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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 673–696 of 1,169 matching vacation rentals, page 29 of 49. Closest capacity matches first.

About Anna Maria Island & Holmes Beach
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Gold Anna Maria Four Bedroom Vacation Home Canal View
Anna Maria Island & Holmes Beach

Anna Maria Four Bedroom Vacation Home Canal View

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $899 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Luxury Four Bedroom Vacation Pool Home Sleeps 8
Anna Maria Island & Holmes Beach

Anna Maria Luxury Four Bedroom Vacation Pool Home Sleeps 8

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,959 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Vacation Home 4 Bedrooms Plus Loft Sleeps 12 North End
Anna Maria Island & Holmes Beach

Anna Maria Vacation Home 4 Bedrooms Plus Loft Sleeps 12 North End

4 Bedrooms · 4 Bathrooms · Sleeps 12
From $2,579 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Bradenton Beach Large Group Vacation Rental 9BR Luxury Home
Anna Maria Island & Holmes Beach

Bradenton Beach Large Group Vacation Rental 9BR Luxury Home

9 Bedrooms · 6 Bathrooms · Sleeps 22
From $2,639 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Rental - Bean Point Beach Family Getaway
Anna Maria Island & Holmes Beach

Anna Maria Island Rental - Bean Point Beach Family Getaway

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $991 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Great Anna Maria Family Rental Short Walk to Beach Private Pool
Anna Maria Island & Holmes Beach

Great Anna Maria Family Rental Short Walk to Beach Private Pool

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,257 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful Anna Maria Four Bedroom Across from Beach
Anna Maria Island & Holmes Beach

Beautiful Anna Maria Four Bedroom Across from Beach

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,749 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island 5 Bedroom Home Approx 30 Seconds to Beach
Anna Maria Island & Holmes Beach

Anna Maria Island 5 Bedroom Home Approx 30 Seconds to Beach

5 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,809 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Brand New Vacation Home - Two Bedrooms Sleeps 6 Guests
Anna Maria Island & Holmes Beach

Brand New Vacation Home - Two Bedrooms Sleeps 6 Guests

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $995 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria 2 Bedroom Vacation Home with Private Heated Pool
Anna Maria Island & Holmes Beach

Anna Maria 2 Bedroom Vacation Home with Private Heated Pool

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $795 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold 3 Bedroom Vacation Rental - On the Intracoastal Waterway
Anna Maria Island & Holmes Beach

3 Bedroom Vacation Rental - On the Intracoastal Waterway

3 Bedrooms · 4 Bathrooms · Sleeps 7
From $1,195 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Pool Vacation Home Wow look at the Outdoor Area
Anna Maria Island & Holmes Beach

Luxury Pool Vacation Home Wow look at the Outdoor Area

4 Bedrooms · 3 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold This 5 Bedroom is All About The Beach
Anna Maria Island & Holmes Beach

This 5 Bedroom is All About The Beach

5 Bedrooms · 5 Bathrooms · Sleeps 10
From $2,245 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Waterfront Rental Close to Anna Maria with a Boat Dock
Anna Maria Island & Holmes Beach

Waterfront Rental Close to Anna Maria with a Boat Dock

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $574 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island North End Vacation Rental Walk To Beach
Anna Maria Island & Holmes Beach

Anna Maria Island North End Vacation Rental Walk To Beach

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,295 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Amazing Anna Maria Beach House that Sleeps Eight Guests
Anna Maria Island & Holmes Beach

Amazing Anna Maria Beach House that Sleeps Eight Guests

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $2,921 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Close to Beach! Holmes Beach Vacation Rental w/Private Pool!
Anna Maria Island & Holmes Beach

Close to Beach! Holmes Beach Vacation Rental w/Private Pool!

2 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury 3 Bedroom Pool Home on Anna Maria Island-Holmes Beach
Anna Maria Island & Holmes Beach

Luxury 3 Bedroom Pool Home on Anna Maria Island-Holmes Beach

3 Bedrooms · 3 Bathrooms · Sleeps 10
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beachfront Rental on North End Anna Maria with Boat Dock
Anna Maria Island & Holmes Beach

Beachfront Rental on North End Anna Maria with Boat Dock

5 Bedrooms · 3 Bathrooms · Sleeps 8
From $2,703 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold The Ultimate Anna Maria Island Vacation Home Four Bedrooms
Anna Maria Island & Holmes Beach

The Ultimate Anna Maria Island Vacation Home Four Bedrooms

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,789 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold So Close to an Actual Anna Maria Island Beach House Sleeps 8
Anna Maria Island & Holmes Beach

So Close to an Actual Anna Maria Island Beach House Sleeps 8

4 Bedrooms · 3 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Luxury Four Bedroom Vacation Home
Anna Maria Island & Holmes Beach

Anna Maria Island Luxury Four Bedroom Vacation Home

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $2,225 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Anna Maria Island Three Bedroom Home for Rent- Vacation Pool
Anna Maria Island & Holmes Beach

Anna Maria Island Three Bedroom Home for Rent- Vacation Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $965 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Holmes Beach 3 Bedroom Plus Den Walk to Beach Rental
Anna Maria Island & Holmes Beach

Luxury Holmes Beach 3 Bedroom Plus Den Walk to Beach Rental

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,258 / night
Call to confirm availability941.500.4555 Request a callback & quote

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