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

A modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.

Home in Naples

4.96 out of 5 average rating, 115 reviews

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

Top guest favorite

The open living and dining space is illuminated by natural light, featuring a neutral palette and modern furnishings. Floor-to-ceiling windows provide unobstructed views of the ocean, while a cozy seating area and a dining table invite relaxation and enjoyment of the surroundings.

Condo in Marco Island

5 out of 5 average rating, 15 reviews

$150 (no pool Sep-Oct): Beachfront w/amazing views

Enjoy the stunning ocean views from every room, watch the colorful sunsets from the comfort of this home! Feel at home as this condo is truly set up to provide you with everything you need during your stay – kitchen, bedroom and bathroom essentials, beach gear, you name it! Access to Crescent beach and Tigertail beach, outdoor heated pool, fitness center in the building, outdoor tennis and pickleball courts; best restaurants and boutique shops within walking distance or just a short ride away.

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, 162 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

A charming blue cottage with an inviting entrance is surrounded by lush tropical vegetation. The exterior features a garage and large windows that enhance the cottage's character. Palm trees gently sway in the breeze, adding to the relaxed island atmosphere.

Home in Marco Island

4.97 out of 5 average rating, 117 reviews

Boater’s Paradise at the Coastal Cottage!

Perfect ENTIRE HOME for a seaside retreat! Direct access 3/2 with boat lift and dock. Charmingly furnished and designed to delight. Enjoy amazing access to Florida's best boating, fishing and beaches- just 4 minutes from the dock to end of no wake zone and a 12 minute car drive to stunning local beaches. Enjoy upstairs screened lanai overlooking tranquil waters and feel your troubles melt away as you relax in the tranquil island vibe of Old Florida! Boat rental available at near by marina.

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

4.9 out of 5 average rating, 31 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

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, 140 reviews

Top-rated luxury pool home in prime location

*No AirBnB or Cleaning Fees!* 🏠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! 🧻Household supplies and personal amenities included ✅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!

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

4.8 out of 5 average rating, 194 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 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, 316 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

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, 120 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.