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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 985–1,008 of 1,169 matching vacation rentals, page 42 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Gold Four Bedroom Luxury Island Vacation Rental Home Sleeps 8
Anna Maria Island & Holmes Beach

Four Bedroom Luxury Island Vacation Rental Home Sleeps 8

4 Bedrooms · 4 Bathrooms · Sleeps 10
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Gold Three Bedroom Anna Maria Vacation Home with Pool
Anna Maria Island & Holmes Beach

Three Bedroom Anna Maria Vacation Home with Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $995 / night
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Gold Three Bedroom Rental Home on Anna Maria with Pool
Anna Maria Island & Holmes Beach

Three Bedroom Rental Home on Anna Maria with Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,195 / night
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Gold Anna Maria 3 Bedroom Vacation Rental Cottage With Pool
Anna Maria Island & Holmes Beach

Anna Maria 3 Bedroom Vacation Rental Cottage With Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,295 / night
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Gold Anna Maria Island Cottage with Pool Sleeps Nine
Anna Maria Island & Holmes Beach

Anna Maria Island Cottage with Pool Sleeps Nine

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $988 / night
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Gold Anna Maria Island Luxury Vacation Rental - Gulf Front Beach Home
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Rental - Gulf Front Beach Home

3 Bedrooms · 3 Bathrooms · Sleeps 8
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Silver Canal-Front Vacation Home on Anna Maria Island Private Pool
Anna Maria Island & Holmes Beach

Canal-Front Vacation Home on Anna Maria Island Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
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Silver Bradenton Vacation Rental - Private Pool Home Near Anna Maria Island
Anna Maria Island & Holmes Beach

Bradenton Vacation Rental - Private Pool Home Near Anna Maria Island

4 Bedrooms · 2 Bathrooms · Sleeps 9
From $234 / night
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Silver Anna Maria Island Beachfront Vacation Rental - Gulf Coast Condo
Anna Maria Island & Holmes Beach

Anna Maria Island Beachfront Vacation Rental - Gulf Coast Condo

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $611 / night
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Silver Bradenton Estate Home Main House & Guest House Private Luxury
Anna Maria Island & Holmes Beach

Bradenton Estate Home Main House & Guest House Private Luxury

8 Bedrooms · 6 Bathrooms · Sleeps 23
From $1,953 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton Vacation Pool Home Two Bedroom
Anna Maria Island & Holmes Beach

Bradenton Vacation Pool Home Two Bedroom

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $370 / night
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Silver Holmes Beach Vacation Home Two Bedrooms Short Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home Two Bedrooms Short Walk to Beach

4 Bedrooms · 2 Bathrooms · Sleeps 8
From $556 / night
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Silver Three Bedroom Vacation Home In Anna Maria Island Private Pool
Anna Maria Island & Holmes Beach

Three Bedroom Vacation Home In Anna Maria Island Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,104 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Lovely 3 Bedroom Home with Private Pool & Spa
Anna Maria Island & Holmes Beach

Lovely 3 Bedroom Home with Private Pool & Spa

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $575 / night
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Silver 3 BR Coastal Home with Pool in Holmes Beach A Block to Beach
Anna Maria Island & Holmes Beach

3 BR Coastal Home with Pool in Holmes Beach A Block to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
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Silver Four Bedroom Luxury Vacation Rental in Holmes Beach
Anna Maria Island & Holmes Beach

Four Bedroom Luxury Vacation Rental in Holmes Beach

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,268 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Anna Maria 4 Bedroom Pool House Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria 4 Bedroom Pool House Walk to Beach

4 Bedrooms · 3 Bathrooms · Sleeps 8
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Call to confirm availability941.500.4555 Request a callback & quote
Silver Canal View Bradenton Vacation Pool Home Three Bedrooms
Anna Maria Island & Holmes Beach

Canal View Bradenton Vacation Pool Home Three Bedrooms

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $130 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bradenton 3 Bedroom Vacation Home with Dock Sleeps 6
Anna Maria Island & Holmes Beach

Bradenton 3 Bedroom Vacation Home with Dock Sleeps 6

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $439 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Beautiful Bradenton Vacation Home with Private Pool Sleeps 6
Anna Maria Island & Holmes Beach

Beautiful Bradenton Vacation Home with Private Pool Sleeps 6

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $323 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Bay Front Vacation Home in Anna Maria Island 12 Guests
Anna Maria Island & Holmes Beach

Bay Front Vacation Home in Anna Maria Island 12 Guests

3 Bedrooms · 4 Bathrooms · Sleeps 12
From $35,939 / month
Call to confirm availability941.500.4555 Request a callback & quote
Silver Short Walk to Beach Holmes Beach Vacation Home Private Pool
Anna Maria Island & Holmes Beach

Short Walk to Beach Holmes Beach Vacation Home Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,090 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver Charming Four Bedroom Home in Bradenton Sleeps 12
Anna Maria Island & Holmes Beach

Charming Four Bedroom Home in Bradenton Sleeps 12

4 Bedrooms · 3 Bathrooms · Sleeps 12
From $727 / night
Call to confirm availability941.500.4555 Request a callback & quote
Silver 2 Minute Drive to Beach in West Bradenton
Anna Maria Island & Holmes Beach

2 Minute Drive to Beach in West Bradenton

5 Bedrooms · 3 Bathrooms · Sleeps 10
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