Chokoloskee Island Vacation Packages
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Top Chokoloskee Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
CA $1,347
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
The hotel is new. Rooms are very spacious. Hotel pool is cute, although small. The boat ride to the beach is a nice touch but keep in mind you must reserve ahead of time. Having the coffee shop in the lobby was convenient. The location is a bit weird behind a small shopping center.
Reviewed on Sep 26, 2026
Ready to book your vacation to Chokoloskee Island?
Chokoloskee Island Hotel Deals
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 May 24, 2026
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Chokoloskee FL
9.6/10 Exceptional! (136 reviews)
"Everything was awesome! It was the perfect place for our Everglades adventures!"
Reviewed on Aug 10, 2026
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.
Stay near popular Chokoloskee Island attractions
Smallwood Store
You can spend time exploring the galleries in Smallwood Store during your trip to Chokoloskee. You can seek out the fishing spots while in the area.
Frequently asked questions
How much does a Chokoloskee Island vacation package cost?
Starting from as low as CA $1,040, a package is your ticket to affordable travel. Put together your Chokoloskee Island escape by selecting from our comprehensive range of hotels, flights and rental cars.
How do I get a cheap travel package to Chokoloskee Island?
Track down flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with a Chokoloskee Island vacation package. It's that easy! From flights and hotels to tours and rental cars, Expedia makes traveling on a budget easy. And with over 550 air carriers and 1,000,000 hotels globally to select from, you'll never be short of choice.
How far in advance should I book my Chokoloskee Island vacation?
Earlier is always better. Air carriers usually release flight tickets up to 12 months in advance, and this is an excellent opportunity to land some of the lowest prices. Boss just told you to take some vacation time next week? That's fine too — Expedia are never short on fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Chokoloskee Island travel package include?
From airfares and hotels to rental cars, Expedia can help you shape a Chokoloskee Island package that's ideal for you. Heading off for a while? Check out a rental car, flight and hotel bundle. If your break is short, a hotel and flight deal could be more your style. Tours and activities can be added after you've booked. Our travel packages make it easy to plan and save.
What should I know before booking a Chokoloskee Island travel package?
Whether it's relaxation or adventure you're chasing, a Chokoloskee Island vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Chokoloskee Island Expedia vacation package?
Yes, so take your pick! Expedia has access to more than 550 airlines around the world, so you can tailor your Chokoloskee Island adventure according to your style and budget.
If I'm not able to travel, can I cancel my Chokoloskee Island vacation 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 made your booking in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
