Gasparilla Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Gasparilla Island vacation rentals

Gasparilla Island beachfront vacation rentals

Guest favorite
Villa in Sarasota
4.96 out of 5 average rating, 165 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

LindsayRating, 5 stars5 months ago
The place was beautiful, clean and had everything you want when you’re in Florida: Strong AC, beach chairs, umbrellas, a cooler, etc AND it’s super close to a nice beach and pool! It’s also close to great coffee shops, ice cream places and cool local bars. Would recommend this to anyone! If you’re arriving late at night it’s easy to miss your turn so just be on the lookout. Thank you for the amazing stay!!
Guest favorite
Condo in Englewood
4.95 out of 5 average rating, 109 reviews

Sunset Beach

MichelleRating, 5 stars3 months ago
The location has a perfect beachfront view to enjoy coffee outside in the morning. The area was still recovering from the hurricane but walking on the beach was still enjoyable. All of the amenities and items available for use in the condo left very little to be needed.
Superhost
Condo in Sarasota
4.77 out of 5 average rating, 22 reviews

Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach

KhrystynaRating, 5 stars7 months ago
We are very pleased with the rest, the apartments are wonderful all that is needed for rest, we found there😊
Guest favorite
Condo in Siesta Key
4.93 out of 5 average rating, 115 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

MarcyRating, 5 stars1 month ago
Amy is an excellent host! I had a fantastic weekend at the beach. Amy is a very responsive and helpful host. I look forward to returning soon.
Superhost
Home in Fort Myers Beach
4.83 out of 5 average rating, 12 reviews

Lone Palm Retreat is a beachfront home

TeresaRating, 5 stars2 months ago
The location was fantastic, very private and perfect for families with kids. When we arrived, I was initially a bit disappointed to discover a second rental space upstairs, I must have missed that upon booking but fortunately, it remained unoccupied throughout our stay. The views were stunning, and the convenience of being within walking distance of a grocery store and restaurants was a major plus. I highly recommend this place to anyone looking for a relaxing beach getaway. Hoping to return soon!
Superhost
Condo in Captiva
4.79 out of 5 average rating, 71 reviews

Ultra Luxe Beach Villa at South Seas Resort

GabeRating, 5 stars4 weeks ago
Fantastic stay. Great location just inside the South Seas complex, walkable to Starbucks and the Island Provisions store. Beachfront, ocean view with plenty of beach gear provided in the accompanying locker. The condo was nicely appointed, newly updated with comfortable bedding and was clean. Pictures accurately reflect the unit. The unit is one level up and the building has an elevator. 100% would stay again. Several places on Captiva remain closed, but there was plenty open to keep us fed and entertained (Jan 2025).
Superhost
Condo in Sarasota
5 out of 5 average rating, 4 reviews

Beachfront Condo on Famous Siesta Key!

JenRating, 5 stars8 months ago
Been to Siesta several times and this by far was the best location. Very clean, and the view was 100% the greatest to wake up to. We def will return next year, if not sooner. Thanks for sharing your piece of paradise with us.
Guest favorite
Vacation home in Englewood
4.92 out of 5 average rating, 38 reviews

Ocean view, Totally remodeled, Beach Home!

MaggieRating, 5 stars1 month ago
This house was perfect for our family and our needs. Loved having the main living area on the 2nd floor so we could enjoy the view of the water even when the weather wasn’t great (late Dec/early Jan). The hot tub was awesome and got a ton of use! The hurricane really had a huge impact on the area, so when we were there there was a lot of construction and desolation around, but this house was rehabbed beautifully. The outdoor shower was really cool and the beds were super comfy. We had everything we needed! Quick notes: No dishwasher so we also used paper plates sometimes but they do have plenty of dishes; Because of the storm, some of the local restaurants are still closed. It’s a very residential area, which we loved. Overall we didn’t really mind because it truly excused us to do nothing but chill. The neighborhood is quiet and walkable if you don’t want to walk the beach.

Gasparilla Island house rentals

Guest favorite
Home in Cape Coral
4.87 out of 5 average rating, 149 reviews

LUXURIOUS LARGE OPEN OCEAN BLUE POOL VACATION HOME

IvyRating, 5 stars3 weeks ago
This home and location was perfect for us! Peaceful, beautiful, a private back yard, and a great neighborhood-yet grocery stores and restaurants just around the corner. We loved the screened in pool and outdoor area! There were a lot of special touches put into the house that made us feel special!
Guest favorite
Home in Sarasota
4.96 out of 5 average rating, 57 reviews

2223 Doud Street, Sarasota, FL

JoanRating, 5 stars4 months ago
Great location for accessing a wide range of local services & amenities. Very comfortable home which suited our family very well. The warm pool was great. Lovely & quiet despite being just off a main road. We had a great holiday in Sarasota despite the recent hurricanes. Thanks!!
Guest favorite
Home in Bonita Springs
4.93 out of 5 average rating, 140 reviews

Pool house near Hyatt Regency Coconut Point

KerryRating, 5 stars7 months ago
Thank you, Henrieta! We had a great stay & definitely plan to return. Our host is welcoming, friendly & provided us with everything we could have needed or wanted.
Guest favorite
Home in North Port
4.79 out of 5 average rating, 151 reviews

3 bdrm Pool Home / Quiet Cul De Sac

GerardRating, 5 stars1 month ago
this place is nice and quiet,every thing is perfect I highly recommend it
Superhost
Home in Cape Coral
4.88 out of 5 average rating, 32 reviews

Blue Abaco - Beautiful Waterfront House

RachelRating, 5 stars7 months ago
Perfect time at Blue Abaco! Lovely villa, clean and comfortable, with everything you could need - real home away from home. Plenty space for our family of 4. Everyone enjoyed pool overlooking waterway! Vesteva Vacation Rentals great with communication too. Within easy driving distance - 5 mins- of local shops/restaurants. So could comfortably walk to shops too. Only short drive to Cape Coral Water Park - about 10 mins and about 20/30 minute drive to lovely Fort Myers beach. Located in quiet neighbourhood so really relaxing. Would highly recommend and would certainly do a return visit
Superhost
Home in Lehigh Acres
4.83 out of 5 average rating, 129 reviews

LIVING in PARADISE 🌴 ⛱️ 😎

SherriRating, 5 stars4 weeks ago
Dario’s place was nice. Very quiet neighborhood with nice neighbors. During the week we had a couple issues, one with the pool heater not turned on and one with the tv, but both times Dario was super quick to respond and had someone out right away to fix any issues! He is a super nervous very guy!!
Superhost
Home in Cape Coral
5 out of 5 average rating, 3 reviews

Cape Cottage

KimRating, 5 stars2 months ago
Should the need arise again we would definitely stay at Angel's place.
Guest favorite
Home in Port Charlotte
4.91 out of 5 average rating, 35 reviews

Charming home near the Beach and Punta Gorda.

TeresaRating, 5 stars3 weeks ago
It was a lovely stay, we really enjoyed ourselves. Thank you, Angel for everything.. He responded quickly to questions that we had.. The last night I locked myself out of the house and he was very helpful and calling us back to get in the house. Thanks Teresa Smith

Beachfront house rentals in Gasparilla Island

Superhost
Home in Placida
4.72 out of 5 average rating, 29 reviews

3/2 LGI Gulf Front w/Dock

CourtneyRating, 5 stars7 months ago
The house was fantastic! So peaceful and tranquil… the house was stocked with trowels and kitchen accoutrements and condiments . Her suggestions of golf cart service and grocery delivery were spot on with the nicest, friendliest people ever. The peaceful atmosphere was so welcoming and wonderful. Can’t imagine a more beautiful vacation spot. Hurricane Debby ousted us early but and act of God can’t be helped!!! I’d go back tomorrow!!!!! Thank you Amber for letting us gather in your home!!!! Love love love
Guest favorite
Home in Manasota Key
5 out of 5 average rating, 28 reviews

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

JerryRating, 5 stars2 weeks ago
What a great property! Chris and Kaylyn thought of everything and what a great location on Manasota Key. While there are still signs of damage from Hurricane Milton in the area, you wouldn’t know while in the house. Great amenities and location for the beach, dining or just relaxing at a great house. The beach was just a few steps away and is coming back! We’ll be back as this is our favorite place to get away from Wisconsin winters!
Guest favorite
Home in Boca Grande
4.95 out of 5 average rating, 65 reviews

Perfect Beach House Excellent Location

ShannonRating, 5 stars1 month ago
It was the perfect spot for a family wedding. The house exceeded every one of our expectations and the owner was a dream to work with.
Superhost
Home in Captiva
4.71 out of 5 average rating, 112 reviews

Beachfront home with stunning views

AnaRating, 5 stars6 months ago
House’s location is perfect. The house needs some updates but very functional. The kitchen has everything you need to cook meals. Plenty of towels, bed sheets and games. Paul was awesome answering all our questions. We really enjoyed the Island lifestyle. Exploring on the golf cart, having ice cream at the Shop. My family had a blast at the beach and watching the amazing sunsets!!!! Definitely coming back!!!
Superhost
Home in Bonita Springs
4.78 out of 5 average rating, 36 reviews

Modern Direct Beachfront | 3-Bedroom & 2.5 Bath

KathleenRating, 5 stars3 months ago
This was everything we had hoped for and more. A gorgeous beachfront home with spectacular ocean views! The pictures are exactly what it looks like in person. We stayed a week and ended it on my birthday. Strolls along the long shoreline, pelicans flying by, dolphins swimming right out front, morning runs with beautiful sunrises and of course some of the most amazing sunsets! The property manager, Arlan, was on it and made sure we were well taken care of. We even met the owner who came by a couple of times to meet some workers. Also, Very nice and courteous! We really enjoyed our stay and hope to return again soon! Thank you! Trehern family
Guest favorite
Home in Cape Coral
4.93 out of 5 average rating, 14 reviews

Dolphin Shores Beach House

MattRating, 5 stars2 months ago
The house is in a great location as it’s very walkable to the Cape Coral beach. The house is also well stocked with plates, pots, glasses as well lots of beach chairs and toys for the kids. Overall A+
Superhost
Home in Fort Myers
4.84 out of 5 average rating, 155 reviews

Blue Beach Bungalow

CliffRating, 5 stars2 weeks ago
Andy's place was clean and tidy. The pool is very nice and the lounge chairs, fire pit and sand outside is amazing.
Guest favorite
Home in Bonita Springs
5 out of 5 average rating, 7 reviews

Bonita Breeze Retreat - 1 minute walk to the Beach

BarronRating, 5 stars2 months ago
We stayed at Crissy’s place over Christmas with our two little kids (1 and 3 years old) and it was fantastic. The place was clean, with nice furniture, a great aesthetic, and a good use of space. Crissy had stocked the place thoughtfully with everything from great beach gear to kitchen gadgets to games. Crissy even setup a Christmas tree because she knew we were bringing young children (which really brought the place together for the holidays). The location was great with a 3-4 minute walk to the beach and a 10-15 minute walk (all side walk) to a popular beach restaurant / bar / breakfast spot / jet ski rental place named Doc’s. There are only a few beach access points along Bonita Beach and Crissy’s property is right next to one of them. Highly recommended and would absolutely stay again.

Your guide to Gasparilla Island

All About Gasparilla Island

Aquamarine waters, endless stretches of white-sand beaches, and palm-lined walking paths adorn this barrier island in the waters of southwest Florida’s Gulf Coast. Gasparilla Island functioned as a fishing village for much of its history, and today is also a popular wintering destination among a certain celebrity set. Along Gasparilla Island’s waterfront, golf carts zip up and down the coast, and you’ll find bohemian cafes, fresh seafood restaurants, and a shopping complex inside a converted 20th-century train station.

A gateway to Gasparilla Sound and Charlotte Harbor, Gasparilla Island is renowned for its world-class tarpon fishing, easy access to surrounding nature reserves, and a continuous seven-mile stretch of pristine beach. Swimming, kayaking, and hiking through the region’s mangrove forests are some of the region’s more popular activities. Visiting the area’s historic lighthouses and enjoying sunset picnics on the beach are among the many memorable experiences you can enjoy here.


The best time to stay in a vacation rental in Gasparilla Island

Gasparilla Island’s sunny Gulf Coast climate bestows it with pleasant year-round conditions — sunlit days, clear blue skies, and breezy afternoons among the miles of palm-lined beaches. Temperatures vary between the summer and winter months somewhat, but they tend not to drop below uncomfortable levels for swimming or other ocean-bound recreation. Rainfall tends to increase towards the latter half of summer with the arrival of hurricane season, though visitors can still be found in the area during this time. The shoulder season’s warmer temperatures, lack of accompanying rainfall, and myriad events in the surrounding communities make this an excellent time to look for vacation rentals on Gasparilla Island. One of the more prominent events in the region is a large sand sculpting festival that takes place every November in Fort Myers. This 10-day competition welcomes sand sculptors from around the world.


Top things to do in Gasparilla Island

Port Boca Grande Lighthouse & Museum

Beginning operation in 1890, this lighthouse is the oldest structure on Gasparilla Island and the only beacon on Florida’s west coast open to the public. Located in the Gasparilla Island State Park, the lighthouse formerly housed a private residence on its ground level, now transformed into a museum detailing the region’s cultural history, ranging from indigenous cultures that date back more than 12,000 years to the now-famous fishing the area is known for.

Cape Haze Aquatic Preserve

This collection of protected mangrove islands and seagrass ecologies is home to more than 200 species of fish and several species of migratory birds. Bordered by the Gasparilla Sound to the west and Charlotte Harbor to the south, Cape Haze Aquatic Preserve is a popular snorkeling spot. You can also rent a kayak to explore the winding mangrove forests along the waterfront.

Little Gasparilla Island

The smaller cousin of Gasparilla Island, this rural retreat is cut off from the mainland and is only accessible to private boats or water taxis. Along the wide sandy paths, you’ll find golf carts — the only form of motorized transport allowed on the island — cruising up and down the coast amid a picturesque backdrop of pristine beaches.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Gasparilla Island