Family-friendly holiday rentals in Gasparilla Island

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

A lil country, A lil beach time

* Enjoy the lovely setting of this romantic spot in nature, a full acre with a small pond! Only 45 minutes to most beaches. Beautiful country with small antique town and parks to explore. Private acre close to farm. Walk out the door and see farm animals and a lovely pond. 2 loft bedrooms with queen beds. Downstairs has a daybed. Kitchenette complete with fridge sink and cook stove. Outside bar area on one side and the other has a fire pit and hammock. So the WiFi iffy. . plenty of DVD’s!

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE FALL SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

2 Bedroom Flat: Downtown Boca Grande:#1

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!

Summer Sunsets just 50 steps to uncrowded beach

Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Green Bamboo - saltwater pool, great backyard.

Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Pool Home: Near the Beach

Come and relax at the perfect vacation getaway for your family in peaceful Englewood Florida. Only 12 minutes from Gulf beaches. Go out and explore the many amazing beaches, bays, lakes and rivers or lay back, relax and enjoy the beautiful private pool and dining on the lanai from your back door. Fully equipped kitchen for all your cooking needs: coffee maker, blender, and more. Clean, new home that will make you feel cozy and comfortable while on vacation.

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Private Hot Tub | King Bed Loft | Hammock Swings

🛜500mbps+ WiFi 🏠Fully private + Private entrance 🌴Hammock Swings ☀️ Outdoor Patio 🦩Private Hot Tub 🥑Kitchenette w/ electric hot plate 😴King Size Bed Loft 📚Work Desk 📺 55 inch Smart TV + Roku ❄️ Cold A/C 🚘 1 parking space NOTE: Accessing the bed requires climbing a ladder. While sturdy and secure, it may not be suitable for guests with mobility limitations, so please consider this before booking.