Holiday 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.
Holiday 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
16–23 Nov
Home in Anna Maria
4.96 out of 5 average rating, 51 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
10–17 Dec
Home in Holmes Beach
5.0 out of 5 average rating, 49 reviewsPrivate Luxurious Ground Level Home
5–12 Sep
Home in Anna Maria
4.94 out of 5 average rating, 18 reviewsWhispering Winds by Beach Boutique Rentals
14–21 Aug
Home in Anna Maria
4.92 out of 5 average rating, 91 reviewsCharming house w/heated pool,steps to beach-Unit A
28 Aug – 4 Sep
Home in Anna Maria
5.0 out of 5 average rating, 60 reviewsNew Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
28 Sep – 5 Oct
Home in Anna Maria
5.0 out of 5 average rating, 10 reviews༄ Sunset Shore on Anna Maria Island ༄
22–29 Aug
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsAmie House Chef’s kitchen Fun pool - walk to beach
20–27 Oct
Condo rentals with a pool
Condo in Longboat Key
4.93 out of 5 average rating, 144 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
2–9 Dec
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
6–13 Apr
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
10–17 Dec
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
2–9 Jul
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
25 Oct – 1 Nov
Condo in Longboat Key
4.8 out of 5 average rating, 212 reviewsSRQ/Longboat Key Beach - kid friendly/romantic B1
9–16 Nov
Condo in Holmes Beach
4.91 out of 5 average rating, 158 reviewsAnna Maria Beach Place...footsteps to the sands
23–30 May
Condo in Redington Beach
4.85 out of 5 average rating, 570 reviewsCondo II:Beach 2 min walk:Heated Pool:2Bikes:Grill
6–13 Dec
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