Chokoloskee Island Vacations from $729
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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
Save 100% on your flight
Price was $1,111, price is now $729 per person
$729
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,000 reviews)
It took more than two hours to check in after check point of 4:00 pm - We supposed to get a call to confirm that the room was ready, a call that never happened. There has been a lot of rain so it did not help to have a clear view of the whole property. Restaurants are of good quality and the staff was very nice.
Reviewed on Aug 1, 2026
Shell Island Beach Club
East End
Save 100% on your flight
Price was $1,379, price is now $926 per person
$926
per person
Oct 3 - Oct 10
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (24 reviews)
Great place to stay on the beach! Woman at the front desk was rude!
Reviewed on Jun 7, 2026
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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 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
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.
