Vacation rentals in Pineland

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Top-rated vacation rentals in Pineland

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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 Bokeelia

4.98 out of 5 average rating, 51 reviews

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to the Florida retreat - The Clubhouse. Nestled on a quiet island 🏝️ location, the well appointed home is ready for you to breath deep and relax in the Florida sunshine. Use the bikes to explore the tropical Island, or walk just two blocks to the Marina and launch your boat. This is the perfect getaway for anyone who loves to boat, fish or relax. Enjoy a relaxed stay with your family and friends in the outdoor kitchen, fire pit and hot tub in the lanai. New bunk beds in lower level!

Superhost

An outdoor dining area features a round table surrounded by four wrought iron chairs, shaded by a striped umbrella. A charcoal grill stands nearby on a concrete patio, framed by a simple, white building with black accents and a door.

Guesthouse in Bokeelia

4.89 out of 5 average rating, 44 reviews

Adorable & spacious efficiency w/ full kitchen

Relax on island time in this adorable & spacious efficiency. It is equipped with wifi, full kitchen, full bathroom, and full closet. There is also a queen sized bed and futon to accommodate guests. Indoor and outdoor dining options. Charcoal grill on site. Designated outdoor smoking section in rear of efficiency with a firepit. Located just 2 miles from the BEST fishing pier in Southwest Florida. Tour the island and experience local restaurant yummy bites. Please *no pets, smoking, or parties *.

Guest favorite

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.

Home in Bokeelia

5 out of 5 average rating, 13 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!

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, 140 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!

Top guest favorite

A two-story canal front home is surrounded by lush greenery and palm trees. A boat dock is visible with a boat ready for use. The clear water reflects the sky and nearby structures, conveying easy access to the canal and Gulf.

Home in Bokeelia

5 out of 5 average rating, 12 reviews

2/2 Home in Bokeelia, Boat Lift Included!

This two level 2 bedroom, 2 bathroom canal front home is exactly what's needed for an excellent vacation on beautiful Pine Island! This property has beautiful tropical décor to get you settled into the island lifestyle. You can relax and enjoy the views and wildlife on the back patio or grill the day's catch. This canal has incredible Gulf access and you will be out to the intra-coastal in minutes for some of the best fishing in not just the country, but the world. Bring your boat!

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 Bokeelia

5 out of 5 average rating, 18 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

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.

Home in Bokeelia

4.96 out of 5 average rating, 24 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.

Top guest favorite

The living area features sleek marble flooring and modern furnishings. A light gray sofa is positioned against the wall, while a square dining table is surrounded by four white chairs. A ceiling fan and wall-mounted TV enhance the space's functionality.

Guesthouse in Cape Coral

5 out of 5 average rating, 11 reviews

Cape Coral Tropical Paradise

"What sets our Cape Coral apartment apart is its combination of comfort, privacy, and tranquility. The spacious private terrace offers a peaceful retreat with stunning views, perfect for enjoying morning coffee or unwinding after a day of exploring. You'll love the thoughtful touches like the king-size bed for restful sleep, the convenience of in-unit laundry, and the flexibility of an air mattress for families. Located in a quiet neighborhood, you’ll feel right at home".

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 Bokeelia

5 out of 5 average rating, 23 reviews

Tranquil Lakeview Home w/ Porch | Bokeelia Retreat

Escape to this tranquil lakeview retreat on Pine Island. Enjoy a screened-in porch, cozy living room, two peaceful bedrooms with smart TVs, and clean, modern bathrooms. Cook with ease in the fully stocked kitchen or explore local seafood spots nearby. Perfect for birdwatching, fishing, and relaxing. Fast Wi-Fi, in-unit laundry, pet-friendly, and close to trails, marinas, and nature. A comfortable, quiet getaway with all the essentials you need.

Top guest favorite

An open-concept living area is showcased, featuring a modern sectional sofa and a sleek coffee table. Large glass doors lead to the outdoor space, allowing natural light to fill the room. A contemporary dining area with stylish fixtures is visible in the background.

Villa in Cape Coral

5 out of 5 average rating, 52 reviews

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Top guest favorite

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

4.98 out of 5 average rating, 106 reviews

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!

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 Bokeelia

4.82 out of 5 average rating, 73 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.