Holiday rentals in Pineland

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!

4.89 out of 5 average rating, 44 reviews

Guest house in Bokeelia

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 *.

4.99 out of 5 average rating, 140 reviews

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!

Guest suite in Burnt Store

4.85 out of 5 average rating, 355 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!

4.77 out of 5 average rating, 171 reviews

Guest house in Bokeelia

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.

5 out of 5 average rating, 16 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.

4.6 out of 5 average rating, 58 reviews

Flat in Bokeelia

Doublemint Duplex A- on Quaint Pine Island!

Take a break and unwind at this peaceful oasis. The Doublemint Duplex A has the necessities and comfort you need for your getaway in paradise. This is an older unit, but the comfortable bed and cozy living room gives you a soft place to land at the end of a day in the sun! This is a bottom floor unit in a duplex located on a quiet street on the quaint Pine Island. Pine Island, which includes Bokeelia, Matlatcha, and St. James City, is one of the gulf coasts' best kept secrets!

Guest house in Cape Coral

4.94 out of 5 average rating, 144 reviews

Pool Modern Apartment fishing paradise

Location! Location! This apartment is close distance to Deli, restaurants and supermarket . The house faces the canal with breathtaking views we have cameras facing the canal and pool area in order to protect guests. The apartment is attached to the main house but private entrance totally separate. Functional full kitchen in the Lanai area Is only for 2 persons. No children allowed. After May 2025 pool will be shared by 1 or 2 more guest. No service dogs or comfort pets allowed.

Guest house in Cape Coral

5 out of 5 average rating, 9 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".

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.

4.98 out of 5 average rating, 106 reviews

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!

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.

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Other great holiday rentals in Pineland

5 out of 5 average rating, 3 reviews

Gorgeous Private Getaway - Heated Pool w/ NEW Cage

EmilyRating, 5 stars5 months ago

The house was very clean and spacious! We had lots of room for our kids to play. The host was very helpful and accommodating throughout the stay. The island was still very much in repair from the hurricane but we did find lots of great restaurants in the area. Definitely recommend!

4.89 out of 5 average rating, 9 reviews

The Little Yellow Retreat with boat parking

ElisabethRating, 5 stars2 months ago

Spacious and we liked the outdoor screen porch. Walkable to ice cream, gifts, and taco truck.

4.63 out of 5 average rating, 8 reviews

Bokeelia Cottage w/ Private Pool

BarbaraRating, 5 stars4 months ago

If you want peace and quiet to just chill out, this is the place. Go ahead and book it. You won't regret it. The house is on a beautiful piece of property. We definitely did not want to go back to the tundras of Ohio! Thanks Kerry for sharing your home! Barb, Ed and Josie

Guest suite in Bokeelia

5 out of 5 average rating, 4 reviews

The Harbor House

EmilioRating, 5 stars1 month ago

I had a wonderful stay! The place was spotless — super clean and well-maintained, which made it feel really comfortable and welcoming. The host was incredibly helpful and responsive, always quick to answer any questions and made the whole check-in process smooth and easy. The property itself is beautiful, even better than the photos — peaceful, stylish, and in a great location. I’d definitely stay here again and highly recommend it to anyone looking for a relaxing getaway!

5 out of 5 average rating, 15 reviews

‘San Carlos Fish Cottage’ by Boca Grande Pass

WilliamRating, 5 stars11 months ago

if you love Florida, and what it's all about you have to stay at San Carlos Fish Camp. If you don't yet know Florida and what it's all about, you have to stay at San Carlos Fish Camp. Stepping into San Carlos Fish Camp is like stepping back in time, but taking air-conditioning and a good refrigerator with you 😉 It is the quintessential old Florida fishing cabin, but with modern conveniences, and a very comfortable bed. The pictures and the description are extremely accurate, but it's better in person. if you have an opportunity to stay here, do it. You will be glad you did. And Carlos is an outstanding host, responsive and helpful, and has an obvious understanding of how to equip the residence for an amazing stay for his guests. Could not have asked for anything more or anything better. Thank you, Carlos.

4.91 out of 5 average rating, 11 reviews

Guest house in Matlacha

Casa Del Franco

GeorgeRating, 5 stars6 days ago

Samantha was an awesome host! Her studio was exactly as advertised. It was cozy, clean, had everything that you could possibly need. I would definitely recommend and would return.

4.97 out of 5 average rating, 119 reviews

Guest suite in Bokeelia

Chateau Soleil Island Estate

JohnRating, 5 stars3 months ago

Valerie and Wayne guided us in from a few miles out.The bridge to Pine Island was closed one way and once clear no problem.Valerie had business to attend to away but was very accomadating at check-in and upon leaving.Wayne was surperb throughout.The property covers 5 acres.We covered Pine Island thoroughly and also the islands nearby,Cape Coral,and a Visit to Naples with relatives.We purchased some provisions at the .Publics Grocery a short distance from the 4 way stop on rt 78 going in.Had a good Pizza at that stop .We didn’t get to too many restaurants at Bokeelia.We did have an enjoyable dinner at the Flamingo.Valerie’s Place is very up scale and Mary And I appreciate the efforts it takes to keep it that way..We really enjoyed our visit.Thanks