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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 625–648 of 1,169 matching vacation rentals, page 27 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Gold Three Bedroom Pool Home in Holmes Beach Sleeps Eight Guests
Anna Maria Island & Holmes Beach

Three Bedroom Pool Home in Holmes Beach Sleeps Eight Guests

3 Bedrooms · 3 Bathrooms · Sleeps 10
From $895 / night
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Gold Just Steps Beach 4 Bedroom Anna Maria Island Vacation Home
Anna Maria Island & Holmes Beach

Just Steps Beach 4 Bedroom Anna Maria Island Vacation Home

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,579 / night
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Gold A New Anna Maria island Rental Home Three Bedrooms & Pool
Anna Maria Island & Holmes Beach

A New Anna Maria island Rental Home Three Bedrooms & Pool

3 Bedrooms · Sleeps 6
From $795 / night
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Gold Three Bedroom Vacation Home in Bradenton Beach
Anna Maria Island & Holmes Beach

Three Bedroom Vacation Home in Bradenton Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $2,083 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Rental North Holmes Beach Rental Home
Anna Maria Island & Holmes Beach

Anna Maria Vacation Rental North Holmes Beach Rental Home

3 Bedrooms · 3 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Holmes Beach Vacation Rental Home with Pool
Anna Maria Island & Holmes Beach

Three Bedroom Holmes Beach Vacation Rental Home with Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,003 / night
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Gold Anna Maria 4 Bedroom Vacation Home Canal View and Pool
Anna Maria Island & Holmes Beach

Anna Maria 4 Bedroom Vacation Home Canal View and Pool

4 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Holmes Beach Vacation Rental Home with Pool
Anna Maria Island & Holmes Beach

Beautiful Holmes Beach Vacation Rental Home with Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,191 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Vacation Rental Home Two Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Luxury Vacation Rental Home Two Bedrooms

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $695 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Home Sleeps Six Guests Private Pool
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home Sleeps Six Guests Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Spectacular Beach House Amazing Gulf Views
Anna Maria Island & Holmes Beach

Anna Maria Spectacular Beach House Amazing Gulf Views

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,014 / night
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Gold Luxury Holmes Beach Six Bedroom Vacation Homes Sleeps 12
Anna Maria Island & Holmes Beach

Luxury Holmes Beach Six Bedroom Vacation Homes Sleeps 12

6 Bedrooms · 6 Bathrooms · Sleeps 12
From $1,208 / night
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Gold Charming Beach Retreat on Sunny Holmes Beach
Anna Maria Island & Holmes Beach

Charming Beach Retreat on Sunny Holmes Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $974 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold North Anna Maria Island 2 Bedroom Vacation Rental Pool Home
Anna Maria Island & Holmes Beach

North Anna Maria Island 2 Bedroom Vacation Rental Pool Home

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $895 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Private Pool at this Five Bedroom Anna Maria Vacation Rental
Anna Maria Island & Holmes Beach

Private Pool at this Five Bedroom Anna Maria Vacation Rental

5 Bedrooms · 4 Bathrooms · Sleeps 10
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Lovely Three Bedroom & Pool
Anna Maria Island & Holmes Beach

Holmes Beach Lovely Three Bedroom & Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $25,580 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach 4 Bedroom Vacation Home Sleeps 10
Anna Maria Island & Holmes Beach

Holmes Beach 4 Bedroom Vacation Home Sleeps 10

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $665 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach 6 Bedroom Vacation Rental Sleeps 14
Anna Maria Island & Holmes Beach

Holmes Beach 6 Bedroom Vacation Rental Sleeps 14

6 Bedrooms · 4 Bathrooms · Sleeps 14
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Townhome Sleeps 6 with Private Pool & Spa
Anna Maria Island & Holmes Beach

Holmes Beach Townhome Sleeps 6 with Private Pool & Spa

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $469 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Canal Front Home with Dock - Direct Bay Access
Anna Maria Island & Holmes Beach

Holmes Beach Canal Front Home with Dock - Direct Bay Access

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,295 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach 3 Bedroom Vacation Home Short Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach 3 Bedroom Vacation Home Short Walk to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,120 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Almost Beachfront - Luxury Anna Maria Island Vacation Home
Anna Maria Island & Holmes Beach

Almost Beachfront - Luxury Anna Maria Island Vacation Home

7 Bedrooms · 5 Bathrooms · Sleeps 14
From $2,050 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 3 Bedroom Rental Sleeps 6 Short Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria 3 Bedroom Rental Sleeps 6 Short Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $995 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold HOLMES BEACH 3 BEDROOM POOL HOME BLOCK TO BEACH
Anna Maria Island & Holmes Beach

HOLMES BEACH 3 BEDROOM POOL HOME BLOCK TO BEACH

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote

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