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
4.89 out of 5 average rating, 142 reviewsSiesta Beach House
Jan 21 – 28
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
Sep 1 – 8
Home in Sarasota
4.97 out of 5 average rating, 110 reviewsGorgeous Home / Heated Pool and Spa
Nov 7 – 14
Home in Sarasota
4.87 out of 5 average rating, 133 reviews5 minutes to private Siesta Key Beach + 2 pools
Apr 15 – 22
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
Oct 16 – 23
Home in Sarasota
4.93 out of 5 average rating, 150 reviewsModern, Bright Downtown SRQ A-Frame West of Trail
Apr 25 – May 2
Home in Sarasota
4.94 out of 5 average rating, 297 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Jul 19 – 26
Home in Siesta Key
4.89 out of 5 average rating, 100 reviewsSpacious & Modern Gem ~ Walk to Gated Beach ~ Pool
Oct 31 – Nov 7
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
Nov 22 – 29
Condo in Longboat Key
4.97 out of 5 average rating, 149 reviewsCharming Condo on the Coast!
Nov 22 – 29
Condo in Sarasota
4.97 out of 5 average rating, 166 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Aug 13 – 20
Condo in Sarasota
4.95 out of 5 average rating, 125 reviewsCozy Beach Side 1BD/2BA, Walk to Beach & Pool
Sep 13 – 20
Condo in Siesta Key
4.83 out of 5 average rating, 122 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Jan 17 – 24
Condo in Sarasota
4.89 out of 5 average rating, 128 reviewsGateway to Siesta Key 1/2 mile to the Beach!
Oct 30 – Nov 6
Condo in Siesta Key
4.81 out of 5 average rating, 285 reviews[Beach Elements] pool view + private beach & bikes
Nov 12 – 19
Condo in Siesta Key
4.92 out of 5 average rating, 180 reviewsBright and Beachy - Steps to the Water!
Oct 10 – 17
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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