
Vacation rentals with a pool in Siesta Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Siesta Beach
Guests agree: these stays 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 Beach rentals with a pool
House rentals with a pool

Gorgeous Home / Heated Pool and Spa

The Sand Castle - Backyard Oasis Mins from Siesta!

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

Toes In The Sand | Private Pool, Walk to Beach!

Beach! Spa, PuttPutt, Beach Gear, Pool Table&More

Stunning Siesta Home | 4 Bedroom | Walk to Village

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Siesta Key Retreat 1mi to Beach!
Condo rentals with a pool

Stunning Siesta Vistas Direct Beach Access & Pool

Beach Haven on Siesta Key Beach

Best Siesta Key Condo

Beautiful White Sand Siesta Key Beach

Bright and Beachy - Steps to the Water!

Siesta Key Ground Floor Condo 2BR On Trolley Line

Condo with a View 1: Open August 22nd & 23rd!

Top Floor Beautiful View Condo-Shore To Please
Other vacation rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Penthouse Expansive Ocean Views

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

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

Upscale Villa in the heart of Siesta Key!

Spacious 2BR 2nd floor Siesta Key condo - GBB 1274

Sarasota Surf & Racquet Club Siesta Key Condo
Quick stats about vacation rentals with a pool in Siesta Beach
Total rentals
1.5K properties
Nightly prices starting at
ﺩ.ﺇ220 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
130 properties allow pets
Rentals with dedicated workspaces
730 properties have a dedicated workspace
Destinations to explore
- Rentals with a fire pit Siesta Beach
- Beach house rentals Siesta Beach
- Pet-friendly rentals Siesta Beach
- Rentals with breakfast Siesta Beach
- Villa rentals Siesta Beach
- Rentals with a fireplace Siesta Beach
- Cottage rentals Siesta Beach
- Beachfront rentals Siesta Beach
- Luxury rentals Siesta Beach
- Condo rentals Siesta Beach
- Rentals with an EV charger Siesta Beach
- Kid-friendly rentals Siesta Beach
- Rentals with a kayak Siesta Beach
- Townhouse rentals Siesta Beach
- Rentals with a patio Siesta Beach
- Rentals with outdoor seating Siesta Beach
- Rentals with a hot tub Siesta Beach
- Rentals with lake access Siesta Beach
- Rentals with a washer and dryer Siesta Beach
- Apartment rentals Siesta Beach
- Rentals with beach access Siesta Beach
- Fitness-friendly rentals Siesta Beach
- Family-friendly rentals Siesta Beach
- Waterfront rentals Siesta Beach
- Rentals with a sauna Siesta Beach
- House rentals Siesta Beach
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Cabins United States
- Treehouses United States
- Tiny Houses United States
- Beach Houses United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Crescent Beach
- John's Pass
- Turtle Beach
- Anna Maria Public Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Amalie Arena
- Lido Key Beach
- Coquina Beach
- Cortez Beach
- Gulfport Beach Recreation Area
- Fort De Soto Park
- Vinoy Park
- Manasota Key Beach
- Jannus Live
- North Beach
- Streamsong Resort
- Curtis Hixon Waterfront Park
- Splash Harbour Water Park
- Myakka River State Park
- North Beach At Fort DeSoto Park
- Alafia River State Park