Family-friendly holiday rentals in Little Gasparilla Island

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Top-rated family-friendly rentals in Little Gasparilla Island

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Cottage in Matlacha

4.9 out of 5 average rating, 156 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.

Guest favourite

Apartment in Boca Grande

4.92 out of 5 average rating, 133 reviews

2 Bedroom Flat Historic Boca Grande: #4

We’ve weathered the storms of Hurricanes Helene and Milton, and now we’re thrilled to welcome you! This beautifully renovated 2-bedroom, 1-bath flat is nestled in the heart of historic Boca Grande on stunning Gasparilla Island. The ground-floor location and a private outdoor sitting area, it’s your perfect island retreat. Steps away from The Temp Restaurant, a 3-minute stroll to the Gasparilla Inn, and only 2 minutes to the beach. Everything you need for an unforgettable vacation awaits!

Guest favourite

Hotel room in Venice

4.86 out of 5 average rating, 217 reviews

Near Downtown/Beach | Tropical Villas Venice Beach

Tropical Villas of Venice Beach offers 10 Villas on the Island of Venice FL. The Villas give the Old time Florida vibe with a convenient location to the beach, stores and restaurants. - 3 blocks from the beach - 2 blocks from the downtown - Near the Legacy Bike trail - In front of the beautiful John N. Park (Picnic) - Tropical gardens & swimming pool - Smart TV : NFLX, DIS +, Hulu, Espn+ - BBQ and Bikes and beach gears provided - Shark teeth equipment - Farmer Market every Saturday

Guest favourite

Home in Cape Coral

4.94 out of 5 average rating, 306 reviews

Luxurious Escape

Centrally located close to restaurants, supermarkets and malls , is 30 minutes to Fort Myers Beach, Sanibel and Captiva. All amenities provided. Guests that have stayed at this property have stress how clean and spotless is this house, UV system in air conditioner system to eliminate viruses, meticulously cleansed after each guest stay. Beach towels, chairs, umbrella provided. Beach in town 5 minutes from the house. We do not accept pets, service pets or comfort pets owner is allergic.

Guest favourite

Holiday home in Venice

4.85 out of 5 average rating, 136 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

Superhost

Condo in Englewood

4.93 out of 5 average rating, 136 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.

Superhost

Home in Port Charlotte

4.76 out of 5 average rating, 119 reviews

Pool Home on Saltwater Canal Accommodating 10

Unique opportunity to rent this gorgeous, pool home overlooking the saltwater canal. The home has accommodations for up to 10. Two homes in one connected by a common interior sitting area. Beautifully decorated and equipped with all the modern conveniences of home. With 7 bedrooms and 4.5 baths, multiple families can vacation together without feeling cramped. Dock with davits is found at the rear and can accommodate your vessel. This makes for a convenient day on the water.

Guest favourite

Home in Port Charlotte

4.85 out of 5 average rating, 168 reviews

Reduced Rates on this waterfront property

REDUCED PRICE - Our home is in a small quiet neighborhood and completely ready for your vacation, extended stay, or work away from home. We are located on a canal with a dock with quick access to the Peace River and the intracoastal waterway via boat. There are many local restaurants, activities, and fun things to do. Watch the sunset from your dock or take a 5 minute car ride to Punta Gorda to watch from numerous local restaurants on the water.

Guest favourite

Home in Cape Coral

4.94 out of 5 average rating, 179 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

This elegant spacious 3 Bedroom + Den, 3 Bathroom house with split floor plan and large living room will truly make you feel home! High ceilings, a lot of natural light, large rooms, amazing Florida canal view, large heated pool. Fully remodeled in 2017 and feels like new. Location is amazing, close to Marina, Cape Harbour, restaurants. Excellent, beautiful and safe neighborhood. This home is perfect for your vacation!

Guest favourite

Home in Englewood

4.87 out of 5 average rating, 106 reviews

Luxury Lemon Bay 6 BR villa w/ pool & tennis court

This beautiful house is located at the Lemon Bay and close to the Manasota Beach. The beach is just a 0.6 mile walk or 0.8 drive away. The property offers a 1/2 acre lot. This house offers, with a 34x12 feet swimming pool and own tennis court, a completely new rental experience. You will find the barbecue area outside of the pool area. The charging of EV is not allowed and an extra fee will be charged.

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 324 reviews

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and 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!

Superhost

Apartment in Englewood

4.82 out of 5 average rating, 125 reviews

BeachBay SeaHouse - 1521

Best location/value on Manasota Key in Englewood, FL... 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 off the 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.