Photo by Noel Benadom

Chokoloskee Island vacation rentals

We found 72 vacation rentals — enter your dates for availability

Experience the serene beauty of Chokoloskee Island, where lush landscapes meet the enchanting waters of Chokoloskee Bay. This tranquil haven invites you to indulge in outdoor adventures like fishing and kayaking while immersing yourself in the rich history of Old Florida. With diverse accommodations ranging from cozy condos to luxurious villas, it’s the perfect backdrop for family vacations or romantic getaways, offering the comfort and convenience of a home away from home.

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Find out more about Chokoloskee Island

Why visit Chokoloskee Island

  • Outdoor adventures: Engage in fishing, kayaking, and exploring the breathtaking scenery of Chokoloskee Bay and the nearby Florida Everglades.
  • Rich history: Discover historic sites and experience the charm of Old Florida through local excursions.
  • Tranquil atmosphere: Enjoy a relaxing retreat in a peaceful environment ideal for romantic getaways or family vacations.
  • Diverse accommodations: Choose from cozy condos, private vacation homes, or luxurious villas tailored to fit any budget.
  • Wildlife experiences: Immerse yourself in the unique wildlife and natural beauty that Chokoloskee Island has to offer.

Popular types of accommodation around Chokoloskee Island

You've chosen the beautiful Chokoloskee Island for your getaway, and now it's time to find the perfect place to stay. From cozy condos and houses to luxurious villas, there’s something for everyone. Explore top options like Chokoloskee Island Park, Chokoloskee Island Resort, and Chokoloskee RV Park, or consider the nearby hotels for added convenience. Discover your ideal vacation home in Chokoloskee and make your stay unforgettable.

  • Condos: The top choice for vacation rentals in Chokoloskee Island, offering modern amenities and stunning views.
  • Houses: A favored option for families and groups seeking spacious accommodations and a home-like atmosphere.
  • Villas: Luxurious retreats that provide comfort and beautiful surroundings for an upscale getaway.
  • Apartments: Convenient and cozy spaces ideal for couples or solo travelers looking for a simple stay.
  • Caravan Parks: A unique choice for those who enjoy outdoor living with camping facilities and communal amenities.**

Top attractions near Chokoloskee Island

Chokoloskee Island is a fantastic destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and cultural experiences. Visitors can explore historic sites, enjoy fishing in Chokoloskee Bay, and visit the nearby national and state parks. Whether you're interested in Chokoloskee tourism or simply soaking up the sun on the beach, this island has something for everyone looking to experience the beauty of Florida's nature and rich history.

  • Everglades City Hall: A historic civic government building that showcases the vibrant culture of the area. Its charming architecture offers a glimpse into the local history and serves as a hub for community activities.
  • Museum of the Everglades: A fascinating history museum that highlights the rich cultural heritage of the Everglades. Engaging exhibits tell the story of the region's past, making it a must-visit for history enthusiasts.
  • House Hammock Bay: A picturesque bay perfect for outdoor activities and relaxation. With stunning scenery and a tranquil beach atmosphere, it’s an ideal spot for kayaking, fishing, and enjoying the natural beauty of Florida.

Things to do recommended for couples

For a romantic getaway on Chokoloskee Island, explore the scenic waterways on a sunset kayak tour, savor a candlelit dinner at a waterfront restaurant, or take a leisurely stroll along the beach. Embrace the island's tranquil atmosphere for a perfect couple's retreat.

Things to do recommended for families

Families can explore the beautiful Everglades National Park, where kids can enjoy wildlife spotting and guided airboat tours. Additionally, the nearby Ten Thousand Islands offer opportunities for kayaking and fishing, making it a perfect spot for family adventures.

Things to do recommended for groups

Groups visiting Chokoloskee Island can embark on an exciting airboat tour through the Everglades, enjoy fishing trips in the Gulf of Mexico, and explore the local history at the Smallwood Store. Don’t miss the chance to savor fresh seafood at nearby waterfront restaurants.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Chokoloskee Island

When planning your trip, whether you're traveling with a group, a family, pets, or seeking extended stays, it's important to filter your options based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chokoloskee Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and much more on Vrbo.
  • Traveling to Chokoloskee Island with young kids: Traveling with little ones can be a bit daunting. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chokoloskee Island: For many families, a vacation isn’t truly satisfying without their furry companions by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chokoloskee Island: If you're in search of vacation rentals with special rates for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chokoloskee Island

Chokoloskee Island invites you to explore its stunning natural beauty and rich history. Ideal for outdoor enthusiasts, this hidden gem offers adventures in the nearby Florida Everglades, where you can experience the region's unique wildlife and breathtaking scenery. Discover the charm of Old Florida through local excursions and family-friendly activities, making it the perfect romantic getaway or relaxing retreat. Don't miss the chance to immerse yourself in the tranquil atmosphere of Chokoloskee.

  • Chokoloskee: Chokoloskee is a charming city located a mere 0.2 miles from Chokoloskee Island, offering an authentic experience for outdoor enthusiasts. Known for its stunning scenery and abundant recreational opportunities, visitors can engage in activities such as fishing, kayaking, and hiking nearby. The area features a variety of attractions, including the scenic national parks and nature reserves that surround it, making it a perfect spot for eco-tourism. Be sure to explore local resorts and recreational areas that cater to both relaxation and adventure seekers alike.
  • Everglades City: Situated about 4 miles from Chokoloskee Island, Everglades City is a gateway to the vast wilderness of the Everglades National Park. This city is celebrated for its outdoor adventures and scenic beauty, with numerous opportunities for exploring the unique ecosystem. Visitors can enjoy recreational areas, local resorts, and even some shopping in the charming downtown area. Everglades City is surrounded by lush nature reserves and parks, making it an ideal base for eco-exploration and wildlife viewing.
  • Plantation Island: Located 3 miles from Chokoloskee Island, Plantation Island is a quaint village known for its peaceful ambiance and outdoor activities. This picturesque spot invites travelers to engage in golf at local courses or relax in the recreational areas. The area is rich in natural beauty, with nearby national parks and nature reserves offering stunning views and wildlife encounters. Plantation Island is perfect for those looking to unwind while enjoying the breathtaking scenery of Florida's coastal landscape.

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your ongoing plans, or review and organize your bookings. All the properties you've saved or reserved are categorized into Potential, Upcoming, or Current Trips for easy access. To discover Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Chokoloskee Island getaway

Experience the unique character of Chokoloskee Island with a stay in a vacation home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Exploring the natural features in Chokoloskee Island

Whether you're looking for adventure or just want to spend some time taking in the scenery, Chokoloskee Island is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Gulf Coast Visitor Center (2.9 mi / 4.6 km)
  • Big Cypress National Preserve (21.3 mi / 34.3 km)
  • Chokoloskee Bay (2.4 mi / 3.8 km)
  • Fakahatchee Strand Preserve State Park (15.7 mi / 25.2 km)
  • Union Key (11.5 mi / 18.5 km)
  • Remuda Key (11.8 mi / 19 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chokoloskee Island?
The most in-demand types of vacation rentals in Chokoloskee Island are mobile homes. Looking for something different? Vrbo has a variety of options to match the unique needs of our guests, so you'll see vacation properties in all sizes and shapes. The perfect fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Chokoloskee Island?
A number of things can affect the price of a vacation rental in Chokoloskee Island, like the time of year, length of stay and property type. However, all of our vacation homes have one thing in common — excellent value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Chokoloskee Island?
The average price for a vacation home near the beach in Chokoloskee Island depends on when you're traveling and the style and size of property you're looking for. Find prices easily and quickly on Vrbo by entering the dates you'll be traveling. Then use the filter tool to pick the number of bedrooms and amenities that you require, like air conditioning, a pool and WiFi.
Are there pet-friendly vacation rentals in Chokoloskee Island?
With five properties that welcome pets, your little buddy can also come along on your Chokoloskee Island break. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
Are there large group vacation rentals in Chokoloskee Island?
Yes, there are nine vacation homes in Chokoloskee Island that can accommodate five or more people. From family get-togethers to special occasions like birthday parties, these stays have enough room to gather with the people that matter the most.
Are there one-bedroom vacation rentals in Chokoloskee Island?
Yes, there are 4 one-bedroom properties in Chokoloskee Island to choose from. A one-bedroom vacation property is a superb choice if it's just you and your partner or if you're vacationing alone. Add in more privacy, space and convenience than a standard hotel, and you have yourself a trip to remember.
Can I find two-bedroom vacation rentals in Chokoloskee Island?
Chokoloskee Island has six two-bedroom properties for you to pick from. Book a vacation home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Chokoloskee Island?
Chokoloskee Island has six vacation rentals with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to sending emails, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Chokoloskee Island?
Chokoloskee Island has 13 vacation rentals where you'll be able to chill out in air-conditioned comfort. To locate a stay on Vrbo featuring this amenity, choose your travel dates and use the convenient filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Chokoloskee Island?
You'll have to check with the Chokoloskee Island vacation home you're looking at on Vrbo as the minimum age varies. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Chokoloskee Island for?
The amount of time you can rent a Chokoloskee Island vacation rental for varies depending on the property. Simply tap in your dates of travel to find options that offer extended stays. They include all you require to make your extended getaway more enjoyable like kitchens and laundries. Some vacation homes might also offer discounted weekly or monthly prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Chokoloskee Island?
Short stay or extended escape, Vrbo has some fantastic deals and discounts in Chokoloskee Island that'll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what's just been added with one of our newly listed homes. Whatever you're after, you'll find the perfect place to stay — at an affordable rate.

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