
Chokoloskee Island Vacations from $450
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.



Olde Marco Island Inn and Suites
Olde Marco
$872
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,001 reviews)
I loved this hotel!
The room was beautiful! The pictures don’t do it justice. It felt so homey, yet out of my league at the same time.😉
It was walking distance to several yummy restaurants. I stayed at this hotel alone for a few days and felt very safe at the hotel and walking to the restaurants and shops nearby, which are literally within a 5 minute walk. I spotted dolphins yesterday while eating lunch at one of the restaurants, another huge bonus to the area!
The pool and hot tub were great and had lots of pretty plants and trees with seats thru-out for shade. The price is right, it was perfect for me, 10 out of 10, I’m going again.😎
Reviewed on Sep 27, 2026

Casa Ybel Resort
Mid Island
$561
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (432 reviews)
I really liked how all the rooms have an ocean view, and how close the room was to the ocean.
Reviewed on Sep 27, 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

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

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL

Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands
Chokoloskee FL
9.6/10 Exceptional! (136 reviews)
"Everything was awesome! It was the perfect place for our Everglades adventures!"
Reviewed on Aug 10, 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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