
Holiday houses in Pine Island
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Top-rated holiday rentals in Pine Island
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A Frame Stream Dream-Weeki Wachee
This charming A-Frame Cedar Cabin is a perfect retreat on the Weeki Wachee River. Families enjoy kayaking, fishing, or relaxing on the dock by the water. In the evening, the atmosphere transforms with underwater lighting and LED dock lights. The cabin features 2 cozy Cedar bedrooms, including one with a spiral staircase and a master suite with water views. The main bathroom has a waterfall faucet and there's a heated outdoor shower nestled in nature. Create unforgettable memories on Weeki Wachee

Weeki Wachee Pirate House - 6703 W. Richard Dr.
Embellish in this once in a lifetime, perfect getaway on Weeki Wachee River. A local favorite! Fully furnished pirate themed, 500 sq ft home with 1 bedroom 1 bath full kitchen and sofa bed. It has everything needed to create unique memories. Swim with manatees in the crystal clear spring-fed river. Have your coffee on the porch over looking the water and your favorite drink around the fire at night. Kayaks are included. Minutes from Weeki Wachee mermaids, Pine Island Beach and Homosassa Springs.

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.

Waterfront at Weeki Wachee
This riverfront playground is perfectly located to experience the best that the Weeki Wachee River system has to offer! Use the provided kayaks for close encounters with beautiful manatees in the crystal clear water, or bring the boat. We have DIRECT gulf access and drive-on jet ski lift! Unwind after a day of playing in the river, in the brand new heated saltwater pool with a built-in Sun Shelf lounge! It's all about the outdoors here, and it's all about you. Owner is experienced Superhost.

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.

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.

Bayport Pearl. Steps to sunrise, sunset, & fishing
Welcome to the Bayport Pearl, your cozy escape nestled in the heart of Weeki Wachee. This charming studio, 1 bath retreat is just steps from the water, making it the ideal spot to sit in serenity, kayak the river, fish, soak up sun at Pine Island, or catch the mermaid show. Breezy, quiet, laid-back vibes & Old Florida charm, The Pearl invites you to slow down, unwind, and embrace the natural beauty all around. Catch sunrise to the east or the sunset to the west. Both are just steps away

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.

Dreamy Waterfront Getaway in Weeki Wachee
Experience life on the river in this relaxing waterfront home, where every day brings a new opportunity to unwind or explore. Start your mornings with peaceful water views and end your evenings with breathtaking sunsets around the fire pit. Whether you're enjoying quiet moments by the water, heading out for a day on the river, or gathering with friends and family, this home offers the perfect balance of relaxation and memorable experiences. Your river escape awaits.

Welcome to Weeki River Escape!
Keep your vacation simple yet glamorous in this coastal themed home that sleeps 7. Enjoy kayaking on the crystal clear waters of Weeki Wachee River. The main house offers a large BR, full BA, beautiful updated kitchen and living room with bunk beds. Screened in patio with dining/seating area. The guest house offers a queen bed, full BA & washer/dryer. Enjoy all the conveniences and comforts of home while enjoying beautiful waters and sunsets.

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!

Sea Glass Cabin on the Weeki with kayaks
You'll have a great time at this comfortable place to stay. The river is amazing ! This is the best location and truly is a slice of the nature coast. We are a new listing and have our host Tony on property if guest need anything. There is a separate fisherman cottage that he utilizes. Come enjoy some time on the porch swing or fish from the dock. This is a great spot to just chill and watch all the people enjoy the river
Popular amenities for Pine Island holiday rentals
Other great holiday rentals in Pine Island

Nature Coast Retreats 3/2 Heated Pool, Gulf Access

Hernando Beach Pool & Relaxation Home

Lakeside Villa

Weeki Wachee Riverfront Home with Amazing View!

Golf Cart +Fire Pit +Pedal Boat + Kayaks + Fishing

Weeki Wachee River | Clear Kayak | Waterfront

Reel Retreat | Lakefront Home with Hot Tub

The White House at Weeki Wachee Waterfront Cottage
Destinations to explore
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- Weeki Wachee Springs
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Rainbow Springs State Park
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Hard Rock Casino
- University of South Florida
- Epperson Lagoon
- Sand Key Beach
- Weeki Wachee Springs State Park
- MidFlorida Credit Union Amphitheatre
- Busch Gardens
- Splash Harbour Water Park
- Fort Island Beach
- Three Sisters Springs
- ZooTampa at Lowry Park
- Crystal River Archaeological State Park
- Adventure Island
- World Equestrian Center
- Pier 60
- Honeymoon Island State Park
- Fred Howard Park





