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 house rentals
Home in Brooksville
4.98 out of 5 average rating, 137 reviewsOff the Beaten Path
Home in Hernando Beach
4.94 out of 5 average rating, 197 reviewsSunset View | Waterfront | 4 Kayaks | Weeki Wachee
Home in Spring Hill
4.82 out of 5 average rating, 242 reviewsBoutique Above the River
Home in Floral City
4.94 out of 5 average rating, 117 reviewsLatitude 28 a little Patch of Paradise!
Home in Weeki Wachee
4.97 out of 5 average rating, 120 reviewsWasted Time on the Weeki Wachee - Kayak & Manatees
Home in Spring Hill
4.91 out of 5 average rating, 256 reviewsThe Chubby Mermaid (Weeki Wachee)
Home in Spring Hill
4.93 out of 5 average rating, 136 reviewsNewly remodeled Weeki Wachee river retreat!
Home in Spring Hill
4.98 out of 5 average rating, 133 reviewsLanding at Weeki River Retreat -Kayaks included
Pine Island cottage rentals
Cottage in Crystal River
4.97 out of 5 average rating, 312 reviews1BR~Near Water + Heart of Cr. River | Manatee-Scallop-Golf-Fish-Boat-Beach-Food-Fun
Cottage in Homosassa Springs
4.97 out of 5 average rating, 113 reviewsTranquil Waterfront Cottage
Cottage in Spring Hill
5.0 out of 5 average rating, 106 reviewsSummer Getaway: Waterfront, Clear Kayak, Fire Pit
Cottage in Spring Hill
4.91 out of 5 average rating, 122 reviewsWeeki Wachee Barefoot Cottage, Waterfront, Kayak’s
Cottage in Weeki Wachee
4.93 out of 5 average rating, 321 reviewsKayak Kottage: waterfront, kayaks, bikes, dockage
Cottage in Weeki Wachee
4.84 out of 5 average rating, 154 reviewsRelax Canalside at our Cottage, fast 200mbps wifi
Cottage in Floral City
4.93 out of 5 average rating, 184 reviewsWaterfront Cottage 2BR 1B
Cottage in Tavares
4.97 out of 5 average rating, 207 reviewsLakeside Cottage on Lake Dora
Pine Island condo rentals
Condo in Crystal River
4.95 out of 5 average rating, 121 reviewsRetreat, waterfront condo/boat slip Crystal River
Condo in Crystal River
4.82 out of 5 average rating, 124 reviewsCrystal River Bungalow with boat slip
Condo in Redington Beach
4.86 out of 5 average rating, 318 reviewsRoyal Orleans and Redington Beach ( Studio )
Condo in Tampa
4.97 out of 5 average rating, 179 reviewsPondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Condo in Madeira Beach
4.95 out of 5 average rating, 243 reviewsSteps Away 1st Floor-Bikes/Beach Access/ WI-FI
Condo in St. Pete Beach
4.91 out of 5 average rating, 216 reviewsSunset Beach Condo in Treasure Island
Condo in Redington Beach
4.97 out of 5 average rating, 466 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Condo in Tampa
4.94 out of 5 average rating, 148 reviewsLovely Waterview Condo/ heated pool
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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