Photo by Tom Hunt

Search Little Gasparilla Island Cottage Rentals from CA $123

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Little Gasparilla Island Cottages

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)
"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
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, (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
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
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, (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
Beach nearby

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (142)
"Clean"
Villa Mojito Dazzles
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!
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!
Canal-front Home in Rotonda West Near Golf + Beach
House (3 Bedrooms) | Front of property

Canal-front Home in Rotonda West Near Golf + Beach

3.0 star property
Canal-front Home in Rotonda West Near Golf + Beach
Studio#1-Back Bay Sunsets in Matlacha
Interior

Studio#1-Back Bay Sunsets in Matlacha

9.6 out of 10, Exceptional, (10)
"We were very impressed with the cleanliness, comforts and the central location!!"
The price is CA $123
CA $279 total
includes taxes & fees
Aug 14 - Aug 15
Studio#1-Back Bay Sunsets in Matlacha
Cozy Beach Cottage
On the beach, sun loungers, beach towels

Cozy Beach Cottage

9.4 out of 10, Exceptional, (21)
"Wonderful location for a peaceful getaway "
Cozy Beach Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Little Gasparilla Island Hotel Reviews

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

10/10 Excellent
"Customer service was impeccible. Both office managers treated my family and myself with high esteem and did not want for anything! The suite we stayed at was also vibrant and a cozy place to relax. Absolutely a beautiful suite. Will be back!"
cheryl 3-night trip
Posted 15 hours ago
The Suites at Fishermen’s Village- 2 Bedroom Suites