Vacation rentals in Pine Island
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Top-rated vacation rentals in Pine Island
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Other great vacation rentals in Pine Island
Undebatable
Me and my family had a beautiful stay here, when fishing in the gulf and saw many dolphins and wildlife. We really appreciated the nice boat ramp as well. We can’t wait to visit again!
Spring Hill, Florida Quaint Paradise
We totally enjoyed staying at Conny’s place. So private, comfortable, and convenient. One of the best AirBnBs that we have stayed in. It’s so nice to be in a house and not a hotel room. Many thanks!!
Adelynn Suite
I will surely be back. Elvis’s airbnb was clean, comfortable, quiet, private and perfect for my visit. The hosts were kind, flexible and quick to respond. I recommend this to anyone. Thank you Elvis
Aframe Cabin Tent in an Olive Grove.
We had an absolutely amazing time during our stay. The dog “Joe” was so cute and sweet! We will definitely visit Brooksville again!
Weeki Wachee, Florida Entire House- 2 bed 2 bath
This place is better than the pictures! The place was super clean. It looked like the inside had been newly renovated and it was beautiful. It was bigger than we thought. Having the kayaks was a big plus! We met a few neighbors while kayaking and they were super nice which added to our overall experience. The bed upstairs (the only one we used) was super comfy as were the pillows. We were in the area for my niece’s high school graduation and plan to stay here again for any future visits! Highly recommend this place. Also, Jennifer was an amazing host and was always quick to respond. We did not need much from her as everything was self explanatory thanks to the thoughtful notes! Thank you for an amazing stay!! Amy M.
Weeki Waterfront Airstream Glamping Experience
We had an amazing stay! The space was clean and very inviting! Sarah was super responsive and helpful! Beautifully curated experience and certainly one I’d recommend!
Hudson Waterfront Home Weekly/Monthly Discount
This home was absolutely beautiful! The area and surroundings were a sight to see! The hosts were very responsive and accommodating!
Tiny Home Glamping - fishing, springs, manatees
Such an adorable tiny home—perfect for a solo getaway or with a friend! It was clean, cozy, and had just the right setup for a comfortable stay. Loved the clever use of space and the warm, welcoming vibe. A great spot to unwind and feel right at home.
Your guide to Pine Island
All About Pine Island
Despite being the largest island off Florida’s Southwestern Gulf Coast, Pine Island has an Old Florida feel, with small villages and miles of farmland, mangroves, palm trees, and tropical fruit groves. Its secluded, small-town atmosphere is unlike the high-rise buildings and commercial businesses in the region’s more popular tourist destinations. You can spend a day or two exploring the 17-mile island’s boutiques and small waterfront restaurants, many of which feature clam and crab chowders and freshly caught seafood.
Although lacking beaches, Pine Island provides some of the best fishing in Florida. On the Matlacha Pass Bridge, which connects the island to the mainland, you’ll often see visitors reeling in redfish, snook, grouper, or mackerel. Kayaking and canoeing are popular ways to experience the waters, and nature trails scattered around the island allow visitors to explore the land and local wildlife.
The best time to stay in a vacation rental in Pine Island
The island’s subtropical climate provides mild, dry winters and hot, wet summers. Visitors seeking rentals in Pine Island, Florida often find that October through May may offer the best weather for fishing. These months generally see clear skies, comfortable temperatures, and minimal rainfall. That half of the year is when many of the region’s major events occur. A festival held in nearby Cape Coral every January is one of the most significant art shows in Southwest Florida, with over 300 artists and numerous culinary options. In March, a food festival features delicacies from more than 20 Cape Coral restaurants.
The island experiences the most rainfall June through September, but it doesn’t stop singer-songwriters from all over from flocking to Fort Meyers and Captiva Island for a major music extravaganza every September.
Top things to do in Pine Island
Randell Research Center
The Randell Research Center teaches visitors about Southwest Florida’s ecology, archaeology, and history through its museum, heritage trail, and 100-acre shellmound site. The Calusa Heritage Trail, well marked with interpretive signs, winds through nearly one mile of the mounds and canals of the Pineland archaeological site.
Museum of the Islands
This small museum features a look into the island’s rich history, with an extensive collection of vintage household artifacts, tools, generations of dolls, and newspaper articles. In addition to more than 1,700 shells, the nature collection features exhibits of the island’s plants and animals.
Cayo Costa State Park
While Pine Island is not known for its luxurious beaches, the barrier island of Cayo Costa, which is only accessible via boat, features nine miles of beautiful white-sand beaches and six miles of hiking and biking trails. During the 50-minute boat ride from Pine Island, you may even spot manatees and dolphins. Once you arrive, you can fish, snorkel, or watch for snowy plovers, tricolored herons, and other coastal birdlife.
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