Vacation rentals in Chokoloskee Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chokoloskee Island

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

An inviting living area features a light-colored sofa adorned with colorful striped cushions. A nautical-themed artwork is displayed on the wall above. A wooden table holds decorative items, while natural light enters from nearby windows, casting a warm glow across the space.

Tiny home in Naples

4.99 out of 5 average rating, 252 reviews

BIG Memories TINYHouse Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, step inside our “Tiny House" and ease into beach life! Sailor’s knot rope tied around anchored cleats create a banister railing to a 5’6” loft bedroom nestled above a 6’2” full kitchen and bath with Surfboard Shower. The 12' living room makes the 360 sq ft space feel more expansive. The new construction is separated from the main house by a breezeway. The private entrance and courtyard was designed for absolute privacy.

Guest favorite

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, 163 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.

Superhost

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

4.91 out of 5 average rating, 32 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!

Guest favorite

A hot tub offers a relaxing retreat surrounded by lush greenery. A gazebo can be seen in the background, featuring an inviting lounge area adorned with potted plants. Natural light filters through the canopy, enhancing the tranquil outdoor setting.

Home in Naples

4.96 out of 5 average rating, 121 reviews

Tropical paradise 5 minutes from the beach

Come on in and unwind in this peaceful and one-of-a-kind oasis just a short 5-minute drive from Wiggins Pass beach! Feeling adventurous? Hop on a bike and you'll be there in a little over 15 minutes. Located in North Naples, this charming house is fully stocked with everything you need to cook, discover, unwind, and rejuvenate, this space even boasts its own private backyard facing the preserve. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

Guest favorite

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.

Condo in Everglades City

4.81 out of 5 average rating, 196 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.

Guest favorite

The illuminated pool glistens in a tranquil setting, adorned with floating yellow lily candles. Lounge chairs with striped towels are positioned beside the water, while soft lights provide ambiance around the area, creating a serene space for relaxation.

Home in Marco Island

4.97 out of 5 average rating, 141 reviews

Top-rated luxury pool home in prime location

💰No nickel & diming — AirBnb & cleaning fees in nightly rate! 🏠Newly renovated & professionally designed 👙Amazing pool and outdoor kitchen (including grill, pizza oven, fridge)! 🏖️4 mins to beach 🌊Beach chairs, umbrellas, beach wagon & bikes 🐶Low pet fee; we love our 4-legged guests! ✅Fully stocked chef’s kitchen 🛌🏽Super comfortable beds for ultimate comfort and sleep 💻 High speed internet with dedicated workspace 😊24/7 local & professional host support!

Top guest favorite

The exterior of the cottage features a welcoming entrance flanked by two comfortable chairs on a brick paved patio. Lush greenery and palm trees surround the space, creating a serene atmosphere. Large glass doors lead into the interior, inviting natural light.

Cottage in Goodland

4.98 out of 5 average rating, 125 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. Dockage, kayaks, and bikes available.

Top guest favorite

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, 80 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.

Top guest favorite

The image depicts a screened-in swimming pool area with a clear blue water surface. The surrounding patio features a smooth concrete finish. Lush greenery lines the pool's edge, and a calm waterway is visible in the background, framed by palm trees and waterfront homes.

Home in Marco Island

4.98 out of 5 average rating, 320 reviews

⭐ Rare Waterfront Western Exposure Vacation Home

This dream getaway home is located in the heart of Marco Island with everything you need for an unforgettable trip! Enjoy the convenience of being only minutes away from South Marco Beach, with its white sand and clear blue skies, and the best restaurants such as Da Vinci's, Marco Prime, The Snook Inn, The Oyster Bar and shopping on the Island! Wind down your day watching breathtaking Western exposure sunsets from your own waterfront patio and dock...

Guest favorite

Cottage in Marco Island

4.97 out of 5 average rating, 117 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 favorite

A stilted home is set in a spacious yard, surrounded by a chain-link fence and lush greenery, including banana plants. A flight of stairs leads to a raised porch with a railing. A variety of trees provide shade, with vehicles visible at the edge of the property.

Home in Chokoloskee

5 out of 5 average rating, 48 reviews

Chokoloskee/Everglades City

Enjoy this cozy stilted home on Chokoloskee Island, located in the Everglades. The double lot makes it easy to travel with your boat, trailer or RV. 2 boat ramps are located less than 5 minutes away. There is plenty to do such as exploring Everglades National Park, kayaking or fishing the Ten Thousand Islands, and enjoying the freshest seafood. 6 bikes are available to use. The entire property is fenced in making it great for pets.

Top guest favorite

An outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.

Home in Naples

4.98 out of 5 average rating, 121 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.