Family-friendly holiday rentals in Gasparilla Island

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Popular amenities for Gasparilla Island family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Sarasota
4.98 out of 5 average rating, 140 reviews

Gorgeous Home / Heated Pool and Spa

svitlanaRating, 5 stars2 weeks ago
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.
Superhost
Villa in Cape Coral
4.92 out of 5 average rating, 36 reviews

Sunset Paradise - Beautiful Sunsets and waterfront

AlbertoRating, 5 stars33 months ago
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.
Guest favourite
Villa in Rotonda West
4.95 out of 5 average rating, 59 reviews

Shangri-La, full refund*, heated pool, sleeps 6

KabirRating, 5 stars5 months ago
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
Top guest favourite
Home in Cape Coral
4.99 out of 5 average rating, 90 reviews

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

ChristineRating, 5 stars1 month ago
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 !
Superhost
Home in Cape Coral
4.87 out of 5 average rating, 150 reviews

Villa Scottsdale -Waterfront Home with Pool

CarlosRating, 5 stars4 weeks ago
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.
Guest favourite
Home in Cape Coral
4.87 out of 5 average rating, 39 reviews

Luxury on Eight Lakes - Gulf Access & Pool table

StephenRating, 5 stars6 months ago
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.
Guest favourite
Home in Fort Myers
4.95 out of 5 average rating, 125 reviews

Private Heated Pool and Spa

MelindaRating, 5 stars1 week ago
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.
Guest favourite
Home in Englewood
4.97 out of 5 average rating, 32 reviews

Private pool and well equipped for vacay!1071HS

MarkRating, 5 stars3 months ago
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

Superhost
Apartment in Sanibel
4.73 out of 5 average rating, 132 reviews

Sanibel Romantic Getaway

MicheleRating, 5 stars1 month ago
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.
Superhost
Home in Fort Myers Beach
4.89 out of 5 average rating, 233 reviews

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

MandyRating, 5 stars5 months ago
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!
Top guest favourite
Home in Cape Coral
4.83 out of 5 average rating, 126 reviews

Villa Oasis - Beautiful Pool/SPA Home on Canal

AshleighRating, 5 stars4 weeks ago
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.
Superhost
Home in Port Charlotte
4.84 out of 5 average rating, 156 reviews

Waterfront Pool and Dock! Great Family Retreat

IsaacRating, 5 stars18 months ago
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.
Superhost
Home in Cape Coral
4.81 out of 5 average rating, 154 reviews

Villa Coral with boat dock & waterview- own pool

ChristieRating, 5 stars2 months ago
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
Superhost
Home in Grove City
4.81 out of 5 average rating, 37 reviews

Comfortable cottage only 5 min. to the beach

FranzRating, 5 stars2 months ago
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
Superhost
Townhouse in Fort Myers
4.87 out of 5 average rating, 172 reviews

Gorgeous Townhome Close to the beaches

KathrynRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Venice
4.76 out of 5 average rating, 136 reviews

Vacation home by Shasta Rd

JudithRating, 5 stars2 months ago
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

Guest favourite
Home in Siesta Key
4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars2 weeks ago
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!
Guest favourite
Hotel room in Venice
4.86 out of 5 average rating, 224 reviews

Near Downtown/Beach | Tropical Villas Venice Beach

KristinRating, 5 stars1 day ago
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.
Guest favourite
Holiday home in Englewood
4.88 out of 5 average rating, 77 reviews

Manasota Beach Vacation Rental

BryanRating, 5 stars2 weeks ago
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!!
Guest favourite
Home in Cape Coral
4.89 out of 5 average rating, 57 reviews

PARADISE SUNSET

NancyRating, 5 stars3 months ago
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.
Superhost
Apartment in Punta Gorda
4.77 out of 5 average rating, 121 reviews

Little Piece of Paradise

Valerie SBRating, 5 stars1 week ago
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!
Top guest favourite
Home in Cape Coral
4.91 out of 5 average rating, 271 reviews

Your Private Waterfront Escape: Pool & Gulf Access

ShaynnaRating, 5 stars4 weeks ago
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
Top guest favourite
Apartment in Englewood
4.95 out of 5 average rating, 44 reviews

Tiki on the Bay

MichaelRating, 5 stars12 months ago
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!
Top guest favourite
Apartment in Englewood
4.91 out of 5 average rating, 64 reviews

On Manasota Key with Direct access to our Beach B)

MaryRating, 5 stars1 month ago
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!

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