
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
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Popular amenities for Siesta Key rentals with a pool
House rentals with a pool

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Spacious 2 Bedroom Home | Near Beach | Heated Pool

“Enfuego!”

5 minutes to private Siesta Key Beach + 2 pools

Beach, Village, Dock & Private Pool! One-of-a-kind

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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

Mid-Century Oasis with Pool in Arlington Park 1
Condo rentals with a pool

Best Siesta Key Condo

Steps away from beach and village! #1 in Siesta!

Cozy 1BR Beach Condo on Siesta Key!

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky

Siesta Key Ground Floor Condo 2BR On Trolley Line

[Beach Elements] pool view + private beach & bikes

Beach & Pool Open! Beachfront View Every Room

2Min Walk to Beach, Main SK Pavillion, Heated Pool
Quick stats about vacation rentals with a pool in Siesta Key
Total rentals
1.4K properties
Nightly prices starting at
R1,069 ZAR before taxes and fees
Total number of reviews
24K reviews
Family-friendly rentals
1.2K properties are a good fit for families
Pet-friendly rentals
210 properties allow pets
Rentals with dedicated workspaces
670 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Fort De Soto Park
- Vinoy Park
- North Beach
- Manasota Key Beach
- Jannus Live
- Streamsong Resort
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- Myakka River State Park
- North Beach At Fort DeSoto Park