Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pine Island vacation rentals
Pine Island house rentals
Home in Spring Hill
Weeki Wachee, Florida Entire House- 2 bed 2 bath
Home in Hernando Beach
Sunset View | Waterfront | 4 Kayaks | Weeki Wachee
Home in Spring Hill
Newly remodeled Weeki Wachee river retreat!
Home in Weeki Wachee Gardens
Bigfoot's Bungalow: Enjoy Clear Main River Waters
Home in Weeki Wachee
Wasted Time on the Weeki Wachee - Kayak & Manatees
Home in Hernando Beach
Seascape - WHOLE HOUSE 360 water views, pool, gulf
Home in Floral City
Latitude 28 a little Patch of Paradise!
Home in Spring Hill
The Chubby Mermaid (Weeki Wachee)
Pine Island condo rentals
Condo in Crystal River
Crystal River Bungalow with boat slip
Condo in Crystal River
Retreat, waterfront condo/boat slip Crystal River
Condo in Tampa
PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Condo in Redington Beach
Beautiful Coastal Couples Get-Away 2 min to beach.
Condo in Redington Beach
Beach Condo, Heated Pool, 2 Minute Walk to Ocean
Condo in Lakeland
Spacious 1 bed 1 bath with office and free parking
Condo in Madeira Beach
Steps Away 1st Floor-Bikes/Beach Access/ WI-FI
Condo in Tampa
Lovely Waterview Condo/ heated pool
Pine Island cottage rentals
Cottage in Homosassa Springs
Tranquil Waterfront Cottage
Cottage in Crystal River
1BR~Near Water + Heart of Cr. River | Manatee-Scallop-Golf-Fish-Boat-Beach-Food-Fun
Cottage in Hernando
The Hernando Lake House
Cottage in Spring Hill
Summer Getaway: Waterfront, Clear Kayak, Fire Pit
Cottage in Weeki Wachee
Kayak Kottage: waterfront, kayaks, bikes, dockage
Cottage in Weeki Wachee
Relax Canalside at our Cottage, fast 200mbps wifi
Cottage in Indian Rocks Beach
Cottage w/ Private Patio | 3 Min Walk to the Beach
Cottage in Dunedin
BeachBunkies Cottage 2. Four miles to the beach!
Your guide to Pine Island
All About Pine Island
Despite being the largest island off Floridaās 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 regionās more popular tourist destinations. You can spend a day or two exploring the 17-mile islandās 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, youāll 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 islandās 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 regionās 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 doesnāt 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 Floridaās 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 islandās 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 islandās 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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