Holiday houses in Gasparilla Island

4.99 out of 5 average rating, 216 reviews

Home in Cape Coral

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!

4.88 out of 5 average rating, 139 reviews

Cottage in Englewood

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.

5 out of 5 average rating, 29 reviews

Salty Mermaid on Little Gasparilla Island/LGI

Charming beach house on Little Gasparilla Island (LGI) The Salty Mermaid offers a unique tropical paradise on a private barrier Island, with 7miles of undisturbed white sandy beaches. Embrace the old Florida island vibe. Enchanted island steeped in pirate lore, legend has it, the spanish pirate Jose Gaspar, nicknamed Gasparilla, made this beautiful island his secret base hideaway. Local legends whisper of buried treasures hidden beneath the islands sandy shores. Come get Salty!

5 out of 5 average rating, 39 reviews

Coconut Paradise POOL! Little Gasparilla Island

Just Ask!! Beach pics since storms. All cCleaned up! House is 100% and Beautiful! Relax with the whole family at this peaceful place to stay on Little Gasparilla Island! Newer Pool Home! Fast STARLINK Internet!! Heated pool/Hot tub. Private beach access and dock access. Boat Access only. Take the private water taxi across the bay to a true island paradise. Or bring your own boat! Boats must be 24’ of less. Over 50 coconut palms. Pool table, kayaks, house fully stocked!

Superhost

4.95 out of 5 average rating, 40 reviews

CocoHut

CocoHut has a private beach on a secluded barrier island; accessible only by boat to owners+guests. 2 vacant lots to the south & vegetation to the north, mean there is absolutely no overlook from neighbors. It’s THE ultimate spa for your soul! Look out onto the sea shimmering in the sun; commune with the clouds crossing a canvas of blue; soak in sunsets & gaze at a galaxy full of stars, free from light pollution. Choose 1 or all, just know you'll relax & refresh your body & soul.

5 out of 5 average rating, 23 reviews

Home in Englewood

Lux Home on Gulf w/Private POOL & 100ft 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 100 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!

4.98 out of 5 average rating, 48 reviews

Cottage in Placida

West Coast Island Retreat, Simply Adrift Cottage

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off FL'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.

4.9 out of 5 average rating, 31 reviews

Villa in Boca Grande

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.

Superhost

Condo in Englewood

4.88 out of 5 average rating, 190 reviews

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.

4.98 out of 5 average rating, 121 reviews

Loft in Boca Grande

The Loft on Park Ave--Boca Grande FL

We survived the old 1-2 of Huricaines, Helene and Milton and are ready to host you! A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

4.97 out of 5 average rating, 327 reviews

Island in Sarasota

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

4.76 out of 5 average rating, 34 reviews

3/2 LGI Gulf Front w/Dock

Gulf of America Beachfront Island Home is a perfect getaway! Enjoy the beach in your front yard and dock your boat on the bay! This three-bed, 2 bath gulf front home has an open floor plan with multiple dining areas both indoor and outdoor. Pocket sliders can be opened to extend the living space and hear the sound of the waves while you sip your morning coffee.

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Other great holiday rentals in Gasparilla Island

5 out of 5 average rating, 32 reviews

Home in Englewood

New house w/pool close to beach & mineral springs

NicolasRating, 5 stars2 weeks ago

This "home' was an absolute gem for our family retreat! We stayed for a few days with my mom and my in-laws, and the setup was truly perfect. The modern, clean space was ideal for families, offering a peaceful environment with a beautiful pool and stunning waterfront access. We highly recommend this place for anyone looking for a relaxing and enjoyable family getaway.

4.97 out of 5 average rating, 37 reviews

Home in Boca Grande

BG Beach House North Unit-Great Price & Location

MichelleRating, 5 stars6 months ago

Cute cozy house right across the street from the ocean! You can walk to the beach and shops! The house was comfy and extremely clean. Would definitely come back! Be prepared, though, with bug spray as the no-see-um little bugs were rampant (but that’s Florida for ya!). Fun trip!!

4.5 out of 5 average rating, 4 reviews

Sunset Beach House

EngelinaRating, 5 stars3 months ago

Paradise, beach was wonderful. Amazing views and sounds right on the beach. The island is recovering from the hurricane and all the people we met that live there were so friendly and helpful. Would definitely come back.

4.86 out of 5 average rating, 14 reviews

Home in Captiva

2/2 SandDollars, CLUB, Boat Slip

Haydee IsabelRating, 5 stars1 week ago

The host is fantastic, very responsive and very helpful. The place was very nice, clean and equipped with everything we needed, including beach chairs and floaties. It was walking distance to the beach. We will definitely be going back.

Cottage in Little Gasparilla Island

4.98 out of 5 average rating, 57 reviews

Happily Ever After

JuliaRating, 5 stars1 week ago

Michele’s place was the perfect place for my husband and myself. The house was very clean and comfortable. We brought our boat and rented Michele’s golf cart. Michele’s instructions for docking our boat and using the cart was helpful and precise. Michele was very flexible and gracious when we asked to arrive a day earlier. We very much enjoyed our stay and would absolutely stay again and recommend her place to others.

Cottage in Boca Grande

4.83 out of 5 average rating, 106 reviews

Charming beach cottage house with pool.

JosephRating, 5 stars3 months ago

This was the perfect place on Boca Grande for our family. A short walk from the beach and a quick gold cart ride to downtown. The cottage was very clean and having the pool access was a huge plus.

4.99 out of 5 average rating, 69 reviews

Home in Fort Myers

Modern City Loft in Downtown River District

AdamRating, 5 stars2 weeks ago

This was by far one of our favorite Airbnb’s. It was perfect for us (and our two dogs). And just as beautiful as the pictures! The Airbnb is very clean and organized. Everything we needed was provided. There were clear instructions written out, but if we had any questions, Loree responded quickly. We mostly hung out at the Airbnb, but walked into town, which was less than a 10 minute walk. We met Loree, who is one of the nicest people we have met. She went above and beyond to make sure everything was okay throughout our entire stay. Looking forward to going back and renting her Airbnb too!