Holiday houses in Gasparilla Island

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Top-rated holiday rentals in Gasparilla Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Don Pedro Island
4.94 out of 5 average rating, 16 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

Guest favourite
An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.
Bungalow in Englewood
4.83 out of 5 average rating, 120 reviews

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

Top Guest favourite
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.
Condo in Don Pedro Island
4.97 out of 5 average rating, 66 reviews

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

Top Guest favourite
Cottage in Don Pedro Island
4.99 out of 5 average rating, 77 reviews

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.

Top Guest favourite
An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.
Home in Englewood
5.0 out of 5 average rating, 65 reviews

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

Guest favourite
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.
Home in Don Pedro Island
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!

Top Guest favourite
Cottage in Don Pedro Island
4.99 out of 5 average rating, 73 reviews

Happily Ever After

Welcome to our treehouse!! Surrounding our home are wonderful sea grapes and palms. If you like privacy look no further. We are off the main path. We encourage our guests to unwind on our spacious screen porch with chairs, and tables. Be prepared for loads of sun and fun. Our rental includes all paper products, spices, plastic ware, toiletries, coffee, tea, all linens, beach chairs, noodle, sun screen, bug spray and GOLF CART available for RENT during your stay.

Guest favourite
The charming villa is framed by lush palm trees and vibrant greenery, with a private dock visible at the water's edge. A boat is moored nearby, and the sky is bright with scattered clouds, while the three-story structure exhibits a classic coastal design.
Villa in Boca Grande
4.88 out of 5 average rating, 42 reviews

Luxury Retreats at Boca Grande - Boca Bay Watch

Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

Top Guest favourite
Home in Don Pedro Island
5.0 out of 5 average rating, 8 reviews

little Gasparilla Island Beach house-Dog friendly

Escape to Beach Hair Don’t Care on Little Gasparilla Island! This cozy 2BR, 2BA retreat sleeps 5 and is just steps from the bay and 100 yards from a private beach. Enjoy uncrowded beaches, fishing, wildlife, and water sports. Pet-friendly with a fully stocked kitchen, beach gear, boat slip, and golf cart access. Experience the serenity of this car-free island paradise, perfect for relaxing, unwinding, and making memories. Book your escape today!

Top Guest favourite
Condo in Boca Grande
5.0 out of 5 average rating, 13 reviews

ArtSea Beachfront Remodeled Pool Old Florida

Welcome to ArtSea -- a beautifully remodeled beachfront condo on Gasparilla Island's Gulf shore. where Old Florida lives on in the best possible way. Step outside your door and you're on the sand: a wide shell-strewn beach where the Gulf of America stretches out in front of you and the sky ignites with color every evening at sunset. Tis is Boca Grande--unhurried, authentic, and unlike anything else on Florida's Gulf Coast.

Guest favourite
A spacious living area is highlighted by a comfortable blue sofa and a glass-top coffee table, resting on a soft area rug. Exposed timber beams and stylish light fixtures create a warm ambiance. A spiral staircase leads to the upper level, while a modern kitchen is visible in the background.
Loft in Boca Grande
4.98 out of 5 average rating, 144 reviews

Beach Loft · King Bed · Adults Only · Boca Grande

A timber-framed loft in the heart of Boca Grande village — king bed up the spiral staircase, village views from above, and everything within walking distance. Adults only: this is the couples retreat in the portfolio. Beach: 120 steps. The Temp: across the street. Hudson's Market: half a block. Golf carts from Gasparilla Adventures — 10% off with your reservation.

Top Guest favourite
Home in Don Pedro Island
5.0 out of 5 average rating, 24 reviews

"Salt of the Sea" - beachfront and pet friendly!

Experience the ultimate escape at "Salt of the Sea," a charming 1 bedroom/ 1 bathroom beachfront cottage located on the serene Little Gasparilla Island, a unique bridge-less barrier island. Here, you'll find no stores, no restaurants, no bars, and no cars – just pure relaxation and a chance to unplug from the hustle and bustle of everyday life.

Popular amenities for Gasparilla Island holiday rentals

Frequently Asked Questions

  • Where is Gasparilla Island located?

    Gasparilla Island lies along Florida's southwest Gulf Coast, nestled between Charlotte Harbor and the Gulf of Mexico. The island has vibrant local neighborhoods and waterfront areas with easy access to beaches.

  • When is the best time to visit Gasparilla Island?

    Spring and fall are frequently suggested for their pleasant temperatures, ranging from 59 to 86°F (15–30°C), and lighter rainfall. Many travelers come during these seasons to explore outdoor activities and enjoy milder weather.

  • What are some things to do near Gasparilla Island?

    Gasparilla Island has sandy beaches, wildlife viewing spots, and traditional fishing opportunities. Visitors often explore local shops, galleries, and parks around the island’s lively center.

  • How is the weather near Gasparilla Island?

    Gasparilla Island experiences warm, humid summers, often reaching 90°F (32°C), and mild winters around 49–74°F (10–23°C). Rainfall peaks in summer months, so visitors sometimes pack lightweight layers and rain gear for outdoor activities.