Holiday rentals in Chokoloskee

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.

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.

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!

The Everglades House

We welcome you to your next adventure! This 3-bedroom home is located in a unique, historic "Old-Florida" style town known as Everglades City (a.k.a. Ochopee). Home includes beautiful & serene waterfront views where you can lie back, relax, read a book or have a drink, while your kids can fish from the dock! You can enjoy activities like airboat tours, eco/wildlife-tours, fishing guides, bicycling, kayaking, walk the nature trails local bars and restaurants. We look forward to hosting you!

Stilt Home in Paradise

This waterfront house is walking distance from four different restaurants, and just a 10 minute drive from the nearest beach in Marco Island. The property is on a corner lot which gives optimal privacy for our guests! This vacation rental also comes with a covered boat lift, a kayak and paddle board for your enjoyment. Guests can catch snook and tarpon off their own private dock, for the true south Florida experience! Book your stay for a vacation that is fun for the whole family.

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.

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

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.