Holiday rentals in Pineland

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa

Experience Cape Coral like never before all from this gorgeous 3bedroom, 3bath villa. This elegant villa boasts a vibrant interior decorated with Italian furniture and fully equipped kitchen. Begin your day with a few laps in the private pool before heading to the Yacht Club Public Beach, Sun Splash Family Waterpark or Pine Island to soak up some sun! After adventurous days, continue making memories back home with a family barbecue and a soak in the hot tub or have a movie night with loved ones!

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!

Beach Centric & Cozy 3BR Home

POOL CONSTRUCTION IN YARD Come relax in the Cape! Spacious living room with a 75-inch 4K TV with: Netflix, Disney+, and Prime Video. The kitchen is fully equipped with a coffee and espresso station, and a very well equipped kitchen. Enjoy a master bedroom with a king-size bed, a 55 inch 4K TV, and an ensuite bathroom. A second bedroom with a queen-size bed and a third bedroom with 2 twin-size beds and a work from home office space with high-speed wifi. There is a second bathroom with a bathtub.

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!

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!

Susie's Old Florida Cottage

Explore Pine Island & the Florida Gulf Coast from this retro 2-room cottage set in a pretty back yard. 45 min from Ft. Myers Beach/Sanibel. Wi-fi, A/C, kitchen, v small bathroom w/shower, 1 bedroom, cozy private deck, screened lanai. Perfect for 1 or 2. Avoid the motel feel & enjoy your privacy. Discounts for weekly/monthly bookings. No beaches on PIne Island, but enjoy kayaking, birding, biking, tennis, boating, & fishing. May 2023: Pine Island is still recovering from Hurricane Ian.

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.

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.

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.

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!

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.

Paradise Found! - 3/2 Pool Home

Escape to our Tropical Oasis in Bokeelia, Pine Island, Florida! This 3-bed pool home offers comfort and style. Enjoy a private pool, lush surroundings, and amenities galore. Minutes from SWFL's best beaches, Cape Coral, Fort Myers, Matlacha, and Pine Island's restaurants and shops. Book now for a perfect blend of relaxation and adventure!