
Family-friendly holiday rentals in Gasparilla Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Gasparilla Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Gasparilla Island family-friendly rentals
Family-friendly home rentals with a hot tub

Sommergluck

Gorgeous Home / Heated Pool and Spa

Villa Oasis - Beautiful Pool/SPA Home on Canal

Cottage Secluded in Palms 1 minute walk to Beach

Villa Scottsdale -Waterfront Home with Pool

Luxury on Eight Lakes - Gulf Access & Pool table

Coastal Modern Retreat with Heated Pool and Spa

Amazing Lagoon | Rock Grotto Swimming Pool | Spa
Family- and pet-friendly home rentals

La Casa On Mango, heated pool-5 min walk to Beach

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

2BR, 2BA home in the heart of downtown Sarasota

2bed/2bath with POOL house, close by SIESTA KEY!!!

Private Siesta Beach House Oasis with Heated Pool.

Sarasota Sandpiper: 4 Bed/3 bath + Pool

The Cottage, very close to Siesta Beach!

"Chill Time” Great Location in Sarasota
Family-friendly home rentals with a pool

5 Star Paradise Plus/Canal/Pool/Spa/Kayaks

Manasota Beach Vacation Rental

8 Lakes Location 3/2 Gulf Access w/Pool + Hot Tub

Amazing villa with great water view.

Gulf side condo be on the beach in minutes!

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

Rotonda River Villa pool home #1125

Myakka River Retreat In Port Charlotte
Destinations to explore
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- 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
- Siesta Beach
- Captiva Island
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Manasota Key Beach
- Lovers Key Beach
- Clam Pass Park
- Barefoot beach Bonita Springs,FL
- Myakka River State Park
- The Club at The Strand
- Delnor-Wiggins Pass State Park
- North Jetty Beach
- Marie Selby Botanical Gardens
- South Jetty Beach
- Worthington Country Club
- Englewood Beach
- Seagate Beach Club
- Heritage Bay Golf & Country Club
- Spanish Wells Country Club
- Gasparilla Island State Park
- Blind Pass Beach
- Lakewood National Golf Club