Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Popular amenities for Pine Island vacation rentals
Pine Island cottage rentals
Cottage in Weeki Wachee
4.85 out of 5 average rating, 163 reviewsRelax Canalside at our Cottage, fast 200mbps wifi
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 265 reviewsVintage Florida Beach Cottage B
Cottage in Indian Shores
4.96 out of 5 average rating, 127 reviewsBeautiful Beachfront Cottage on the Water
Cottage in Spring Hill
5 out of 5 average rating, 125 reviewsClear Kayak / Waterfront / Fire Pit / Screen Lanai
Cottage in Crystal River
4.97 out of 5 average rating, 336 reviews1BR House
Cottage in Coleman
4.97 out of 5 average rating, 117 reviewsPeaceful Chic Cottage Mini Farm Near The Villages
Cottage in Spring Hill
4.92 out of 5 average rating, 140 reviewsWeeki Wachee Barefoot Cottage, Waterfront, Kayakâs
Cottage in Tavares
4.97 out of 5 average rating, 221 reviewsLakeside Cottage on Lake Dora
Pine Island house rentals
Home in Plant City
4.99 out of 5 average rating, 487 reviewsThe Strawberry Field Stilt House
Home in Hudson
4.82 out of 5 average rating, 34 reviewsSunWild Ventures Home *Golf Cart & Kayaks*
Home in Inverness
4.92 out of 5 average rating, 101 reviewsInverness 2 bedroom/2 bathroom featuring a hot tub
Home in Spring Hill
4.84 out of 5 average rating, 79 reviewsFlip Flop River Stop
Home in Weeki Wachee
4.99 out of 5 average rating, 157 reviewsSEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!
Home in Spring Hill
4.83 out of 5 average rating, 121 reviewsLegacy Lagoon-Peaceful on Canal w/ 2 Clear Kayaks!
Home in Hernando Beach
4.99 out of 5 average rating, 109 reviewsParadise! Golf Cart-Kayaks-Firepit+more
Home in Spring Hill
4.88 out of 5 average rating, 137 reviewsFlorida Gulf Coast. Sunshine and warm breezes!
Other great vacation rentals in Pine Island
Home in Hudson
4.96 out of 5 average rating, 23 reviewsFlorida Keys escape in Hudson
Home in Hudson
5 out of 5 average rating, 96 reviewsRachel's Place
Guest suite in Spring Hill
4.91 out of 5 average rating, 191 reviewsKing Suiteâ˘Private Entryâ˘Drivewayâ˘Wi-Fiâ˘Self C/I
Cabin in Brooksville
4.96 out of 5 average rating, 23 reviewsOrange Blossom Retreat
Guesthouse in Spring Hill
5 out of 5 average rating, 15 reviewsThornberry Guesthouse
Guest suite in Spring Hill
4.98 out of 5 average rating, 47 reviewsAttached Private Suite | Heated Pool NOT Shared
Home in Weeki Wachee
4.89 out of 5 average rating, 28 reviewsWaterfront Cottage
Rental unit in Spring Hill
4.93 out of 5 average rating, 60 reviewsThe Perfect Blend
Your guide to Pine Island
All About Pine Island
Despite being the largest island off Floridaâs 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 regionâs more popular tourist destinations. You can spend a day or two exploring the 17-mile islandâs 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, youâll 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 islandâs 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 regionâs 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 doesnât 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 Floridaâs 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 islandâs 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 islandâs 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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