Cottage holiday rentals in Pine Island

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Top-rated cottage rentals in Pine Island

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Top Guest favourite

Two kayaks glide through calm waters, surrounded by lush greenery and residential properties along the canal. Brightly colored kayaks in orange and yellow contrast against the serene blue water. Sunny trees provide shade and reflections are visible on the water's surface.

Cottage in Weeki Wachee

4.92 out of 5 average rating, 378 reviews

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.

LocationFamilyView

Top Guest favourite

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

4.99 out of 5 average rating, 387 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Stroll to Dunedin's stunning sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

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Top Guest favourite

The stilt home features a light-colored exterior with multiple windows allowing natural light. A wide staircase leads to the covered porch, surrounded by green grass and palm trees. The backdrop includes a clear blue sky, emphasizing the coastal setting.

Cottage in Crystal River

4.97 out of 5 average rating, 152 reviews

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.

FamilyValueLong stay

Top Guest favourite

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

4.98 out of 5 average rating, 267 reviews

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.

FamilyValueHospitality

Top Guest favourite

A cozy living area features a turquoise and white beach-themed couch, complemented by a neutral armchair. A coffee table sits in front of a flat-screen TV on a white mantel. Soft lighting is provided by lamps near the windows, which are adorned with sheer curtains.

Cottage in Weeki Wachee

4.96 out of 5 average rating, 320 reviews

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.

ValueFamilySleep quality

Guest favourite

The cottage is situated on a peaceful corner lot by the canal, offering views of its blue exterior and a welcoming porch. Lush greenery surrounds the property, and a clear blue sky reflects in the calm water, enhancing the serene atmosphere.

Cottage in Spring Hill

4.88 out of 5 average rating, 194 reviews

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 .

LocationValueBathroom

Top 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

4.97 out of 5 average rating, 199 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.

LocationFamilyPets

Guest favourite

A screened porch offers a view of the water and surrounding landscape, with seating options including a red leather chair and a light-colored sofa. Natural light fills the space, enhancing the connection with the outdoors.

Cottage in Inverness

4.96 out of 5 average rating, 140 reviews

Serendipity Lake private dock, canoes & kayaks

Please note the 15.5% Host Service Fee is an Airbnb fee, they chose the name, host do not collect this fee. FL is in a drought, water levels are 8ft + lower than normal. You can still enjoy fishing and kayaking on our direct waterway. 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, Dunnellon or Homosassa. Simply perfect!

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Top Guest favourite

Cottage in Clermont

4.93 out of 5 average rating, 147 reviews

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.

FamilyLocationWi-Fi

Top Guest favourite

A wooden dock extends into a serene canal, flanked by lush palm trees and vibrant greenery. A gazebo and outdoor seating area are visible in the background, providing inviting spaces for relaxation amidst the tranquil surroundings.

Cottage in Spring Hill

4.99 out of 5 average rating, 169 reviews

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!

FamilyValueComfort

Guest favourite

A stone pathway meanders through lush greenery, leading towards a serene seating area. Tall palmetto plants are situated on either side of the path, with vibrant seating visible in the background. Sunlight filters through the surrounding foliage, creating a peaceful invitation to relax outdoors.

Cottage in Brooksville

4.94 out of 5 average rating, 493 reviews

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.

ValueFamilyQuiet

Top Guest favourite

Lush greenery features prominently in the scene, highlighting various palm trees and colorful flowering plants. The vibrant yellow flowers contrast with the greenery, while a soft lawn extends through the landscape. A sense of tranquility is suggested by the natural setting.

Cottage in Weeki Wachee

4.96 out of 5 average rating, 140 reviews

A Dream Cottage!!!

This property has 200 feet of river frontage. It is located next to Rogers Park & beach on the Weeki Wachee river. The living facility is a renovated trailer and large vestibule with a bar and screened patio area. There are a charcoal grill, kayaks, cable TV and Wifi available for entertainment. The location is peaceful for your enjoyment!

LocationFamilyParks