Holiday rentals with a pool in Longboat Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longboat Key
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 Longboat Key rentals with a pool
House rentals with a pool
Home in Bradenton Beach
4.97 out of 5 average rating, 154 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Home in Sarasota
4.94 out of 5 average rating, 299 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSet AMI
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Home in Sarasota
4.93 out of 5 average rating, 14 reviewsFruit /Botanical Garden Estate 2 miles to downtown
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Home in Holmes Beach
4.91 out of 5 average rating, 46 reviewsGorgeous Bay house in AMI! 5 min walk to beach!
Home in Holmes Beach
4.93 out of 5 average rating, 28 reviewsBackyard Bliss Anna Maria Island
Condo rentals with a pool
Condo in Redington Beach
4.97 out of 5 average rating, 464 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Condo in Bradenton Beach
4.86 out of 5 average rating, 103 reviewsCharming and Updated 1 Bedroom in Runaway Bay
Condo in Englewood
4.93 out of 5 average rating, 116 reviewsDiscounted Ground Floor Beach Studio on the Gulf!
Condo in Treasure Island
4.98 out of 5 average rating, 121 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Condo in Bradenton
4.94 out of 5 average rating, 109 reviewsNewly remodeled cozy 2 bed/2.5 bath townhome
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
650 properties
Rentals with dedicated workspaces
220 properties have a dedicated workspace
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
490 properties are a good fit for families
Total number of reviews
6.6K reviews
Nightly prices starting at
$65 NZD before taxes and fees
Destinations to explore
- Anna Maria Island Holiday rentals
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- Rentals with pools United States
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