Beachfront vacation rentals in Little Gasparilla Island

Find and book unique beachfront homes on Airbnb

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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Superhost

A light blue two-story beach cottage features a spacious front deck with two umbrellas and outdoor seating. The lower level includes a concrete driveway leading to two garage doors. Lush greenery and palm trees surround the property, providing a tropical ambiance.

Cottage in Englewood

4.85 out of 5 average rating, 110 reviews

Free Kayaks/bikes/walk to beach/pet friendly #3

"Perfect for family / friends/pets, who want to escape the stress into paradise on Manasota Key. One block from beach. 1 bed 1 bath beach cottage 1st floor has great spaces, queen size bed and aqueen sofa bed, full kitchen, private lanai, electric grill/ garage/laundry area/free bikes/kayaks/ that you can enjoy at the beach or the bay. Great restaurants/bars/trails and much more just walking distance from the house. Beach toy, chairs/umbrellas/snorkeling gear included. Just come relax and enjoy.

Guest favorite

A pathway lined with tiles leads to a sandy beach, framed by lush greenery and flowering plants. A seating area with a fire pit is visible, accompanied by a wicker chair. The serene ocean can be seen in the distance under a clear sky.

Home in Englewood

5 out of 5 average rating, 34 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Located right on the Gulf, our renovated beach cottage is equipped with everything you need for a relaxing getaway. With private beach access and outdoor dining area, take in the views and enjoy with your family, friends or a solo trip to reset with a little R&R. This 2-bedroom, 2-bath bungalow has all the accoutrements for your a home-away-from-home, complete with beach chairs, boogie boards, beach games and of course, sun tan lotion. Come for some fun in the sun, your beachfront oasis awaits!

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

Aerial view of a coastal property featuring palm trees and a paved path leading to the beach. The image shows multiple buildings, parking spaces, and a glimpse of the ocean in the background, enhancing the beachside environment.

Condo in Englewood

4.79 out of 5 average rating, 117 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 exterior of the building showcases a modern design with outdoor seating areas illuminated by string lights. Tropical plants enhance the inviting atmosphere, while palm trees are seen in the background. Stairs lead to the entrance of the flats, creating easy access.

Apartment in Boca Grande

4.91 out of 5 average rating, 208 reviews

Downtown Boca Grande Flat#3

We beat the old 1-2 of Huricaines Helene and Milton and are ready to host you. This is a great, renovatred , one bath flat, in the heart of Boca Grande on the gorgeous Gasparilla Island. Located across the street from The Temp Rest. Going to the beach, no worries, it is just down the road. Please note: there is a small fridge and coffee maker in this flat, but no other cooking facilities. Rent our place through Air BnB and receive a 10% discount on golf cart and bike rentals.

Superhost

An aerial view captures a coastal condo complex nestled along a sandy beach. The vibrant turquoise waters of the Gulf of Mexico meet the shore, framed by lush greenery and winding pathways. Nearby structures feature a blend of nature and architecture, embodying a serene coastal lifestyle.

Condo in Englewood

4.93 out of 5 average rating, 134 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.

Superhost

Bungalow in Nokomis

4.86 out of 5 average rating, 7 reviews

Retro Reef! Walk to Beach, Boats +Restaurants!

Welcome to The Retro Reef! 🎙️🪸 📍Unbeatable location - directly across the street from the intercoastal waterway & Pop’s Sunset Grill & Pelican Alley. ☀️🌊You’ll just be 1,000 feet from the pristine Gulf of Mexico beaches, and across the street from boat & jet ski rentals, offering endless opportunities for relaxation and fun! 🌴 One of the original homes in the area, this duplex shows off its Florida roots with genuine terrazzo flooring, and unique detail.

Superhost

Condo in Englewood

4.89 out of 5 average rating, 186 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.

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 323 reviews

NEW MAY SALE 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

Home in Captiva

4.83 out of 5 average rating, 12 reviews

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

Discover the allure of Beach Paradise, a brand-new listing boasting unparalleled luxury. This recently furnished 4-bedroom rental property rests directly on the pristine Gulf of Mexico shores, nestled amidst lush tropical surroundings adorned with swaying coconut palms and pristine white sands adorned with exquisite seashells.

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What guests are saying

Bay view and possible two family rental!

5 out of 5 average rating, 8 reviews3 weeks ago

we had a wonderful time at Robert's place. Everything was as described. the island is a perfect getaway for anyone that wants to go on an adventure and get away from the hustle and bustle. The kitchen had everything you would need to cook, it was perfect! Everything was well thought of in this home. On a side note, golf carts need to be booked months in advance and are pretty pricey and we hoped to walk around the island but we're told upon checkin that was not allowed. we could only go to the beach and back to the property. You could walk along the beach though.

Home in Placida

What guests are saying

Private Waterfront 2 Bedroom Condo

5 out of 5 average rating, 23 reviews2 weeks ago

My daughters & I stayed in Nokomis for a spring break beach trip. Dan's place was exactly as described in the listing. The entire place was clean and tastefully decorated. It had everything we needed for our stay. We used the paddle boards and kayaks during our stay, as well as the beach chairs & umbrella. It was so nice to have everything for the beach available for us to borrow. Nokomis Beach is only a few minutes from the condo. We enjoyed several short trips to Venice for restaurants and coffee shops. Dan responded quickly to any questions I sent. We had an excellent stay at Dan's and would definitely stay there again!

Condo in Nokomis

What guests are saying

STUNNING 3/2 beach+pool property! 2 kings/2 bunks!

4.95 out of 5 average rating, 98 reviews9 months ago

We loved staying here especially having the beach just a few feet away! Although there was construction taking place in the development, it did not interfere with our stay at all! We didn’t even notice the workers on site. If you get a chance to book this home, do it. April is an amazing host and has thought of every amenity possible! We look forward to booking again soon!

Villa in Englewood

What guests are saying

Casita Salida del Sol-Waterfront

5 out of 5 average rating, 10 reviews1 week ago

My family and I enjoyed our stay at Casita Salida Del Sol very much! The condo was clean, comfortable, and nicely updated and decorated. The hosts were very responsive and accommodating before and during our stay, and the property manager was very helpful as well. We had everything we needed to feel right at home in the townhouse. It is located right next to the marina which was convenient, and fun to watch the ferry come and go throughout the day. The deck faces the east which is perfect for watching the sunrise. We saw dolphins from the deck one day. We enjoyed the kayaks, bikes, sand toys, and of course used the golf cart daily. We hated to leave and would definitely stay here again!

Townhouse in Captiva

What guests are saying

"Pelican" Beaches, Bikes & Beautiful Sunsets!

4.77 out of 5 average rating, 66 reviews2 weeks ago

loved this little place close to the beach. It was perfect for our spring break get away. the beach was close, the heated pool was definitely a favorite. there was plenty of room for our whole group to have their own space and great common area. kitchen was well stocked with all pots, pans, utensils exc that you would need to cook your own food. the only negative thing in can say is the bikes all need a little work.

Vacation home in Nokomis

What guests are saying

Manasota Key to Relaxation

5 out of 5 average rating, 9 reviews1 month ago

Linda’s home was truly a gem! So peaceful and relaxing! The ocean is literally steps away, with sunsets, swimming, sand, shells and shark’s teeth to hunt all day long!! We had everything we needed to feel at home, and more! Manasota Key was amazing and Linda’s home was a perfect location for our family’s get away!

Home in Englewood

What guests are saying

Quaint Surf Cottage on Beach - Hurricane Milton!

4.9 out of 5 average rating, 30 reviews6 months ago

Dear Jeff Thanks for hosting us. Even though the hurrican helene hit this area so hard, you made us feel safe and at home! We enjoyed the lonely beach walks and collecting sea shells. The neighbourhood is extremely friendly. Especially Matt and Peppy. They were always there for a nice chat or a helping hand (our car ran out of battery). We enjoyed every second of our stay! Thanks so much for everything and we hope to come back one day, or maybe you visit us in switzerland :) Greeting Florian & Sina

Home in Englewood