Holiday houses in Chokoloskee

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Top-rated holiday rentals in Chokoloskee

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Guest favourite
Cottage in Marco Island
4.94 out of 5 average rating, 162 reviews

Goodland Water view Cottage

Experience the breathtaking beauty of a sunrise from our charming coastal cottage in Goodland FL. With a stunning direct view of the water right from the living room, you can immerse yourself in the tranquility of island life. Our cottage is thoughtfully equipped to meet all your basic needs, ensuring a comfortable stay for up to three guests. Enjoy the convenience of boat dockage and trailer parking, making it easy to explore the surrounding waters and embrace the natural beauty that awaits you

Top Guest favourite
A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.
Condo in Naples
4.92 out of 5 average rating, 169 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Top Guest favourite
Villa in Everglades
5 out of 5 average rating, 18 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.

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, 173 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, 41 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
A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.
Home in Bonita Springs
4.97 out of 5 average rating, 115 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

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
4.81 out of 5 average rating, 217 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, 86 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
4.96 out of 5 average rating, 129 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 bright and airy open-concept living area features light blue walls and a spacious seating arrangement. A dining table is set for meals, while the nearby kitchen showcases minimal cabinetry and a dining nook with a table and chairs. Large windows provide natural light.
Home in Marco Island
4.88 out of 5 average rating, 195 reviews

"Waterfront & OceanAccess Oasis with Private Pool"

Discover your perfect getaway at our stunning 3-bedroom, 2-bathroom home on Marco Island, accommodating up to 6 guests. Relax in your private pool or bring your boat and use our boat lift, easy Gulf access. Enjoy beautiful beaches, world-class dining, and shopping nearby in Naples. Our home is equipped for ultimate comfort, offering peaceful, family-friendly vibes. (No pets allowed, $$$ fine for violations), no loud music, trailers, or parties.

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, 50 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
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
4.92 out of 5 average rating, 174 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.

Popular amenities for Chokoloskee holiday rentals

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