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Holiday houses in Chokoloskee

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Top-rated holiday rentals in Chokoloskee

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Guest favourite
An outdoor deck area features four Adirondack chairs surrounding a circular fire pit. The deck is surrounded by white gravel and lush greenery, providing a peaceful view of the nearby tidal creek, enhanced by clear skies and natural sunlight.
Guesthouse in Ochopee
5 out of 5 average rating, 12 reviews

Waterfront Everglades Cottage

Waterfront private guest house on the creek. Get your own private view of mangroves and birds just off halfway creek in Everglades city Florida. Modern with rainfall shower in bath room, pull out sleeper queen memory foam couch and master bedroom can be set up as either 2 twin xl or a king bed. Fully equipped kitchen, and 65” tv for relaxing in the evenings. Outdoor deck and fire pit for evening lounging and enjoyment. Sit on the dock and enjoy the tidal creek or relax in the Adirondack chairs.

Top Guest favourite
A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.
Condo in Park Shore
4.94 out of 5 average rating, 104 reviews

Lush tropical 1st floor getaway in Naples

Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

Top Guest favourite
A private patio area features a smooth surface bordered by lush tropical plants and colorful flowers. A three-tiered blue water fountain adds a calming element, accompanied by comfortable seating arrangements. The space is set against a backdrop of vibrant greenery, presenting a serene outdoor escape.
Guest suite in Naples
4.97 out of 5 average rating, 410 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

Guest favourite
A wooden dock juts out over calm water, flanked by mangrove vegetation. Two adirondack chairs are positioned for relaxation, offering unobstructed views of the water. A cozy cottage is visible in the background, surrounded by palm trees, under a clear blue sky.
Cottage in Everglades City
4.98 out of 5 average rating, 168 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

Top Guest favourite
A bright living area features large glass sliding doors that open to a private patio with views of lush greenery. A round dining table with four chairs is positioned adjacent to the doors, while a dark sofa is placed nearby, creating a welcoming and open atmosphere.
Cottage in Naples
4.98 out of 5 average rating, 184 reviews

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

Guest favourite
A spacious building with a modern design is flanked by palm trees under a clear blue sky. The entrance is marked by a covered area, with a parking lot visible in the foreground, offering ample space for vehicles.
Condo in Everglades City
4.81 out of 5 average rating, 202 reviews

Everglade Isle Palms Condotel w/ Pool & Boat Ramp

It’s island time! Welcome to your home base for exploring the Florida Everglades. With all the comforts of home, our Condotel will be your ideal vacation spot. Explore Everglades National Park, the 10,000 islands, airboat tours, and more! Bring your boat or rent one for saltwater, brackish, & freshwater fishing- all from this unique & pristine area. Located in the heart of town, you’ll be in walking distance of several restaurants, ice cream parlors, and the grocery store.

Top Guest favourite
A stilt home is surrounded by lush greenery, featuring palm trees and manicured grass. The entrance is accessible via a white staircase leading up to a screened porch, emphasizing the elevated structure among the tropical landscape.
Home in Chokoloskee
5 out of 5 average rating, 81 reviews

The Reel'em Inn, Chokoloskee Island Paradise

Take in the tropical feel of Chokoloskee Island in an impeccably maintained 3 bedroom/2 bath single family stilt home nestled in the canopy of Royal Poinciana trees and palms. This fisherman's paradise is a unique find in a small fishing village in the heart of the Everglades National Park. Captain Brock Wagner is available for full day private fishing charters. After a day of fishing or kayaking simply relax in a rocking chair on the 600 sqft screen porch.

Guest favourite
Cottage in Marco Island
4.97 out of 5 average rating, 119 reviews

Coastal Paradise! Kayaks+Bikes+Fishing+Boat Dock

Direct back bay access+ boat dock & lift+ kayaks + bikes. 1 mile to Everglades National Park! Minutes to shops & dining! Adorable spacious home- perfect for a seaside retreat!. Designed for dockside enjoyment: hammocks, swing chairs, outdoor dining - 5 minute boat ride to beach -12 minute car ride to beach -Walk to waterfront dining & live music -Kayak in the Everglades -Fish off the dock -Cool, rustic Old Florida vibe -Bring your boat or rent one

Guest favourite
A stilted home is set in a spacious yard, surrounded by a chain-link fence and lush greenery, including banana plants. A flight of stairs leads to a raised porch with a railing. A variety of trees provide shade, with vehicles visible at the edge of the property.
Home in Chokoloskee
5 out of 5 average rating, 49 reviews

Chokoloskee/Everglades City

Enjoy this cozy stilted home on Chokoloskee Island, located in the Everglades. The double lot makes it easy to travel with your boat, trailer or RV. 2 boat ramps are located less than 5 minutes away. There is plenty to do such as exploring Everglades National Park, kayaking or fishing the Ten Thousand Islands, and enjoying the freshest seafood. 6 bikes are available to use. The entire property is fenced in making it great for pets.

Top Guest favourite
A cozy living area is highlighted with a light sofa and green accent chair, complemented by a glass-topped table. A large vibrant palm tree artwork adorns the wall, while a staircase leads to the upper sleeping area. Natural light fills the space through nearby windows.
Tiny home in Pelican Bay
4.99 out of 5 average rating, 292 reviews

TINY House BIG Living Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, step inside our “Tiny House" and ease into beach life! Gallery white walls, oversized art and 12' living room ceiling make the 360sf space feel more expansive. Sailor's knot rope tied around anchored cleats create a banister railing to the 5'6" loft bedroom nestled above a 6'2" kitchen and bathroom. The private entrance was designed for absolute privacy.

Top Guest favourite
The exterior of a cozy cabin is depicted, featuring a porch with a screened area. A gravel pathway leads to the entrance, while two green waste bins are positioned beside the building. A well-maintained shrub adds greenery to the setting.
Cabin in Everglades City
4.91 out of 5 average rating, 164 reviews

Everglades City waterfront cabin

Bring your boat to this waterfront community in the heart of the Everglades and the 10,000 Islands. Across from Everglades National Park. Great fishing and boating community.. cozy cabin Sleeps up to 4 guests. Large outdoor living space. Community heated pool. 20$ boat launch fee to be paid next door at Glades store. Loft space and utility room are off limits to guests.

Guest favourite
A modern kitchen features white cabinetry with gold hardware, complemented by open shelving. Stainless steel appliances, including a microwave and dishwasher, are visible. A two-sided kitchen island with two brown bar stools offers additional seating and workspace.
Villa in Naples
4.98 out of 5 average rating, 119 reviews

Las Casitas in Naples # 3

Welcome to your home away from home! Beautifully renovated condo, located close to shops, restaurant, and the beach. This condo is located at the edge of a natural preserve; giving you the best of both worlds: you can sit in the backyard and enjoy a quiet and relaxing afternoon, or take a short walk and find yourself at local restaurants, the beach, wine bars, or shops.

Popular amenities for Chokoloskee holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Collier County
  5. Chokoloskee