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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Matlacha

4.88 out of 5 average rating, 135 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

23–30 Nov

$165 SGD per night

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

19–26 Oct

$147 SGD per night

Guest favourite

Guest house in Fort Myers

4.98 out of 5 average rating, 621 reviews

Hints of Key West in Fort Myers' Historic District

Tucked away in tranquil Dean Park Historic District. Built in 1925, this carriage house has been completely renovated in 2016. It is over a garage, there are stairs. Stroll to downtown Fort Myers River District, and enjoy the restaurants, nightlife, and cultural events. Take advantage of all the activities the area has to offer, and at the end of the day come back to this peaceful oasis. Our place can accommodate couples, older child (twin air mattress available), business travelers. No pets.

23–30 Jul

$180 SGD per night

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

NEW 4 Day MAY opening Sarasota #1 Luxury Villa

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

11–18 Nov

$857 SGD per night

Guest favourite

Home in Cape Coral

4.87 out of 5 average rating, 178 reviews

Recently Renovated Home with Pool in SW Cape Coral

The perfect getaway for families at our recently renovated house with pool and grill! Half an hour by car from famous beaches. Create lasting memories. Relax in the comfortable living area, and unwind in well-appointed bedrooms. Outside, make a splash in the refreshing pool or sizzle up a feast on the grill. Explore beaches, dine at charming restaurants, and enjoy outdoor activities. We ensure a memorable stay. Book now for an unforgettable family vacation! Pool heater from November to March.

9–16 Oct

$201 SGD per night

Superhost

Home in Fort Myers

4.85 out of 5 average rating, 595 reviews

Tiny house 5 miles from Sanibel / free amenities

Tiny Paddle Board House 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. Breakfast items (eggs, bagels, apples, coffee and tea) 2. Bicycles 3. SUP - inflatable paddle board 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

18–25 Jun

$140 SGD per night

Guest favourite

Home in Captiva

4.97 out of 5 average rating, 107 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

12–19 Jun

$822 SGD per night

Guest favourite

Home in Venice

4.89 out of 5 average rating, 161 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Relaxing pool home with 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

21–28 Sep

$199 SGD per night

Guest favourite

Apartment in Englewood

4.94 out of 5 average rating, 116 reviews

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

23–30 Dec

$300 SGD per night

Guest favourite

Home in Englewood

4.96 out of 5 average rating, 104 reviews

Waterfront Cottage by Manasota Key

A 2 bedroom 2 bathroom* waterfront house on Forked Creek in Englewood, Florida 2.5 miles away from Manasota Key. This is a 1,100 sq. ft. single family home on a natural deep water creek with a boat dock. House comes fully furnished and fully equipped. King size and queen size beds in the 2 bedrooms. Full size sofa and IKEA recliners in the "Florida Room", high speed wireless internet and cable and Netflix ready TV, towels, beach chairs, grill, etc. Air mattress is provided.

12–19 Sep

$186 SGD per night

Guest favourite

Villa in Englewood

4.92 out of 5 average rating, 110 reviews

Magnificent Waterfront! Kayaks-Pool-Beach! gs

Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & cozy family room. On-site resort pool overlooks stunning Lemon Bay. 5-minute walk to ocean-side beach or enjoy “Bay-front beach” out back. Quiet island street. low-key quiet respectful vacationers. 1 car parking spot. No visitor parking. No boats. No pets. No smoking. Free use of kayaks!

20–27 Oct

$211 SGD per night

Guest favourite

Home in Englewood

4.99 out of 5 average rating, 102 reviews

Paradise on the Bay

Waterfront pool home with all the amenities. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fish from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 2 Kayaks and 1 pebble boat is available for your enjoyment.

26 Nov – 3 Dec

$572 SGD per night