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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
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, 115 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!

Top guest favourite
Home in Hernando Beach
4.99 out of 5 average rating, 161 reviews

Fire pit, Golf Cart, Kayaks, PedalBoat, 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, 274 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 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!!

Top guest favourite
Home in Homosassa
5.0 out of 5 average rating, 21 reviews

Reel Serenity-Waterfront Escape in Old Homosassa-I

Welcome to Reel Serenity, your private slice of waterfront paradise in Old Homosassa. Nestled along the tranquil waters of the Nature Coast, our retreat offers the perfect balance of relaxation and adventure. Step out the back door and onto your private dock. Sip your morning coffee as dolphins or manatees glide by, launch a kayak or paddleboard for a peaceful cruise, or cast a line for some of Florida’s best inshore fishing. Here, the water isn’t just a view — it’s part of your daily rhythm.

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, 241 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, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

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.

Top guest favourite
Camper/RV in Spring Hill
4.99 out of 5 average rating, 176 reviews

Weeki Waterfront Airstream Glamping Experience

Nature Oasis 🤩 Glamping (Glamorous Camping) Experience in 25-foot Airstream Travel Trailer (RV) ✅ Lush forest views ✅ Tranquil waterfront location (paddle down the canal to the pristine Weeki Wachee River) ✅FREE amenities - hot tub, outdoor shower, firepit, griddle, bikes, yoga mats, kayaks, & stand-up paddle boards. SELF CARE UPGRADE is $100/person. It includes access to shared space: food forest, garden & waterfront wellness studio with experiences curated for you by your hostess.

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, 202 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 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 homes in Spring Hill
4.99 out of 5 average rating, 104 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🔥.

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, 27 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!

Top guest favourite
A two-story house is positioned beside a private canal, featuring large windows that invite natural light. A spacious deck with outdoor seating is visible, along with a wooden dock and a kayak moored nearby. Lush greenery and a large tree frame the scene, creating a serene atmosphere.
Home in Spring Hill
4.97 out of 5 average rating, 125 reviews

Charming 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, 1 paddle board, 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