Vacation rentals in Chokoloskee Island

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Top-rated vacation rentals in Chokoloskee Island

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

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Guest favorite

Farm stay in Naples

4.84 out of 5 average rating, 154 reviews

Happy Little Camper on Modern Farm #4

Cabin tent has been upgraded to handcrafted 🏕️ glamping camper✨ Same luxurious, boho décor & scenic view of farm animals, w/ year-round protection from the elements. Extra creature comforts: WiFi, AC, TV, mini fridge. Camp-like amenities: Detached restroom & shower, fire pit 🪵, outdoor kitchen, private deck. Camper on 2.5 acre farm, cows, goats, chickens, & Caribbean garden. Come glamp w/ a partner or BFF. Enjoy the freedom & closeness of backyard camping without the uncomfortable, scary parts!

Guest favorite

Guesthouse in Naples

4.91 out of 5 average rating, 107 reviews

Ecofriendly Yoga Retreat 6 min to Beach

Guests can enjoy an adult only, clean, quiet, TV-free, 300 sq. ft indoor space and a tropical bathhouse surrounded by a serene garden setting, and private entrance. Entire property is non-smoking. Perfect for yoga, meditation, creative work and nature lovers. Garden and patios can be enjoyed between 7 am and 10 pm. Guests have free use of bikes. Property does not accept third party bookings, guest must be at least 21 years, no animals (no exceptions) or guests that like to party or smoke.

Guest favorite

Guesthouse in Naples

5 out of 5 average rating, 152 reviews

By the Beach and 5th - Studio Home with Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Guest favorite

Guest suite in Naples

4.97 out of 5 average rating, 340 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

Guest favorite

Rental unit in Naples

4.99 out of 5 average rating, 125 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

Guest favorite

Cottage in Ochopee

4.99 out of 5 average rating, 136 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 favorite

Rental unit in Naples

4.98 out of 5 average rating, 212 reviews

Bear Necessities - 1 Bdrm 1 Bthrm w/Kitchen/Lvrm

Relax and enjoy Florida indoors and outdoors in this "mini-apartment". You can watch for roaming wildlife and enjoy the tall pine trees, palm trees, and cypress trees from the patio. The "mini-apartment" is within walking distance of the canal where you can go bird watching and possibly see other wildlife. The apartment is outside of the busy hustle and bustle of the city but within driving distance of the beach. There are several restaurants with indoor or outdoor dining options.

Guest favorite

Cottage in Goodland

4.97 out of 5 average rating, 101 reviews

No Storm Damage: 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. Dockage, kayaks, and bikes available.

Guest favorite

Condo in Marco Island

4.94 out of 5 average rating, 210 reviews

Marco Island Beach Club 310 1 bed/1 bath Renovated

Come enjoy the comforts of this clean, bright 3rd floor condo in Marco Island's Beach Club. Save money over high hotel rates and have all the amenities of home. Plenty of room in this 700sf condo for the perfect couples getaway or a family vacation. Located at Marco Island's south end, the Beach Club is at a very quiet part of the island. Just a three block walk to 6+ bars/restaurants, movie theater and mini-golf. The Marriott is one mile away.

Guest favorite

Guest suite in Naples

4.96 out of 5 average rating, 132 reviews

Kismet Cottage- Private Guesthouse

A tropical paradise positioned in the middle of all Naples has to offer! Kismet Cottage is our private guest house, complete with a full kitchen, bathroom with shower/tub, living room, and patio in a tropical setting with a private keyless entry and plenty of plants, bamboo, trees, and parking. Here are some popular sights: Clam Pass Beach-5.3 mi Mercato-4.9 mi 5th Ave-S 9 mi Naples Pier-11 mi Waterside Shops-5.2 mi Lowdermilk-6.4 mi

Superhost

Guesthouse in Naples

4.8 out of 5 average rating, 313 reviews

Waterfront Sea Cottage

Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

Guest favorite

Rental unit in Everglades City

4.96 out of 5 average rating, 492 reviews

Everglades City Getaway - 2 BR Apartment

Escape from the big city to the little City of Everglades! Centrally located to explore the Everglades and other parks in Southwest Florida. This Airbnb accommodates 4 people and is within walking distance of boat tours and local restaurants. The base price is for 2 people. Additional guests over 2 are charged $15/ per person per night.