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, 142 reviewsSiesta Beach House
Oct 13 – 20
Home in Sarasota
4.87 out of 5 average rating, 133 reviews5 minutes to private Siesta Key Beach + 2 pools
Aug 11 – 18
Home in Sarasota
4.97 out of 5 average rating, 207 reviewsYour private retreat near Siesta Key Beach.
Jun 15 – 22
Home in Sarasota
4.97 out of 5 average rating, 110 reviewsGorgeous Home / Heated Pool and Spa
Nov 7 – 14
Home in Siesta Key
4.89 out of 5 average rating, 100 reviewsSpacious & Modern Gem ~ Walk to Gated Beach ~ Pool
Jan 25 – Feb 1
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
Mar 8 – 15
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
Aug 25 – Sep 1
Home in Sarasota
4.98 out of 5 average rating, 160 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Jun 27 – Jul 4
Condo rentals with a pool
Condo in Sarasota
4.96 out of 5 average rating, 121 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Dec 1 – 8
Condo in Siesta Key
4.93 out of 5 average rating, 215 reviewsPrivate Siesta Key Escape
Oct 3 – 10
Condo in Sarasota
4.91 out of 5 average rating, 216 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
Jan 3 – 10
Condo in Siesta Key
4.94 out of 5 average rating, 140 reviewsSea Club 2-Relaxing Siesta Key Condo-Mermaids Rest
Dec 24 – 31
Condo in Sarasota
4.89 out of 5 average rating, 128 reviewsGateway to Siesta Key 1/2 mile to the Beach!
Nov 8 – 15
Condo in Sarasota
4.97 out of 5 average rating, 166 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Aug 7 – 14
Condo in Siesta Key
4.93 out of 5 average rating, 183 reviewsSteps away from beach and village! #1 in Siesta!
Feb 6 – 13
Condo in Siesta Key
4.97 out of 5 average rating, 110 reviewsSiesta Key For Me @ The Palm Bay Club
Sep 15 – 22
Destinations to explore
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