
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 Youâll Love: â˘đś Kayaks for exploring the waterways â˘đ Water Mat for fun on the water â˘đĽ Fire Pit for cozy evenings under the stars â˘đŻ Cornhole Boards for friendly competition â˘.đ Golf Cart â˘đż 5 Minutes to Weeki Wachee River â perfect for kayaking, paddleboarding, or spotting manatees â˘đľ Nearby Bars & Restaurants with live entertainment every night!!

The Bohemian Studio Countryside Gem Separate Entry
đ¨ Deal Alert! Our cozy studio won't last long at this unbeatable price from November- February. Enjoy a PRIVATE countryside escape minutes from hospitals, dining, springs, & beaches. Self-check-in & SEPARATE ENTRY offer total privacy Features include: fenced patio, fully equipped kitchen, high-speed internet, FREE Netflix, ample FREE parking on 2 acres & flexible check-in. Perfect for traveling nurses, snowbirds, or a romantic escape. No hidden fees or deposits. Book your perfect getaway now!

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.

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.

Ozello Keys Cottage on Crystal Bay
2/1 Ozello coastal cottage on stilts surrounded by nature, tranquility, and endless views of the water and estuary. Nature lovers paradise. World renowned fishing and scalloping. Regular dolphin and manatee sightings. Relax with the whole family on the large screened back porch providing gorgeous views of the Nature Coast and stunning sunrises over the salt marsh. The open floor plan opens up to a large screened porch with a dining and lounging space with private and expansive water views.

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!

Relaxing Luxury Private Suite ⢠SpaBathroom Chic
Discover unmatched luxury and comfort in our private suite. Drift into a queen bed or queen sofa bed, enjoy a Toshiba 55â TV, or curl up in a comfortable reading chair. The compact kitchen with a large fridge adds convenience, while the spa-inspired bathroom enchants with a sculptural freestanding tub beneath an arched window, a double rain shower, dual sinks, and sunlight that warms the space. Step onto your private, fully fenced, tranquil patio and immerse in serene elegance and calm.

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 youâll 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

Weeki Wachee River Escape Waterfront Home w/Kayaks
Stay at this Weeki Wachee River Escape! 2 BR, 2 BA, updated coastal-themed home on the river that sleeps up to 6 people with a floating dock! The main house has a large master BR with king bed, full bath, beautiful kitchen and living room with bunk beds (twin and full) The patio is screened-in and has a dining and seating area. The little house has a queen bed, full bath and washer/dryer. Relax out back by a fire pit or cookout on the grill and enjoy the 5 kayaks and paddle board!

Stilted 2BR canal home, full kitchen, yard, pets!
This unique place has a style all its own. Nestled upon an actual island within the Ozello Keys, Crystal River! Backwater canals to the Gulf of Mexico is the view from this loft style, stilt home. Recently renovated with all the conveniences guests love into the overall design. The property offers plenty of parking for all your toys (RV's require prior Host approval). Easily fits up to 8 vehicles. Dog friendly! FOUR Kayaks/Paddles included with your stay! Fully equipped home!

PARADISE POINT on Weeki Wachee (Boat Welcome)
Find tranquility at Paradise Point, a charming, private STUDIO home so there is not a separate bedroom. Our canal feeds into the Weeki Wachee River just before Rodgers Park. Short, easy paddle, (less than a quarter mile) to the amazingly clear, turquoise rivers. Stunning views from the back porch. Don't miss breathtaking sunsets on the water and watch for manatees, dolphins, and otters. âď¸ PLEASE NOTE: đž NO pets!

Harbormasterâs Loft-Nature and Kayak
Find your zen...Relax in the surroundings of an 150 acre bird sanctuary. Hear the sounds of the birds and star gaze into the night. Paddle to the crystal clear waters of the weeki wachee from bay lake pond, then 15-20 min nature paddle down canal to river . Observe manatees, birds, otters and turtles , or spend the afternoon at the beach watching dolphins or cast a fishing line into the pond or river..
Popular amenities for Pine Island vacation rentals
Pine Island condo rentals

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Relax in a Newly Renovated Beach Front Paradise

Crystal River Bungalow with boat slip

Condo On The Beach - Heated Pool - Self Check-in

GORGEOUS SUNSETS Starting at $69 night

Florida Breeze

Modern Waterfront Condo - Captivating Sunset Views

Newly Remodeled Condo In The Heart Of Innisbrook
Pine Island house rentals

Private waterfront house with large outdoor bar

Rachel's Place

Weeki Wachee Pirate House-6703 W. Richard Dr.

Riverfront Escape on the Weeki Wachee with Kayaks

"Ruf'n It" On The River w/kayaks

Gulf of Mexico Waterfront Retreat.

Florida Fishing and Kayaking Paradise

Waterfront home heated pool+jacuzzi+game room+golf
Other great vacation rentals in Pine Island

Beautiful sunsets, waterfront 2/2 pool home

HORSE FARM Retreat, Newer Built Private Guesthouse

Mason Creek River House

The Banyon House 2br 2Ba on Canal + Kayaks

Orange Blossom Retreat

The Palm Tree Getaway

Budget-Friendly Getaway ⢠Nature, Trails & Springs

Cozy & Stylish Studio Getaway
All about Pine Island
Despite being the largest island off Floridaâs 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 regionâs more popular tourist destinations. You can spend a day or two exploring the 17-mile islandâs 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, youâll 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 Floridaâs 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 islandâs 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 islandâs 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
- Central Florida Vacation rentals
- Miami Vacation rentals
- Saint Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- 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
- Weeki Wachee Springs State Park
- Black Diamond Ranch
- Ben T Davis Beach
- Hunter's Green Country Club
- World Woods Golf Club
- Bird Creek Beach
- Gandy Beach
- Homosassa Springs Wildlife State Park
- Honeymoon Island State Park Pet Beach




