Holiday houses in Pine Island

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Top-rated holiday rentals in Pine Island

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

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Top Guest favourite

An aerial view of a spacious three-story home is presented, bordered by lush greenery and palm trees. A private dock extends into the water, featuring seating areas for relaxation. The surrounding area is tranquil, showcasing a blend of natural and residential scenery.

Home in Spring Hill

4.98 out of 5 average rating, 116 reviews

Newly Offered-Great Location - Sleeps 12 + Kayaks

Gulf Access +LOCATION!The whole group will enjoy easy access to everything from this centrally located place. See the drone photos on this ad. This home is ONLY a 5 min via kayaks to : The Main Weeki Wachee River + Rogers Park Playground + Rogers Park Beach + Rogers park Boat Ramp + Jon Boat Rentals + Upper Deck Resturaunt & located on a Deep- Water channel just a couple streets off Shole Line Blvd. Bicycles and Kayaks are included so you can experience the River Life to the fullest!

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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, 275 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.

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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

4.87 out of 5 average rating, 95 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!!

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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, 353 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.

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Superhost

A serene view of the ocean at sunset, with vibrant hues of orange and pink reflected on the water's surface. Palm trees frame the image, while lush foliage adds to the natural setting, creating a peaceful coastal atmosphere.

Home in Weeki Wachee

4.82 out of 5 average rating, 165 reviews

Island House, Gulf Views Pine Isl., Tampa, Orlando

Private, island -house with breathtaking ocean views (+tons of space indoor & out to relax!) You'll have the privacy of the entire home, & screened in patio in this updated stilt house. Enjoy memory foam mattresses, stainless steel appliances, WiFi, Smart TV's - everything guests need to make your stay on this quaint island a cherished memory. Breathtaking Gulf views from nearly every window of the house! Watch dolphins frolic from your private deck. 10 min walk to the island beach-park.

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Superhost

A spacious waterfront property is set on a canal, surrounded by greenery and palm trees. The structure features a large screened-in area, showcasing the outdoor living space and pool, while reflecting the tranquil water nearby.

Home in Spring Hill

4.86 out of 5 average rating, 126 reviews

PALM CREEK GETAWAY spring meets gulf+pool/spa

Enjoy natural spring yet only minutes kayaking to the gulf: 4BR, 3 full baths + living + dining + outdoor dining by screened & heated salt-water pool and spa ($30/nite extra) + screened patios. Get away to kayaking, scalloping, fishing, crabbing, biking, watching dolphins/manatees, fire pit, hammock in Florida sun... 5 mins drive to Weeki Wachee State Park, 7 mins drive to Pine Island, 30 mins to Homosassa, 1 hr to Tampa, 2 hrs to Disney. Close to restaurants, stores, grocery...

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Top Guest favourite

Home in Weeki Wachee

4.99 out of 5 average rating, 228 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.

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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

4.98 out of 5 average rating, 207 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.

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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

4.99 out of 5 average rating, 107 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🔥.

FamilyValueRiver

Top Guest favourite

The image captures the serene Weeki Wachee River, characterized by its clear waters and lush greenery lining both banks. A wooden dock with a ladder leads down to the water, while gentle ripples and blue sky complement the natural landscape.

Home in Spring Hill

4.98 out of 5 average rating, 106 reviews

Home On the River - Weeki Wachee Cabin

Escape to our peaceful Weeki Wachee River retreat, where relaxation meets adventure. Nestled on the clear part of the river, our family-friendly getaway offers everything you need for a memorable vacation. Tube down the crystal-clear waters, kayak through stunning scenery, and snorkel in the pristine river. Enjoy swimming, fishing, and wildlife sightings. Discover the perfect blend of tranquility and excitement at our Weeki Wachee River oasis.

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Top Guest favourite

Two teal lounge chairs are positioned on a private deck, offering a view of a calm waterway reflecting a vibrant sunset. In the background, a kayak is visible on the water, with lush greenery along the shore adding to the serene setting.

Home in Spring Hill

5.0 out of 5 average rating, 28 reviews

Pine Island Escape | Kayaks, Sand, Sunsets & Games

Tucked away on a rare double lot just steps from Pine Island’s sandy beach, Coastal Cozy Cabana is perfect for beach lovers, anglers, and nature seekers. This 3BR, 2BA home offers kayaks (4 adult, 2 youth), 2 docks, and space to unwind. Watch dolphins from shore, paddle calm Gulf waters, or grill your catch and stargaze at night. Inside, enjoy a cozy, beachy vibe with all the comforts of home—your laid-back Old Florida escape awaits!

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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

4.98 out of 5 average rating, 43 reviews

Island/Beachfront House - Majestic Sunsets

Welcome to the stunning, recently-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. [Please review recent nightly rate changes under details]

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