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Featured Cottages in Gasparilla Island

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (135)
"We have stayed at this cottage before, and it’s always been obvious how much love the owners put into the cottage, and how much effort they put into making your stay an enjoyable one. Knowing how much work they had to do to get it rehabbed after last year’s hurricanes makes you appreciate it even more. The cottage is very clean and has everything you need for your stay. You are right on the beach with a spectacular view of the sunset. Communication with the hosts is a breeze and they are quick...
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

Island Life! King Bed Studio-Steps to beach

9.6 out of 10, Exceptional, (166)
"Beautiful area and unit. We will be back."
Island Life! King Bed Studio-Steps to beach

Island-Life-Steps to Stunning Beach! Pool!

9.4 out of 10, Exceptional, (11)
"Oir host was amazing and on point. She quckly answered any all questions and immediately addressed any issues. Had an amzing workation. 10 out of 10 stars."
Island-Life-Steps to Stunning Beach! Pool!

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"Had a great family vacation. We spent lots of time on the beach & fishing off the dock. We were especially grateful for your turtle education thank you for letting us partake in that. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

Honeymoon or Anniversary getaway beachfront with bay dock!

10.0 out of 10, Exceptional, (109)
"We had a wonderful stay. The house and property exceeded expectations! Rebecca and Andy were super accomodating, attentive, and went above and beyond to make our stay as special as was possible. House was equipped with everything we could ever need. Beautiful, peaceful location. We will be back!"
Honeymoon or Anniversary getaway beachfront with bay dock!

Near beaches! 2100 square foot heated pool home on the Golf Course!

2.0 star property
9.8 out of 10, Exceptional, (14)
"Great property- we especially enjoyed the pool area and viewing the sunset from thereWell stocked kitchen and comfortable beds. In the area try Coffee & Friends for breakfast, Sassy tarts for baked goods, Placida Fish market for fresh seafood, Englewood farmers market for fresh produce And don’t forget to visit Gasparilla Island - the sun always seems to shine thereWe will be back!"
Near beaches! 2100 square foot heated pool home on the Golf Course!

Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!

10.0 out of 10, Exceptional, (65)
"Our family of four had a fantastic stay at this condo. It was incredibly clean and had wonderful amenities. We loved the kayaks and bikes. The location was perfect and the beach access was close by. We look forward to booking here again! "
Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (145)
"Great location, easy beach access. Will definitely stay again."
Villa Margarita Sparkles

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (110)
"Great place to stay. Very clean. "
Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Charming Waterfront Cottage on peaceful Matlacha! FULL RENOVATION DECEMBER 2024

10.0 out of 10, Exceptional, (2)
"Well equipped, very clean, new and comfortable! "
Charming Waterfront Cottage on peaceful Matlacha! FULL RENOVATION DECEMBER 2024

Spacious "Crab Cakes" Cottage on N. Captiva Island,FL with GolfCart and Starlink

8.8 out of 10, Excellent, (13)
"Cute house as described, beautiful island, would love to return"
Spacious "Crab Cakes" Cottage on N. Captiva Island,FL with GolfCart and Starlink

Private Pool: Beachy Cape Coral Getaway!

3.0 star property
9.4 out of 10, Exceptional, (3)
"Very comfortable, inviting stay at the Beachy Cape Coral getaway after a long journey from Minnesota, trying to get ahead of back to back Winter storms. So when we arrived at this beautiful home, it was such a beautiful place to rest and rejuvenate. Everything worked as advertised, we had no trouble connecting to wifi or the NFL playoff games when we arrived. Thank you for sharing your beautiful home with us!"
Private Pool: Beachy Cape Coral Getaway!

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

9.4 out of 10, Exceptional, (193)
"Cottages for my daughter and I were adjacent. Having a pool was nice. The free washer and dryer was a plus. "
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (143)
"We had a wonderful vacation. The cottage was cute, very clean, and the host was great! Great location! The beach is a very short 2 minute walk, the bay just a 1 minute walk. Short walk to local restaurants. We had a short stay, so we didn't get to use the kayaks, but we did take advantage of the pool. Loved that the property had grills, and a cute outdoor area as well. Lots of dolphins on the bay side, and we even saw some while at the beach for sunset. We really enjoyed our...
Villa Mojito Dazzles

White Pelican at Shorebirds, Beach sunsets 3 min walk! Kayaks, Bikes and more!

10.0 out of 10, Exceptional, (64)
"Very clean property with everything you need. Small but excellent in terms of having it all for a 2-7 day stay. The area is still recovering from hurricanes in the fall of 2024 but this property is in great shape."
White Pelican at Shorebirds, Beach sunsets 3 min walk! Kayaks, Bikes and more!

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

9.8 out of 10, Exceptional, (24)
"Our family absolutely loved our time at this beach cottage!! It was an easy walk from the dock and even easier to the beach! We loved how safe and welcoming the island was! Our kids had endless fun with sea shelling/shark tooth hunting/swimming/boogie boarding and hanging out at our home away from home! We’ll be back for sure! "
Beach Cottage on Private Little Gasparilla Island, relax & unwind!

The Shore Bird-Private Captiva Escape Bay to Gulf Cottage!

6.0 out of 10, (1)
"Nails are protruding above decking and a safety hazard. The slider needs a new lock and currently not secure. The dish washer quit working. And, we had demolition next door with loud construction equipment and the smell of diesel exhaust. Considering the cost, we were quite disappointed. We enjoyed ourselves when we were not at the property."
The Shore Bird-Private Captiva Escape Bay to Gulf Cottage!

Little Gasparilla Island a 2-bedroom cottage wth WiFi and AC on a private island

10.0 out of 10, Exceptional, (2)
"Love that the house was just steps from the dock and the beach was a short walk. It was nice to have chairs and an umbrella so that we didn't have to bring those with us. The house was wonderful with everything we needed. Communication was great with questions answered quickly. Would definitely book here again."
Little Gasparilla Island a 2-bedroom cottage wth WiFi and AC on a private island

Pet-friendly Englewood Home - 4 Mi to Beach!

3.0 star property
Pet-friendly Englewood Home - 4 Mi to Beach!

Canal-front Home in Rotonda West Near Golf + Beach

3.0 star property
Canal-front Home in Rotonda West Near Golf + Beach
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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Top Gasparilla Island Hotel Reviews