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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Gasparilla Island and around

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

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

10.0 out of 10, Exceptional, (135)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Island Life! King Bed Studio-Steps to beach
Beach nearby

Island Life! King Bed Studio-Steps to beach

9.6 out of 10, Exceptional, (164)
"This is a fantastic place to stay. We will be back next year without a doubt. Thank you!!!"
Island Life! King Bed Studio-Steps to beach
Island-Life-Steps to Stunning Beach! Pool!
Beach nearby

Island-Life-Steps to Stunning Beach! Pool!

9.4 out of 10, Exceptional, (10)
"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
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (34)
"We were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Honeymoon or Anniversary getaway beachfront with bay dock!
Outdoor dining

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!
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (13)
"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!
Outdoor dining

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
Beach nearby

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!
Fridge, microwave, oven, stovetop

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
Smart TV, books

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
Fridge, microwave, oven, stovetop

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!
House (3 Bedrooms) | Interior

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.
Beach nearby, beach towels

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

9.4 out of 10, Exceptional, (192)
"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
Beach nearby

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (142)
"Clean"
Villa Mojito Dazzles
Cozy and warm 3-bedroom cottage with a pool in the island
Fridge, microwave, oven, stovetop

Cozy and warm 3-bedroom cottage with a pool in the island

8.2 out of 10, Very good, (11)
"Firstly let me say the property was better than advertised as it was extremely clean upon arrival. The location is perfect for those looking for peace and quiet and that love to relax. Pool was perfect. 100% will stay again."
Cozy and warm 3-bedroom cottage with a pool in the island
White Pelican at Shorebirds, Beach sunsets 3 min walk! Kayaks, Bikes and more!
Outdoor dining

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!
Beach nearby, sun-loungers, beach towels

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!
Interior

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
Beach

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!
House (3 Bedrooms) | Interior

Pet-friendly Englewood Home - 4 Mi to Beach!

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

Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside

10/10 Excellent
"Very pleased with service & quality of hotel. "
Becky 2-night trip
Posted 15 hours ago
Four Points by Sheraton Punta Gorda Harborside