Vacation rentals with a pool in Anna Maria Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Anna Maria Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Anna Maria Island rentals with a pool
House rentals with a pool
Home in Holmes Beach
4.99 out of 5 average rating, 154 reviewsCaptain's Quarters at Spinnakers Vacation Cottages
Home in Anna Maria
4.96 out of 5 average rating, 51 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
Home in Holmes Beach
5.0 out of 5 average rating, 49 reviewsPrivate Luxurious Ground Level Home
Home in Anna Maria
4.94 out of 5 average rating, 18 reviewsWhispering Winds by Beach Boutique Rentals
Home in Anna Maria
4.92 out of 5 average rating, 91 reviewsCharming house w/heated pool,steps to beach-Unit A
Home in Anna Maria
5.0 out of 5 average rating, 10 reviews༄ Sunset Shore on Anna Maria Island ༄
Home in Anna Maria
5.0 out of 5 average rating, 60 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsAmie House Chef’s kitchen Fun pool - walk to beach
Condo rentals with a pool
Condo in Longboat Key
4.93 out of 5 average rating, 144 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Condo in St. Pete Beach
4.91 out of 5 average rating, 212 reviewsSunset Beach Condo in Treasure Island
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Condo in Longboat Key
4.8 out of 5 average rating, 212 reviewsSRQ/Longboat Key Beach - kid friendly/romantic B1
Condo in Holmes Beach
4.91 out of 5 average rating, 158 reviewsAnna Maria Beach Place...footsteps to the sands
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