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

4.85 out of 5 average rating, 118 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!

Jan 21 – 28

€ 119 per night

Superhost

Vacation home in Bonita Springs

4.8 out of 5 average rating, 105 reviews

Amazing home w canal views, a mile from the beach!

New&Amazing location Walk or bike riding distance from the best escape to the most beautiful beach locations in Southwest Florida . This 1-bedroom, 2-bed and fold up bed spacious home has an open floor to allow the family to enjoy time away from home. The porch has seating to watch the sunsets with canal views. Step outside to relax play board games or just enjoy the fireplace while you chat with the family. This great place with lots of room for fun. Short distance to Fort Myers, Naples.Miami2

Sep 27 – Oct 4

€ 142 per night

Superhost

Guesthouse in Naples

4.81 out of 5 average rating, 294 reviews

Waterfront Sea Cottage

*Newly rebuilt after Hurricane Ian. Expect some construction within the main home. 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.

Aug 13 – 20

€ 107 per night

Guest favorite

Cottage in Ochopee

4.99 out of 5 average rating, 107 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.

Jan 3 – 10

€ 418 per night

Guest favorite

Guest suite in Naples

4.97 out of 5 average rating, 299 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the 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.

Sep 12 – 19

€ 135 per night

Guest favorite

Tiny home in Naples

5.0 out of 5 average rating, 140 reviews

BEACHYVibes TINY House Pickleball Ct Mile to Beach

From the minute you step inside our “Tiny House" the beachy vibe gently reminds you of why you came! The 12' living room makes the 400 sq ft space feel more expansive. Sailor’s knot rope tied around anchored cleats create a banister/railing to the 6’2” spacious loft bedroom. Nestled below an eat-in kitchen and full bath. Located less than one mile from the beach in the center of the city hustle, the stand alone new construction has a private entrance and luscious outdoor private patio.

Sep 21 – 28

€ 170 per night

Guest favorite

Apartment in Naples

4.98 out of 5 average rating, 167 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.

Jul 25 – Aug 1

€ 92 per night

Guest favorite

Guesthouse in Naples

4.93 out of 5 average rating, 112 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

Jul 30 – Aug 6

€ 162 per night

Guest favorite

Home in Naples

4.97 out of 5 average rating, 109 reviews

Everglades Nature House.

Attention Nature Lovers! The house is on 3 acres of Florida Everglades landscape. You will enjoy the sound of the wind through the pine, oak and palm trees surrounding the property. You may be to able see wildlife such as hawks, owls, kites, turkey, deer, bears, bobcats, or panthers. A canal is a short walk down the street, you may see alligators and wading birds. The property is very relaxing, a great place to get away and gaze at the stars and hear owls hoot.

Oct 29 – Nov 5

€ 136 per night

Guest favorite

Home in Naples

5.0 out of 5 average rating, 124 reviews

Peaceful Gulf Access, Kayaks, Bikes, ebikes

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.

May 24 – 31

€ 200 per night

Guest favorite

Apartment in Everglades City

4.94 out of 5 average rating, 294 reviews

Explore the Everglades! - Private 1 BR Apartment

This 1 bedroom/ 1 bath apartment located in Everglades City is clean, simple, and comfortable. It is perfectly located to explore Everglades National Park as well as other preserves and wildlife refuges in southwest Florida. Everglades City is a tiny little town literally at the end of the road on the West coast of Florida, approximately 45 minutes from Marco Island and Naples.

Jun 1 – 8

€ 112 per night

Guest favorite

Cabin in Everglades City

4.9 out of 5 average rating, 114 reviews

Everglades City waterfront cabin

Bring your boat to this waterfront community in the heart of the Everglades and the 10,000 Islands. Across from Everglades National Park. Great fishing and boating community.. Sleeps 4 Large outdoor living space. Community heated pool. Loft space and utility room are off limits to guests.

Sep 1 – 8

€ 167 per night