Vacation rentals in Bokeelia

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Top-rated vacation rentals in Bokeelia

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Guest favourite

Home in Bokeelia

4.97 out of 5 average rating, 34 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.

Guest favourite

Home in Captiva

4.97 out of 5 average rating, 114 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Guest favourite

Rental unit in Bokeelia

5 out of 5 average rating, 22 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.

Guest favourite

Home in Captiva

4.92 out of 5 average rating, 106 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Guest favourite

Guest suite in Burnt Store

4.84 out of 5 average rating, 331 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

4.98 out of 5 average rating, 189 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayak

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 person kayak 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

4.79 out of 5 average rating, 53 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

Guest favourite

Cottage in Bokeelia

4.99 out of 5 average rating, 119 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. 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

Home in Bokeelia

5 out of 5 average rating, 7 reviews

Bountiful Bokeelia

Escape the cold! Great rates for March and April 2025, one week minimum, monthly discounts. Forget your worries in this spacious and serene oasis. Professionally decorated, Coastal Chic, extremely quiet, 3 acre fenced and gated property off the beaten path on Pine Island. So close yet so far away! The immediate mainland has all that you could possibly need. The property boasts a unique clean natural swimming pond pool.

Guest favourite

Rental unit in Bokeelia

4.84 out of 5 average rating, 88 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

4.98 out of 5 average rating, 59 reviews

Peaceful Pine Island House 🌿 Top Floor

Welcome to your getaway home in Bokeelia- top floor two bedrooms and one bathroom. Quiet and peaceful setting, enjoy one of the most natural reserved islands of Southwest Florida. Located near Pineland Marina and Fourwinds Marina. Perfect town for biking, kayaking, fishing, golfing, sightseeing, etc.