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Vacation rentals in Pineland

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Top-rated vacation rentals in Pineland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A screened lanai features a heated pool and two lounge chairs positioned beside it. Lush palm trees are visible in the background, alongside a scenic view of the waterway that enhances the outdoor space.
Home in Cape Coral
5 out of 5 average rating, 18 reviews

Water Front, Heated Pool, Tiki, Large Lanai

Enjoy the view of Meadowview Lake from the comfort of the large screened-in lanai or tiki hut overlooking the lake. Begin your day with a cup of coffee while enjoying the view. Take a dip in the heated pool or lounge under the Florida sun. Prepare a great meal with the fully equipped kitchen or outdoor grill. Or check out one of the great restaurants on Matlacha Island. Whether you are looking to just unwind or take an adventure, this home provides ample opportunities for relaxation & recreation

Top guest favorite
Home in Cape Coral
4.96 out of 5 average rating, 24 reviews

Villa Coral

¡Escapada familiar a Villa Coral. Tu oasis en Cape Coral. Esta espaciosa casa es perfecta para el descanso: 4 habitaciones, 4 camas, 2 baños, sala, cocina y comedor integrados. Cada habitación tiene su TV. Disfruta de una terraza cubierta ideal para compartir y un patio espacioso para niños y mascotas. Cerca de los proyectos más importantes de la zona y a solo 40 minutos en coche de las playas del área, como Fort Myers Beach o Sanibel Island. Garaje para 2 autos. Reserva ya, vive tu experiencia

Top guest favorite
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.
Home in Pineland
4.98 out of 5 average rating, 61 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!

Top guest favorite
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
4.99 out of 5 average rating, 141 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! Jug Creek Marina is steps away with food & music!

Superhost
A pool area is visible, showcasing clear blue water surrounded by a screened lanai. A wide canal can be seen beyond, with houses lining the opposite shore. Palm trees frame the scene, and bright blue skies enhance the peaceful waterfront setting.
Home in Cape Coral
4.8 out of 5 average rating, 5 reviews

Seaside Villa Majestic

Welcome to our beautiful and modern Seaside Villa Majestic, which was built in 2012 and completely renovated in 2019. Thereby not only all floors were renewed but also the kitchen was replaced. In 2023 the Seaside Villa Majestic was repainted inside and out. The villa has a perfect location in the Rosegarden area overlooking a wide canal. In just a few minutes you can reach the open river by boat. From the pool area the great location is further enhanced by the large heated infinity pool.

Guest favorite
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.
Home in Pineland
5 out of 5 average rating, 28 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.

Top guest favorite
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.
Home in Pineland
5 out of 5 average rating, 35 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.

Superhost
An aerial view of the waterfront condo complex is displayed, showcasing a serene body of water surrounded by lush greenery and palm trees. The building's modern architecture is highlighted, with several units visible and a well-maintained pathway leading to the docks.
Home in Bokeelia
4.67 out of 5 average rating, 12 reviews

Condo in Four Winds! 2/2 Incredible Water Views!

This condo offers the finest in island getaway accommodations. Beautiful waterfront 2 bedroom/2 bath unit with abundant amenities to round out a relaxing boating and fishing vacation experience. Unit 302 has a screened-in lanai and a water view. It is beautifully appointed with a complete kitchen, washer/dryer, wi-fi, cable television, 48 state free long distance, boat docks, and a swimming pool on site. This condo building has an elevator for easier access.

Top guest favorite
A spacious living area is highlighted by a comfortable blue sofa and a glass-top coffee table, resting on a soft area rug. Exposed timber beams and stylish light fixtures create a warm ambiance. A spiral staircase leads to the upper level, while a modern kitchen is visible in the background.
Loft in Boca Grande
4.98 out of 5 average rating, 134 reviews

The Loft on Park Ave--Boca Grande FL

We survived the old 1-2 of Huricaines, Helene and Milton and are ready to host you! A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

Guest favorite
Home in Cape Coral
5 out of 5 average rating, 12 reviews

New Villa Alhambra Lake at the lake-gameroom-dock

Brand new villa with heated infinity pool, spa/whirlpool and low-water area in waterfront south-facing orientation including fantastic views over Lake Alhambra for sole use. Modern and tastefully furnished villa in an absolutely quiet cul-de-sac. The concept and focus of the house are on the unique lake and the extremely spacious outdoor area, which invites you to relax, linger and recharge your batteries. New Gameroom

Top guest favorite
A spacious bedroom features a wooden bed with a light-colored blanket and accent pillows. Natural light streams through two windows and French doors, highlighting the wood flooring and area rug beneath the bed. A decorative lamp and a nightstand add to the room's charm.
Home in Cape Coral
4.94 out of 5 average rating, 195 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

This elegant spacious 3 Bedroom + Den, 3 Bathroom house with split floor plan and large living room will truly make you feel home! High ceilings, a lot of natural light, large rooms, amazing Florida canal view, large heated pool. Fully remodeled in 2017 and feels like new. Location is amazing, close to Marina, Cape Harbour, restaurants. Excellent, beautiful and safe neighborhood. This home is perfect for your vacation!

Guest favorite
A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry and a tiled backsplash complement the granite countertops. A round glass dining table with decorative chairs is positioned in the foreground, creating an inviting dining area.
Home in Pineland
4.81 out of 5 average rating, 79 reviews

Bokeelia Charming Island House

Welcome to your getaway home- a newly remodeled 2 bed 1 bath house, the first floor of a 2 unit duplex. Quiet and peaceful setting, enjoy one of the most natural reserved islands of Southwest Florida. Catch the ferry for a beach daytrip to famous nearby islands of Cayo Costa & Captiva or visit local art galleries and shops in nearby Matlacha. Perfect for biking, kayaking, fishing, sightseeing, etc.

Popular amenities for Pineland vacation rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Pineland