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
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Popular amenities for Siesta Beach rentals with a pool
House rentals with a pool
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
Nov 9 – 16
Home in Siesta Key
4.89 out of 5 average rating, 140 reviewsSiesta Beach House
Jan 21 – 28
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Oct 10 – 17
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
Sep 3 – 10
Home in Sarasota
4.98 out of 5 average rating, 125 reviewsNew remodel- 150 Yds to Beach and Restaurants!
Aug 30 – Sep 6
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
4.94 out of 5 average rating, 297 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Aug 2 – 9
Condo rentals with a pool
Condo in Siesta Key
4.96 out of 5 average rating, 103 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Dec 20 – 27
Condo in Siesta Key
4.81 out of 5 average rating, 285 reviews[Beach Elements] pool view + private beach & bikes
Aug 20 – 27
Condo in Sarasota
4.89 out of 5 average rating, 127 reviewsGateway to Siesta Key 1/2 mile to the Beach!
Aug 12 – 19
Condo in Siesta Key
4.88 out of 5 average rating, 122 reviewsPrivate Beach Siesta Key Resort Jamaica Royale
Jan 3 – 10
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
4.93 out of 5 average rating, 215 reviewsPrivate Siesta Key Escape
Jul 28 – Aug 4
Condo in Siesta Key
4.85 out of 5 average rating, 132 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Nov 11 – 18
Condo in Siesta Key
4.89 out of 5 average rating, 118 reviewsSiesta Key Beach Escape
Dec 5 – 12
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