Holiday rentals in Pineland

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Top-rated holiday rentals in Pineland

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Guest favourite

Cottage in Matlacha

4.88 out of 5 average rating, 137 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.

Guest favourite

Home in Bokeelia

5.0 out of 5 average rating, 19 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!!

Guest favourite

Cottage in Bokeelia

4.99 out of 5 average rating, 112 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!

Guest favourite

Flat in Bokeelia

5.0 out of 5 average rating, 16 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.

Superhost

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 320 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!

Superhost

Cottage in Bokeelia

4.82 out of 5 average rating, 74 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!

Guest favourite

Home in Matlacha

5.0 out of 5 average rating, 145 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Guest favourite

Home in Matlacha

4.98 out of 5 average rating, 184 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 & 2 person kayaks for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

Guest favourite

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.

Guest favourite

Flat in Bokeelia

4.83 out of 5 average rating, 84 reviews

Family & Fisherman Get-a-way

This is a great vacation rental on a small island away from the hustle and bustle. The home is located right across the road from the boat ramp which makes it easy and convenient for a day out on the water. However, there isn't any dock access at the property. If you are not interested in going out, the home is fully equipped with a television, board games, and a kitchen & BBQ grill to make it a cozy stay!

Guest favourite

Home in Bokeelia

4.97 out of 5 average rating, 61 reviews

Island Time Begins Here at Bokeelia Rd PINE ISLAND

Island Time Begins when you cross over the Bridge!! The people of Pine Island are super friendly and not stressed out at all. This vacation home has brand new furnishings throughout. Brand New 70" & 50" HD SmartTV's. Wi-Fi There is a Fresh Water Pond that borders the back of the property.The pond is loaded with beautiful schools of Nile Perch and Sun Fish.

Guest favourite

Flat in Englewood

4.92 out of 5 average rating, 398 reviews

BEACH FRONT Unit w/Pool Sandy Toe's #4

Directly Beach front unit. Listen to the waves, walk the beach, hunt for beautiful shells and prehistoric shark teeth, take a swim in the gulf, watch the dolphins, manatees swim by. You can even try your luck at fishing from your 75 feet of private beach. Life is good! 1 of 5 units for rent, please inquire if interested in another. 3 night minimum stay.