Chokoloskee Island Vacation Packages
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Top Chokoloskee Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Casa Ybel Resort
Mid Island
CA $1,099
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (391 reviews)
Great place to stay. Always check your invoice because they had extra charges on my bill and place a huge hold on CC for deposit and takes time for return. It could be the bank too. They also charged me by error and refunded but still haven’t received after few days.the amenities were great and the beach! Also entrance with wood little bridge really scared us. I believe they fixed while we were there. Lots of bugs !! Maybe property should clean up trees and fumigate because we were bit by noseeums
Reviewed on Aug 5, 2026
Marriott Sanibel Harbour Resort & Spa
Punta Rassa
CA $1,053
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,015 reviews)
My husband and I enjoyed our time at the resort. The staff were incredibly welcoming and helpful with all our needs and the dining options were fantastic for the area. However, the main pool area felt like a state of chaos as kids were screaming running all around the pool deck and paying to attention to other people in the pool. I would not classify that as relaxing.
Reviewed on Aug 7, 2026
Ready to book your vacation to Chokoloskee Island?
Chokoloskee Island Hotel Deals
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 Jul 19, 2026
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
Ochopee FL
9.8/10 Exceptional! (21 reviews)
"Great host"
Reviewed on May 23, 2026
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL
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 $996, 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.
