
Pine Island vacation rentals
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Top-rated vacation rentals in Pine Island
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Vacation rentals for every style
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Popular amenities for Pine Island vacation rentals
Pine Island house rentals

Attached Beautiful 2 Bedroom/2 Bathroom Home.

3 Miles from Disney.. Perfect for large families

New 2023 3 bedroom home

Stylish Seminole Heights House

2 BR Home in an Amazing Location With 4-Seat Cart!

2B/2B Newly Renovated Home in Silver Lake!

Cozy 2-Bedroom Oasis with Pool (NOT heated)

Patio Villa, 5 mins from Sumter, FREE Gas Cart!
Pine Island cottage rentals

Redbird cottage and farm. Equestrian lake cottage

Little Manatee River Cottage

Tranquil Waterfront Cottage

The Hideaway - Quaint and Peaceful Cottage

💯 Remodeled Cottage, Animal free property

Coastal Cottage Getaway

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

Cozy Cottage - Walk to Historic Downton-King Bed
Pine Island condo rentals

Amazing main floor condo at Avalon

Renovated Condo! Across the Street From The Beach

Beachfront w/ Stunning Sunsets in Prime Location.

Arie Dam 302, Beach Front Condo - 2Bed/2Bath

2/2 Newly remodeled Beach Front - Sunset Vistas

Indian Shores Gulf Front Rental

Beautiful and spacious condo centrally located

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.
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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- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Clearwater Beach
- Rainbow Springs State Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Plantation Inn and Golf Resort
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Fort Island Beach
- Clearwater Marine Aquarium
- Fred Howard Park
- Sand Key Beach
- Tampa Palms Golf & Country Club
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- Black Diamond Ranch
- Honeymoon Island State Park
- Florida Botanical Gardens
- Bayou Club
- Ben T Davis Beach
- Clearwater Country Club
- Honeymoon Island State Park Pet Beach