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!
9–16 Dec
Home in Sarasota
4.94 out of 5 average rating, 296 reviews☀Coastal Gem☀Heated pool & amazing location!☀
2–9 Aug
Home in Siesta Key
4.9 out of 5 average rating, 105 reviewsSiesta Key, FL - Casa Berano
19–26 Aug
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
24 Sep – 1 Oct
Home in Siesta Key
4.89 out of 5 average rating, 139 reviewsSiesta Beach House
29 Sep – 6 Oct
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
29 Aug – 5 Sep
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
15–22 May
Home in Sarasota
4.87 out of 5 average rating, 132 reviews5 minutes to private Siesta Key Beach + 2 pools
8–15 Apr
Apartment rentals with a pool
Apartment in Siesta Key
4.82 out of 5 average rating, 233 reviewsSiesta Key 1/1 King bed “Sunset Suite” Pool Kayaks
10–17 May
Apartment in Sarasota
4.89 out of 5 average rating, 127 reviewsGateway to Siesta Key 1/2 mile to the Beach!
22–29 Oct
Apartment in Sarasota
4.95 out of 5 average rating, 123 reviewsCozy Beach Side 1BD/2BA, Walk to Beach & Pool
13–20 Sep
Apartment in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
24–31 May
Apartment in Longboat Key
4.97 out of 5 average rating, 148 reviewsSunset Views - Open May 13 & 14 - $175/nt!
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
10–17 Oct
Apartment in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
14–21 Dec
Apartment in Siesta Key
4.82 out of 5 average rating, 131 reviewsThe Key to a Great Vacation!
2–9 Nov
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
€ 56 before taxes and fees
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