Vacation rentals in Pine Island
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Top-rated vacation rentals in Pine Island
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Fire pit, Golf Cart, Kayaks, PedalBoat, Fishing!
Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River,perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!
Weeki Wachee Pirate House-6703 W. Richard Dr.
Embellish in this once in a lifetime, perfect getaway on Weeki Wachee River. A local favorite! Fully furnished pirate themed, 500 sq ft home with 1 bedroom 1 bath full kitchen and sofa bed. It has everything needed to create unique memories. Swim with manatees in the crystal clear spring-fed river. Have your coffee on the porch over looking the water and your favorite drink around the fire at night. Kayaks are included. Minutes from Weeki Wachee mermaids, Pine Island Beach and Homosassa Springs.
Weeki Wachee, Florida Entire House- 2 bed 2 bath
Come and relax in our newly remodeled river front cottage. This spacious two bedroom two full bath home sits nestled between beautiful tropical trees on the crystal clear river that leads out to the gulf of mexico. The 20 x 20 master suite consist of a king bed, custom two person rain shower and walk out private balcony. First level has an open floor plan with a fully stocked kitchen ready to entertain family and friends. The garage has 6 kayaks, life jackets, fishing gear, washer and dryer.
The Chubby Mermaid (Weeki Wachee)
The "Chubby Mermaid" is a brand new (2020) manatee themed 3/2 waterfront home on a pristine canal just yards away from the Weeki Wachee River. Manatees frequent the canal year round. It sits amid towering old trees, directly across the street from a nature preserve and its large 28' porch overlooks the water. Canoe and kayaks are included. Ideally located so close to the river yet without the crowds of kayakers constantly passing by, you'll enjoy the Old Florida charm and peace offered here.
Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)
Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.
Weeki Waterfront Airstream Glamping Experience
Nature Oasis 🤩 Glamping (Glamorous Camping) Experience in 25-foot Airstream Travel Trailer (RV) ✅ Lush forest views ✅ Tranquil waterfront location (paddle down the canal to the pristine Weeki Wachee River) ✅FREE amenities - hot tub, outdoor shower, firepit, griddle, bikes, yoga mats, kayaks, & stand-up paddle boards. SELF CARE UPGRADE is $100/person. It includes access to shared space: food forest, garden & waterfront wellness studio with experiences curated for you by your hostess.
"Ruf'n It" On The River w/kayaks
"Ruf'n IT" is a 2/1 Waterfront home w/ TV/WiFi just off the main river w/ 7 single kayaks and a youth paddle board. There is dock space for your boat, canoe, or kayaks w/ space to park your trailer. The living space provides 1250 squ ft w/dining area. Enjoy the peace and quiet on the screened lanai and a spiral staircase up to the loft w/TV and kid space. The master bedroom provides a king size bed while the 2nd bedroom has 2 queens and bunks. ASK ABOUT OUR JON BOAT RENTAL!
SEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!
The house is on the main river close to Weeki Wachee springs and has great access to the Gulf of Mexico. You can dock up to a 24' boat. It is only minutes from Pine Island Beach Park, Hernando Beach and Sun West Park. It is also about an hour and half from world renowned Clearwater beach. Get the best experience Florida can offer. You’ll love Weeki Wachee and the freshwater spring that feeds seventy two degree water year round. This house has 4 bedrooms and sleeps 10!
Riverfront Escape on the Weeki Wachee with Kayaks
Relax and enjoy the peaceful beauty of the Weeki Wachee River in this riverfront retreat with kayaks included and boat rentals available. Our 2BR/2BA home sleeps 8 with two queen beds and two futons, perfect for families and friends. Lounge on the deck, sip drinks in the lanai, or launch into crystal-clear springs for kayaking and wildlife watching. Minutes from Weeki Wachee Springs State Park, beaches, dining, and shopping — the ideal mix of adventure and relaxation.
Screened Lanai /Clear Kayak / Waterfront / Fire Pi
Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.
Charm and comfy tiny house
Enjoy the lovely setting of this romantic💘 spot in nature. Comfort and charm await you in our tiny 🏡 , just 6 minutes from Weeki Wachee State Park. It is completely private, no shared spaces. Located in the middle of a spacious and fenced lot. Immerse yourself in the quiet atmosphere surrounding by nature. Enjoy a beautiful 🌅 under the shade and refreshing breeze of the 🌳 , a delicious ☕️ , a good 🍷 , a grill barbecue 🍗 or some marshmallows by the fire pit🔥.
Home On the River - Weeki Wachee Cabin
Escape to our peaceful Weeki Wachee River retreat, where relaxation meets adventure. Nestled on the clear part of the river, our family-friendly getaway offers everything you need for a memorable vacation. Tube down the crystal-clear waters, kayak through stunning scenery, and snorkel in the pristine river. Enjoy swimming, fishing, and wildlife sightings. Discover the perfect blend of tranquility and excitement at our Weeki Wachee River oasis.
Popular amenities for Pine Island vacation rentals
Pine Island house rentals
Adult-Only Retreat w/ Pool & Spa | 18+, Private
PALM CREEK GETAWAY spring meets gulf+pool/spa
Little Bohemia! Waterfront+kayaks+dock+tikitub
Boutique Above the River
"Come Sail Away" | Gulf Waterfront Stilt House
Island/Beachfront House - Majestic Sunsets
Pine Island Escape | Kayaks, Sand, Sunsets & Games
Island House, Gulf Views Pine Isl., Tampa, Orlando
Other great vacation rentals in Pine Island
Gulf Sunsets! Island Life but minutes to spring!
Sea Glass Cabin on the Weeki with kayaks
Waterfront at Weeki Wachee
Sunshine Escape Hernando Beach Direct Gulf Access
Welcome to Weeki River Escape!
Weeki Wachee Riverfront Home with Amazing View!
New house only minutes from Weeki Wache State Park
Main River: Hot Tub, Jon boat, hot tub
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.
What are the 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.
Destinations to explore
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- Weeki Wachee Springs
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