Vacation rentals in Pine Island

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Popular amenities for Pine Island vacation rentals

Other great vacation rentals in Pine Island

Top guest favorite
Guesthouse in Orlando
5 out of 5 average rating, 248 reviews

Livingston Pool House- In The Heart of Downtown

MollyRating, 5 stars3 weeks ago
This beautifully decorated guest house and out door space including a refreshing pool is an oasis in the midst of a vibrant historical neighborhood. One can enjoy daily walks around Lake Eola, pick up groceries, eat out, visit a spa, or browse at one of the outdoor markets, all within a few blocks. Always nice to return to the cheerful rooms and sit by the pool or enjoy other outdoor activities in this private garden. Everything is provided for a carefree stay. The hosts are especially friendly & helpful. Definitely look forward to a return visit.
Guest favorite
Apartment in Spring Hill
5 out of 5 average rating, 20 reviews

Cozy Studio Near Weeki Wachee

MarianRating, 5 stars1 week ago
Estervinas place is exactly like the pictures, extremely clean and easy to find. Recommend 100%… very quite place … Love it! Thank you!! Truly a rare find.
Top guest favorite
Home in Port Richey
4.99 out of 5 average rating, 235 reviews

Heated & Screened in Pool-All Essentials Provided

TimRating, 5 stars1 week ago
Very clean and very well equipped. House was very responsive and even checked in on us mid stay to see if we needed anything! Would definitely rent again
Guest favorite
Home in Spring Hill
4.94 out of 5 average rating, 217 reviews

Weeki Wachee, Florida Entire House- 2 bed 2 bath

AmyRating, 5 stars1 week ago
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.
Top guest favorite
Cottage in Spring Hill
4.99 out of 5 average rating, 122 reviews

PARADISE POINT on Weeki Wachee (Boat Welcome)

MakenzieRating, 5 stars1 week ago
An absolutely wonderful stay! Planning on coming back again next year to this same AirBnb! This host had everything we could need or use and she was very helpful. Loved our stay here.
Top guest favorite
Home in Weeki Wachee
4.97 out of 5 average rating, 152 reviews

Wasted Time on the Weeki Wachee - Kayak & Manatees

MorganRating, 5 stars3 weeks ago
We had an amazing stay at "Wasted Time!" The house was clean and stocked with everything we needed and more. Plenty of kitchen accessories, dishes, spices, etc. Loads of linens and towels, and an air mattress. The kayaks were so convenient and we felt like having them there really saved us money in the long run. We explored the springs, jumped off rope swings and tall trees, played at the beach, and pulled up to eat at the local restaurant. The neighbors were friendly. And we had a momma and baby manatee that payed us a long visit on our last night. It was incredible! We hope to stay again!!
Guest favorite
Camper/RV in Hudson
4.97 out of 5 average rating, 32 reviews

Manatee Cove Saltwater Canal Gulf access hot tub

ClarissaRating, 5 stars2 weeks ago
The place was wonderful and for the price, you can’t beat it! The surroundings were beautiful, the hosts are friendly responsive, and there’s so much to do around the area. Definitely would recommend this place to anyone!
Top guest favorite
Campsite in Thonotosassa
5 out of 5 average rating, 217 reviews

The Palm Tree Getaway

KennethRating, 5 stars5 days ago
I would like to Thank Wendy and Michael for letting my Wife, Son, our Dog Bugsy and I stay in their Beautiful Serene Tiny House. What a Spectacular set up, private, clean, nostalgic, everything about the Palm Tree Getaway is exactly as advertised and then some. My Family and I have never felt so peaceful and comfortable at an Airbnb like we did here. We enjoyed every minute we spent here. If your thinking about staying here stop and book it now. You will love it. Michael and Wendy are very attentive and make sure you are a Happy Camper. Our Coffee in the mornings on the back deck were amazing. We used the fire pit one night in the front to make scores incredible. The Sundeck in the front is amazing with a ramp to easily get up to. The Windows with the Beautiful trees and forest in the back and waking up in the morning to it was just incredible. The Butterflies flying all around had my Wife in Awe. We will definitely be back and hopefully try to stay a little longer next time. Thank you

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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