Vacation rentals in Chokoloskee

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Top-rated vacation rentals in Chokoloskee

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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.

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.

Guest favorite

A private dock extends over calm waters, reflecting the clouded sky and surrounding greenery. Sturdy posts provide support along the water's edge. Colorful outdoor furniture can be seen in the background, offering a relaxed space to enjoy the waterfront views.

Home in Goodland, Marco Island

4.9 out of 5 average rating, 397 reviews

SWFl waterfront home with direct Gulf access

Private waterfront home in the quaint fishing village of Goodland. We are on a deep water canal with 40 foot of dock space to park your fishing boat, with direct access to the Gulf of Mexico and the 10000 Islands National Park. We have 3 marinas ,walking distance , to launch your boat and get gas. Our home has a 300 square foot screened in porch and a 450 square foot dock with southern exposure to watch the sunrise and sunsets . The Marco Island shopping and beaches are 5 miles away.

Top guest favorite

A screened-in outdoor area features a clear blue inground pool alongside a jacuzzi, both surrounded by stone pavers. Lush greenery is visible beyond the enclosure, providing a serene backdrop. Comfortable seating awaits for relaxation in this private oasis.

Home in Naples

4.94 out of 5 average rating, 131 reviews

Venetian Photoshoot - La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

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, 195 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

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, 318 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, 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.

Top guest favorite

The exterior of a cozy cabin is depicted, featuring a porch with a screened area. A gravel pathway leads to the entrance, while two green waste bins are positioned beside the building. A well-maintained shrub adds greenery to the setting.

Cabin in Everglades City

4.91 out of 5 average rating, 157 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.. cozy cabin Sleeps up to 4 guests. Large outdoor living space. Community heated pool. 20$ boat launch fee to be paid next door at Glades store. Loft space and utility room are off limits to guests.

Superhost

A bright and airy bedroom features a spacious bed with patterned bedding, complemented by a wooden ceiling and natural light. A cozy chair and small table are positioned near a window, with a shelf displaying decorative items and a lamp providing additional lighting.

Tiny home in Marco Island

4.86 out of 5 average rating, 303 reviews

Camp Cocktail

Located in quaint Goodland FL on waterfront canal. Walking distance to Goodland Boating Park where you can launch your boat to the gulf and 10,000 Islands. Boat trailer and vehicle parking. Short walk to restaurants/bars Little Bar, Stan’s, Crabby Lady, Paradise found and Kirk’s Fish House. Minutes to restaurants and shops on Marco Island.