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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 337–360 of 1,169 matching vacation rentals, page 15 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Gold Luxurious Lakewood Ranch Pool Residence
Anna Maria Island & Holmes Beach

Luxurious Lakewood Ranch Pool Residence

3 Bedrooms · 2 Bathrooms · Sleeps 5
From $16,557 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely 4 Bedroom Home in Palmetto with Pool
Anna Maria Island & Holmes Beach

Lovely 4 Bedroom Home in Palmetto with Pool

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $614 / night
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Gold Bradenton Vacation Pool Home Four Bedrooms Sleeps 11
Anna Maria Island & Holmes Beach

Bradenton Vacation Pool Home Four Bedrooms Sleeps 11

4 Bedrooms · 3 Bathrooms · Sleeps 11
From $658 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Bradenton 3 Bedroom Home Sleeps 6 With Private Pool
Anna Maria Island & Holmes Beach

Luxury Bradenton 3 Bedroom Home Sleeps 6 With Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Water Views Holmes Beach Vacation Pool Home Five Bedroom
Anna Maria Island & Holmes Beach

Water Views Holmes Beach Vacation Pool Home Five Bedroom

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,388 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Anna Maria Vacation Home with Pool & Hot Tub
Anna Maria Island & Holmes Beach

Beautiful Anna Maria Vacation Home with Pool & Hot Tub

5 Bedrooms · 4 Bathrooms · Sleeps 14
From $1,789 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Gorgeous Anna Maria Vacation Home with Private Pool & Spa
Anna Maria Island & Holmes Beach

Gorgeous Anna Maria Vacation Home with Private Pool & Spa

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,802 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Waterside Vacation Rental Home
Anna Maria Island & Holmes Beach

Anna Maria Island Waterside Vacation Rental Home

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $547 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Three Bedroom
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Three Bedroom

3 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Four Bedroom Vacation Home in Holmes Beach Close to Beach
Anna Maria Island & Holmes Beach

Four Bedroom Vacation Home in Holmes Beach Close to Beach

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,608 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming 3 Bedroom Vacation House Sleeps 8 Guests
Anna Maria Island & Holmes Beach

Charming 3 Bedroom Vacation House Sleeps 8 Guests

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $1,146 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Two Bedroom Full Ocean View Vacation Condo
Anna Maria Island & Holmes Beach

Two Bedroom Full Ocean View Vacation Condo

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $1,573 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Canal Front Retreat with Private Pool and Dock
Anna Maria Island & Holmes Beach

Anna Maria Island Canal Front Retreat with Private Pool and Dock

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $401 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Partial Gulf Views Holmes Beach Vacation Condo Three Bedroom
Anna Maria Island & Holmes Beach

Partial Gulf Views Holmes Beach Vacation Condo Three Bedroom

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $675 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful & Cozy 4 Bedroom Pool Home in Anna Maria Island
Anna Maria Island & Holmes Beach

Beautiful & Cozy 4 Bedroom Pool Home in Anna Maria Island

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,943 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning Vacation Home away from Home in Holmes Beach
Anna Maria Island & Holmes Beach

Stunning Vacation Home away from Home in Holmes Beach

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,495 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Anna Maria Pool Vacation Villa
Anna Maria Island & Holmes Beach

Luxury Anna Maria Pool Vacation Villa

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,029 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Canal Views Holmes Beach Vacation Pool Home Five Bedroom
Anna Maria Island & Holmes Beach

Canal Views Holmes Beach Vacation Pool Home Five Bedroom

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,868 / 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 · 3 Bathrooms · Sleeps 8
From $1,053 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Pool Home With Four Bedrooms
Anna Maria Island & Holmes Beach

Anna Maria Vacation Pool Home With Four Bedrooms

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $946 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Vacation Home Two Bedroom
Anna Maria Island & Holmes Beach

Anna Maria Island Vacation Home Two Bedroom

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $606 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Rental - Bean Point Beach Cottage with Pool
Anna Maria Island & Holmes Beach

Anna Maria Island Rental - Bean Point Beach Cottage with Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $611 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Holmes Beach 3 Bedroom Pool Home Sleeps 6 Walk To Beach
Anna Maria Island & Holmes Beach

Holmes Beach 3 Bedroom Pool Home Sleeps 6 Walk To Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $806 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Vacation Home with Pool & Spa in Holmes Beach
Anna Maria Island & Holmes Beach

Charming Vacation Home with Pool & Spa in Holmes Beach

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $670 / night
Call to confirm availability941.500.4555 Request a callback & quote

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