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Vacation rentals in Pine Island

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Top-rated vacation rentals in Pine Island

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Top guest favorite
A covered outdoor seating area features four dark blue Adirondack chairs arranged around a small fire pit. Wooden decking provides a warm contrast underfoot, while lush greenery lines the waterway in the background, enhancing the serene riverside setting.
Cabin in Spring Hill
5 out of 5 average rating, 104 reviews

A Frame Stream Dream Cedar Cabin-WeekiWachee River

This charming A-Frame Cedar Cabin is a perfect retreat on the Weeki Wachee River. Families enjoy kayaking, fishing, or relaxing on the dock by the water. In the evening, the atmosphere transforms with underwater lighting and LED dock lights. The cabin features 2 cozy Cedar bedrooms, including one with a spiral staircase and a master suite with water views. The main bathroom has a waterfall faucet and there's a heated outdoor shower nestled in nature. Create unforgettable memories on Weeki Wachee

Top guest favorite
A charming cottage exterior is surrounded by tropical trees and well-maintained grass. The building features a mix of blue siding and stone accents, while large windows offer natural light. A cozy patio area with lounge chairs invites relaxation.
Home in Spring Hill
4.93 out of 5 average rating, 244 reviews

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.

Guest favorite
Several boats are docked alongside a wooden pier, surrounded by lush greenery and trees. A soft, golden light enhances the serene scene, while a rainbow stretches across the sky, adding a touch of color to the tranquil waters.
Condo in Crystal River
4.95 out of 5 average rating, 161 reviews

Retreat, waterfront condo/boat slip/pool

This exclusive complex offers old Florida charm. Raised boardwalks, pool, dock with boat slip, scallop cleaning station and abundance of wildlife to watch. Perfect for a couple, allows up to four. We offer breath taking sunrise and sunset floor to ceiling views. Kayaking, scalloping, birdwatching, fishing, golf and swimming with manatees are all available locally. Fantastic seafood restaurants, grocery stores, and shopping all close by. Come experience the best Crystal River has to offers

Top guest favorite
The bathroom features a freestanding bathtub and two elegant showerheads within a marble-tiled enclosure. Natural light enters through a round window, highlighting the floral accents on the counter. Gold fixtures add a luxurious touch to the modern design.
Guest suite in Spring Hill
4.99 out of 5 average rating, 226 reviews

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 55” TV, or curl up in a comfortable reading chair. The compact kitchen with a full-size 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 yourself in serene elegance and calm…

Guest favorite
A sandy area beside the canal features a wooden picnic table and several brightly colored Adirondack chairs. Kayaks are neatly arranged along the shore, while lush greenery and towering trees provide a serene backdrop overlooking the calm waters.
Home in Spring Hill
4.93 out of 5 average rating, 327 reviews

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.

Top guest favorite
A screened-in outdoor space features a large patio area with several lounge chairs and a dining table, all overlooking the river. A kayak is stored nearby, and a built-in ladder leads down to the water for convenient access.
Home in Weeki Wachee
4.97 out of 5 average rating, 174 reviews

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!

Top guest favorite
Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.
Cottage in Tampa
4.98 out of 5 average rating, 244 reviews

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.

Guest favorite
A modern kitchen features blue cabinets and stainless steel appliances. Natural light fills the space, highlighting the countertop's clean design. The open layout connects seamlessly to a living area, which includes light-colored furnishings and decorative rugs, creating a welcoming environment.
Home in Spring Hill
4.96 out of 5 average rating, 114 reviews

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!

Guest favorite
A cozy living area features a turquoise and white beach-themed couch, complemented by a neutral armchair. A coffee table sits in front of a flat-screen TV on a white mantel. Soft lighting is provided by lamps near the windows, which are adorned with sheer curtains.
Cottage in Weeki Wachee
4.96 out of 5 average rating, 300 reviews

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.

Top guest favorite
A river house is depicted, featuring a wide deck with yellow railings. Below, a sandy area is surrounded by stones, with two blue lounge chairs and a sliding board leading into the water. Kayaks and a boat are visible nearby, along with greenery and a clear blue sky.
Home in Weeki Wachee
4.99 out of 5 average rating, 201 reviews

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.

Top guest favorite
A wooden dock extends into a serene canal, flanked by lush palm trees and vibrant greenery. A gazebo and outdoor seating area are visible in the background, providing inviting spaces for relaxation amidst the tranquil surroundings.
Cottage in Spring Hill
4.99 out of 5 average rating, 147 reviews

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. ⭐️ PLEASE NOTE: 🐾 NO pets!

Top guest favorite
A wooden dock extends along a tranquil canal, bordered by lush trees and potted plants. Adirondack chairs are positioned on the patio, offering a peaceful view of the water and surrounding homes reflected in its surface.
Home in Spring Hill
4.98 out of 5 average rating, 101 reviews

Seahorse River House @ Weeki Wachee

Located in Weeki Wachee Gardens, FL launch right off the back deck for a short paddle to the crystal clear Weeki Wachee River. Enjoy the area by using one of our provided 7 adult & 2 youth kayaks, 2 paddle boards, 1 canoe and life jackets of all sizes. Swim with manatees in the backyard canal or fish right from our private dock where you can also tie up your boat or enjoy a short boat ride to the Gulf of Mexico.

Popular amenities for Pine Island vacation rentals

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.

  1. Airbnb
  2. United States
  3. Florida
  4. Hernando County
  5. Pine Island