
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

Beautiful 3 Bd, 2 bth Pool Home Near Siesta Key!

Beautifully Remodeled Home with Pool Near Siesta

5 minutes to private Siesta Key Beach + 2 pools

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

St Armand's Mid-Century Oasis

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Siesta Key, FL - Casa Berano
Condo rentals with a pool

Best Siesta Key Condo

Beach Retreat - Jamaica Royale Unit #52

Crystal House on Siesta Key Beach

LIDO KEY 1 BR/1Bath Heated Pool 16

Siesta Key Condo: Beach, Pool & Village Fun!

Sunset and beach view from your balcony Unit 403

Amazing beach view! Entire unit renovated!

Anchor house +6 min. from Siesta Beach+heated pool
Other vacation rentals with a pool

Siesta Sunsets Suite

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

Relax in a Private Tropical Retreat on Siesta Key!

Coastal Home in Sarasota-8min from Siesta Key

The Blessing House- Htd Pool/Spa, Close to Beaches

Beachfront Villa | Pool + Lanai | Hosts 6

Graceful Getaway Studio

Designer Home| Sleeps 10| Walk to Beach & Village|
Quick stats about vacation rentals with a pool in Siesta Key
Total rentals
1.6K properties
Nightly prices starting at
$84 CAD before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
1.3K properties are a good fit for families
Pet-friendly rentals
240 properties allow pets
Rentals with dedicated workspaces
800 properties have a dedicated workspace
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- Rentals with pools Sarasota County
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- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Coquina Beach
- Anna Maria Public Beach
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Vinoy Park
- Gulfport Beach Recreation Area
- Streamsong Resort
- Jannus Live
- Manasota Key Beach
- North Beach
- Splash Harbour Water Park
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Englewood Beach
- Fort De Soto Park