Family-friendly holiday rentals in Don Pedro Island

A private swimming pool is surrounded by lush tropical foliage and colorful flowering plants. A decorative fish sculpture adds a whimsical touch, while comfortable seating is visible in the background beneath palm fronds.

5.0 out of 5 average rating, 18 reviews

Paradise Cottage Island Oasis

An enchanting, GROUND LEVEL tropical Palm Island paradise that delivers the epitome of off the grid, private island living. 7 minute walk to sugar sand beaches offering buckets of seashells, shark’s teeth & award winning sunsets! Return home to your private, swimming pool surrounded by mature, tropical foliage that has the look and feel of a Caribbean resort. Follow the winding path that leads to the harbor with dock: toss a line, boat to no bridges out to GOM, launch kayaks, take in nature!

FamilyKitchenHospitality

4.92 out of 5 average rating, 24 reviews

Sunset Beach House

This beautiful beachfront house is located on Little Gasparilla Island with three-bedroom/two-baths. It is tucked away, just off the main drag of this quiet, “off the beaten path” island. Escape your busy life on the mainland and enjoy outdoor living space with amazing 180-degree views of the Gulf of Mexico. Enjoy your private beach path and shared dock, which is perfect for fishing! You can catch your dinner and come back to the house and grill it on deck while watching a breath-taking sunset.

KitchenFamilyWi-Fi

4.94 out of 5 average rating, 17 reviews

Modern Island Oasis: steps2beach

🏝️Island fun + luxury🥂living = the perfect getaway! 👣 Just steps to the beach & the bay/dock 🦋 High-end fixtures & fittings: -Custom LED lighting modes -Stunning kitchen -Stylish tile floor -Gorgeous granite counter tops -Micromesh screened balcony: 100% bug free 🏠 The most luxurious home on LGI 🏓 Packed with toys+games 🛝THIS is your Paradise Playground 🥇 Guest Favorite: Rated Top 5% 🙋 For those who want to max out on fun, in luxury, style & comfort… 🎯 Look no further: this is the #1

KitchenFamilyHospitality

4.95 out of 5 average rating, 37 reviews

Home in Placida

Seaside Boca (Pool + Sauna + Mini Golf + Spa)

As seen on TV fun for the whole family at this new Airbnb. With its Key West vibes you’ll be sure to have a great time here! Boca Grande is just minutes away, Publix and shopping center are a short bike ride and boats are welcome as the marina is right next door. House is located in the tranquil area of Cape Haze close to Golf courses where you can stroll or bike to you hearts content. We just added a Game Room, a Pool with jacuzzi, Sauna, plus a multi court and Mini Golf (pics jus refreshed)

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Condo in Don Pedro Island

An aerial view captures the Tropical Island Getaway, showcasing structures with teal roofs nestled among lush greenery. A pool is visible on the left, while the coastline stretches in the background, revealing sandy shores and the serene blue Gulf waters.

Island Getaway Pool-Ferry-Grocery Delivery Incl.

10-minute passenger ferry ride to this boat-access-only, car-free island Locally Owned & Operated Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Uncrowded shelled beach with Birds, Dolphin and Manatee -Venture out for Prime Fishing & Kayaking SWFlorida has to Offer There are no grocery stores or restaurants on the island, plan to bring everything you’ll need with you

Indoor spacesFamilyAccuracy

4.97 out of 5 average rating, 66 reviews

4.93 out of 5 average rating, 15 reviews

Dolphin Watch | Beachfront on private Beach

Dolphin Watch Welcome to Dolphin Watch, an exquisite beachfront villa located in the serene Cape Haze, Florida. This stunning five-bedroom property offers breathtaking ocean views and is designed for unforgettable beach vacations. Spanning over 3,461 square feet, Dolphin Watch comfortably accommodates up to 10 guests, making it perfect for families or groups seeking relaxation and adventure. The villa features four well-appointed bathrooms, ensuring convenience and privacy for all.

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Cottage in Don Pedro Island

Island Getaway, Beach House, Dock, Pet Friendly

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off Florida’s West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

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4.99 out of 5 average rating, 79 reviews

The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.

4.9 out of 5 average rating, 30 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

Welcome to the most secluded spot on Little Gasparilla Island! Our Beach Cottage property is on the beach with all-natural surroundings: a state park, a mangrove lagoon, and the Gulf of Mexico. It boasts front views of the water and gorgeous island sunsets year-round. You'll have boat space on our private dock and amenities including kayaks, paddle boards, an outdoor bayside dining area, coffee bar with complimentary coffee, private grilling area, fire pit, and much more!

FamilyKitchenAccess

4.99 out of 5 average rating, 143 reviews

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

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4.96 out of 5 average rating, 101 reviews

A serene beach scene showcases gentle waves lapping at a sandy shore. Lush greenery is visible along the coastline, with a residential property nestled among the trees. The clear blue sky complements the tranquil waters, creating a peaceful environment.

Home in Englewood

Welcome to one of Florida’s best hidden gems! A beautiful beach home with private beach access, a butterfly garden and a game room. Enjoy a dream stay by the sea in one of most beautiful Keys in Florida.

Relax with the whole family at this peaceful place to stay.Our home offers you at-home comfort for up to 8 people. Large spacious bedrooms, a fully equipped kitchen with breakfast bar, and multiple patios and balconies to enjoy. For winding down after a long day, spend some quality family time in our game room. Your little ones can pretend to grill up some burgers while mom and dad play a round of ping pong or get the whole family together for some board games!

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A spacious living area is filled with natural light, featuring a large sectional couch adorned with orange accent pillows. A modern kitchen is visible in the background, equipped with stainless steel appliances and a dining area with wooden chairs and a table. Soft lighting illuminates the space.

5.0 out of 5 average rating, 36 reviews

Island Escape • Deep Water Dock • Quiet Beaches

Escape to Coastal Sol, a newly built 3-bedroom, 2.5-bath retreat on peaceful Don Pedro–Knight–Palm Island. A short 5-minute car ferry brings you to this bridgeless barrier island, where seven miles of uncrowded Gulf beaches, warm coastal breezes and spectacular sunsets await. Enjoy nearby deep-water dock access for boating and fishing, explore the island by golf cart or bike, and experience the laid-back Old Florida charm that makes Palm Island so special.

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