
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!

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

Coastal Home in Sarasota-8min from Siesta Key

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

St Armand's Mid-Century Oasis

Private Siesta Beach House Oasis with Heated Pool.

Siesta Key, FL - Casa Berano

The Wisteria Oasis W/ heated pool & hot tub
Condo rentals with a pool

Beautiful White Sand Siesta Key Beach

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

The Honeymoon Suite on Siesta Key Beach

Cozy 1BR Beach Condo on Siesta Key!

Sea Shell Ocean view On Beach Walk everywhere Pool

Siesta Key Ground Floor Condo 2BR On Trolley Line

6 min to Siesta Beach | Heated Pool | Lake View

Sunset and beach view from your balcony Unit 403
Other vacation rentals with a pool

Amazing SK beach views... Newly renovated condo!!!

Beachfront Getaway in Siesta Key

Legacy's Palm of Paradise | Pool+ Putt Putt Course

Stunning Siesta Home | 4 Bedroom | Walk to Village

Modern 2/1+ shared, heated pool +4 min Siesta

Private Pool - Beach 100 steps, Village 5-min walk

Seaside on Siesta Key Beach

Sarasota Surf & Racquet Club Siesta Key Condo
Quick stats about vacation rentals with a pool in Siesta Key
Total rentals
1.6K properties
Nightly prices starting at
$83 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
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Raymond James Stadium
- Caspersen Beach
- Bean Point Beach
- Anna Maria Public Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Gulfport Beach Recreation Area
- Vinoy Park
- Streamsong Resort
- Jannus Live
- North Beach
- Manasota Key Beach
- Splash Harbour Water Park
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Ben T Davis Beach