Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Other great vacation rentals in Pine Island
Home in Homosassa
4.88 out of 5 average rating, 151 reviewsChassahowitzka/Homosassa Waterfront Home
Sep 10 – 17
Home in Brooksville
4.98 out of 5 average rating, 135 reviewsOff the Beaten Path
Jan 13 – 20
Home in Weeki Wachee
4.89 out of 5 average rating, 190 reviewsAngie's Acre
Oct 13 – 20
Home in Inglis
4.93 out of 5 average rating, 222 reviewsYellow bird
Sep 19 – 26
Home in Weeki Wachee Gardens
4.95 out of 5 average rating, 130 reviewsBigfoot's Bungalow: Enjoy Clear Main River Waters
Dec 9 – 16
Home in Lady Lake
4.97 out of 5 average rating, 270 reviewsCozy Lady Lake Guest House
May 20 – 27
Home in Weeki Wachee
4.97 out of 5 average rating, 118 reviewsWasted Time on the Weeki Wachee - Kayak & Manatees
Apr 4 – 11
Home in Floral City
4.94 out of 5 average rating, 114 reviewsLatitude 28 a little Patch of Paradise!
Jul 20 – 27
Pine Island condo rentals
Condo in Crystal River
4.95 out of 5 average rating, 116 reviewsRetreat, waterfront condo/boat slip Crystal River
Nov 11 – 18
Condo in Crystal River
4.82 out of 5 average rating, 119 reviewsCrystal River Bungalow with boat slip
Oct 2 – 9
Condo in Redington Beach
4.97 out of 5 average rating, 458 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Sep 18 – 25
Condo in Indian Shores
4.89 out of 5 average rating, 116 reviewsGulf Side Florida Charm 1/1 Condo 60 Steps To Sand
Nov 2 – 9
Condo in St. Pete Beach
4.91 out of 5 average rating, 209 reviewsSunset Beach Condo in Treasure Island
Nov 6 – 13
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Dec 14 – 21
Condo in Redington Beach
4.86 out of 5 average rating, 313 reviewsRoyal Orleans and Redington Beach ( Studio )
Apr 12 – 19
Condo in Redington Beach
4.94 out of 5 average rating, 356 reviewsBeach Condo, Heated Pool, 2 Minute Walk to Ocean
Aug 2 – 9
Pine Island cottage rentals
Cottage in Hudson
4.84 out of 5 average rating, 125 reviewsMy Happy Place!
Aug 21 – 28
Cottage in Homosassa Springs
4.97 out of 5 average rating, 109 reviewsTranquil Waterfront Cottage
Apr 3 – 10
Cottage in Dunnellon
4.94 out of 5 average rating, 163 reviewsThe Lakeside River House
Aug 8 – 15
Cottage in Spring Hill
4.91 out of 5 average rating, 150 reviewsThe Aripeka Shack
Aug 29 – Sep 5
Cottage in Spring Hill
5.0 out of 5 average rating, 99 reviewsSummer Getaway: Waterfront, Clear Kayak, Fire Pit
Apr 10 – 17
Cottage in Weeki Wachee
4.92 out of 5 average rating, 316 reviewsKayak Kottage: waterfront, kayaks, bikes, dockage
Feb 4 – 11
Cottage in Dunnellon
4.96 out of 5 average rating, 162 reviewsCozy Cottage. Surrounded by nature, not neighbors.
Jun 21 – 28
Cottage in Weeki Wachee
4.84 out of 5 average rating, 151 reviewsRelax Canalside at our Cottage, fast 200mbps wifi
Oct 6 – 13
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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