Holiday houses in Chokoloskee

HGTV’s “Vacation House for Free” Marco Island Home

Beautifully decorated fishing, ocean, beach themed home. Featured on HGTV. Renovated and located on Marco’s only golf course. Private heated pool, hot tub, gourmet kitchen. We have a private gated side fence area that will accommodate your private fishing vessel if you so desire. Located only 3-5 Minutes from the beach, shops, parks and restaurants. Public boat ramps provide easy access to the 10,000 Islands and Everglades National Park is only a 45 min drive. Enjoy! It’s an island getaway!

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

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Oasis Downtown Naples 3 BD/2 BA full house w/ a HEATED pool, outdoor entertaining, BBQ grill, lanai seating/dining for 8, outdoor games, 2 living rooms w/ large TVs (main room has a 75" screen TV), master suite w/ ensuite bathroom & flatscreen TV, all 3 bedrooms have king beds. Close to downtown restaurants/shopping (9 min), beaches/Naples Pier (14 min). DOG POLICY: Only after owner's approval, a non-shedding small dog is allowed with $100 per dog non-refundable fee (2 dog maximum).

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.

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

🏡 THIS LUXURY PROPERTY IS IDEAL FOR FAMILIES/SMALL GROUPS (SLEEPS 8) YOU HAVE MADE IT! You are now viewing one of the most unique properties in Naples 🌴 & here is why: 🌳 This property is on 2.5 acres of land & VERY private 🏖️ Beach is only 12 minutes away 🍽️ 10 minutes from heart of the city (Dining, shopping, nightlife) 🏊‍♂️ Heated saltwater pool/spa ⛳ Golf putting green 🎾 2 Pickleball Courts 🏓 Ping Pong table W/AC in garage 🏀 Adjustable Basketball Hoop 💻⚡ Blazing fast WIFI

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.

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Boat Parking, Dockage, kayaks, and bikes available.

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.