Holiday houses in Chokoloskee

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.

2 bed/2 bath Beachfront unit w/stunning views

Enjoy the stunning ocean views from every room, watch the colorful sunsets from the comfort of this home! Feel at home as this condo is truly set up to provide you with everything you need during your stay – kitchen, bedroom and bathroom essentials, beach gear, you name it! Access to Crescent beach and Tigertail beach, outdoor heated pool, fitness center in the building, outdoor tennis and pickleball courts; best restaurants and boutique shops within walking distance or just a short ride away.

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.

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!

Everglades Fishing Cabin

Escape to the heart of the Everglades in this serene waterfront cabin. This 1 bedroom 1 bath cabin is designed for anglers and nature lovers, with a private dock, fish cleaning station, and plenty of space to store your gear. No boat? No problem! Enjoy activities like shoreline fishing, air boating , kayaking or kick back and float in the heated pool. Whether you're a seasoned fisherman or just looking for a peaceful escape, this cabin offers the perfect blend of adventure and relaxation.

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.

Lost in the Glades

Welcome to Paradise! Kick back and relax like a local after a day in our charming fishing town. Two minute walk to the Barron River. Short walk or drive to local restaurants and bars. Enjoy the unique perk of discounted fishing trips when booked with Captain Derrick. Sleeps 6!! Modern comforts including Keurig, whiskey ice ball machine, and a fully stocked kitchen. *Dock available for $75 fee for the length of your stay **Option to book both duplex units for larger groups

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.

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.

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.

3BD 1-Acre Oasis: Private Pool Estate near Beaches

✨ Experience the 'Casa Bonita Florida’ Standard—where 1-acre privacy meets 5-star hospitality. ✨ Discover the unrivaled guest experience at Casa Bonita Florida—a secluded 1-acre retreat in Bonita Springs designed for ultimate privacy and coastal luxury. Spotlessly clean, pet-free, and fully stocked, we offer a "Top Shelf" stay backed by a flexible cancellation policy. Book with total confidence and relax in your own private resort!

Everglades City Getaway - 2 BR Apartment

Escape from the big city to the little City of Everglades! Centrally located to explore the Everglades and other parks in Southwest Florida. This Airbnb accommodates 4 people and is within walking distance of boat tours and local restaurants. The base price is for 2 people. Additional guests over 2 are charged $15/ per person per night.