Chokoloskee vacation rentals

We found 73 vacation rentals — enter your dates for availability

Welcome to Chokoloskee, where the serene beauty of Florida’s coastline meets the adventurous spirit of the Everglades. This charming island invites nature lovers to kayak through tranquil waters, fish in abundant bays, and hike scenic trails, all while immersing themselves in the rich local history. With a variety of accommodations—from cozy cottages to spacious villas—travelers can enjoy a home-like experience that offers comfort and convenience for family gatherings or group getaways, making every moment unforgettable.

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Find out more about Chokoloskee

Why visit Chokoloskee

  • Outdoor Adventures: Engage in exciting activities like kayaking, fishing, and hiking in the beautiful natural surroundings.
  • Scenic Beauty: Experience breathtaking views of Chokoloskee Bay and the Gulf Coast, ideal for relaxation and photography.
  • Historic Sites: Discover the rich history of the area through its historic landmarks and local culture.
  • Island Exploration: Rent a boat to explore nearby islands and enjoy the unique ecosystems.
  • Family-Friendly Activities: Enjoy a variety of activities suitable for all ages, ensuring a memorable vacation for everyone.

Popular types of accommodation in Chokoloskee

Planning your getaway to Chokoloskee? Exciting adventures await, and finding the perfect place to stay is the first step. Discover an array of vacation rentals, including cozy condos, inviting houses, and luxurious villas. Whether you’re looking for Chokoloskee Island vacation rentals or a relaxing resort experience, we have options to suit every traveler. Explore the best vacation homes and house rentals to make your stay unforgettable.

  • Condos: The top choice for vacation rentals in Chokoloskee, offering modern amenities and stunning views.
  • Houses: A favorite for families and groups, providing space and comfort for a home-like experience.
  • Villas: Elegant and spacious, these rentals offer luxury and privacy for a relaxing getaway.
  • Apartments: A convenient option for solo travelers or couples, featuring essential amenities in a cozy setting.
  • Caravan Parks: A unique and affordable choice for those looking to enjoy the great outdoors and community atmosphere.**

Top attractions near Chokoloskee

Chokoloskee, Florida, is a perfect destination for outdoor and adventure enthusiasts, offering stunning scenery and a range of activities. Explore popular attractions like Chokoloskee Island and Chokoloskee Bay, or consider renting a boat for a unique experience. With its historic sites and family-friendly activities, Chokoloskee promises an unforgettable vacation for travelers of all ages.

  • Gulf Coast Visitor Center: Located 3 miles from Chokoloskee, this visitor center offers a gateway to adventure. Engage in outdoor activities, enjoy family-friendly experiences, and immerse yourself in the breathtaking natural beauty of the Gulf Coast.
  • Everglades City Hall: A historic civic government building situated 3 miles from Chokoloskee, this site showcases the rich cultural heritage of the area. Admire its architecture and learn about the local history that shaped the community.
  • Museum of the Everglades: Just 3 miles away, this history museum provides a fascinating look into the region's past. Discover exhibits highlighting the culture and history of the Everglades, making it a must-visit for history enthusiasts.

Things to do recommended for couples

Ready for a romantic getaway in Chokoloskee? Explore the stunning Everglades on a private airboat tour, savor a sunset picnic on the beach, or enjoy a cozy evening at a local seafood restaurant. Unwind together amidst nature's beauty and create unforgettable memories.

Things to do recommended for families

Families will delight in exploring the scenic Everglades National Park, where they can take guided airboat tours and spot wildlife. Fishing and kayaking in the peaceful waters of Chokoloskee Bay offer fun, hands-on experiences for all ages, creating lasting family memories.

Things to do recommended for groups

Explore the unique ecosystem of the Everglades with a guided airboat tour, or gather your friends for a fishing trip in the Gulf of Mexico. Experience local wildlife and enjoy breathtaking sunsets on the beach—perfect for creating unforgettable memories together.

*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 in Chokoloskee

If you're traveling with a group, family, or pets, or if you're seeking longer stays, be sure to use filters that align with your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chokoloskee with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chokoloskee with young kids: Traveling with young kids can be quite demanding. It’s important to prioritize their comfort and safety, along with finding suitable amenities, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Chokoloskee: For many families, a vacation isn’t truly complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chokoloskee: If you're in search of vacation rentals that offer discounts for stays of a month or more, 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 consider adding amenities like parking, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Chokoloskee

Chokoloskee, Florida, offers a unique blend of outdoor adventure and serene beauty, making it an ideal vacation spot. Explore the idyllic Gulf Coast and nearby islands, where you can unwind in a friendly, welcoming atmosphere. Enjoy romantic getaways or family-friendly activities as you soak in the stunning scenery and vibrant local culture. Whether you're seeking recreation or relaxation, Chokoloskee and its surrounding areas promise an unforgettable experience.

  • Chokoloskee Island: Chokoloskee Island is a stunning destination that embodies the essence of natural beauty and outdoor adventure. Situated a mere 0.2 miles from Chokoloskee, this island invites travelers to immerse themselves in its scenic landscapes. Visitors can enjoy a variety of outdoor activities, from exploring the recreational areas to relaxing at local resorts or country clubs. The proximity to significant landmarks like the national park, state park, and nature reserve provides ample opportunities for wildlife viewing, hiking, and photography, making it a perfect spot for nature lovers and adventure seekers alike.
  • Everglades City: Located 3 miles from Chokoloskee, Everglades City is a charming community that serves as a gateway to the wonders of the Everglades. This city is renowned for its outdoor experiences and stunning scenery. Travelers can indulge in various activities such as visiting resorts, exploring recreational areas, or shopping at local mall centers. The nearby national park and nature reserve offer breathtaking views and chances to engage with Florida's unique ecosystems, making it an ideal destination for those looking to experience the great outdoors and enjoy the tranquility of nature.
  • Plantation Island: Just 2 miles away from Chokoloskee, Plantation Island is a quaint village that attracts visitors with its serene atmosphere and outdoor experiences. This village features recreational areas and shopping venues, catering to both adventure enthusiasts and those seeking a leisurely day out. Surrounded by natural landmarks like the national park, state park, and nature reserve, Plantation Island provides an excellent backdrop for hiking, birdwatching, and enjoying the picturesque landscapes of Florida's unique environment.

Best time to go to Chokoloskee

If you're planning a trip to Chokoloskee, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January, March and September, while off-peak times, like June, August and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyAverageSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnySlightly HighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnyAverageAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnySlightly LowAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnySlightly LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnySlightly HighSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnyAverageAverage
December69.4°F (20.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you eager to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy even greater savings. To discover a Vrbo property that matches your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing itineraries, and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The waterfront setting of Chokoloskee is ready to explore

The island views and other outdoor surroundings create an inviting atmosphere in Chokoloskee. This relaxing and welcoming city is known for its fishing, boating and seafood restaurants. 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

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chokoloskee. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Chokoloskee Bay (2.2 mi / 3.6 km)
  • Gulf Coast Visitor Center (2.8 mi / 4.4 km)
  • Big Cypress National Preserve (21.4 mi / 34.4 km)
  • Fakahatchee Strand Preserve State Park (15.6 mi / 25.1 km)
  • Collier Seminole State Park (19.6 mi / 31.5 km)
  • Union Key (11.4 mi / 18.3 km)

Frequently asked questions

What is the best area to stay in Chokoloskee, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Chokoloskee, Florida, the area around the historic Chokoloskee Island is a fantastic choice. This charming neighborhood offers a unique blend of tranquility and access to the natural beauty of the Everglades. Visitors often enjoy exploring the nearby Everglades National Park, where you can immerse yourself in the stunning landscapes and diverse wildlife. Another top attraction is the Smallwood Store, a historic site that offers a glimpse into the area's rich history and local culture.

In terms of vacation rentals, this area tends to have a range of properties that cater to different preferences, from cozy cottages to waterfront homes. Staying here provides a great opportunity to enjoy the peaceful atmosphere while being close to outdoor adventures and cultural experiences.
How much does it cost to rent a vacation home in Chokoloskee?
Prices for vacation rentals in Chokoloskee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chokoloskee to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chokoloskee vacation house rentals?
You can find great discounts on house rentals in Chokoloskee on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chokoloskee?
For renting a beach house in Chokoloskee, travelers should explore the charming coastal areas along the Gulf of Mexico, particularly around the beautiful Ten Thousand Islands National Wildlife Refuge. This region is known for its stunning natural scenery and opportunities for outdoor activities. Many beach houses in Chokoloskee feature amenities such as private docks, outdoor seating areas, and views of the water, making them ideal for fishing enthusiasts and those seeking a peaceful retreat.

Additionally, properties located near the small community of Chokoloskee Island often come equipped with modern kitchens, spacious living areas, and access to nearby beaches where guests can enjoy sunbathing or shelling. The close proximity to Everglades National Park also provides opportunities for eco-tours and wildlife viewing, with many rentals offering kayaks or bicycles for exploring the surrounding areas.

The local atmosphere is laid-back, with a few quaint shops and restaurants nearby, ideal for travelers looking to enjoy a quiet getaway.
What is the most popular type of vacation rental accomodation in Chokoloskee?
In Chokoloskee, vacation houses are the most common type of rental, with several options available throughout the area. These homes typically feature multiple bedrooms, full kitchens, and spacious living areas, making them ideal for families or groups looking to enjoy a relaxing getaway. The rentals often come with outdoor patios or decks, allowing guests to soak in the serene surroundings and warm Florida weather. Additionally, mobile homes and cottages are also popular in Chokoloskee, providing more affordable yet comfortable alternatives for travelers. Condos are available as well, often located near the water, and they usually include amenities like pools and communal areas.
Are there any family house rentals in Chokoloskee?
In Chokoloskee, Florida, there are some family-friendly house rentals available, with around 11 options to choose from. This charming locale offers a unique blend of natural beauty and outdoor activities, making it an appealing destination for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor decks where kids can enjoy the fresh air.

Visitors will find that the area is close to attractions such as the Everglades National Park, superb for exploring wildlife and engaging in water sports like kayaking and fishing. The tranquil surroundings also provide opportunities for leisurely bike rides or nature walks.
Can I rent a vacation home with a pool or hot tub in Chokoloskee?
In Chokoloskee, there are several vacation homes available for rent that feature pools and hot tubs. This charming area offers a unique blend of natural beauty and tranquility, ideal for travelers looking to unwind. Many of these rentals come with private pools, outdoor spaces for lounging, and hot tubs for relaxation after a day of exploring.

The properties often include amenities such as fully equipped kitchens and spacious living areas, making them great for families or groups.
Can I find long-stay vacation rentals in Chokoloskee?
A long-stay vacation rental in Chokoloskee is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chokoloskee?
In Chokoloskee, travelers will find several pet-friendly house rentals that cater to both comfort and convenience. Many of these vacation homes come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. This charming area is known for its proximity to the beautiful Everglades National Park, offering outdoor adventures like hiking and kayaking, which are great for pet owners looking to explore the natural surroundings together with their furry companions.
Are there any remote work vacation rentals in Chokoloskee?
In Chokoloskee, there are several options for remote work vacation rentals, with around 13 properties available. This unique area in Florida offers a peaceful environment ideal for productivity, surrounded by stunning natural beauty. Many rentals come equipped with essential amenities such as high-speed internet and Wi-Fi, ensuring a seamless work experience.

Travelers can expect comfortable living spaces that may include dedicated work areas, full kitchens for meal preparation, and outdoor areas for relaxation during breaks. The proximity to the Everglades National Park provides opportunities for outdoor activities, allowing for a great balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chokoloskee vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chokoloskee with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chokoloskee?
In Chokoloskee, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and spacious decks or patios for enjoying the warm Florida weather. Many rentals also offer onsite parking for convenience, and porches or lanais provide additional outdoor space to relax and take in the serene surroundings.
When is the best time to visit Chokoloskee for a vacation rental?
The best time to visit Chokoloskee for a vacation rental is during the peak season from January to March. This period attracts a wide range of travelers looking to escape colder climates, making it the ideal time for those seeking warm weather and outdoor adventures. With average temperatures ranging from the mid-60s to low 80s Fahrenheit, it's great for enjoying activities like kayaking through the mangroves or exploring the beautiful Everglades National Park.

January is particularly popular, as visitors can experience comfortable temperatures while engaging in birdwatching and fishing in the tranquil waters. The natural beauty of the area shines during this time, with opportunities for sightseeing that can easily be enjoyed in a leisurely manner.

For those looking for a more budget-friendly option, consider visiting in August when the crowds thin out. While summer temperatures can rise into the 90s Fahrenheit, this quieter time offers the chance for a more serene experience and the opportunity to enjoy the local wildlife in a less hectic setting.

Ultimately, the best time to visit Chokoloskee hinges on your preference for vibrant, bustling activity during peak season or a more laid-back experience in the summer months.
How early should I book a Chokoloskee vacation rental?
Book your Chokoloskee vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chokoloskee, Florida, United States of America?
In Chokoloskee, Florida, visitors can immerse themselves in the natural beauty and unique attractions of the Everglades. The area is known for its proximity to the vast Ten Thousand Islands National Wildlife Refuge, where travelers can explore pristine mangroves and spot diverse wildlife such as manatees, dolphins, and various bird species. Vacation rentals in this region often offer easy access to kayak and boat tours, allowing guests to navigate the serene waterways and experience the rich ecosystem.

The historic Smallwood Store, located nearby, provides a glimpse into the area's past and serves as a museum showcasing the history of Chokoloskee and the surrounding region. For outdoor enthusiasts, nearby Everglades National Park offers hiking trails and opportunities for fishing, birdwatching, and photography.
Can I change or cancel my Chokoloskee home rental booking on Vrbo?
To find Chokoloskee vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chokoloskee vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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