Gasparilla Island vacation rentals

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Top-rated vacation rentals in Gasparilla Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Tiny home in Port Charlotte

5 out of 5 average rating, 6 reviews

A Slice of Paradise for a Fraction of the Price!

EricRating, 5 stars3 months ago
We transferred over to Richard’s Airbnb location seamlessly during the last hurricane. The place was very spacious, comfortable, with high end finishings, easily accommodating myself, daughter, granddaughter, and pet. Richard was a great host especially considering the circumstances. Very responsive and openly communicative when needed or necessary. We would definitely stay at Richard’s Place again when in the area. Eric - out of state traveler
Guest favorite

Home in Sarasota

4.89 out of 5 average rating, 53 reviews

Lakefront Getaway in Sunny FL

RebeccaRating, 5 stars4 months ago
We had a lovely time
Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 147 reviews

5 minutes to private Siesta Key Beach + 2 pools

SusanRating, 5 stars5 days ago
Beautiful condo that felt like a separate residence. Looks exactly as shown in the photos. Very thoughtfully and well equipped in the kitchen and throughout the home. Easy walk to the private beach. Solen was very responsive and helpful with any questions we had. Definitely recommend this condo to anyone visiting Siesta Key.
Superhost

Home in Venice

4.78 out of 5 average rating, 9 reviews

Sunset Breeze Retreat

DouglasRating, 5 stars1 month ago
Very responsive host. Acted on our 2 concerns promptly. Easy to use home, good layout, large enough open spaces for the whole family to congregate. Had children’s toys available and were much appreciated. Beach equipment was also available (sand sifting tools, buggy, etc.). Appliances were well-appointed, either new or only gently used. Large TV and the wall of recliner/sofa were much appreciated. We look forward to staying here again.
Guest favorite

Condo in Sarasota

4.97 out of 5 average rating, 37 reviews

Siesta Key Village & Beach w pool & pet friendly

NatalieRating, 5 stars4 months ago
Great location, exactly as listed. Came with all the essentials plus more. The condo was perfect for us and our 18 month old and the brand new pack and play was much appreciated. Very friendly beach town with the softest white sand!
Guest favorite

Home in North Fort Myers

5 out of 5 average rating, 16 reviews

Paradise Found

EricaRating, 5 stars3 weeks ago
Very spacious place! Perfect for what I was looking for and needed
Guest favorite

Cottage in Englewood

4.89 out of 5 average rating, 167 reviews

Good after Milton - Waterfall Pool! Beach! am

MiladysRating, 5 stars4 months ago
Very nice place to stay. Perfect location to the beaches and nice restaurants/hang out spots that were very close. Very quiet and peaceful. September is a quiet month - not lots of tourists. Lovely place that was clean and nicely decorated. My only issue was that the shower water never got above luke warm. I like hot showers. Otherwise, very nice place to stay. I would definitely recommend.
Superhost

Cottage in Fort Myers Beach

4.89 out of 5 average rating, 27 reviews

DEJA BLUE 1000 FT from Beach Great for Families

MaddyRating, 5 stars8 months ago
The place was great! Perfect size for 3 or 4 people. The beach supplies (wagon, chairs, umbrella) were SOOO handy! It was just a short walk over to the beach. The kitchen was well stocked with supplies to cook if desired. Since the hurricane, there was a limited amount of restaurants open. We didn’t mind this since we cooked but just a heads up!
Guest favorite

Home in Punta Gorda

5 out of 5 average rating, 10 reviews

Stunning! Luxury waterfront home

RitaRating, 5 stars1 week ago
We enjoyed our time in Troy’s place in Punta Gorda. The home is beautiful and equipped with everything we needed. Kitchen was well stocked. The pool is amazing and fishing from the dock was fun.
Guest favorite

Home in Siesta Key

4.96 out of 5 average rating, 103 reviews

Beachfront home with private access, walk to town!

ToddRating, 5 stars1 month ago
Great location!!!!! We would definitely consider a return trip. Easy, short walk to restaurants, shops and the beach. Stephanie was a fantastic host. Very responsive up to and during our stay. The home exceed our expectations. Very clean and spacious enough for our family and pets. Without hesitation, I would highly recommend this home. Thank you Stephanie.
Guest favorite

Condo in Sarasota

5 out of 5 average rating, 11 reviews

100' from the beach, Spacious 2BR Beachside Oasis

SaraRating, 5 stars1 month ago
Perfect spot, everything you could possibly need for cooking or cleaning. I wish there was a small divider of some kind for the shared deck upstairs.
Guest favorite

Home in Venice

4.77 out of 5 average rating, 133 reviews

Vacation home by Shasta Rd

JosephRating, 5 stars2 months ago
It was a lovely experience at a beautiful home on a lake. We were totally satisfied.

Popular amenities for Gasparilla Island vacation rentals

Gasparilla Island beach 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 stars4 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 Nokomis

5 out of 5 average rating, 17 reviews

Private Waterfront 2 Bedroom Condo

LiubovRating, 5 stars1 month ago
Our family had a great time at Dan’s place. Kayaks and paddle board were amazing for kids and adults, the beach is only 10 mins walk away, we enjoyed the farmers market in Venice on Saturday and the ice cream place across the street. The place was clean, the instruction and all communications with Dan were clear and quick. One of the best airbnb experiences we had. Highly recommend!
Superhost

Home in Bonita Springs

4.78 out of 5 average rating, 36 reviews

Modern Direct Beachfront | 3-Bedroom & 2.5 Bath

KathleenRating, 5 stars2 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
Superhost

Home in Fort Myers Beach

4.83 out of 5 average rating, 12 reviews

Lone Palm Retreat is a beachfront home

TeresaRating, 5 stars1 month 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!
Guest favorite

Condo in Venice

4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

MarleneRating, 5 stars5 months ago
This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!
Guest favorite

Vacation home in Nokomis

4.99 out of 5 average rating, 75 reviews

Modern Beach Home. 2 Blocks to Beach. 3BD/2BA

MatthewRating, 5 stars3 weeks ago
Great beach cottage within walking distance to beach, restaurant, ice cream, fishing charters, etc. One of the nicest homes when it comes to interior design and comfort. Venice is just a short drive a way and you are a quick drive to the grocery store. Nokomis Beach is a hidden spot that is worth the visit. Thank you Ty and Olivia. Such a great place to stay.
Guest favorite

Home in Nokomis

4.88 out of 5 average rating, 32 reviews

Beach house

TayaRating, 5 stars3 weeks ago
Jaime’s place was fabulous! It was spacious and super-comfortable ~ plenty of indoor and outdoor space to hang out, and such a short walk to the beach. The kitchen was well-equipped for cooking, the wifi was fast and the street was quiet. Jaime was very responsive with any questions and easily accommodated our request for early check-in. The stay far exceeded our expectations! We didn’t want to leave the Airbnb :) though we did because it was nearby so much beauty! Thank you, Jaime!
Superhost

Condo in Siesta Key

4.83 out of 5 average rating, 6 reviews

Our House at the Beach- Endless Summer

VladimirRating, 5 stars7 months ago
Beautiful apartment! Two bedrooms, two full bathrooms, toys for the kids, umbrellas, beach chairs, towels, great kitchen with all the spices and utensils. Pool was perfect, and I was happy for gas grill by the pool. Walk to the beach. Really perfect place, and we will come again.

Gasparilla Island house rentals

Guest favorite

Home in Cape Coral

4.87 out of 5 average rating, 146 reviews

LUXURIOUS LARGE OPEN OCEAN BLUE POOL VACATION HOME

RoselynRating, 5 stars6 months ago
The pool and the comfy beds the kitchen the grill the list goes on. It all made our stay even more enjoyable. I highly recommend this place to anyone looking for a wonderful stay in Cape Coral Thank you,for a fantastic experience! We can’t wait to come back. I promise I will recommend it to my friends and family
Guest favorite

Home in Bonita Springs

4.93 out of 5 average rating, 140 reviews

Pool house near Hyatt Regency Coconut Point

KerryRating, 5 stars6 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 stars4 weeks 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 stars6 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, 128 reviews

LIVING in PARADISE 🌴 ⛱️ 😎

MichaelRating, 5 stars4 months ago
Was a great place and he was very pleasant will definitely rent again
Superhost

Home in Cape Coral

5 out of 5 average rating, 3 reviews

Cape Cottage

KimRating, 5 stars4 weeks ago
Should the need arise again we would definitely stay at Angel's place.
Superhost

Home in Bonita Springs

5 out of 5 average rating, 4 reviews

Feelin’ Bonita - 2 mi to the Beach! Heated Pool!

JoanneRating, 5 stars10 months ago
House was very welcoming and beautiful. Felt like home. Loved having a pool to swim in anytime we wanted. If we had one dislike it would have been lack of hot water for the whole family to shower. Neighbors were super friendly.
Guest favorite

Home in Port Charlotte

4.94 out of 5 average rating, 32 reviews

Charming home near the Beach and Punta Gorda.

JosephRating, 5 stars1 month ago
Angel has an awesome place and was super helpful, highly recommend you book this Airbnb !

Beach house rentals in Gasparilla Island

Guest favorite

Home in Captiva

5 out of 5 average rating, 15 reviews

Tropical Family Oasis: Pool, Spa, Golf Cart

BeckyRating, 5 stars2 months ago
Green Tortuga was everything we could have hoped for and more for a little family Thanksgiving getaway. North Captiva is a little slice of paradise that’s a well kept secret from the majority so it can be a little difficult to access as a result. However, our hosts went above and beyond with providing all the information needed for arrival, during the stay, and departure. We loved riding golf carts around the island, enjoying the lovely beaches, hunting for seashells, seeing lots of dolphins and manatees, as well as enjoying the pool at the house. The house is well maintained and excellently stocked and I was very impressed with the job the island has already done to clean up after a very active season.
Guest favorite

Home in Bonita Springs

5 out of 5 average rating, 11 reviews

Secluded Bayfront Paradise: Oasis on the Gulf

PulkitRating, 5 stars1 month ago
Fantastic place. Just as advertised. Would definitely go there again. Chrissy was extremely communicative. The pool heater was unexpectedly not working the day we got there. She tried to fix the problem right away and gave us a discount. Also arranged for us to use a different property just for the pool.
Guest favorite

Home in Port Charlotte

5 out of 5 average rating, 13 reviews

Waterfront Escape on canal ocean access kayaks

TiffanyRating, 5 stars5 months ago
This wasn't our first time staying, still wish we could give 10 stars. We will definitely be back again in the future!
Guest favorite

Home in Nokomis

5 out of 5 average rating, 24 reviews

Two bedroom cottage near beach, downtown Venice

LaurieRating, 5 stars2 months ago
This was our third time staying in this home. We have always found it, comfortable, clean and peaceful. Richard is a great communicator. We would never hesitant to visit again!
Superhost

Home in Captiva

4.95 out of 5 average rating, 110 reviews

Welcome to Paradise!

JaredRating, 5 stars1 month ago
This was our second stay and they were just as friendly as the first time everything worked out very well. Right in the heart of Captiva. Ryan is very responsive if you have any questions thanks
Superhost

Home in Venice

4.87 out of 5 average rating, 54 reviews

Always Eden- a dreamy oasis near a sunny beach

EricaRating, 5 stars1 month ago
Beautiful home and very convenient for my family and what our plans were. Not too far from anything, great location.
Superhost

Home in Fort Myers Beach

4.8 out of 5 average rating, 36 reviews

Life's a Beach Cottage

JonathanRating, 5 stars7 months ago
Really nice peaceful place to stay close to the beach and restaurants overall will stay again
Superhost

Home in Englewood

4.73 out of 5 average rating, 15 reviews

Belvidere Beach Bungalow

CharleneRating, 5 stars2 months ago
Kimberly was an excellent host! Great location, quiet neighborhood, walkable to beach and close to shopping. Clean and tidy home that was comfortable as home.

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