Holiday houses in Chokoloskee Island

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!

Attention Naples Lovers! Entire Home w/Pool&HotTub

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

The Captain's Quarters

Waterfront One-Bedroom Retreat with Private Dock Access Escape to the water and enjoy a relaxing stay in this charming one-bedroom waterfront apartment, perfect for boaters, anglers, and anyone looking to unwind by the water. Features a comfortable bedroom, bathroom, living area, and equipped kitchenette. Enjoy waterfront views from the outdoor patio. Includes Wi-Fi, Smart TV, A/C, free parking, and boat trailer parking. Close to hiking, beaches, fishing, kayaking, and outdoor adventure.

Pool Home Minutes to the Beach

Enjoy our family’s bright, renovated home and experience indoor/outdoor Florida living at its best! The open floor plan living area has high vaulted ceilings and fully-retractable glass sliders that open out to a beautiful, south-facing lanai featuring a brand-new, heated, salt-water pool complete with a waterfall-edge spa, a sun shelf and in-pool loungers! Perfect for entertaining and outfitted with all new outdoor furniture including a new sofa & lounge chairs, dining table & grill.

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.

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

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 or soak in our new pool!

Beach Paradise with Pool and Spa

Kick back and relax in this calm, stylish house. 3 minutes away from the beautiful beaches and 2 minutes away from Mackle Park. This exclusive house offers 3 sizable bedrooms two with queen size and one with king size beds, 2 full bathrooms and a fully Equipped kitchen, all with charming coastal decor and newly furnished. Every detail has been designed to ensure your comfort. Our perfect Lanai area is a perfect spot for BBQ lounging or enjoying the heated pool and Spa.

Heated Pool & Spa | Game Room | 5 Min Beach

Welcome to Sunset Serenity, a beautifully remodeled Marco Island retreat designed for unforgettable family vacations. Enjoy a heated pool, relaxing spa, game room, and spacious indoor and outdoor living areas. Located just 5 minutes from the beach, you'll be close to restaurants, parks, shopping, and scenic bike trails. Whether you're exploring the island, relaxing poolside, or unwinding under the stars, Sunset Serenity is the perfect place to create lasting memories.

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.