Family-friendly vacation 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.

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Superhost

Townhouse in Siesta Key

4.86 out of 5 average rating, 145 reviews

"Relax Here" -Royal Palm Suite- Siesta Key Beach

The pampering begins HERE: 3 bed/ 2.5 baths townhouse, sqft 1,850, 2 kings & 1 queen bed, an enchanting loft bedroom with it's own balcony and incredible Gulf / Beach views All 3 balconies have Gulf views!! Imagine sitting on your patio and watching people at the beach. Gumbo Limbo Rentals is a mini resort, 60 steps to the beach with only 2 duplexes sharing a black bottom lagoon pool which is heated during the colder winter months. Free: Wifi, beach chairs & sun umbrellas, 2-3 parking spaces

Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Superhost

Apartment in Englewood

4.83 out of 5 average rating, 120 reviews

BeachBay SeaHouse (1519)

Best location/value on Manasota Key. 300 yards to pristine gulf beaches, 300 yards to boat ramp and dock on Lemon Bay if you have a boat or want to see dolphin or fish from dock. 4/10s of a mile to several great restaurants and 1 mile to Stump Pass State Park and a few more miles to walk via the park to Stump Pass. 1519 Beachway Bungalows has one bedroom with a queen bed and a pull-out sofa. There is a full kitchen and a great outside screened in patio that is shared with SeaHouse 1521.

Top guest favorite

Home in Sarasota

4.96 out of 5 average rating, 234 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Guest favorite

Cottage in Sarasota

4.76 out of 5 average rating, 126 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

Superhost

Condo in Sanibel

4.74 out of 5 average rating, 129 reviews

Sanibel Romantic Getaway

Sanibel; named by Travel & Leisure as one of the top 50 “Best Places” internationally to visit in 2025, with its restaurants, shops and of course, Sanibel’s incredible beaches, rebuilt and open for business. Fully equipped kitchen, sheets, towels, etc included. Great restaurants and shopping, lighthouse and parks. Bike rentals and trails throughout the island allow you to access all the hidden treasures on Sanibel. A 2 minute walk to access our pristine white beaches .

Top guest favorite

Home in Siesta Key

5 out of 5 average rating, 140 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Superhost

Home in Fort Myers

4.85 out of 5 average rating, 656 reviews

Cozy Cabin Next To Sanibel With Paddle Boards

Paddle Board Canin Stay on adventure's doorstep! 5 miles to FMB and Sanibel island (beaches, salt water fishing, paddle boarding, kayaking ). Are guests enjoy free amenities: 1. Coffee/tea/bottled water 2. Bicycles 3. SUP - inflatable paddle boards 4. BBQ gas grill 5. Beach chairs and umbrella 6. Cooler and beach towels 7. Secured Wi-Fi 8. Amazon TV, Netflix, Hulu, Disney +, ESPN+ 9. Parking 2 cars 10. Washer and dryer in house 11. Kids toys and books

Guest favorite

Guest suite in Sarasota

4.95 out of 5 average rating, 243 reviews

2 Miles to Siesta Key

Comfortable Accommodations with Private Entrance & Quiet Surroundings. This is a Private Guest Suite in a home with a king size bed, full bathroom, and kitchenette with sink and countertop, fridge and freezer, microwave, and coffee maker. This provides ample utility to prepare simple meals but is not suitable for cooking since there is no stove or oven.

Superhost

Townhouse in Fort Myers

4.86 out of 5 average rating, 169 reviews

Gorgeous Townhome Close to the beaches

Nestled in a charming townhouse community, this lovely home offers a prime location near Sanibel Island and Fort Myers Beach. Boasting three spacious bedrooms, it caters to families, friends, and couples. Furry companions are welcome too. Enjoy all the comforts of a well-appointed home, and take a dip in the inviting community pool.

Superhost

Home in Sarasota

4.79 out of 5 average rating, 195 reviews

Relaxing 3BR/2Ba Oasis with Heated Pool.

Welcome to our charming and inviting house, the perfect retreat for a private and comfortable stay. Feel at home with self check-in, cleanliness, and high-speed WiFi. Enjoy streaming on Roku and Sling TV. Relax in the private heated pool. Ideal for couples, solo adventurers, business travelers, and families.

Superhost

Condo in Sarasota

4.73 out of 5 average rating, 128 reviews

Best Deals on Siesta Key

Siesta Key Studio with 1 Bathroom We are proud of our Siesta Key Condo at Ebb Tide. It is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short one minute walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.

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What guests are saying

Serenity in Paradise-Heated Pool-10 min to Beach!

5 out of 5 average rating, 22 reviews3 weeks ago

This home has everything we needed to relax on our vacation. It is very clean, spacious (we are a family of 4), and the heated private pool was such a nice bonus! Tena met us at the house as soon as we arrived to give us a tour and to go over little details such as light switches for the outdoor space etc. The neighborhood itself was quiet and close to stores, restaurants and beaches. Both Tena and Tim were incredible hosts, and responded to any needs we had within minutes of texting. We highly recommend staying here!

Home in Naples

What guests are saying

Waterfront fun! Boat, Pool, Hot tub, Near Beach

5 out of 5 average rating, 12 reviews1 week ago

We absolutely loved our stay at this beautiful home. Everything was clean and nicely updated. Location was great and the backyard felt very private. The host always responded to us in a timely manner and took care of any questions/concerns we had right away. Would definitely recommend staying here!

Home in Cape Coral

What guests are saying

Blue Abaco - Beautiful Waterfront House

4.88 out of 5 average rating, 32 reviews9 months ago

Perfect time at Blue Abaco! Lovely villa, clean and comfortable, with everything you could need - real home away from home. Plenty space for our family of 4. Everyone enjoyed pool overlooking waterway! Vesteva Vacation Rentals great with communication too. Within easy driving distance - 5 mins- of local shops/restaurants. So could comfortably walk to shops too. Only short drive to Cape Coral Water Park - about 10 mins and about 20/30 minute drive to lovely Fort Myers beach. Located in quiet neighbourhood so really relaxing. Would highly recommend and would certainly do a return visit

Home in Cape Coral

What guests are saying

Great Resort! Large Heated Pool / Hot Tub

4.7 out of 5 average rating, 100 reviews1 month ago

The photos are not updated, so to our surprise, the unit has been beautifully updated and we were so excited when we walked in! Rob was a great host, made check in so easy, and gave great recommendations to restaurants in the area. The food and atmosphere at Junkaroos was awesome! We went two nights in a row and they have a great happy hour! We were there over spring break, so we were told on the property to go early or the wait will be long. Great advise…we went at 4:30 one night and 5:30 the 2nd and didn’t wait longer than 20 minutes! The beach is across the street, entrance 1 block away and Rob had chairs and some beach toys which was great for our little one. The pool is huge and heated and the hot tub was a great bonus! We will definitely be back! So relaxing and fun! We highly recommend this place. Great location.

Apartment in Fort Myers Beach

What guests are saying

LUX VILLAs close to sparkling Siesta Beach.

4.86 out of 5 average rating, 29 reviews5 months ago

My two boys and I truly enjoyed the condo. It was clean, tidy, roomy, well-equipped, and conveniently located. The community was quiet and peaceful. My boys loved the pool and I loved the hot tub. We were extremely pleased. While we were given a unit that differed from our original request, we understood the reason given and we were in no way disappointed with the new arrangement. The unit was perfect for us and we would definitely return. Bea and her assistant were quick to respond to my questions prior to arrival. We had no issues during our stay, so we never needed to communicate while we were there. Check-in and check-out were both extremely easy.

Apartment in Sarasota

What guests are saying

Sea Turtle Heaven 2

5 out of 5 average rating, 29 reviews2 weeks ago

We absolutely loved our stay! The house had literally everything we needed. Eric has done everything to make it a smooth and easy process for check in and check out. Everything in the house was labeled, which made it super easy to find things and put them back as we used them. The kids loved having their own rooms and would have stayed in the pool all night if we had let them! The walk to the beach is a little farther than we had anticipated with kids, but that wasn’t a problem. Vanderbilt Beach parking is right down the road so we loaded up the car, dropped everyone off at the beach and parked. They also had everything we needed for the beach. It truly felt like home for 7 days. We will definitely be back! Thanks for sharing your home.

Home in Naples

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