Vacation 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.
Vacation 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
4.89 out of 5 average rating, 142 reviewsSiesta Beach House
Home in Sarasota
4.97 out of 5 average rating, 111 reviewsGorgeous Home / Heated Pool and Spa
Home in Siesta Key
4.87 out of 5 average rating, 119 reviews"Safe & Clean" Palm Oasis - Relax in comfort!
Home in Siesta Key
5.0 out of 5 average rating, 22 reviewsBeachfront 180-Degree View, Walk to Village!
Home in Siesta Key
4.98 out of 5 average rating, 63 reviewsYour Tropical Siesta Key Beach House - Top 1% Host
Home in Siesta Key
5.0 out of 5 average rating, 46 reviewsCoolest House in Siesta Key Village
Home in Sarasota
4.98 out of 5 average rating, 42 reviewsSun-filled cottage with pool, walk to beach
Home in Sarasota
5.0 out of 5 average rating, 43 reviewsSea Esta | Heated Saltwater POOL + Putting Green!
Condo rentals with a pool
Condo in Longboat Key
4.97 out of 5 average rating, 151 reviewsOceanfront Condo Mid-Island: Open May 30th, $165!
Condo in Sarasota
4.89 out of 5 average rating, 129 reviewsGateway to Siesta Key 1/2 mile to the Beach!
Condo in Siesta Key
4.96 out of 5 average rating, 104 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Condo in Siesta Key
4.85 out of 5 average rating, 133 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Condo in Sarasota
4.97 out of 5 average rating, 167 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Condo in Siesta Key
4.92 out of 5 average rating, 182 reviewsBright and Beachy - Steps to the Water!
Condo in Siesta Key
4.83 out of 5 average rating, 123 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Condo in Siesta Key
4.92 out of 5 average rating, 131 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
Quick stats about vacation 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
$60 before taxes and fees
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