
Cottage holiday rentals in Pine Island
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Top-rated cottage rentals in Pine Island
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Kayak Kottage: waterfront, kayaks, bikes, dockage
Ideal for nature lovers & adventurers! Located at end of cul-de-sac in a quiet friendly neighborhood on canals w/10 min paddle to crystal clear waters of the Weeki Wachee River & Hospital Hole. Close drive, kayak or bike to Rogers Park, boat ramp, marina & restaurants. Corner lot w/2 sides canal frontage & 20 ft dock you can safely swim off or dock your boat. Not on main river;serene wildlife viewing instead of crowds. Manatees right off the dock. 5 kayaks & 4 bikes included. 4 guests, no pets.

Serendipity Lake private dock, canoes & kayaks
What a view, what a really good view, YES IT IS! Watch the sunrise and sunset over the water on a private dock. We have 2 canoes and 2 kayaks to enjoy the water or bring your boat! This is a place you will want to come back to time and time again. Water views from all angles, you will feel like you're on a houseboat there's so much water! Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!

Weeki Wachee cottage getaway
Weeki Wachee cottage that sleeps 4. Bedroom has a king and the couch pulls out and sleeps 2(kids). Plenty of space outside to park your boat, trailer, or toys. There is a 10x20 RV pad with 30A hookup available for extra. No dump station. Two kayaks, fish cleaning table, fire pit, horseshoes, cornhole, netted gazebo, smartTV, propane grill, board games, laundry. 1 dog w/fee. Hammock outside. WW Springs Park- 3 min drive. Rogers Park - 6 mins /Jenkins, & Linda P are 7 mins. Bayport Park 10 min.

Cooper Cottage: Cozy, Convenient and Comfortable
Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Ozello Keys Cottage on Crystal Bay
2/1 Ozello coastal cottage on stilts surrounded by nature, tranquility, and endless views of the water and estuary. Nature lovers paradise. World renowned fishing and scalloping. Regular dolphin and manatee sightings. Relax with the whole family on the large screened back porch providing gorgeous views of the Nature Coast and stunning sunrises over the salt marsh. The open floor plan opens up to a large screened porch with a dining and lounging space with private and expansive water views.

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.

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.

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.

Cozy Renovated Cottage, Pet-Free Retreat
Our cottage is the perfect retreat, offering a peaceful escape in a true nature’s paradise. We are an animal‑free property due to the owners’ and their families’ severe allergies, making this a clean, allergen‑friendly stay for all guests. Just 5 minutes from all the best land and water activities, the cottage gives you quick access to everything Homosassa has to offer. You’ll love our convenient location making it easy to explore and enjoy your time on the river.

Ozello Waterfront Cabaña - minutes from the Gulf!
Calling all outdoor adventurers—this cozy waterfront cabin is your perfect basecamp. Launch straight from your private boat slip, then return to clean your catch at your own fish/scallop station. Grill up dinner on the back deck while soaking in epic water views. Whether you're fishing, scalloping, kayaking, or exploring Florida’s wild coast, this spot puts you in the heart of it all—rustic comfort meets real adventure.

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!

Cozy Cottage! “ Steps away from Kings Bay!”
This Cozy Cottage is centrally located in Crystal River, steps away Kings Bay! Heated pool, ( October til May) under the oaks, large fenced in yard, take the 4 bikes out for a cruise around the neighborhood or get the family out kayaking in the Bay, 1 double, 3 single kayaks, 1 paddle board , paddles and life jackets, 1/4 mile to 3 sisters springs! Our family has been coming here years and love the area
Popular amenities for cottage rentals in Pine Island
Cottage rentals with a hot tub

Lush Harbor Oasis with Private Hot Tub

Beachy Keen Cottage A only steps to the Beach

Cozy Lake Cottage w/ Hot Tub + Boat Parking

Lemon Cottage Steps from Beach

Breezy Botanical Bungalow

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

𖤓Updated Stilt home: just steps to the beach!𖤓
Pet-friendly cottage rentals

Gasparilla Bayshore Good Vibes cottage

3 - Lake Life House 1 bed/1bath - Unit 15

Anneliese's Cottage

Luxury Beach Bungalow | Walk to Dining & Sunset

Cozy up in a French Country nest NEAR EVERYTHING

Refreshing 1930s Cottage in Mount Dora

Serene Waterfront Cottage with Tranquil Setting

Waterfront Cottage on The Harris Chain in Leesburg
Private cottage rentals

Lakefront Boho Cottage w/ Fire Pit | Still Waters

Live Life Now Canal Cottage: Dock, Kayaks, & Bikes

B - BEACH HOUSE 3 MIN WALK TO THE BEACH

Adorable Villa 1 min to Downtown Dunedin

Spotted Dance Ranch

BeachBunkies Cottage 2. Four miles to the beach!

Historic Sweetwater Cottage |Fenced Yard & Firepit

Kamp Komfort Historic Family Beach House
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Panama City Beach Holiday rentals
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Weeki Wachee Springs
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Rainbow Springs State Park
- Hard Rock Casino
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- University of South Florida
- Fort Island Beach
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- Crystal River Archaeological State Park
- Yuengling Center
- Weeki Wachee Springs State Park
- Fred Howard Park
- Three Sisters Springs
- Ben T Davis Beach
- World Equestrian Center
- MidFlorida Credit Union Amphitheatre





