Chokoloskee Island Vacations from $466
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
$913
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,074 reviews)
We had a pleasant stay. The hotel is very modern and the staff is friendly. Our room was very nice and clean. The only issue we had was trying to reach guest services over night. I left a message with guest services and also messaged them through the expedia app and no one replied to my request to have a later check out. When I called in the morning, they said they had already met the amount of courtesy late check out requests and that I would have to pay for any extra time. Anyways, don’t know if I would come back when visiting seed to table.
Reviewed on Aug 30, 2026
Lehigh Resort Club
Joel
$491
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (115 reviews)
I like the hotel however needs upgrade they have bicycles and stuff but most they were flat or not working
Reviewed on Aug 20, 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.
