Vacation rentals in Pineland

An outdoor patio is presented with a colorful array of furniture, including a blue table and yellow benches. A shaded area features a seating arrangement with cushions, while vibrant greenery can be seen in the background. Natural light enhances the welcoming space.

4.98 out of 5 average rating, 55 reviews

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to The Clubhouse – Your Private Island Escape Experience laid-back luxury on the serene Florida island 🏝️ just two blocks from the marina. This beautifully appointed retreat features an outdoor kitchen, fire pit, hot tub, and elegant indoor-outdoor living. Cruise the island on provided bikes, kids get to stay the new designer bunk space. Perfect for boating, fishing, or simply soaking in the sun. Refined comfort meets coastal charm — reserve your stay today — your island retreat awaits!

The exterior of the home features a modern design with light blue siding and large windows. Lush palm trees surround the property, adding a tropical touch. A gravel driveway leads to the entrance, which includes a set of stairs leading to the main level.

5 out of 5 average rating, 18 reviews

Antigua Cay Retreat

Stylish and classy, with plenty of space to relax and enjoy one of Floridas most unique and special hidden treasures. Bokeelia on Pine Island! Beautifully remodeled home has 3 full bedrooms, as well as a bonus room with double futon downstairs at pool lanai. Lots of outdoor space around the pool, on the new boat dock as well as an upper level outdoor breakfast area that can be fully opened up to both main bedrooms via the oversized sliding glass doors to each bedroom. Also includes an elevator!

4.99 out of 5 average rating, 140 reviews

A modern living area is highlighted by a spacious white sectional sofa, accented with a mustard yellow pillow. A glass coffee table sits atop a striped rug, while a charming yellow front door adds a pop of color. Decorative oars are mounted on the wall.

Cottage in Bokeelia

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! Jug Creek Marina is steps away with food & music!

A dining area features a white table surrounded by six chairs, topped with blue placemats. A decorative vase filled with flowers sits in the center. The walls are lightly colored and display a wall sign that reads 'RELAX.' Pendant lights provide warm illumination.

4.92 out of 5 average rating, 13 reviews

The Little Yellow Retreat with boat parking

Welcome to The Little Yellow Retreat! Your cozy escape on Bokeelia Island awaits. This charming home features a bright living room, fully equipped kitchen, and cheerful bedrooms, perfect for families, couples, or solo travelers. Relax in the lush backyard with fruit trees and a covered patio, or walk to nearby restaurants and a pool. Two scooters are available for $20/day for both, perfect for exploring the island. Beaches and marinas are close by. Your island getaway is waiting—book now!

Guest suite in Matlacha Isles-Matlacha Shores

A spacious pool area is viewed with a clear turquoise pool reflecting sunlight. Five lounge chairs are positioned around the pool, with a wooden dock extending towards the water. Lush greenery and potted plants add a natural touch to the surroundings.

4.85 out of 5 average rating, 363 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!

4.85 out of 5 average rating, 89 reviews

A well-appointed living space is observed, featuring a comfortable couch adorned with decorative pillows. A wooden coffee table occupies the center, complemented by a mounted television across from the seating area. Stairs lead to the loft, with an entry door visible to the right.

Cottage in Bokeelia

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!

An open-concept living and dining area is showcased, featuring a comfortable gray sofa and vibrant red accent table. A dining table for six is positioned nearby, complemented by stylish decor and ample natural light from large windows.

5 out of 5 average rating, 23 reviews

Bokeelia Golf Retreat

Welcome to BOKEELIA GOLF, a modern and stylish vacation retreat located in the popular Bokeelia, FL. This renovated house features a contemporary modern style with 6-beds, 4-Baths, an inviting open-concept living, dining area, IN/OUT kitchen, pool & play game room. Quiet neighborhood with free parking and a spacious yard featuring a BBQ for family enjoyment. Bokeelia Golf seamlessly combines a Golf Campus & Marina, creating an ideal setting for both golf and fishing enthusiasts.

The exterior of the home is illuminated at dusk, highlighting a welcoming entrance with decorative stone pathways. Lush greenery surrounds the property, and two palm trees add a tropical element. A soft glow from the porch light enhances the inviting atmosphere.

4.97 out of 5 average rating, 29 reviews

Fishing and Nature Paradise

Savor Nature, Sip Cocktails and Embrace Sunsets. Beautifully designed 2 Bedroom home located right on the water. Take a kayak or Paddleboard down the canal and you are instantly in the most pristine waters of the Gulf of Mexico. Located one block away from the Jug Creek Marina where you will find Live entertainment, fresh seafood and any boating needs. Sit on the extensive screened in porch and watch the Manatees. We have everything you need to enjoy a wonderful getaway.

The exterior of a charming home is showcased, featuring tropical palm trees and vibrant bougainvillea bushes. A large sliding door is present, allowing natural light to brighten the interior. The textured white walls contrast with the greenery, creating a relaxed atmosphere.

4.92 out of 5 average rating, 38 reviews

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

A two-story house with a light-colored exterior and a metal roof is showcased under a bright blue sky. Lush tropical landscaping surrounds the property, including palm trees. A paved driveway leads to the two garage doors at the front of the home.

5 out of 5 average rating, 27 reviews

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

4.98 out of 5 average rating, 106 reviews

The small heated pool is surrounded by a screened lanai, featuring mature hedges for privacy. Lounge chairs are positioned nearby on the stone patio, complemented by tropical foliage and vibrant flowers that enhance the serene atmosphere.

Guest suite in Bokeelia

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, living area with kitchen and patio. This suite is separate from the upstairs main house. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of screened guest lanai - kitchen, fridge, BBQ, gardens, secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun!