Holiday rentals in Chokoloskee

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chokoloskee

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

%{current} / %{total}1 / 1

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, 129 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

Top guest favourite

A spacious bedroom is furnished with a comfortable bed dressed in white luxury linens. Two bedside lamps provide soft lighting, and a small table with a chair is positioned nearby. Decorative wall art with palm leaf designs frames the bed, while dark curtains complement the room.

Guest suite in Naples Park

4.82 out of 5 average rating, 219 reviews

#Blocks2Beach Lower Studio Palm Villa Close2 #RITZ

Gorgeous newly renovated private one King bedroom with en-suite bathroom. This 1st floor studio has modern updates with new furniture, comfortable mattress, fluffy pillows & luxury linens. Small refrigerator, microwave & Keurig in studio for guests to use. Just BLOCKS to the best beach where the sunsets are divine at Vanderbilt Beach. Easy walk to the Ritz Carlton Naples Beach Resort with the finest ocean front dining. Enjoy beach activities including shelling, SUP, fishing, kayaking & more!

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, 172 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.

Top guest favourite

A bright living area features large glass sliding doors that open to a private patio with views of lush greenery. A round dining table with four chairs is positioned adjacent to the doors, while a dark sofa is placed nearby, creating a welcoming and open atmosphere.

Cottage in Naples

4.98 out of 5 average rating, 188 reviews

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

Superhost

The exterior of the cabin is shown, featuring wooden siding and a screened porch with blue curtains. A staircase leads to the entrance, and a 'For Sale' sign is prominently displayed on the latticework. Greenery surrounds the structure, adding a natural touch.

Cabin in Everglades City

4.81 out of 5 average rating, 69 reviews

cabin2A screen room view of your dock nice view

come and fish relax heated pool cooking facilites for you bbq área with table and chairs you have your own dock park your trailer right in front of your cabin enjoy your stay please no smoking in our cabins tiky bar and restaurant acrooss your cabin note this are fishing cabins there are docks on deepwater basan not recomendado to bring children take advantage our cabins are super clean and our cleaning fee is only 30 others are100 and up save money be c0mfortable and clean

Guest favourite

A spacious building with a modern design is flanked by palm trees under a clear blue sky. The entrance is marked by a covered area, with a parking lot visible in the foreground, offering ample space for vehicles.

Apartment in Everglades City

4.81 out of 5 average rating, 212 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

An open-concept living area features a comfortable sofa and a cozy chair, oriented towards a 55" HDTV mounted on the wall. A dining table with seating for four is nearby. Natural light streams in from large windows, enhancing the welcoming atmosphere.

Flat in Marco Island

4.94 out of 5 average rating, 279 reviews

Best JW Marriott Alternative Prime~ Location~Pool

Retreat to the gorgeous 1BR 1Bath coastal oasis located across the street from JW Marriot, offering easy access just steps to the amazing beach on Marco Island. The condo's comforts, amenities, and wonderful location provide everything you need to relax, recharge, and have a perfect Gulf Coast stay! ✔ Large 1bd w King Bedroom ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Community Amenities (Pool, Hot Tub, Free Designated Parking)

Top guest favourite

A spacious living area is filled with natural light, featuring a comfortable sectional sofa and armchair arranged around a coffee table. A flat-screen TV is mounted on the wall, with access to the open kitchen visible through an adjoining doorway.

Apartment in Marco Island

4.93 out of 5 average rating, 221 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, 83 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, 124 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 spacious balcony offers views of the bay, with a palm tree framing the scene. Comfortable outdoor seating is arranged for relaxation, while distant boats are visible along the water. The bright blue sky enhances the tranquil atmosphere.

Flat in Marco Island

4.87 out of 5 average rating, 232 reviews

Amazing Olde Marco Condo, Beautiful Sunsets & Dolphins

No Damage from Hurricanes Ian, Helene, or Milton! We'd love to host you if you had planned to travel to an area affected by any of these storms in other parts of Florida. Great One Bedroom, One Bath condo in Olde Marco Island. You'll enjoy great views of the bay and amazing sunsets over the Gulf Of Mexico. You'll love all of the boats that float by and the daily dolphin sightings sitting on our back porch.