Beachfront vacation rentals in Little Gasparilla Island

4.91 out of 5 average rating, 270 reviews

A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guesthouse in Englewood

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.

4.9 out of 5 average rating, 120 reviews

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

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.

5 out of 5 average rating, 30 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!

4.79 out of 5 average rating, 127 reviews

An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.

Condo in Englewood

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.

A spacious dining area is set with a colorful tablecloth and comfortably accommodates multiple guests. The large windows offer unobstructed views of the ocean, allowing natural light to fill the room and creating a bright, inviting space.

4.95 out of 5 average rating, 42 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.

4.93 out of 5 average rating, 145 reviews

A view from the porch captures a vibrant sunset over the Gulf of Mexico, with silhouettes of palm trees and nearby buildings. The warm colors of the sky blend into the horizon, creating a serene backdrop that enhances the coastal atmosphere.

Condo in Englewood

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with 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 sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

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.

4.88 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!

4.88 out of 5 average rating, 195 reviews

Condo in Englewood

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.

4.75 out of 5 average rating, 106 reviews

A screened-in patio features a pool illuminated by soft lighting under a vibrant sunset. Lush palm trees provide a tropical backdrop, while a dining area is visible to the side. The pool deck includes a slide and is surrounded by a spacious enclosure.

Home in Cape Coral

Ultra Modern Pool home With Astroturf

Welcome to The Swangalow, where you’re royalty 👑 As soon as you step in, a crown magically appears on your head. Is this Cape Coral or did you just ascend to heaven? 😇 Take selfies with our custom accent wall, strut on our Astroturf (because dirt is for peasants, obviously), and enjoy the fact that CALORIES DON’T COUNT here. 🍕🍷but be warned, your friends... theyll be jealous of you!! Book now and let your inner celebrity run wild!

4.96 out of 5 average rating, 101 reviews

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

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.

5 out of 5 average rating, 8 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.