Beachfront vacation rentals in Little Gasparilla Island

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Little Gasparilla Island

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Guest favorite

Condo in Englewood

5 out of 5 average rating, 24 reviews

Gorgeous Direct Beachfront 2/2 Condo with Pool

Newly renovated direct beachfront 2 bdrm/2 bath unit at the the ever popular Boardwalk. Stylish and updated with higher end furnishings, you will love this oceanfront unit with three balconies! Chef's kitchen w/induction range, w/d in unit, fully equipped for your beach getaway. Walk to restaurants/nightlife of Englewood Beach, 5-10 minute drive to major shopping areas and historic Dearborn St. 85 paces to the beach, tiki grill area, fire pit and heated pool! 7 day minimum stay. Paradise awaits!

Guest favorite

Home in Englewood

5 out of 5 average rating, 26 reviews

Vacation Condo- Beach Access!

DIRECT GULF FRONT, SPECTACULAR VIEWS, ONLY STEPS TO THE BEACH! Enjoy the Gulf Coast lifestyle with direct beach access. Manasota Key is famous for its old Florida charm, and relaxed, comfortable pace. This meticulously maintained, second-floor residence has been updated with a contemporary, coastal feel. Relax on your private balcony with views of dolphin, manatee, plus the seasonal turtle nesting and tarpon run. Lounge by the heated pool or walk to local shops, restaurants, and seafood market!

Guest favorite

Rental unit in Boca Grande

4.9 out of 5 average rating, 194 reviews

Downtown Boca Grande Efficiency Flat#3

We survived Ian and are ready to host you! A great efficiency, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Located across the street from The Temp Restaurant, down the block from Hudson's Market and around the corner from Sister's Pizza. Going to the beach, no worries, it is just down the road. Rent our place through Air BnB and receive a 10% discount on golf cart and bike rentals. You’ll love my place because of the location, and the neighborhood.

Superhost

Rental unit in Sarasota

5 out of 5 average rating, 4 reviews

Just Dune Our Thing Beach Front 2/2, Siesta Key

**Jan-April is a one month minimum stay per HOA*This BEAUTIFUL 2 bed/ 2 bath beach front is located on Siesta Key. Enjoy your morning coffee from the balcony with a direct ocean view. The unit comes with a small cabana stocked with beach chairs, buggy and fridge to keep your beverages cold! After the beach take a dip in the heated pool and enjoy the sun. A free trolly runs morning to night and will take you to all your favorite Siesta Key Local bars, restaurants, and shops up and down the key!

Superhost

Guesthouse in Englewood

4.91 out of 5 average rating, 249 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

Home in Captiva

4.97 out of 5 average rating, 115 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Guest favorite

Cottage in Englewood

4.93 out of 5 average rating, 82 reviews

Luxury Beach Resort Style Cottage

Escape to our 1-bed beachfront cottage, steps from a serene shoreline. Enjoy private beach access, an outdoor shower, and lush surroundings for a secluded paradise. Walk to local spots, indulge in watersports, and unwind in nightlife nearby. Clean and well-equipped, our cottage offers comfort with beach gear, and a private path to the beach. Experience a honeymoon-worthy stay with a spacious bathroom and seamless amenities. It's a worry-free escape. A getaway that goes beyond the ordinary.

Superhost

Condo in Englewood

4.78 out of 5 average rating, 111 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

Condo in Englewood

4.95 out of 5 average rating, 129 reviews

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.

Guest favorite

Condo in Venice

4.93 out of 5 average rating, 54 reviews

Beachfront Venice Villas 1-bed Condo

Great location! Beautiful Beachfront Condo conveniently located on the private Venice Beach, only one mile away from historic downtown, shops and restaurants. Key-less entry enables check-in/check-out without person-to-person contact. This property is heaven for beach-lovers or someone interested in fishing, shark teeth hunting, snorkeling or swimming. No stairs, no lobby, just walk outside the door to enjoy less crowded private Venice Beach or a swimming pool.

Guest favorite

Condo in Englewood

4.89 out of 5 average rating, 178 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

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.