Vacation rentals with a pool in Siesta Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Siesta Beach
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 Beach rentals with a pool
House rentals with a pool
Home in Siesta Key
4.89 out of 5 average rating, 141 reviewsSiesta Beach House
Nov 7 – 14
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
Apr 6 – 13
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
May 18 – 25
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
Jan 18 – 25
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Nov 7 – 14
Home in Sarasota
4.95 out of 5 average rating, 410 reviewsThe Cottage At Central Park
Mar 16 – 23
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
Dec 8 – 15
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Oct 20 – 27
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*
Jul 14 – 21
Condo in Siesta Key
4.85 out of 5 average rating, 132 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Jul 6 – 13
Condo in Sarasota
4.96 out of 5 average rating, 120 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Sep 18 – 25
Condo in Siesta Key
4.93 out of 5 average rating, 215 reviewsPrivate Siesta Key Escape
Jul 10 – 17
Condo in Sarasota
4.89 out of 5 average rating, 128 reviewsGateway to Siesta Key 1/2 mile to the Beach!
Aug 21 – 28
Condo in Siesta Key
4.93 out of 5 average rating, 182 reviewsSteps away from beach and village! #1 in Siesta!
Oct 29 – Nov 5
Condo in Siesta Key
4.81 out of 5 average rating, 285 reviews[Beach Elements] pool view + private beach & bikes
Aug 23 – 30
Condo in Siesta Key
4.9 out of 5 average rating, 204 reviewsSea Club 2 Condo Siesta Key
Jan 25 – Feb 1
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