
Family-friendly holiday rentals in Little Gasparilla Island
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Top-rated family-friendly rentals in Little Gasparilla Island
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Family-friendly home rentals with a hot tub

Rowan's Retreat
Beautiful historic home ! Loved the wrap around porch and the hot tub. Great shower ! Loved the coffee and wine and cozy blankets on the couch . Wish we could have stayed longer . Lots of space ! Close to downtown fort Myers

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.

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.

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.

Amazing villa with great water view.
We had a fantastic stay! The house was incredibly well-equipped—there were plenty of essentials like paper towels, toilet paper, and all the little extras that make a stay comfortable and convenient. The pool and hot tub were both in perfect working order and made for a relaxing time day or night. The canal out back was a real highlight—great fishing with a wide variety of fish, including catfish, gar, and more. The house also came with five bicycles available for tenant use, which was a nice bonus, and there were TVs in every room—perfect for unwinding after a long day. The home felt truly luxurious, especially for the price. Jeff was a great host, and everything went smoothly. Highly recommend!

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.

2nd Floor Beachfront Condo Sanibel Harbour
We had a fantastic stay at this condo! The place was clean, comfortable, and exactly as described. The location was perfect—close to everything but still quiet and relaxing. Check-in was super easy, and the host was friendly and responsive. We loved having coffee on the lanai each morning and looking for dolphins and manatees. We would definitely stay here again! Taylor family

The Parsonage-Private Villa-Heated Pool & Spa.
This was a great “home base” for our event at the Heitman House. It was nearby and walkable, with plenty of space for all our guests. The house and backyard were excellent for hosting meals and hangouts, and the place was really well-stocked, making it feel like home and not a random rental. The beds were comfy and there were plenty of linens, including lots of extras so despite being at full capacity for days we didn’t need to go without. I really appreciated the amount of bath and pool towels that were provided! The hosts were responsive and had anticipated many of our questions and needs. Details like the kitchen having multiple coffee makers, and extra bug spray & beach chairs were nice touches.
Family- and pet-friendly home rentals

Key Condo located on Manasota Key
Great location! Beach was steps away. Wish we could have stayed longer. Would definitely stay here again.

South Venice, FL. Ideal vacation home.
This place was great! We had no problem with check in. Came right over to show us how to use the TV. The neighborhood was quiet and peaceful. Perfect for us. Check out was easy too. Will definitely stay here again, if we need a place in Venice.

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

3 Bed 2 Bath Heated Pool Home in Fantastic Area!
Loved the house was perfect for peaceful vacation and to relax. Very nice neighborhood. Will definitely stay there again for the next vacation.

Turtle Nest Retreat - Manasota Key (upper unit)
Dana was an amazing host. The space was beautiful and magical. We can’t wait to return again. Thank you for everything.

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!

Chameleon Guest Cabana
We had an amazing stay here. It was peaceful and close to downtown fort Myers for shopping and night life.
Family-friendly home rentals with a pool

South Seas Beach Villa 2313
We had a delightful time. Woke up the first morning to discover we had a flat tire. AAA came and put on the spare which limited us from traveling ling to far. But our place was comfortable the beach and pool a short walk and some good restaurants a short drive away. Being home in the evening was awesome seeing the gorgeous sunsets!

South Facing Canal Home Outdoor Living Room Tiki
We had a great stay at this house! The home was spotless and had everything we needed for a comfortable visit. We enjoyed the outdoor space, with the pool being a definite highlight. Easy check-in process and host was very responsive. Highly recommend this place for a relaxing getaway!

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!!

Manasota Key Condo Bay side Beach Access
Great place, great stay.

Peaceful Port Charlotte 2Bd/2Ba on water
We were very relaxed at this home because it felt like home. Home was completely and fully stocked with everything you needed. We even used items in the garage during our stay ( lawn chairs, floating devices and there were even fishing poles if we wanted to use). The HVAC and hot water tank looked new and the washer and dryer was great. In the event we ever travel in that area again I will definitely be staying at this home if it is available. For myself and my family Thanks Troy for making our stay easy and great!

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.

Sanibel Harbour Resort - 137: Stairs to Beach
We recently stayed at the Sanibel Harbor condo with our one year old daughter and her great grandma, and we had the most amazing time! Her uncle also joined us for a fun filled Saturday. We can’t say enough great things about this stay. The immediate access to the water via stairs was a huge plus and one of the main reasons we chose this property. It was absolutely beautiful, especially considering how hard the area was hit just two years ago by Hurricane Ian. The restoration and care put into the property truly show. We’re so grateful for the memories made here!

Sunset Paradise: Book your Summer Vacation
Tom's place is beautifully furnished, comfortable, and spacious. It has everything you need to prepare meals. We used the pool everyday. Living on the canal was peaceful and relaxing. Tom is a great host and very responsive. We had a wonderful vacation and look forward to returning next year.
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Cortez Beach
- Coquina Beach
- Manasota Key Beach
- Barefoot beach Bonita Springs,FL
- Lovers Key Beach
- Myakka River State Park
- River Strand Golf and Country Club
- South Jetty Beach
- North Jetty Beach
- Marie Selby Botanical Gardens
- Englewood Beach
- Lakewood National Golf Club
- Tara Golf & Country Club
- Gasparilla Island State Park
- Stump Pass Beach State Park
- Boca Grande Pass