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 9 – 16
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
Aug 19 – 26
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Aug 25 – Sep 1
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
Nov 22 – 29
Home in Sarasota
4.94 out of 5 average rating, 296 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Aug 2 – 9
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
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Nov 7 – 14
Home in Siesta Key
4.89 out of 5 average rating, 139 reviewsSiesta Beach House
Sep 4 – 11
Condo rentals with a pool
Condo in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
May 25 – Jun 1
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
Dec 14 – 21
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
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
May 28 – Jun 2
Condo in Siesta Key
4.81 out of 5 average rating, 284 reviews[Beach Elements] pool view + private beach & bikes
Dec 16 – 23
Condo in Siesta Key
4.82 out of 5 average rating, 131 reviewsThe Key to a Great Vacation!
Nov 2 – 9
Condo in Siesta Key
4.83 out of 5 average rating, 122 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Jan 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
Oct 11 – 18
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
G$12,545 GYD before taxes and fees
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