Beachfront vacation rentals in Little Gasparilla Island

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Top-rated beachfront rentals in Little Gasparilla Island

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

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Guest favorite

Guesthouse in Englewood

4.91 out of 5 average rating, 274 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Guest favorite

A bright bedroom features a spacious bed adorned with decorative pillows. Large windows allow natural light to flood the room, offering views of the outdoors. Two modern lamps flank the bed and a flat-screen television is mounted on the wall opposite.

Home in Manasota Key

5 out of 5 average rating, 43 reviews

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

Guest favorite

The exterior of a Bahamian-style condo is visible, featuring a multi-level structure with a pitched roof. A wide porch extends from the upper floor, surrounded by greenery and palm trees, creating an inviting atmosphere. The sandy pathway leading to the beach is seen below.

Condo in Englewood

4.93 out of 5 average rating, 150 reviews

Gulf Side Condo Englewood Florida

Monthly bookings will receive a 15% discount at this cozy 2 bed 2 bath condo. The condo has 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 Gulf breezes and sunsets from the porch or the beach.

Top guest favorite

Home

4.9 out of 5 average rating, 121 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Top guest favorite

A charming beach house is nestled among lush greenery, with palm fronds and shrubs surrounding the property. The light-colored exterior and numerous windows reflect the inviting atmosphere. A wooden post with a decorative feature stands in the foreground, enhancing the rustic appeal of the setting.

Home in Placida

5 out of 5 average rating, 35 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 7 miles 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!

Superhost

A view showcases a lush green pathway leading to the sandy beach, bordered by low shrubbery. The calm turquoise waters stretch into the horizon under a lightly clouded sky, with beachgoers visible in the distance, emphasizing a serene coastal atmosphere.

Condo in Englewood

4.77 out of 5 average rating, 132 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY LOCAL RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with pool access. Complimentary grill for your dinner paired with an amazing Gulf sunset. Your morning coffee is on us! Beach chairs & towels supplied. Kitchen is updated and all utensils supplied. Master Bedroom has a queen sized bed. Boat dock slip available upon request. HEATED POOL located directly across the street.

Guest favorite

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 Placida

4.88 out of 5 average rating, 26 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!

Guest favorite

Home in Fort Myers

4.84 out of 5 average rating, 179 reviews

Blue Beach Bungalow

3 large bedrooms (3 king sized beds) with TV in everyroom, plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics,

Guest favorite

Condo in Englewood

4.89 out of 5 average rating, 201 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.

Guest favorite

An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.

Condo in Venice

4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

Soak up the Florida sunshine on Golden Beach which is mere steps away from your front door! This mid-century vacation villa, located on Venice Island, is yours to unwind and relax in and is within minutes of additional beaches, historic Venice, a fishing pier and multiple restaurants. This single-level unit offers the ocean within steps of the unit and also offers a community pool.

Top guest favorite

A spacious screened porch features comfortable seating arrangements with a wooden table at the center. Inviting ocean views are visible through the mesh screens, alongside swaying palms. Decorative throw pillows enhance the cozy feel, and soft lighting is provided by string lights overhead.

Home in Placida

5 out of 5 average rating, 9 reviews

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

Brand New to the Rental Market! 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.

Guest favorite

A wooden pathway leads through lush greenery to a sandy beach. The gentle ocean waves are visible in the distance under a partly cloudy sky. Colorful paddleboards and kayaking equipment are positioned along the shoreline, inviting outdoor activities.

Island in Sarasota

4.97 out of 5 average rating, 334 reviews

RARE Sept SALE! OPEN! 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!