Chokoloskee Island Holidays

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Photo by Noel Benadom

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Chokoloskee Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Miami Intl. Airport (MIA)

Top hotels in Chokoloskee Island

Deep Water Access with a Panoramic View of Chokoloskee Bay

Deep Water Access with a Panoramic View of Chokoloskee Bay

Chokoloskee FL
9.8/10 Exceptional! (65 reviews)
"This is an amazing spot! Perfect for a fishing trip or if you just want to get away from it all and experience old Florida. The views and access to the water can’t be beat. The house was clean, comfortable and well stocked. Lynn is a great, communicative, friendly host who made it easy. I hope to ..."

Reviewed on 19 Jul 2026

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Deep Water Access with a Panoramic View of Chokoloskee Bay
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

Chokoloskee FL
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The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Waterfront 2 bedroom 1 bath with boat slip

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
10/10 Exceptional! (54 reviews)
"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"

Reviewed on 24 May 2026

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Waterfront 2 bedroom 1 bath with boat slip
See all 198 properties in Chokoloskee Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Stay near popular Chokoloskee Island attractions

Smallwood Store

You can spend time browsing the exhibits at Smallwood Store in Chokoloskee. You can seek out the fishing spots while in the area.
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Frequently asked questions

How much does a Chokoloskee Island travel package cost?
Go from looking to booking with our Chokoloskee Island travel packages, which start from a low . Handpick the flights and hotels that fit your travel plans. Then, add on one or two sightseeing activities to round off your unique adventure.
If I'm not able to travel, can I cancel my Chokoloskee Island travel package?
Because we understand life is full of surprises, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've booked your Chokoloskee Island travel package in the last 24 hours, you may be able to cancel or change it with no penalties. Your hotel, airline or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Chokoloskee Island?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best fits you and watch your savings grow. We know a travel package is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 properties from all over the world, which lets you customize your Chokoloskee Island adventure.
Does Expedia offer Book Now, Pay Later Chokoloskee Island holidays?
Yes. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply click on the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:
  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you spot an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you get what you want.
How far in advance should I book my Chokoloskee Island holiday?
Search Expedia to compare international fares as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred air carrier, or you've left things to the last moment, don't worry. Cheap fares to Chokoloskee Island sometimes emerge within weeks of the date of departure.
What does an Expedia Chokoloskee Island travel package include?
You can choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can also add on experiences and tours. Want to pick your fare class? That's also easy to do. The choice is all yours when it comes to planning your dream Chokoloskee Island getaway.
What should I know before booking a Chokoloskee Island travel package?
You'll score amazing savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one place makes trip planning easier. So why waste money or time? Whether you're organising a ritzy city getaway or a budget family adventure, check out our package deals today.
Can I choose my airline with a Chokoloskee Island Expedia travel package?
With a travel package, you're in charge. Whether you'd prefer to fly to Chokoloskee Island in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 airline partners globally.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.