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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 1–24 of 1,169 matching vacation rentals, page 1 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Platinum Luxury 6-Bedroom Vacation Rental Home on Anna Maria Island Private large Pool Spa
Anna Maria Island & Holmes Beach

Luxury 6-Bedroom Vacation Rental Home on Anna Maria Island Private large Pool Spa

6 Bedrooms
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Platinum Luxury Vacation Villa Anna Maria Island Golf Cart Private Pool
Anna Maria Island & Holmes Beach

Luxury Vacation Villa Anna Maria Island Golf Cart Private Pool

7 Bedrooms · 7 Bathrooms · Sleeps 14
From $2,350 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Island Beach Luxury Vacation Rental - Steps to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island Beach Luxury Vacation Rental - Steps to Beach

7 Bedrooms · 6 Bathrooms · Sleeps 15
From $2,285 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Beachfront Anna Maria Island Luxury Vacation Rental - Eight Bedroom Pool Home
Anna Maria Island & Holmes Beach

Beachfront Anna Maria Island Luxury Vacation Rental - Eight Bedroom Pool Home

8 Bedrooms · 6 Bathrooms · Sleeps 16
From $7,280 / night
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Platinum Coastal Luxury Retreat Near Bradenton Beach - 7-Bedroom & Private Pool
Anna Maria Island & Holmes Beach

Coastal Luxury Retreat Near Bradenton Beach - 7-Bedroom & Private Pool

7 Bedrooms · 7 Bathrooms · Sleeps 16
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Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Beach Home in Anna Maria Island - Unforgettable Getaway
Anna Maria Island & Holmes Beach

Luxury Beach Home in Anna Maria Island - Unforgettable Getaway

4 Bedrooms · 4 Bathrooms · Sleeps 8
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Platinum Luxurious 4-Bedroom Pool Home on Anna Maria Island
Anna Maria Island & Holmes Beach

Luxurious 4-Bedroom Pool Home on Anna Maria Island

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,184 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Coastal Retreat in Holmes Beach - 4-Bedroom Exclusive Home with Private Pool
Anna Maria Island & Holmes Beach

Luxury Coastal Retreat in Holmes Beach - 4-Bedroom Exclusive Home with Private Pool

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,203 / night
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Platinum Luxurious Anna Maria Island Retreat - Stunning Views
Anna Maria Island & Holmes Beach

Luxurious Anna Maria Island Retreat - Stunning Views

5 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,835 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxurious Pool Home in Bradenton - Your Dream Getaway
Anna Maria Island & Holmes Beach

Luxurious Pool Home in Bradenton - Your Dream Getaway

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $14,400 / month
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Luxury Luxury Posh Anna Maria Island Retreat- Stroll to Beach Private Island Key Royale
Anna Maria Island & Holmes Beach

Luxury Luxury Luxury Posh Anna Maria Island Retreat- Stroll to Beach Private Island Key Royale

4 Bedrooms · 3 Bathrooms · Sleeps 8
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Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Beachfront Property in Anna Maria Island - Four Bedroom Vacation Home
Anna Maria Island & Holmes Beach

Luxury Beachfront Property in Anna Maria Island - Four Bedroom Vacation Home

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $68,351 / month
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Beach Home in Anna Maria - Exclusive Property with Private Pool & Dock
Anna Maria Island & Holmes Beach

Luxury Beach Home in Anna Maria - Exclusive Property with Private Pool & Dock

6 Bedrooms · 6 Bathrooms · Sleeps 8
From $4,781 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Florida Luxury Vacation Rental | Anna Maria Island Beach Home with Pool & Rooftop Deck
Anna Maria Island & Holmes Beach

Florida Luxury Vacation Rental | Anna Maria Island Beach Home with Pool & Rooftop Deck

7 Bedrooms · 7 Bathrooms · Sleeps 14
From $2,176 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum North Anna Maria Three Bedroom Luxurious Geatway Bay Beachfront
Anna Maria Island & Holmes Beach

North Anna Maria Three Bedroom Luxurious Geatway Bay Beachfront

3 Bedrooms · 3 Bathrooms · Sleeps 8
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Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Vacation 9 Bedroom Rental Private Pool
Anna Maria Island & Holmes Beach

Anna Maria Vacation 9 Bedroom Rental Private Pool

9 Bedrooms · 8 Bathrooms · Sleeps 8
From $3,689 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Seven Bedroom Rental Home in Bradenton Beach
Anna Maria Island & Holmes Beach

Luxury Seven Bedroom Rental Home in Bradenton Beach

7 Bedrooms · 6 Bathrooms · Sleeps 16
From $2,100 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Anna Maria Island Home: Pool, Dock, Rooftop Views
Anna Maria Island & Holmes Beach

Luxury Anna Maria Island Home: Pool, Dock, Rooftop Views

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,424 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Great Escape Bradenton Beach Pool Home
Anna Maria Island & Holmes Beach

Great Escape Bradenton Beach Pool Home

5 Bedrooms · 5 Bathrooms · Sleeps 10
From $3,982 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Brand New Anna Maria Island Luxury Vacation Home WOW factor
Anna Maria Island & Holmes Beach

Brand New Anna Maria Island Luxury Vacation Home WOW factor

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,365 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury 5 Bedroom Vacation Home in Anna Maria 2 Min Walk to Beach
Anna Maria Island & Holmes Beach

Luxury 5 Bedroom Vacation Home in Anna Maria 2 Min Walk to Beach

5 Bedrooms · 4 Bathrooms · Sleeps 8
From $3,129 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Unforgettable Getaway with 6 Bedrooms in Anna Maria Island
Anna Maria Island & Holmes Beach

Unforgettable Getaway with 6 Bedrooms in Anna Maria Island

6 Bedrooms · 6 Bathrooms · Sleeps 8
From $1,895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum 8 Bedroom Anna Maria Island Vacation Rental in Bradenton Beach
Anna Maria Island & Holmes Beach

8 Bedroom Anna Maria Island Vacation Rental in Bradenton Beach

8 Bedrooms · 7 Bathrooms · Sleeps 16
From $2,100 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Anna Maria Six Bedroom Walk to the Beach Vacation Rental
Anna Maria Island & Holmes Beach

Anna Maria Six Bedroom Walk to the Beach Vacation Rental

6 Bedrooms · 6 Bathrooms · Sleeps 8
From $3,902 / night
Call to confirm availability941.500.4555 Request a callback & quote

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