Vacation rentals in Pine Island

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Top-rated vacation rentals in Pine Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
A boat deck is presented with a shaded area featuring a built-in grill and multiple seating arrangements. Lush green grass leads from a paved pathway to the water's edge, while palm trees and tranquil waters create a serene setting.
Home in Hernando Beach
4.99 out of 5 average rating, 131 reviews

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!!

Top guest favourite
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, 241 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.

Top guest favourite
The house stands elevated on stilts, featuring a wrap-around balcony with white railings. The exterior is a soft yellow, complemented by green foliage. A set of stairs leads to the entrance, while a spacious parking area is visible beneath the structure.
Home in Crystal River
4.98 out of 5 average rating, 125 reviews

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.

Guest favourite
A cottage featuring a light blue exterior is surrounded by greenery and mature trees. The front yard is spacious, with a gravel pathway leading to the entrance, and the sunset casts warm colors across the sky.
Cottage in Spring Hill
4.95 out of 5 average rating, 111 reviews

Weeki Wachee cottage getaway

Weeki Wachee cottage that sleeps 4. Bedroom has a king and the couch pulls out and sleeps 2(kids). Plenty of space outside to park your boat, trailer, or toys. There is a 10x20 RV pad with 30A hookup available for extra. No dump station. Two kayaks, fish cleaning table, fire pit, horseshoes, cornhole, netted gazebo, smartTV, propane grill, board games, laundry. 1 dog w/fee. Hammock outside. WW Springs Park- 3 min drive. Rogers Park - 6 mins /Jenkins, & Linda P are 7 mins. Bayport Park 10 min.

Top guest favourite
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
4.96 out of 5 average rating, 170 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 favourite
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, 216 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 Toshiba 55” 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.

Top guest favourite
A gentle-looking fox rests on the ground beneath a fence, surrounded by greenery. Its white fur blends with the natural surroundings, and its dark eyes reflect curiosity. The area is covered with soft earth and decorative wood chips, creating a tranquil setting.
Farm stay in Dade City
4.93 out of 5 average rating, 350 reviews

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

Guest favourite
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, 112 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!

Top guest favourite
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
4.98 out of 5 average rating, 199 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 favourite
An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.
Tiny homes in Dade City
4.98 out of 5 average rating, 175 reviews

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.

Top guest favourite
A blue kayak rests on a wooden dock surrounded by vibrant pink flowers. Still waters reflect the colorful homes in the background under a partly cloudy sky, creating a serene and inviting space for outdoor activities.
Guest suite in Weeki Wachee
4.98 out of 5 average rating, 270 reviews

Harbormaster’s 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..

Top guest favourite
A stone pathway meanders through lush greenery, leading towards a serene seating area. Tall palmetto plants are situated on either side of the path, with vibrant seating visible in the background. Sunlight filters through the surrounding foliage, creating a peaceful invitation to relax outdoors.
Cottage in Brooksville
4.94 out of 5 average rating, 475 reviews

Whispers of Country Where your soul will Wander.

The Shebeen – a charming retreat nestled along the Brooksville ridge, on a picturesque working dairy farm. Here, adventure meets relaxation in a space designed for, reflection, and a bit of romance. Let the rhythmic sound of the farm surround you as you step into a world where time slows, and every moment feels like a sweet escape. Book your stay now and find a little magic in every moment.

Popular amenities for Pine Island vacation rentals

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