Holiday houses in Chokoloskee Island

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Top-rated holiday rentals in Chokoloskee Island

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Top Guest favourite
A spacious living area features a comfortable black sofa and a wooden coffee table. A large flat-screen TV is mounted on the wall. Sliding glass doors lead to a private balcony, offering views of the surroundings. Neutral-colored walls enhance the light and open atmosphere.
Condo in Marco Island
4.89 out of 5 average rating, 238 reviews

Marco Island Beach Club 212 – Clean 1 Bed/1 Bath!

Escape to the comfort and convenience of this bright, welcoming 2nd-floor condo at Marco Island's Beach Club. Enjoy all the amenities of home while saving on expensive hotel rates. With 700 square feet of space, it’s the perfect retreat for couples or a familes. Nestled at the quiet southern end of Marco Island, the Beach Club offers a peaceful atmosphere. Plus, you're just a short 3-block stroll from over 6 bars and restaurants, a movie theater, and mini-golf. The Marriott is only a mile away.

Top Guest favourite
Villa in Everglades City
5 out of 5 average rating, 17 reviews

Villa Serena - Tranquility Redefined

Nestled along the edge of the majestic Everglades, this refined luxury villa is a quiet sanctuary designed for those who seek both sophistication and serenity. It is fully equipped with everything you’ll need during your visit, a private dock, and easy access to restaurants and outdoor adventures. Whether you're here to visit Everglades National Park, go fishing, birdwatch, or just relax and unwind, Villa Serena offers a true retreat for the soul—this is Everglades living at its most refined.

Top Guest favourite
A tranquil pool area is showcased, surrounded by lounge chairs and palm trees. The inviting water reflects the blue sky and waterfront views of lush greenery. The building nearby features a light exterior, complementing the serene atmosphere of the space.
Condo in Marco Island
4.99 out of 5 average rating, 136 reviews

Dolphin Pardise Waterview, Wildlife, Pool &Fishing

Unique Waterfront Condo & Gorgeous Intercoastal Views, Wildlife, Fishing, Boat Dock. 1 block from Snook Inn! Adjacent Pool Steps Away from Patio. NEWLY REMODELED! Pool & 2 Private Patios overlook Beautiful Waterfront, Dolphins, Manatees, Exotic Birds. Main Floor -no steps. If you love water and WILDLIFE, this place is for you! Fishing on the dock-Fishing Poles and Tack Supplied, pull your boat right to the back door. TONS of wildlife. Dock is lit at night, watch the sea life! NON SMOKING UNIT

Top Guest favourite
A modern living area is highlighted by a spacious sofa and two accent chairs, complemented by a large flat-screen TV. Natural light pours in through sliding glass doors, which open to the balcony. A dining table sits in the corner, enhancing the open layout.
Condo in Marco Island
5 out of 5 average rating, 139 reviews

Beach Across the Street! Balcony in the ❤️of Marco

A modern 1 bed 1 bath condo nestled in the heart of Marco Island and packed with everything you need for an unforgettable and effortless trip. Enjoy the convenience of beach access right across the street and JW Marriott a block away! Perfectly located on the main strip with popular restaurants like Da Vinci's and Marco Prime, shops, grocery stores, and major convention centers just down the road. Wind down your day watching breathtaking western exposure sunsets from your own private balcony...

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, 172 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.

Guest favourite
The living area showcases a comfortable seating arrangement featuring a brown recliner sofa and loveseat. A wooden coffee table sits in the center, with a flat-screen TV mounted on the wall. Large windows provide natural light, enhancing the open and airy feel of the space.
Home in Ochopee
4.93 out of 5 average rating, 40 reviews

Paradise House on Chokoloskee Island

Relax with the whole family in this newly remodeled, quiet and peaceful place to stay on Chokoloskee Island. Great location to Big Cypress NPres, Everglades NP, Boating, hiking, kayaking, trails, lots of outdoor activities, museums, in a quiet, peaceful, safe neighbor. You are in walking distance to a fabulous Cuban Restaurant, marina and boat ramp. There is plenty of parking, bring your boat. Because some of our clients have allergies we DO NOT allow pets. ASK US ABOUT OUR KAYAK RENTALS!

Top Guest favourite
Cottage in Goodland
4.98 out of 5 average rating, 139 reviews

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Boat Parking, Dockage, kayaks, and bikes available.

Superhost
The exterior of the cabin is shown, featuring wooden siding and a screened porch with blue curtains. A staircase leads to the entrance, and a 'For Sale' sign is prominently displayed on the latticework. Greenery surrounds the structure, adding a natural touch.
Cabin in Everglades City
4.82 out of 5 average rating, 72 reviews

cabin2A screen room view of your dock nice view

come and fish relax heated pool cooking facilites for you bbq área with table and chairs you have your own dock park your trailer right in front of your cabin enjoy your stay please no smoking in our cabins tiky bar and restaurant acrooss your cabin note this are fishing cabins there are docks on deepwater basan not recomendado to bring children take advantage our cabins are super clean and our cleaning fee is only 30 others are100 and up save money be c0mfortable and clean

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, 213 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, 84 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.

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
4.92 out of 5 average rating, 173 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.

Top Guest favourite
An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.
Condo in Bonita Springs
4.99 out of 5 average rating, 152 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.

Popular amenities for Chokoloskee Island holiday rentals