Chokoloskee Island Vacations from $569
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa
$816
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
The manager was horrible and completely u accommodating. I have never felt so attacked and the unwillingness of the reservations manager to accept payment or the phone even was a joke. It was a great property but the manager was horrible. My fiance tried paying for our room and was denied. Had all our reservations cancelled to be told the were sold out but in fact we're not. I. Brought my family 24 hours away from home only to be denied service. And totally discriminated against
Reviewed on Aug 23, 2026
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See all available trips from Columbus to Chokoloskee Island
View all tripsStay 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.
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
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL
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
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.
Find the Best Chokoloskee Island Vacation Packages
Chokoloskee Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
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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.
