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
4.87 out of 5 average rating, 119 reviews"Safe & Clean" Palm Oasis - Relax in comfort!
Dec 13 – 20
Home in Sarasota
4.94 out of 5 average rating, 297 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Aug 2 – 9
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Oct 11 – 18
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
Aug 21 – 28
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Sep 18 – 25
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Sep 19 – 26
Home in Sarasota
4.95 out of 5 average rating, 410 reviewsThe Cottage At Central Park
Jul 22 – 29
Home in Siesta Key
4.89 out of 5 average rating, 140 reviewsSiesta Beach House
Jan 24 – 31
Condo rentals with a pool
Condo in Sarasota
4.95 out of 5 average rating, 123 reviewsCozy Beach Side 1BD/2BA, Walk to Beach & Pool
Sep 13 – 20
Condo in Sarasota
4.97 out of 5 average rating, 166 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Sep 25 – Oct 2
Condo in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
Jun 27 – Jul 4
Condo in Sarasota
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
May 28 – Jun 2
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
Apr 4 – 11
Condo in Siesta Key
4.96 out of 5 average rating, 103 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Nov 25 – Dec 2
Condo in Siesta Key
4.83 out of 5 average rating, 122 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Dec 16 – 23
Condo in Siesta Key
4.88 out of 5 average rating, 122 reviewsPrivate Beach Siesta Key Resort Jamaica Royale
Jul 23 – 30
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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