Finally! You have decided to cross the glorious Pine Island off your bucket list. This is the perfect chance to unwind in a quiet, laid-back environment, with a scenic, lush, natural environment and plenty of fishing and birdwatching opportunities. Other activities you can enjoy include boating, kayaking, and canoeing. Whether in Pine Island for a short or extended stay, you can live in one of the numerous vacation homes available in the region based on your preference and budget. Beach houses are quite popular for travelers who want direct access to the beach. Other vacation rentals available include cottages and condominiums.

Top 15 Recommended vacation rentals on Pine Island
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Popular Rental Amenities on Pine Island
Waterfront Vacation Rentals on Pine Island

Family Fun and Adventure Activities Aplenty at Pine Island
Take a tour of the Matlacha Art District, home to numerous restaurants, art galleries, and buildings. Take a stroll, a few miles away from one of the island’s vacation rentals, and appreciate the region’s wide-ranging mix of art and beautiful and vibrant buildings. You can also shop for mementos such as home decor and handmade crafts, and treat your taste buds to delicious cuisine in one of the many restaurants. Vacationers are also allowed to attend the many events in the region, including holiday celebrations, concerts, and art festivals held throughout the year.
Leave the comfort of your vacation rentals and explore the Calusa Heritage Trail at the Randell Research Center. Self-guided vacationers are allowed a limited 1000-foot trail every day from sunrise to sunset. There are on-site signage and markings for directional guidance and interpretive signs to educate you on the People of Calusa, the original inhabitants of the Pineland site. Take in the glorious views of the region on the observation platforms conveniently placed at the top of the tallest shell mound on the site.
Mangoes for everyone! Take a fun, guided tour to the gorgeous 25-acre mango plantation for a mango mango-picking adventure. This is a chance for your family to learn about the various mango varieties and everything that goes into growing them. You will also get to pick the mangoes that are in season. The mangoes are fresh, sweet, juicy, fiberless, and the best you have ever tasted. Mangoes can be purchased and shipped anywhere across the nation, including bringing some to your vacation rentals. Even better, you will have some free samples to taste and purchase others to take back to your vacation homes.
Top 3 Best Vacation Spots in Pine Island
Turn Back Time With a Visit to the Museum of the Islands
Located at Pine Island Center and near the island’s best vacation rentals, this museum preserves the history of the island for tomorrow’s generation of Islanders and vacationers alike. It is located in what was the first and only library in the region. The Museum of Islands features Pine Island’s Sound history, numerous unique local artifacts, and a Manatee skeleton boasting gorgeous heart shapes running from each bone extending to the spine.
Explore the Nature Trail at Pine Island Audubon Sanctuary
If you want to leave your vacation homes and connect with nature, visit the Pine Island Audubon Sanctuary. The sanctuary features a 2.5-mile trail open to residents and travelers with a reservation. You can also take kayak trips during spring and summer - April through September - and enjoy one of the most complex Marsh mazes ever.
Explore the Beauty of Pine Island’s Village of Bokeelia
If you want to experience the ultimate peace, calm, and solitude, book one of the small condo vacation rentals in the village of Bokeelia. This remote village brings out the Old Florida charm. Nature enthusiasts can enjoy fishing or take a boat tour at the recently reopened fishing pier for a small fee. You can also visit the Promised Land Mangoes and explore the beautiful Useppa Islands.
Information about vacation rentals on Pine Island
🏡 Vacation rentals available | 42 rentals |
---|---|
🌙 Nightly prices starting at | $76 |
⭐ Popular amenities | Pool, Pets allowed and Fishing |
🐾 Pet friendly homes | 9 homes |
🏊 Vacation rentals with pools | 5 homes |
Frequently Asked Questions
What is the price per night for a vacation home on Pine Island?
The average accommodation on Pine Island is priced at $76 per night. Nightly prices for house rentals are $337 on average. Apartment rentals on Pine Island cost on average $142 per night.
How many vacation rentals are available for booking on Pine Island?
Currently there are 42 vacation homes on Pine Island to browse and book for your upcoming trip.
What are the most popular amenities for vacation homes on Pine Island?
Three most popular amenities for home rentals on Pine Island include accommodations that have: Pool, Pets allowed, and Fishing.
How many vacation rentals with pools are on Pine Island?
Check out 5 vacation rentals available to book on Pine Island.
Are dogs allowed in vacation rentals on Pine Island?
If traveling with a dog on Pine Island, 21% of vacation rentals are pet-friendly.
What's the best month to travel to Pine Island?
If you are booking a vacation rental on Pine Island, consider that rainy season is typically in July or June, with November often being the driest.
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