Vacation rentals in Pineland

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Top-rated vacation rentals in Pineland

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Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 133 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.

May 31 – Jun 7

G$24,195 GYD per night

Guest favorite

Home in Bokeelia

4.97 out of 5 average rating, 32 reviews

Relaxing island home near marina and boat ramp

Enjoy the island life at this newly renovated two-bedroom home. Costa Jack's is within walking distance of Jug Creek Marina and Lavender Landing Boat Ramp so you can bring your boat or kayaks/paddle boards and be out on the water in minutes. You'll feel right at home at this pet and family-friendly home. It's fully equipped with everything you need to relax and explore Pine Island. Great place for anglers, boaters, kayakers, families, vacationers, and anyone looking for time on the island/water.

Apr 21 – 28

G$33,760 GYD per night

Guest favorite

Home in Bokeelia

5.0 out of 5 average rating, 17 reviews

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to this Florida retreat - The Clubhouse. Nestled on a prime island 🏝️ location, the well appointed home is ready for you to breath deeply and relax in the Florida sunshine. Use the bikes to explore the tropical Island, or take a short walk to the Pineland Marina and launch your boat. This is the perfect getaway for anyone who loves to boat, fish or relax. Enjoy a delightful stay with your family and friends in the outdoor kitchen, fire pit and hot tub in the lanai. You will love it!

Dec 27 – Jan 3

G$117,409 GYD per night

Guest favorite

Cottage in Bokeelia

4.99 out of 5 average rating, 109 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!

Aug 7 – 14

G$42,422 GYD per night

Guest favorite

Apartment in Bokeelia

5.0 out of 5 average rating, 12 reviews

Apartment at Treehouse Permaculture Farm

This apartment is on a one-of-a-kind tropical fruit farm. Guests can wander throughout 4 acres of tropical fruit tree groves featuring extremely rare fruits grown as a "Food Forest" using the principles of Permaculture. The apartment has private entrance at poolside. On a paved road in a quiet rural location at the north end of Pine Island, within minutes of Saint James City and Bokeelia! All new kitchen. Queen size bed. Parking for a boat trailer. The large bathroom has a tub and shower.

Oct 25 – Nov 1

G$32,497 GYD per night

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Sep 6 – 13

G$18,926 GYD per night

Superhost

Cottage in Bokeelia

4.82 out of 5 average rating, 73 reviews

The Bokeelia Cottage

This tiny home is perfect for those seeking a peaceful retreat from every day life! Located in the quiet little fishing town of Bokeelia. Minutes from several boat ramps, restaurants, and the Bokeelia fishing pier. Take the local ferry out to the outside islands like Cayo Costa, Captiva, or Cabage Key or enjoy your time on the beautiful front porch overlooking your own private pond. Catch and release is always welcomed and don't be surprised if you see wild peacocks passing through!

Jan 3 – 10

G$30,965 GYD per night

Guest favorite

Home in Bokeelia

4.91 out of 5 average rating, 32 reviews

NEW- Sunny Island Cottage w/ Large Patio

This charming one bed/one bath home is very spacious, tiled throughout, and includes a large privately fenced in back patio to enjoy the Florida weather. The living room includes a Queen sleeper sofa for additional sleeping space. This home is outfitted with mini split AC, newly renovated bathroom, and a washer and dryer inside for your convenience. This home is located near two public marinas and boat, so you are welcome to park your boat trailer on our spacious property

May 5 – 12

G$24,021 GYD per night

Guest favorite

Home in Cape Coral

5.0 out of 5 average rating, 8 reviews

The Cape Escape | Pet-Friendly | Sleeps 7

Welcome to "The Cape Escape", a pet-friendly new construction rental located in North West Cape Coral. This single-level fully furnished home offers 3 bedrooms, 2 full bathrooms, 1,619 sqft, 3-car garage, 2 smart Roku TVs, strong WiFil, fully equipped kitchen & sleeps 7 people in 1 king bed, 2 queen beds, & the living room couch. No more than 2 dogs allowed for an additional $100 per pet per booking fee. Conveniently located to major attractions in our quiet neighborhood.

Jun 4 – 11

G$24,051 GYD per night

Guest favorite

Home in Bokeelia

4.78 out of 5 average rating, 51 reviews

Island Retreat

Located on beautiful Pine Island SW Florida. Recently renovated with new flooring throughout and updated bathroom. Close to community swimming pool, fishing pier, boat ramp, restaurants, and golf course. Take a ride on the 17 mile bike path with 2 bicycles we provide and enjoy 2 kayaks provided to tour the local waters. I also have a private hot tub at Island Retreat for your enjoyment. Island Retreat is a 2 bedroom 2 bathroom private mobile home in a quiet community

Sep 25 – Oct 2

G$26,643 GYD per night

Superhost

Camper/RV in Bokeelia

4.79 out of 5 average rating, 14 reviews

Pine Island Escape

20' Grey Wolf Camper in a quiet residential neighborhood in Bokeelia. There is a smart TV, games, firepit & BBQ grill. A short distance to the boat ramp, area restaurants, and nature trails. Visit Cabbage Key, beautiful Cayo Costa State Park, or Captiva Island with a local boat tour company or ferry. Bicycle the island along a 17-mile bike trail from Bokeelia to St. James City at the south end of the island. Enjoy beautiful sunsets from Bokeelia Fishing Pier.

Nov 14 – 21

G$20,389 GYD per night

Guest favorite

Home in Bokeelia

5.0 out of 5 average rating, 5 reviews

*Newly Renovated* Fishing Getaway Near Boat Ramps

Fish camp is a newly renovated 2 bedroom 1 bath mobile home with a nice yard. The living space has been completely renovated and is all new from floor to ceiling. Private bedrooms at opposite ends of the house make it perfect for two couples or a family of 4 to come and enjoy all that Pine Island has to offer. There are 4 different boat ramps within one mile of fish camp for access to all of Pine Island and Boca Grande pass, home of world-class fishing.

Jul 24 – 31

G$21,644 GYD per night