Vacation rentals in Pineland

Spacious 3/2 50’ Dock-HotTub-Walk 2 restaurants

So much love is put into this home you will see and feel it. Can sleep up to 10. 50’ of dock to Tie up multiple boats. This close to town home is in a quiet neighborhood with Gulf access. You can drink your coffee and mimosas overlooking the tranquil water. Don’t want to cook breakfast? You can walk to town in 10 min or ride one of the bikes to the Perfect Cup or have lunch at another Matlacha restaurant. Your family will enjoy paddle boarding, fishing off the dock, corn hole, bbq, and PacMan.

Boater’s Paradise in Bokeelia!

Welcome to Bokeelia! Forget your worries in this spacious and serene space. Beautiful Newly Remodeled Home located right On the Water with Boat Lifts & Dockage, and plenty of parking for All Come and enjoy a Relaxing and Comfy Home. Boaters! We are across the street from the Public Boat Ramp, Minutes to Captiva & Sanibel Islands, Cayó Costa, Cabbage Key, and Boca Grande which is known for its sugar sand Beaches. Best of all, Amazing Fishing in Florida aka “Tarpon Fishing Capital of the World!”

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, outdoor kitchen and patio. This suite is totally separate from the owners' home/upstairs. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of ground floor screened guest lanai: kitchen, fridge, BBQ. Beautiful gardens, small/secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun! We welcome guests who prefer a low-key getaway.

Island Paradise- Big 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 Snook & Rod Club (Waterfront)

Welcome to the Snook & Rod Club. If you want a place to relax, bring your family, or friends this is the place to be! We are on a canal with a 50' captains walk you can tie your vessel to while you stay. Our island getaway property is located on the northern end of Pine Island (off of FT Myers/ Cape Coral) in the quiet community of Bokeelia FL. We are perfectly located in a neighborhood of canals right down from Jug Creek Marina and are set up for retired couples, families, or fishing buddies

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

The Lookout

This 2 bed 2 bath home sleeps 4 comfortably and there are extra air mattresses. The decor is modern and the home has an old Florida style. Plenty of parking for vehicles and boats. There are 4 older bikes, a single and tandem kayaks. Live music and food are at the end of the street at Jug Creek. Bokeelia is known for its boating, fishing, kayaking and biking. Relax on either of the two decks or patio or hit the water for some fun. The boat ramp and kayak access are both very close.

“The Quarterdeck Cottage” with Dockage!

Other property in this group: www.airbnb.com/h/thewaterside airbnb.com/h/aframeausable Moments from open water and Jug Creek Marina!! This is a fisherman's dream or just relax in the sun. Fresh sheets/towels, grill. Tennis, golf course, library, tennis, yoga, bike ride entire island and beautiful salt water pool just minutes away! Golf carts/kayaks/boats/bikes available at local resources! Jug Creek Marina is a block or so away with fresh seafood, music and sunset views!

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.

Slice of Paradise on Pine Island!

Nestled in a quiet, private wooded area, this peaceful retreat is perfect for embracing the laid-back island lifestyle and timeless Old Florida charm. Whether you’re boating, fishing, kayaking, or bird-watching, you’ll love the abundance of outdoor recreation right at your fingertips. You’ll be staying in a 34' XLR Nitro Travel Trailer, thoughtfully decorated, clean, and well-kept for your comfort. Discover the gorgeous landscape that surrounds this place to stay.

3/3 Loft Style Home in the Heart of Bokeelia!

Discover this stunning brand-new build located in beautiful Bokeelia! This property offers: 3 spacious bedrooms, each featuring king-sized beds and private bathrooms for comfort and privacy. An open loft overlooking the living room and kitchen, providing a modern and airy feel. A balcony with picturesque canal views, with plenty of room for boat trailer parking and the public boat ramp conveniently located just across the street! *Pet Friendly, $150 fee*

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.