

Bradenton 5 Bedroom Vacation Rental Great Views

5 Bedrooms · 3 Bathrooms · Sleeps 18
From $1,695 / night
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Platinum Bradenton Beach Luxury 7 Bedroom Home with Pool
Anna Maria Island & Holmes Beach

Bradenton Beach Luxury 7 Bedroom Home with Pool

7 Bedrooms · 7 Bathrooms · Sleeps 14
From $3,300 / night
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Platinum Anna Maria Island Vacation Home Five Bedrooms Bay Views
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Five Bedrooms Bay Views

5 Bedrooms · 6 Bathrooms · Sleeps 12
From $1,673 / night
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Platinum The Holmes Beach Vacation Home is a Stroll to Beach
Anna Maria Island & Holmes Beach

The Holmes Beach Vacation Home is a Stroll to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,370 / night
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Platinum Luxury Anna Maria Island Vacation Pool Home Six Bedroom
Anna Maria Island & Holmes Beach

Luxury Anna Maria Island Vacation Pool Home Six Bedroom

6 Bedrooms · 6 Bathrooms · Sleeps 8
From $1,829 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Vacation Home Five Bedroom Beachfront
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home Five Bedroom Beachfront

5 Bedrooms · 5 Bathrooms · Sleeps 10
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Platinum Tastefully Decorated Five Bedroom Vacation Rental in Bradenton
Anna Maria Island & Holmes Beach

Tastefully Decorated Five Bedroom Vacation Rental in Bradenton

5 Bedrooms · 4 Bathrooms · Sleeps 18
From $2,222 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Charming Four Bedroom Vacation Rental Holmes Beach
Anna Maria Island & Holmes Beach

Charming Four Bedroom Vacation Rental Holmes Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,107 / night
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Platinum Luxurious Villa by the Beach in Bradenton Beach
Anna Maria Island & Holmes Beach

Luxurious Villa by the Beach in Bradenton Beach

5 Bedrooms · 5 Bathrooms · Sleeps 13
From $3,469 / night
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Platinum Bradenton Beach Luxury Vacation Home Seven Bedroom Beach
Anna Maria Island & Holmes Beach

Bradenton Beach Luxury Vacation Home Seven Bedroom Beach

7 Bedrooms · 7 Bathrooms · Sleeps 14
From $3,400 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Bradenton Vacation Home Four Bedroom
Anna Maria Island & Holmes Beach

Luxury Bradenton Vacation Home Four Bedroom

4 Bedrooms · 2 Bathrooms · Sleeps 12
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Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria 4 Bedroom Luxury Home with Private Pool & Spa
Anna Maria Island & Holmes Beach

Anna Maria 4 Bedroom Luxury Home with Private Pool & Spa

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,840 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Island Bonus Room Home Heated Pool & Spa
Anna Maria Island & Holmes Beach

Anna Maria Island Bonus Room Home Heated Pool & Spa

4 Bedrooms · 4 Bathrooms · Sleeps 10
From $2,295 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxurious Anna Maria Vacation Home with Bay Views, Pool & SPA
Anna Maria Island & Holmes Beach

Luxurious Anna Maria Vacation Home with Bay Views, Pool & SPA

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,437 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum You'll Love this Luxury Home One Block to Beach, Private Pool & Spa
Anna Maria Island & Holmes Beach

You'll Love this Luxury Home One Block to Beach, Private Pool & Spa

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,915 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Coastal Luxury Home with Private Pool & Close to Beach
Anna Maria Island & Holmes Beach

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

6 Bedrooms · 6 Bathrooms · Sleeps 12
From $2,156 / night
Call to confirm availability941.500.4555 Request a callback & quote

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