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Holiday houses in Chokoloskee

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Top-rated holiday rentals in Chokoloskee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Villa in Everglades
5 out of 5 average rating, 29 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 serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.
Home in Naples
4.96 out of 5 average rating, 127 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

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, 145 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
4.98 out of 5 average rating, 178 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, 43 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!

Guest favourite
Home in Chokoloskee
4.96 out of 5 average rating, 27 reviews

Sunset Point, Bayfront Home on Chokoloskee Island

Sunset Point sits directly on Chokoloskee Bay, offering front-row seats to breathtaking sunsets over the water. Perfect for fishing or kayaking adventures in the Ten Thousand Islands, this peaceful getaway captures the charm of a quaint fishing town with a local restaurant and a small museum just around the corner. The home is ideally located right across from the boat ramp and next to a marina store stocked with bait, tackle, beer, and ice—everything you need for a day on the water.

Superhost
Cottage in Marco Island
4.93 out of 5 average rating, 142 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! Delightful rustic home- perfect for a seaside retreat!. Designed for dockside enjoyment: hammocks, swing chairs, outdoor dining. Enjoy a taste of old Florida! - 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

Top Guest favourite
A modern single-story home is showcased with a sleek facade and an inviting entryway. A well-maintained driveway leads to a garage, with green landscaping and carefully arranged plants adorning the front. Large windows allow natural light to fill the interior space.
Home in Marco Island
4.98 out of 5 average rating, 107 reviews

Flamingo Paradise 4 min walk from Beach Access.

Time, and worries of the rest of the world, will melt away as you are captured by the serenity of this beautiful location. This 3 bedroom home accommodates up to 8 guest, all with its own private heated pool. This is the best option to create the story of a perfect vacation with family and friends. This house is newly renovated with a modern look steps away from the beautiful white sanded beach. Its fully equipped with gym, laundry, BBQ, and even with bikes for the whole family.

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
4.93 out of 5 average rating, 188 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 the Marjory Stoneman Douglas Visitor Center, Everglades Gulf Coast Center. Great fishing and boating community. The cabin is cozy and rustic. Sleeps up to 4 guests. There is a screened outdoor living space overlooking the water. 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
Cottage in Goodland
4.98 out of 5 average rating, 146 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.

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
4.82 out of 5 average rating, 226 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.

Popular amenities for Chokoloskee holiday rentals

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