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
4.97 out of 5 average rating, 124 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Home in Holmes Beach
4.99 out of 5 average rating, 154 reviewsCaptain's Quarters at Spinnakers Vacation Cottages
Home in Holmes Beach
4.93 out of 5 average rating, 27 reviewsBackyard Bliss Anna Maria Island
Home in Holmes Beach
5.0 out of 5 average rating, 20 reviewsKey Lime Cottage by Beach Boutique Rentals
Home in Anna Maria
4.96 out of 5 average rating, 52 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
Home in Anna Maria
4.99 out of 5 average rating, 78 reviewsCHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
Home in Anna Maria
4.93 out of 5 average rating, 45 reviewsBeach House w/Private Pool & Hot Tub by Bean Point
Home in Anna Maria
5.0 out of 5 average rating, 60 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
Condo rentals with a pool
Condo in Longboat Key
4.92 out of 5 average rating, 146 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Condo in Redington Beach
4.94 out of 5 average rating, 356 reviewsBeach Condo, Heated Pool, 2 Minute Walk to Ocean
Condo in Longboat Key
4.97 out of 5 average rating, 150 reviewsCharming Condo on the Coast!
Condo in St. Pete Beach
4.91 out of 5 average rating, 213 reviewsSunset Beach Condo in Treasure Island
Condo in Redington Beach
4.85 out of 5 average rating, 570 reviewsCondo II:Beach 2 min walk:Heated Pool:2Bikes:Grill
Condo in Largo
4.89 out of 5 average rating, 181 reviewsModern and Cozy Condo 6 Minutes from the Beach !
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