Vacation rentals 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.

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

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...

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!

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

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.

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.

"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.

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.