Holiday houses in Pine Island

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Top-rated holiday rentals in Pine Island

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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, 249 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 exterior of a converted Chinook helicopter is showcased, featuring a fenced area and a welcoming entryway. The surrounding landscape includes greenery and sky, with details of the helicopter's design visible, blending seamlessly into the natural setting.
Plane in Brooksville
4.98 out of 5 average rating, 140 reviews

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Top Guest favourite
A serene waterfront view captures a vast expanse of calm water reflecting shades of blue, orange, and pink during sunset. The horizon is lined with soft clouds, enhancing the tranquil atmosphere of the beachfront. The sandy shore is visible in the foreground.
Home in Spring Hill
4.9 out of 5 average rating, 78 reviews

Pine Island Paradise in Weeki Wachee

Beautiful 2 Bedroom, 1 Bath Waterfront home in Weeki Wachee Florida with 2 decks providing you a spectacular view the most beautiful sunset imaginable. With fully equipped, kitchen you can create your own delectable meals or grill out on the beautiful patio area with fire pit. Visit any of the nearby restaurants to enjoy some area favorites! Right outside you will find family friendly beach with a park perfect for kids. Kayaks are supplied with life jackets and paddles. Welcome to Paradise!!

Top Guest favourite
Tiny home in Crystal River
4.99 out of 5 average rating, 128 reviews

The Shell Shack! Interactive Stay, King Bed

Welcome to The Shell Shack, where a cozy retreat meets the charm of tortoises and turtles. Immerse yourself in a unique, interactive experience surrounded by various tortoise species in a tranquil, nature-inspired setting. Perfect for animal lovers and those seeking a peaceful escape, The Shell Shack offers comfort and a touch of whimsy for a memorable stay. 🐢 2 miles away from Kings Bay, Crystal River, amazing springs and manatees as well as many restaurant/ shops. $200 smoking fine indoors

Top Guest favourite
The cabin is surrounded by lush greenery, positioned on a private peninsula. A spacious deck with seating faces the water, offering a serene view of the canal. Natural light filters through the trees, illuminating the inviting structure.
Cabin in Floral City
4.97 out of 5 average rating, 163 reviews

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

Guest favourite
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, 330 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 favourite
The cabin is situated alongside a calm river, surrounded by lush trees that display various autumn colors. The two-story structure features a spacious deck and balconies, providing outdoor seating areas. The tranquil water reflects the greenery, creating a peaceful natural setting.
Cabin in Spring Hill
4.97 out of 5 average rating, 38 reviews

River Run Retreat

This charming cabin oasis is nestled in the most serene and sought-after spot along the crystal clear portion of The Weeki Wachee River! Spacious cozy & inviting space with rustic yet modern amenities; 1 bedroom w/ king bed, & 1 loft style "bedroom" w/ 2 sets of bunk beds, + fully equipped kitchen, & a bathroom on each floor. Large windows allow you to view the ever-changing beauty of the river from every room. Step outside where you can lounge by the water, kayak the river, fish, or relax.

Top Guest favourite
A dining table set for six is situated on a covered deck, overlooking the Gulf waters. The sun sets in the distance, creating a gradient of colors in the sky. Palm trees frame the view, enhancing the serene atmosphere.
Home in Weeki Wachee
4.97 out of 5 average rating, 31 reviews

Island/Beachfront House - Majestic Sunsets

Welcome to the stunning, newly-built (2023) Beachfront Bliss! We are directly on the beach in the most desirable west side of the island. Starting with the most spectacular panoramic views of the Gulf, you'll find yourself mesmerized by the seemingly endless water view and beautiful sunsets. See dolphins and wildlife from the covered deck. Or rest in a hammock on the sandy beach for a closer look. Feel a serene constant sea breeze and the sound of gentle waves lapping along the beach.

Guest favourite
The stilt home features a spacious outdoor area with white Adirondack chairs arranged on a wooden deck. Sturdy stairs lead to the entrance, surrounded by palm trees. A clear blue sky and soft clouds provide a serene backdrop, highlighting the inviting nature of this unique property.
Home in Crystal River
4.97 out of 5 average rating, 147 reviews

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!

Top Guest favourite
A wooden dock extends over calm waters, leading to a shaded seating area under a pergola. The two-story house features a pastel exterior and multiple outdoor spaces, surrounded by lush greenery and distant waterfront homes under a partly cloudy sky.
Home in Weeki Wachee
4.99 out of 5 average rating, 177 reviews

SEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!

The house is on the main river close to Weeki Wachee springs and has great access to the Gulf of Mexico. You can dock up to a 24' boat. It is only minutes from Pine Island Beach Park, Hernando Beach and Sun West Park. It is also about an hour and half from world renowned Clearwater beach. Get the best experience Florida can offer. You’ll love Weeki Wachee and the freshwater spring that feeds seventy two degree water year round. This house has 4 bedrooms and sleeps 10!

Top Guest favourite
A tiny house, characterized by its vibrant green exterior and metal roof, is positioned alongside a gently sloping ramp leading to the entrance. Surrounding foliage and gravel pathways offer a natural setting, while the background displays open fields and a fading sunset.
Tiny home in Wesley Chapel
4.97 out of 5 average rating, 162 reviews

King Lake Hideaway

Experience something different Our Tiny house with the amenities of home. Enjoy our very private spot in nature. Beautiful lake view. This is a tiny house. 280 sq feet including the loft. Lots of natural light. It’s perfect for relaxing. We are close to beaches, Sporting venues, museums the aquarium and Busch Gardens in Tampa. Situated between Epperson and Mirada lagoons. Wesley Chapel has movie theaters, mini golf, shopping and restaurants within a short drive.

Top Guest favourite
A large tree with branches adorned with string lights creates a warm ambiance in the outdoor area. Two wooden swings hang from the tree, surrounded by a ground covered in leaves, inviting relaxation in a serene, natural environment.
Tiny home in Spring Hill
5 out of 5 average rating, 68 reviews

Charm and comfy tiny house

Enjoy the lovely setting of this romantic💘 spot in nature. Comfort and charm await you in our tiny 🏡 , just 6 minutes from Weeki Wachee State Park. It is completely private, no shared spaces. Located in the middle of a spacious and fenced lot. Immerse yourself in the quiet atmosphere surrounding by nature. Enjoy a beautiful 🌅 under the shade and refreshing breeze of the 🌳 , a delicious ☕️ , a good 🍷 , a grill barbecue 🍗 or some marshmallows by the fire pit🔥.

Popular amenities for Pine Island holiday rentals

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