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 Anna Maria
4.93 out of 5 average rating, 152 reviewsPrivate 30' Pool and Boat Dock - Rated best on AMI
Sep 2 – 9
Home in Holmes Beach
4.97 out of 5 average rating, 124 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Aug 31 – Sep 7
Home in Anna Maria
4.94 out of 5 average rating, 18 reviewsWhispering Winds by Beach Boutique Rentals
Sep 26 – Oct 3
Home in Holmes Beach
5.0 out of 5 average rating, 49 reviewsPrivate Luxurious Ground Level Home
Sep 24 – Oct 1
Home in Bradenton
4.83 out of 5 average rating, 18 reviews"Paradise" by the Private (Heated) Pool light!
Nov 17 – 24
Home in Anna Maria
4.92 out of 5 average rating, 49 reviewsWhite Pearl-New Premier AMI Home with Sunset Views
Sep 14 – 21
Home in Anna Maria
5.0 out of 5 average rating, 78 reviewsManatee Harbour - heated pool, on the canal
Oct 25 – Nov 1
Home in Anna Maria
4.96 out of 5 average rating, 28 reviewsAnna Maria Chateau. Private Pool home
Nov 6 – 13
Condo rentals with a pool
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Dec 21 – 28
Condo in Longboat Key
4.93 out of 5 average rating, 144 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Sep 5 – 12
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr 20 – 27
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Dec 2 – 9
Condo in St. Pete Beach
4.91 out of 5 average rating, 211 reviewsSunset Beach Condo in Treasure Island
Nov 14 – 21
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec 10 – 17
Condo in Holmes Beach
4.91 out of 5 average rating, 158 reviewsAnna Maria Beach Place...footsteps to the sands
May 23 – 30
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
Apr 3 – 10
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