Holiday rentals in Pine Island

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Top-rated holiday rentals in Pine Island

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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 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, 215 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
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
4.97 out of 5 average rating, 238 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.

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 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, 293 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 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
A colorful cottage with a screened lanai rests along a serene river. Kayaks and a floating island are docked nearby, with reflections shimmering on the water. Lush greenery surrounds the property, creating a tranquil outdoor setting ideal for relaxation and recreation.
Cottage in Spring Hill
4.99 out of 5 average rating, 163 reviews

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.

Top guest favourite
A serene outdoor patio area features blue Adirondack chairs arranged around a central fire pit, with a backdrop of lush greenery and clear waters of the Weeki Wachee River. The setting promotes a peaceful connection to nature, inviting relaxation and enjoyment of the surroundings.
Home in Weeki Wachee
4.99 out of 5 average rating, 354 reviews

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.

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 home in Dade City
4.98 out of 5 average rating, 174 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 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, 141 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!

Popular amenities for Pine Island holiday rentals

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