Holiday rentals with a pool in Siesta Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Siesta 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 Siesta Key rentals with a pool
House rentals with a pool
Home in Siesta Key
Siesta Beach House
Home in Sarasota
The Palms-Heated Private Pool Hot Tub-5mi to beach
Home in Sarasota
Cottage On Bay (private backyard, near beaches)
Home in Siesta Key
"Safe & Clean" Palm Oasis - Relax in comfort!
Home in Sarasota
1 House 1400sq. ft. 12 min from Siesta Key!
Home in Sarasota
Sarasota Pool Home| Hot-tub| 2-miles to Siesta
Home in Siesta Key
Coolest House in Siesta Key Village
Home in Siesta Key
Quiet luxury on Siesta Key!
Condo rentals with a pool
Condo in Siesta Key
Bright and Beachy - Steps to the Water!
Condo in Siesta Key
Sea Club 2 Condo Siesta Key
Condo in Siesta Key
*A Stones Throw from #1 Voted Siesta Key Beach*
Condo in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
Condo in Sarasota
Beachside Siesta Key Cottage steps from the ocean
Condo in Siesta Key
Private Beach Siesta Key Resort Jamaica Royale
Condo in Sarasota
New Renovation! Walk to Beach, Pool, Restaurants!
Condo in Longboat Key
Updated Beachfront Condo at Prestigious Long Boat
Quick stats about holiday rentals with a pool in Siesta Key
Total rentals
1.3K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Pet-friendly rentals
220 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
22K reviews
Nightly prices starting at
$97 NZD before taxes and fees
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