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.
Tiny home in Port Charlotte
5 out of 5 average rating, 6 reviewsA Slice of Paradise for a Fraction of the Price!
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
Home in Sarasota
4.89 out of 5 average rating, 53 reviewsLakefront Getaway in Sunny FL
We had a lovely time
Home in Sarasota
4.88 out of 5 average rating, 147 reviews5 minutes to private Siesta Key Beach + 2 pools
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.
Home in Venice
4.78 out of 5 average rating, 9 reviewsSunset Breeze Retreat
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.
Condo in Sarasota
4.97 out of 5 average rating, 37 reviewsSiesta Key Village & Beach w pool & pet friendly
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!
Home in North Fort Myers
5 out of 5 average rating, 16 reviewsParadise Found
Very spacious place! Perfect for what I was looking for and needed
Cottage in Englewood
4.89 out of 5 average rating, 167 reviewsGood after Milton - Waterfall Pool! Beach! am
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.
Cottage in Fort Myers Beach
4.89 out of 5 average rating, 27 reviewsDEJA BLUE 1000 FT from Beach Great for Families
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!
Home in Punta Gorda
5 out of 5 average rating, 10 reviewsStunning! Luxury waterfront home
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.
Home in Siesta Key
4.96 out of 5 average rating, 103 reviewsBeachfront home with private access, walk to town!
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.
Condo in Sarasota
5 out of 5 average rating, 11 reviews100' from the beach, Spacious 2BR Beachside Oasis
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.
Home in Venice
4.77 out of 5 average rating, 133 reviewsVacation home by Shasta Rd
It was a lovely experience at a beautiful home on a lake. We were totally satisfied.
Vacation rentals for every style
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Popular amenities for Gasparilla Island vacation rentals
Gasparilla Island beach vacation rentals
Villa in Sarasota
4.96 out of 5 average rating, 165 reviewsNewly Renovated- 150 Yards to Beach & Restaurants!
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!!
Condo in Nokomis
5 out of 5 average rating, 17 reviewsPrivate Waterfront 2 Bedroom Condo
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!
Home in Bonita Springs
4.78 out of 5 average rating, 36 reviewsModern Direct Beachfront | 3-Bedroom & 2.5 Bath
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
Home in Fort Myers Beach
4.83 out of 5 average rating, 12 reviewsLone Palm Retreat is a beachfront home
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!
Condo in Venice
4.96 out of 5 average rating, 101 reviewsVintage Villa, Thirty-Five
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!
Vacation home in Nokomis
4.99 out of 5 average rating, 75 reviewsModern Beach Home. 2 Blocks to Beach. 3BD/2BA
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.
Home in Nokomis
4.88 out of 5 average rating, 32 reviewsBeach house
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!
Condo in Siesta Key
4.83 out of 5 average rating, 6 reviewsOur House at the Beach- Endless Summer
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
Home in Cape Coral
4.87 out of 5 average rating, 146 reviewsLUXURIOUS LARGE OPEN OCEAN BLUE POOL VACATION HOME
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
Home in Bonita Springs
4.93 out of 5 average rating, 140 reviewsPool house near Hyatt Regency Coconut Point
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.
Home in North Port
4.79 out of 5 average rating, 151 reviews3 bdrm Pool Home / Quiet Cul De Sac
this place is nice and quiet,every thing is perfect I highly recommend it
Home in Cape Coral
4.88 out of 5 average rating, 32 reviewsBlue Abaco - Beautiful Waterfront House
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
Home in Lehigh Acres
4.83 out of 5 average rating, 128 reviewsLIVING in PARADISE 🌴 ⛱️ 😎
Was a great place and he was very pleasant will definitely rent again
Home in Cape Coral
5 out of 5 average rating, 3 reviewsCape Cottage
Should the need arise again we would definitely stay at Angel's place.
Home in Bonita Springs
5 out of 5 average rating, 4 reviewsFeelin’ Bonita - 2 mi to the Beach! Heated Pool!
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.
Home in Port Charlotte
4.94 out of 5 average rating, 32 reviewsCharming home near the Beach and Punta Gorda.
Angel has an awesome place and was super helpful, highly recommend you book this Airbnb !
Beach house rentals in Gasparilla Island
Home in Captiva
5 out of 5 average rating, 15 reviewsTropical Family Oasis: Pool, Spa, Golf Cart
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.
Home in Bonita Springs
5 out of 5 average rating, 11 reviewsSecluded Bayfront Paradise: Oasis on the Gulf
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.
Home in Port Charlotte
5 out of 5 average rating, 13 reviewsWaterfront Escape on canal ocean access kayaks
This wasn't our first time staying, still wish we could give 10 stars. We will definitely be back again in the future!
Home in Nokomis
5 out of 5 average rating, 24 reviewsTwo bedroom cottage near beach, downtown Venice
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!
Home in Captiva
4.95 out of 5 average rating, 110 reviewsWelcome to Paradise!
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
Home in Venice
4.87 out of 5 average rating, 54 reviewsAlways Eden- a dreamy oasis near a sunny beach
Beautiful home and very convenient for my family and what our plans were. Not too far from anything, great location.
Home in Fort Myers Beach
4.8 out of 5 average rating, 36 reviewsLife's a Beach Cottage
Really nice peaceful place to stay close to the beach and restaurants overall will stay again
Home in Englewood
4.73 out of 5 average rating, 15 reviewsBelvidere Beach Bungalow
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.
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