Chokoloskee Island Vacations from $634
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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
Save 100% on your flight
Price was $1,085, price is now $634 per person
$634
per person
Sep 6 - Sep 13
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (912 reviews)
The rooms we had, had problems with the AC. It was cooling and the rooms were at temp of 75 to 78
Reviewed on Jul 5, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,800, price is now $956 per person
$956
per person
Sep 21 - Sep 27
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
Todo estuvo maravilloso. La instalación muy cómoda. El servicio muy bueno y amable. Las habitaciones confortables. Las piscinas en óptimas condiciones. 100 % recomendable. Definitivamente volvería a ir. Me encantó
Reviewed on Jul 5, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,149, price is now $691 per person
$691
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
We had a lovely stay. I do feel it was somewhat overpriced. The previous week was priced $100 cheaper and I think that would be more appropriate. The rooms are very nice but not exceptionally luxurious and oh that cheap shampoo was brutal. Please, please provide conditioner!! Overall though it was really charming and we had a wonderful time. Shout-out to the coffee girl who decorated every cup. That was delightful.
Reviewed on Jul 1, 2026
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,387, price is now $848 per person
$848
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,005 reviews)
Property is very modern/clean. Staff is amazing. Walking distance to wonderful restaurants and shopping.
Reviewed on Jul 5, 2026
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Chokoloskee Island Hotel Deals
Deep Water Access with a Panoramic View of Chokoloskee Bay
Chokoloskee FL
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise
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.
