Cottage vacation rentals in Little Gasparilla Island

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Top-rated cottage rentals in Little Gasparilla Island

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Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 134 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

Aug 14 – 21

€ 135 per night

Guest favorite

Cottage in Englewood

4.9 out of 5 average rating, 109 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Aug 8 – 15

€ 169 per night

Guest favorite

Cottage in Bokeelia

4.99 out of 5 average rating, 110 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. The dock is shared, but there is plenty of room! Lots of history on this beautiful island, with fishing you’ll be amazed with! Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Mar 2 – 9

€ 239 per night

Guest favorite

Cottage in Englewood

4.9 out of 5 average rating, 150 reviews

Free Kayaks! Waterfall Pool! Beach! am

In a prime Manasota Key location, our talented interior designer created this beach bungalow gem with 2 bedrooms and sofa sleeper, Smart Tv's & granite kitchen with dining set. Walk only 1 minute until your toes are in Gulf of Mexico at delightfully uncrowded beach! 5 walk to Stump Pass. Longer walk or free shuttle to good restaurants with live music. Unwind in on-site Swim Spa with waterfall & massage therapy jets in common area. Spot dolphins with free Kayaks. Peaceful, quiet

Dec 30 – Jan 6

€ 575 per night

Guest favorite

Cottage in Sarasota

4.94 out of 5 average rating, 138 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Nov 18 – 25

€ 166 per night

Guest favorite

Cottage in Placida

4.97 out of 5 average rating, 37 reviews

Simply Adrift Island Cottage

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off FL's West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

Nov 30 – Dec 7

€ 376 per night

Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Bella Vita! (The Good Life!)…that feeling when you wake up each day in this little slice of Paradise. This is the spot to enjoy a warm peaceful getaway from the rest of the world...just arrive with your bathing suit/flip flops and walk 1.5 blocks to the warm Gulf waters. Tranquillity of beach life, beautiful sunsets and lazy days of fishing and bird watching. Visit the Jetties, where you can see dolphins, manatees and rays, is only 1/2 mile away.

Aug 11 – 18

€ 148 per night

Guest favorite

Cottage in Little Gasparilla Island

4.98 out of 5 average rating, 48 reviews

Happily Ever After

We are off the main paths and so it is s quiet place to reconnect with what matters. We encourage our guests to unwind on our spacious comfy porch with fluffy chairs and a futon chair for naps or use our large private outside shower, fully stocked. This is an island so be prepared for loads of sun and sand. Unlike most rentals ours is very stocked with all paper products, spices, plastic ware, toiletries, towels for your use!

Mar 20 – 27

€ 379 per night

Superhost

Cottage in Sarasota

4.83 out of 5 average rating, 150 reviews

Charming Beach Cottage

LOCATION!!! Getaway from the fast paced, high pressure life and slip on some flip flops! Get ready to unwind with the cool sea breeze, sunny adventures on the beach or on the water and explore the meaning of easy island living. Our contemporary designed home is just a few minutes drive from the most picturesque beaches in the nation with LOTS of parking. Feel free to bring your boat:) Restaurants and shopping are plentiful!

Nov 9 – 16

€ 188 per night

Guest favorite

Cottage in Siesta Key

4.89 out of 5 average rating, 143 reviews

Siesta Key Cozy Cottage across from the beach!

Adorable Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with barbecue:) Very nice size kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!

Aug 15 – 22

€ 289 per night

Guest favorite

Cottage in North Fort Myers

4.94 out of 5 average rating, 172 reviews

Cozy Private Pool Cottage

This is a small separate guest house with a large pool just steps from the door. Located in a very safe and quiet secluded neighborhood with only 18 homes, all retirees and famous artists along the caloosahatchee with some Riverfront views from pool deck. Only 1.2 miles to Historic Downtown Fort Myers and Edison Museum, along with numerous downtown events, restaurants and nightlife.

Jan 3 – 10

€ 157 per night

Guest favorite

Cottage in Englewood

4.96 out of 5 average rating, 139 reviews

Family-Friendly Beach Cottage Manasota Key

Perfect for family / friends who want to escape the stress of the real world into paradise on Manasota Key. This family/group-friendly beach cottage sits across the street from the Gulf of Mexico. The closest public beaches are Manasota Beach and Blind Pass beach ( ea. 4 min drive) The property sits bayside and has private dock access !

Feb 22 – Mar 1

€ 260 per night