Holiday rentals in Chokoloskee Island

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Top-rated holiday rentals in Chokoloskee Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.
Home in Naples
4.95 out of 5 average rating, 131 reviews

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

Top guest favourite
A tranquil pool area is showcased, surrounded by lounge chairs and palm trees. The inviting water reflects the blue sky and waterfront views of lush greenery. The building nearby features a light exterior, complementing the serene atmosphere of the space.
Apartment in Marco Island
4.99 out of 5 average rating, 136 reviews

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

Guest favourite
An open living area is viewed from a dining space, featuring a large wooden table set for meals. Comfortable seating is arranged around a coffee table, with large windows providing an unobstructed view of the pool area outside. A television is positioned on a black media console.
Home in Naples
4.95 out of 5 average rating, 241 reviews

3 bdrm up to 6 guest pool walk to Vanderbilt Beach

Our home is located in the heart of North Naples. It is less than 1mi. to the beautiful white sand Vanderbilt Beach. Our brand new remolded non-smoking, 3 bedroom 2 bath home is surrounded by numerous local restaurants, entertainment and shopping centers. It's less than 1mi to the newest Naples hot spot "The Mercato". It's 10 min to downtown Naples, 15mi to Miromar Outlets SWFL top place to shop. You can relax in our open floor plan that leads out to the deck of private Pool and hot tub.

Guest favourite
A wooden dock juts out over calm water, flanked by mangrove vegetation. Two adirondack chairs are positioned for relaxation, offering unobstructed views of the water. A cozy cottage is visible in the background, surrounded by palm trees, under a clear blue sky.
Cottage in Everglades City
4.98 out of 5 average rating, 173 reviews

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.

Guest favourite
The living area showcases a comfortable seating arrangement featuring a brown recliner sofa and loveseat. A wooden coffee table sits in the center, with a flat-screen TV mounted on the wall. Large windows provide natural light, enhancing the open and airy feel of the space.
Home in Ochopee
4.93 out of 5 average rating, 40 reviews

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!

Top guest favourite
A modern stilt home is nestled along a canal, featuring a large deck accessible by wooden stairs. Palm trees frame the exterior, while a private dock provides space for a boat. The tranquil setting is enhanced by the soft glow of the sunset.
Home in Naples
4.99 out of 5 average rating, 173 reviews

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

Top guest favourite
Cottage in Goodland
4.98 out of 5 average rating, 139 reviews

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.

Guest favourite
A well-maintained swimming pool is surrounded by palm trees and lounge chairs. The water reflects clear blue skies, creating a calming ambiance. A fenced area provides security and separation from the surrounding environment, enhancing the inviting look of this open space.
Apartment in Everglades City
4.81 out of 5 average rating, 215 reviews

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.

Top guest favourite
Apartment in Marco Island
4.92 out of 5 average rating, 222 reviews

Marco Island Beach Club 201 - Modern 2 bed/ 2 bath

Enjoy the comfort of this bright, clean 2nd-floor, end-unit condo at Marco Island's Beach Club. Save money compared to expensive hotels and enjoy all the amenities of home. With 1,100 sq ft, this condo is ideal for a couples getaway or family vacation. Located on the peaceful south end of Marco Island, the Beach Club is just a short walk from over six bars, restaurants, a movie theater, and mini-golf—only three blocks away. The Marriott is just a mile away.

Top guest favourite
A stilt home is surrounded by lush greenery, featuring palm trees and manicured grass. The entrance is accessible via a white staircase leading up to a screened porch, emphasizing the elevated structure among the tropical landscape.
Home in Chokoloskee
5 out of 5 average rating, 86 reviews

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.

Guest favourite
Cottage in Marco Island
4.97 out of 5 average rating, 128 reviews

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

Guest favourite
A refreshing pool area features a heated pool surrounded by lounge chairs and a dining table. An inflatable pink flamingo floats in the water, while colorful umbrellas provide shade. Lush greenery frames the outdoor space, creating a bright and inviting atmosphere.
Home in Naples
4.92 out of 5 average rating, 160 reviews

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Popular amenities for Chokoloskee Island holiday rentals