
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

Gorgeous Home / Heated Pool and Spa
Another great stay at this house! Love the location, very clean throughout, has everything you would need and more. We spent most of our time in covered outdoor area which has lots of seating options, the pool/hot tub is perfect! The only small issue we had was the door to the pool does not lock securely, therefore adding a safety risk if you have young children. It needs to have an added safety lock on top or something to that nature.

Sunset Paradise - Beautiful Sunsets and waterfront
The house we reserved was better than expected and everything was immaculate. Neil, the property manager responded right away when we called about a broken vaccum cleaner. Excellent response time and very professional. Unfortunately a thunderstorm damaged the AC and it couldn't be fixed right away, but Sean moved us right away to an even larger house. He even reimbursed us a day for our having to move and the night without AC. We definitely would rent from Sean again.

Shangri-La, full refund*, heated pool, sleeps 6
Spacious, clean , comfortable. They had beach stuff available in the garage that was great for the kids. Door alarm kept going iff when opening doors to the pool. Some instructions on the alarm system inside the house would be great. Kitchen was great. Jacuzzi was great. Pool was great

5 Star Paradise Plus/Canal/Pool/Spa/Kayaks
This is the second time my family has stayed at Connie & Dale’s. We absolutely love it. The home is gorgeous and well equipped with everything you need. The outdoor patio area and pool/ jacuzzi is amazing. So beautiful and relaxing. Will definitely be back !

Villa Scottsdale -Waterfront Home with Pool
We rented the house for a family reunion of 7 people, we ended up going only 6 people. We had a great time , we spent most of the time by the pool and inside the Jacuzzi and the pool. I will suggest to the Host to a couple of Lights or Flood lights in the back patio by the pool area. If you want to cook a BBB, you have to do it before it gets dark, the only light is the one inside the pool.

Luxury on Eight Lakes - Gulf Access & Pool table
We really enjoyed spending our Thanksgiving holiday at this location. Watching the sunsets every night over the lake were spectacular. The pictures of the place were accurate. The host was wonderful and very communicative.

Private Heated Pool and Spa
Alex was very responsive on the occasion we needed him. Followed up with us too. He was a WONDERFUL host. The house and pool could not have been any better. We loved the indoor outdoor living. We found the house to have much more than we expected. Lots of kitchen supplies that were not expected. We live near by and had visitors from out of state and we would highly recommend this place to anyone all ages. Oh and our 2 little pups had a great times. So happy we can take them with us. We would for sure stay again. Thanks Alex.

Private pool and well equipped for vacay!1071HS
Mike was a great host, friendly and very helpful. The house was well appointed and very clean. would definitely stay there again.
Family- and pet-friendly home rentals

Sanibel Romantic Getaway
We had a wonderful week at Nancy’s place! It was just right for my husband, me, and our small dog. Location is great and it’s an easy walk to the beach! While small, the apartment has all the necessities. We particularly liked that there is a bike rack and the house is beside a bike path.

La Casa On Mango, heated pool-5 min walk to Beach
Location is close enough to bike into downtown FMB and to the Publix, and we did both during our stay! The kids enjoyed the pool. House was stocked with everything you'd need for a day at the beach, which was much appreciated!

Villa Oasis - Beautiful Pool/SPA Home on Canal
This house was absolutely incredible! From the moment we arrived, everything was spotless—even the baseboards and ceiling fans were immaculate. The home is super spacious, with room to spread out comfortably (even the garage was huge!). The kitchen was fully stocked with everything you could possibly need to cook indoors or grill outside, and there were multiple dining areas both inside and out. The pool and spa were beyond refreshing—clean, well-maintained, and surrounded by plenty of lounge chairs for everyone. We loved the outdoor eating area and the thoughtful extras like pool toys and bikes, which added a fun touch. My boys especially enjoyed exploring near the canal, which made for some great memories. The beds were super comfy, with plenty of extra linens and cozy throw blankets. The neighborhood was peaceful and quiet, and the house is in a perfect, central location. The hosts were amazing: extremely responsive and helpful.

Waterfront Pool and Dock! Great Family Retreat
Beautiful spot, not far from numerous restaurants and things to do. Not far from the Charlotte Event Center. Good amenities, stocked cupboards (coffee filters, seasonings, etc). Definitely would stay here again if we visit.

Villa Coral with boat dock & waterview- own pool
We spent the month of March at this home and enjoyed the experience. With only solar heat we were afraid we wouldn’t use the pool but it was great and enjoyed lots of floats. We thoroughly enjoyed the outdoor area and beautiful canal views. Everything looked like the pictures. We loved the quiet neighborhood too

Comfortable cottage only 5 min. to the beach
We spend two happy and relaxed weeks in Angelika‘s house. The location is perfectly located among nature, parks, beaches and great shopping opportunities though a own car is highly recommended. Thank you Angelika! Dita & Franz, Switzerland

Gorgeous Townhome Close to the beaches
We stayed for 5 days. It was very easy to get there, check-in, check-out. The place was just as it was described and very clean. Everything we needed/wanted was very close by and easy to accesss. Stores, restaurants, the ocean... Great information from the host about the place and the area. Would definitely stay again!

Vacation home by Shasta Rd
The house was comfortable, and the kitchen was well stocked with all the dishes and cookware we needed. The location overlooking the pond is a highlight. The many kinds of birds that come onto the lawn and right onto the patio are fun to watch. As are the turtles and alligators that swim by all the time! The water in the area isn’t great, so there is a reverse osmosis filter in the kitchen for drinking and cooking water. But the water in the rest of the house isn’t filtered, so the water in the tub and toilets and laundry is a little amber colored. It didn’t affect our clothes in the laundry, and we used bottled water to brush teeth, so it was fine. Overall, we really enjoyed our stay, and would come back again!
Family-friendly home rentals with a pool

Beachfront Getaway in Siesta Key
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!

Near Downtown/Beach | Tropical Villas Venice Beach
The tropical villas were a great place to stay! Very cozy, clean and my favorite part was how accessible it was to everything. They had bikes for us to use which was amazing, we rode them to the beach each day and then to the town for lunch and dinners and shopping. We also made good use of the beach supplies in the closet. The sand sifter helped us find the most amazing shells and shark teeth! We want to come back here asap, loved it here.

Manasota Beach Vacation Rental
This house was better than we had hoped for!! The walk to the beach would have been possible but with free public parking with ample parking spaces, why walk when you can haul everyone and everything to the beach in the car? The garage door opened with a keypad and the owner has a garage door opener for the guests to use during their stay. The garage was appreciated during our stay because we had frequent rain. There were bikes available, a sand flea rake (for sifting for shark teeth), beach chairs, and beach toys available for use in the garage. The pool had heating available but we didn’t use it because the water temperature was already perfect. Master bedroom was on one side of the house and the other two bedrooms were on the opposite side of the house. In between the bedrooms was a spacious kitchen, den, and dining room. Our family of four had plenty of room to relax, work on puzzles, eat, and count the day’s haul of shark teeth. This was one of our favorite trips!! Thanks!!

PARADISE SUNSET
A beautiful location, very quiet neighborhood, yet within 1.5 miles of a large supermarket and drugstores. Pictures are very accurate of the home. We loved the outdoor pool area/lanai. There was an issue with the pool filter causing the pool to become too cold for swimming during the last few days, which was unfortunate for us, but that was not the hosts' fault, and they were very responsive, within minutes. The home as a very comfortable layout with several large sitting areas inside, as well as a very large lanai area. Kitchen is well equipped with everything we could need. We did not use the grill, but there was one available. We had an issue with the smoke detectors and, again, a simple text to our hosts brought immediate response and remedy. Alexina and her husband are lovely and very responsive. I would recommend this beautiful spot and we would return on our next trip to Cape Coral.

Little Piece of Paradise
Thank you Judy! We really enjoyed our stay it was delightful sitting out looking at the Marina watching the boats and the Sunset! Cass Cay is a great place to get dinner, drinks and listen to great music! Met your neighbor Mark and his friends Jim and Debby very nice to meet and talk with them. If we come to the area again we would definitely stay with you again! Thank you!

Your Private Waterfront Escape: Pool & Gulf Access
I would rent this place 1000 times over! They were so kind to us and I hope they are as happy with us as renters as we were with them as hosts

Tiki on the Bay
Deedra and her place were great. A relaxing place on the water with a pool, and a host who was responsive and polite. We couldn't have asked for anything more!

On Manasota Key with Direct access to our Beach B)
Great place to stay on the Bay. The golf was a short walk and was beautiful. Walking distance to several restaurants. My husband was able to catch fish off the dock. Our host, Dave had excellent communication. Thank you for the great time!
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
- 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
- Worthington Country Club
- North Jetty Beach
- South Jetty Beach
- Seagate Beach Club
- Marie Selby Botanical Gardens
- Delnor-Wiggins Pass State Park
- Heritage Bay Golf & Country Club
- Englewood Beach
- Tara Golf & Country Club
- Bonita National Golf & Country Club
- Van Wezel Performing Arts Hall
- LaPlaya Golf Club