
Vacation rentals in Pine Island
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Top-rated vacation rentals in Pine Island
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Firepit, Golf Cart, Kayaks, Pedal Boat, 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!!

The Bohemian Studio Countryside Gem Separate Entry
🚨 Unbeatable Deal! Secure a serene, countryside escape at an AMAZING PRICE (Nov-Feb) This cozy studio offers total PRIVACY with self-check-in & a separate entry. Enjoy a PEACEFUL stay minutes from hospitals, dining, springs, & beaches 🌳 2 Acres & Fenced Patio 🍳 Fully Equipped Kitchen and bathroom 💻 High-Speed Internet & FREE Netflix 🚗 Ample FREE Parking Zero Hidden Costs Perfect for traveling nurses, snowbirds, or a romantic escape. Experience comfort and book your stress-free getaway now

Private waterfront house with large outdoor bar
Enjoy waterfront views while sipping a cocktail at the giant outdoor bar. Two bedrooms offer queen beds in each and a pull-out queen-size sofa bed is in the living room. Close to popular Crumps Landing Restaurant. The Riverside Marina is nearby to launch your boat. There is ample parking for a boat trailer. Canal access to Halls River & Homosassa River for flats boats or pontoon boats only. Must be able to lower bimini to go under Halls River Bridge. Property includes three kayaks and one canoe.

Riverside Cozy Treehouse, Outdoor Movie & Firepit
Immerse yourself in the tranquil allure of Famous Ozello Trail, residing in our cozy, coastal-inspired 2-bedroom house. Here, the magic of nature unfolds daily with wild peacocks making frequent appearances. Delight in BBQs by the gentle river, relax under the starlit sky on our comfy porch, or indulge in a movie night with our outdoor projector. Indulge in home comforts with a full kitchen, WiFi & smart TVs. Local springs and parks are a short drive away. Your dreamy Florida escape is here!

Undebatable
This one bedroom house offers one queen bed and a pull-out sofa to sleep a total of 4 people. The house offers a private boat ramp, docks, and quick access to the gulf. Includes Wifi, 2TVs, washer/drier, fire pit, grill, coffee maker. Enjoy sunsets, nature walks, and fishing from the docks. Clean, Clean, Clean! EVERYTHING is washed after each guest including sheets, towels, All blankets, bed comforters, and even decorative pillow cases. All handles, knobs, remotes and shower are sanitized.

Wasted Time on the Weeki Wachee - Kayak & Manatees
Manatees, fishing, kayaks, crystal clear water and the best location await you at "Wasted Time," our waterfront retreat on the beautiful Weeki Wachee river, minutes from Rogers Park. This 2/2 stilt home is comfortably furnished, sleeps 6 and comes complete with all the essentials and toys you could imagine, including boat dock. It features a large, screened in balcony patio overlooking the river, and an entire screened in entertaining space underneath the home. Direct access to the Gulf!

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Duck Haven - Wildlife Sanctuary - 5 miles to I75
Have you ever wanted the opportunity to feed an egg to a fox? Or feed a lemur? Hand feed a deer or sheep? Dance with a cockatoo? If so you’ll get to have these and many more experiences here during your stay. Our Airbnb is different, and our main focus is on offering rememberal experiences to our guests. We have a small family run 501C-3 wildlife sanctuary here on our 18 acre facility that you will be staying at. We do live on the property, but in a detached house across the driveway

HORSE FARM Retreat, Newer Built Private Guesthouse
Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

The Hideaway - Quaint and Peaceful Cottage
1.5 miles from Weeki Wachee State Park. Charming, quiet, quaint cottage, beach theme, quiet neighborhood. 2 bedrooms, 1 bathroom. Utilities, flat screen TV, cable, Netflix, wireless internet, DVD player, DVDs, towels and linens. Fully equipped kitchen with pots, pans, utensils, plates, glasses, coffee cups, wine glasses, coffee maker, air fryer, toaster and blender. Outdoor sitting area with a charcoal grill and a fire pit. Bring boat or kayaks. Park your boat on the property.

Sasquatch Hideaway: Enjoy Clear Main River Waters
Trust me, you want to be on the main river with direct access to the clear waters of the Weeki Wachee. There's a preserve across the river providing added privacy, and just around the corner from Hospital Hole where manatees love to congregate. Our home has been COMPLETELY updated and can accommodate your large group with four large bedrooms! Bring your boat to tie up or use the six single kayaks and a three person canoe provided.

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, delight in the opportunity to interact with our friendly farm animals, adding a touch of rural charm to your agritourism escape.
Popular amenities for Pine Island vacation rentals
Pine Island house rentals

Weeki Wachee, Florida Entire House- 2 bed 2 bath

Weeki Wachee River Escape Waterfront Home w/Kayaks

Stilted 2BR canal home, full kitchen, yard, pets!

Weeki Wachee Pirate House-6703 W. Richard Dr.

Riverfront Escape on the Weeki Wachee with Kayaks

Sunset Casita with private pool & game room

Retro Retreat, Waterfront,Kayaks,Boatslip

Florida Fishing and Kayaking Paradise
Other great vacation rentals in Pine Island

Mason Creek River House

Hernando Beach Pool & Relaxation Home

Relaxing Luxury Private Suite • SpaBathroom Chic

Luxury getaway, Heated Pool, Weeki Wachee

Breezy Botanical Bungalow

Vintage tiny house on Weeki w/ kayaks and RV site

3br waterfront | pool table | fishing from home!

Waterfront apt. adjoins host home
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
- Seminole Vacation rentals
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- Key West Vacation rentals
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Amalie Arena
- ZooTampa at Lowry Park
- Rainbow Springs State Park
- Tampa Palms Golf & Country Club
- Fort Island Beach
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park
- Busch Gardens
- Fred Howard Park
- Clearwater Marine Aquarium
- Ben T Davis Beach
- Black Diamond Ranch
- Weeki Wachee Springs State Park
- Hunter's Green Country Club
- World Woods Golf Club
- Gandy Beach
- Bird Creek Beach
- Homosassa Springs Wildlife State Park
- Honeymoon Island State Park Pet Beach




