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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 313–336 of 1,169 matching vacation rentals, page 14 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Gold Water Views Bradenton Vacation Pool Home Three Bedroom
Anna Maria Island & Holmes Beach

Water Views Bradenton Vacation Pool Home Three Bedroom

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $895 / night
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Gold Holmes Beach Vacation Duplex Three Bedroom with Pool
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Duplex Three Bedroom with Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Private Pool Game Room Anna Maria Vacation Home
Anna Maria Island & Holmes Beach

Private Pool Game Room Anna Maria Vacation Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $810 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Vacation Duplex Walk to Beach
Anna Maria Island & Holmes Beach

Bradenton Beach Vacation Duplex Walk to Beach

7 Bedrooms · 6 Bathrooms · Sleeps 16
From $1,942 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Home 3 Bedroom Walk to Beach
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home 3 Bedroom Walk to Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $886 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gorgeous 2 Bedroom Vacation Rental in Bradenton Sleeps 6
Anna Maria Island & Holmes Beach

Gorgeous 2 Bedroom Vacation Rental in Bradenton Sleeps 6

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $795 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Luxury Vacation Pool Home Five Bedrooms
Anna Maria Island & Holmes Beach

Bradenton Beach Luxury Vacation Pool Home Five Bedrooms

5 Bedrooms · 4 Bathrooms · Sleeps 12
From $1,842 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Vacation Rental - Canal-Front Home with Pool & Dock
Anna Maria Island & Holmes Beach

Bradenton Vacation Rental - Canal-Front Home with Pool & Dock

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $363 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island & Holmes Beach Home 1022576
Anna Maria Island & Holmes Beach

Anna Maria Island & Holmes Beach Home 1022576

4 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Close to Beach Home with Private Pool Sleeps 6
Anna Maria Island & Holmes Beach

Three Bedroom Close to Beach Home with Private Pool Sleeps 6

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $875 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Walk to Beach Holmes Beach Vacation Pool Home Five Bedroom
Anna Maria Island & Holmes Beach

Walk to Beach Holmes Beach Vacation Pool Home Five Bedroom

5 Bedrooms · 4 Bathrooms · Sleeps 10
From $12,756 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Holmes Beach 3 Bedroom Pool House
Anna Maria Island & Holmes Beach

Luxury Holmes Beach 3 Bedroom Pool House

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,112 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach Vacation Home With Private Heated Pool
Anna Maria Island & Holmes Beach

Holmes Beach Vacation Home With Private Heated Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedrooms Villa with Ocean Views and Private Pool
Anna Maria Island & Holmes Beach

Three Bedrooms Villa with Ocean Views and Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $904 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold North Anna Maria Villa Exceptional Large Private Poolside Entertaining
Anna Maria Island & Holmes Beach

North Anna Maria Villa Exceptional Large Private Poolside Entertaining

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $919 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Stroll To Sandy Beach Stunning Pool JUST IN
Anna Maria Island & Holmes Beach

Anna Maria Island Stroll To Sandy Beach Stunning Pool JUST IN

6 Bedrooms · 5 Bathrooms · Sleeps 12
From $2,008 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Six Bedroom Gorgeous Pool Vacation Home in Holmes Beach
Anna Maria Island & Holmes Beach

Six Bedroom Gorgeous Pool Vacation Home in Holmes Beach

6 Bedrooms · 5 Bathrooms · Sleeps 12
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold 4 Bedroom Getaway with Large Private Pool, Spa & Bay Views
Anna Maria Island & Holmes Beach

4 Bedroom Getaway with Large Private Pool, Spa & Bay Views

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,183 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Vacation Villa West of Gulf Drive
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Vacation Villa West of Gulf Drive

5 Bedrooms · 3 Bathrooms · Sleeps 12
From $1,750 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely Pool Home Away From Home North End Anna Maria
Anna Maria Island & Holmes Beach

Lovely Pool Home Away From Home North End Anna Maria

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,588 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Three Bedroom Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Three Bedroom Walk to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,076 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Home Four Bedroom Walk to Beach
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home Four Bedroom Walk to Beach

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $2,688 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Discover Your Ideal Getaway at Our Cozy Bradenton Home
Anna Maria Island & Holmes Beach

Discover Your Ideal Getaway at Our Cozy Bradenton Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $430 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Bradenton Vacation Rental: Pool, Spa & Golf
Anna Maria Island & Holmes Beach

Luxury Bradenton Vacation Rental: Pool, Spa & Golf

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $11,018 / month
Call to confirm availability941.500.4555 Request a callback & quote

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