Vacation rentals with a pool in Siesta Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Siesta Beach
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 Beach rentals with a pool
House rentals with a pool
Home in Sarasota
4.94 out of 5 average rating, 301 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Home in Sarasota
4.97 out of 5 average rating, 112 reviewsGorgeous Home / Heated Pool and Spa
Home in Sarasota
4.87 out of 5 average rating, 134 reviews5 minutes to private Siesta Key Beach + 2 pools
Home in Sarasota
4.98 out of 5 average rating, 161 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Home in Siesta Key
4.91 out of 5 average rating, 124 reviewsSea Club II Garden House
Home in Siesta Key
4.89 out of 5 average rating, 102 reviewsSpacious & Modern Gem ~ Walk to Gated Beach ~ Pool
Home in Sarasota
4.9 out of 5 average rating, 128 reviewsCottage On Bay (private backyard, near beaches)
Home in Siesta Key
4.98 out of 5 average rating, 63 reviewsYour Tropical & Private Siesta Key Beach House!
Condo rentals with a pool
Condo in Siesta Key
4.82 out of 5 average rating, 124 reviewsSarasota Surf & Racquet Club Siesta Key Condo
Condo in Sarasota
4.96 out of 5 average rating, 124 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Condo in Siesta Key
4.92 out of 5 average rating, 131 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
Condo in Sarasota
4.97 out of 5 average rating, 168 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Condo in Siesta Key
4.93 out of 5 average rating, 215 reviewsPrivate Siesta Key Escape
Condo in Sarasota
4.91 out of 5 average rating, 124 reviewsBeachside Siesta Key Cottage steps from the ocean
Condo in Siesta Key
4.97 out of 5 average rating, 111 reviewsSiesta Key For Me @ The Palm Bay Club
Condo in Sarasota
4.83 out of 5 average rating, 148 reviewsBest Gulf Coast Condo in Siesta Key
Destinations to explore
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Naples Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Rentals with pools United States
- Rentals with pools Florida
- Rentals with pools Florida
- Rentals with pools Kissimmee
- Rentals with pools Tampa
- Monthly Rentals Siesta Beach
- Waterfront rentals Siesta Beach
- Rentals with a hot tub Siesta Beach
- Rentals with a fireplace Siesta Beach
- Rentals with a firepit Siesta Beach
- Rentals with a washer and dryer Siesta Beach
- Rentals with a patio Siesta Beach
- Rentals with breakfast Siesta Beach
- Beachfront rentals Siesta Beach
- Pet-friendly rentals Siesta Beach
- Condo rentals Siesta Beach
- Townhouse rentals Siesta Beach
- Rentals with outdoor seating Siesta Beach
- House rentals Siesta Beach
- Fitness-friendly rentals Siesta Beach
- Rentals with a sauna Siesta Beach
- Wheelchair accessible rentals Siesta Beach
- Family-friendly rentals Siesta Beach
- Rentals with lake access Siesta Beach
- Apartment rentals Siesta Beach
- Rentals with beach access Siesta Beach
- Rentals with a kayak Siesta Beach
- Villa rentals Siesta Beach
- Kid-friendly rentals Siesta Beach
- Rentals with pools Sarasota County
- 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