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Featured Cottages in Gasparilla Island

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (136)
"Amy was a wonderful host. She found a lovely place for us when Manasota Key was devastated by the hurricane. She and her team were great to work with and our stay was wonderful!"
Villa Mojito Dazzles

Island Cottage in Bokeelia - close to fishing and water sports!

10.0 out of 10, Exceptional, (9)
"Home was just as listed. Host was great!! I would definitely stay again "
Island Cottage in Bokeelia - close to fishing and water sports!

Spacious "Crab Cakes" Cottage on beautiful North Captiva Island,FL with GolfCart

9.6 out of 10, Exceptional, (7)
"Delighted to stay at Crab Cakes - a lovely and cozy getaway!"
Spacious "Crab Cakes" Cottage on beautiful North Captiva Island,FL with GolfCart

Beach Cottage on Private Little Gasparilla Island, relax & unwind!

9.8 out of 10, Exceptional, (18)
"The house was charming, comfortable and clean. The photos of the house are very accurate. There was a nice screen porch to relax on. The kitchen was very well equipped, as was the house. It had everything you need. The location was excellent, half way between the beach and the bay— about a 2 or 3 minute walk each way. You could hear the surf at night with the windows open. Michelle the host was super responsive and everything on the place was cleaned up and fixed from whatever hurricane damage...
Beach Cottage on Private Little Gasparilla Island, relax & unwind!

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (104)
"Check in process was easy. Communication with the owner effortless. Location close to the beach, restaurants, yet still private & quiet. We will book again if available when in Venice. "
Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (136)
"We loved this property/location. Unfortunately we had to leave a day early due to Helene. The owner was very concerned about this and offered to refund us the day we missed. I would definitely stay here again. "
Villa Margarita Sparkles

Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

10.0 out of 10, Exceptional, (5)
"This was our first booking with VRBO. Could not have asked for better hosts. Jeff and Lexie went above and beyond to make sure we were comfortable. They were very responsive with any questions we had. Beautiful little cottage with all the amenities you need. Thank you Jeff and Lexie. Looking forward to next time!"
Cozy Cottage - Minutes from Beaches and Historic Dearborn St!

Cozy and Private our island home on North Captiva is the perfect escape

8.6 out of 10, Excellent, (7)
"I booked this house because of the location and fantastic price. It was adorable and exactly as expected. I couldn't get the dryer door to open but I think that may have been operator error. The property managers, Duncan and Laurie with Tortuga, went above and beyond to make my stay not just ok, but exceptional. I would have missed the ferry due to my plane delay had Duncan not reached out to give me additional options. He even called the ferry captain to make sure he new I was coming for the...
Cozy and Private our island home on North Captiva is the perfect escape

Island TreeTop House, Pet friendly

10.0 out of 10, Exceptional, (19)
"We really enjoyed our time here. The house is in a great location with plenty of privacy. We had a lot of fun using the kayaks, and the closeness of the put-in was great. Well stocked with everything we needed - even a stacked washer/dryer. Has a homey feel as another reviewer said. There is a grocery store nearby and a good amount of restaurants around. We would both highly recommend a stay here."
Island TreeTop House, Pet friendly

Bring your boat to our cozy cottage in a quiet waterfront community.

10.0 out of 10, Exceptional, (16)
"The property is immaculate. Everything you need is there and organized. Nicole is great to work with."
Bring your boat to our cozy cottage in a quiet waterfront community.

Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning

8.0 out of 10, Very good, (2)
"Needs improvement"
Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (181)
"We were actually at a property in Venice Beach, a house with private pool. It was very nicely decorated and so comfortable. Close to everything. We had a blast."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

Flamingo Bay Cottage 3 Bedroom Cottage by RedAwning

3.0 star property
Flamingo Bay Cottage 3 Bedroom Cottage by RedAwning

Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

9.6 out of 10, Exceptional, (8)
"Very nice stay. Loved the easy access to the beach and our unit was great."
The price is AU$1,501
includes taxes & fees
1 Feb - 2 Feb
Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

Island Cottage in Quaint Matlacha Florida. Amazing island life is a click away…

10.0 out of 10, Exceptional, (6)
"The spool was an amazing addition while visiting during a cool spell! The owner was very generous in assuring that we had a very warm spool! The sunsets are beautiful! Hope to be able to return in the future!"
Island Cottage in Quaint Matlacha Florida. Amazing island life is a click away…

Cozy Beach Cottage

9.2 out of 10, Wonderful, (17)
"Great fun Surf and bay fishing "
Cozy Beach Cottage

Tropical Port Charlotte Cottage - Walk to Bay!

7.8 out of 10, Good, (11)
"The heater/ac didn't work. The contact brought over 2 space heaters. The front blinds were missing the cord. The bed was soft. We liked the location close to the Bay park."
Tropical Port Charlotte Cottage - Walk to Bay!

Island Life! King Bed Studio-Steps to beach

9.4 out of 10, Exceptional, (153)
"Location of this property is superb. The pictures make it look a little bigger than it is but it is a lovely place to stay. Walkable to a couple great restaurants/bars. Easy 3 minute walk to one of the best beaches in Florida. I have to say, the only criticism I have is the parking spot is a little small. Other wise an amazing 5 star stay. Would go again in a heartbeat "
Island Life! King Bed Studio-Steps to beach

Casa Pina Colada Delights

9.8 out of 10, Exceptional, (153)
"Nice area and plenty of space "
Casa Pina Colada Delights

Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!

10.0 out of 10, Exceptional, (122)
"Great, quiet place near the beach. Host was an excellent communicator. We hope to be back!"
Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (719)
"View, shopping and comfort all in one place."
The price is AU$538
includes taxes & fees
21 Jan - 22 Jan
The Suites at Fishermen’s Village- 2 Bedroom Suites

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (238)
"Quiet area and great little houses. Rented the margarita and was not disappointed. At one point our door lock failed and the manager was there within a few minutes to fix it. Would stay again!"
The price is AU$337
includes taxes & fees
23 Jan - 24 Jan
Matlacha Tiny Village

Privacy in Paradise

10.0 out of 10, Exceptional, (62)
"Just the right size for a family with kids under 10. Quiet, tucked in neighborhood. Very close to family activities and adult nightlife. 5 stars!"
Privacy in Paradise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.