Cottage holiday rentals in Pine Island

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.

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and indulgent stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

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.

Weeki Wachee Barefoot Cottage, Waterfront, Kayak’s

Relax with the whole family at this peaceful corner lot cottage on a canal off of the Weeki Wachee river with two sides of water only a short paddle to crystal clear water just North of hospital hole . And I’m super excited to let everyone know the seawall has just been completed looks amazing definitely has transformed our property. The next phase will be a dock so as of now no dock so if you like to bring a boat only people with power poles will be able to do so .

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.

Serendipity Lake private dock, canoes & kayaks

FL is in a drought, water levels are 8ft + lower than normal. You can still enjoy fishing and kayaking on our direct waterway. Watch the sunrise and sunset over the water on a private dock. This is a place you will want to come back to time and time again. We do provide kayaks and canoes to enjoy the lakes. 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!

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

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!

Whispers of Country Where your soul will Wander.

The Shebeen – a charming retreat nestled along the Brooksville ridge, on a picturesque working dairy farm. Here, adventure meets relaxation in a space designed for, reflection, and a bit of romance. Let the rhythmic sound of the farm surround you as you step into a world where time slows, and every moment feels like a sweet escape. Book your stay now and find a little magic in every moment.

Lush Harbor Oasis with Private Hot Tub

Escape to your private resort-style cottage in the heart of Safety Harbor! This renovated retreat is perfect for a relaxing getaway. Enjoy a private hot tub, a fully fenced yard, a dedicated office, and complimentary EV charging. Perfectly located for exploring Tampa, St. Pete, and Clearwater's famous beaches. Your ideal Florida home base awaits!