Holiday 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.
Holiday 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!
3–10 Sep
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
6–13 Aug
Home in Siesta Key
4.89 out of 5 average rating, 141 reviewsSiesta Beach House
7–14 Nov
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
7–14 Nov
Home in Sarasota
4.95 out of 5 average rating, 410 reviewsThe Cottage At Central Park
16–23 Mar
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
5–12 Apr
Home in Siesta Key
4.91 out of 5 average rating, 122 reviewsSea Club II Garden House
30 Sep – 7 Oct
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
19–26 Oct
Apartment rentals with a pool
Apartment in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
14–21 Jul
Apartment in Longboat Key
4.97 out of 5 average rating, 148 reviewsCharming Condo on the Coast!
6–13 Apr
Apartment in Siesta Key
4.96 out of 5 average rating, 103 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
26 Aug – 2 Sep
Apartment in Sarasota
4.95 out of 5 average rating, 124 reviewsCozy Beach Side 1BD/2BA, Walk to Beach & Pool
13–20 Sep
Apartment in Siesta Key
4.92 out of 5 average rating, 180 reviewsBright and Beachy - Steps to the Water!
6–13 Oct
Apartment in Siesta Key
4.81 out of 5 average rating, 285 reviews[Beach Elements] pool view + private beach & bikes
12–19 Aug
Apartment in Siesta Key
4.93 out of 5 average rating, 182 reviewsSteps away from beach and village! #1 in Siesta!
7–14 Nov
Apartment in Siesta Key
4.93 out of 5 average rating, 215 reviewsPrivate Siesta Key Escape
10–17 Jul
Quick stats about holiday 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
$81 SGD before taxes and fees
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