
Chokoloskee Island Vacations from $353
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The Latest Chokoloskee Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Quality Inn Fort Myers Cape Coral
$353
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
7.6/10 Good! (431 reviews)
I had to change my room because the A/C was not working correctly! And I didn't have water for three hours. Because the hotel had a problem with the water. Then when the water fix the hot water was brown. That took a while to change color. Bad experience with the hotel!!!😡😡 I would like a full refund!!!
Reviewed on Sep 21, 2026

The Perry Hotel Naples
$972
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
We had such a wonderful experience here! ❤️ This is a great place to come with the family. The atmosphere was welcoming, the food was delicious, and everyone made us feel right at home.
We’re visiting from Miami, and we’re so glad we found this place! We would definitely recommend it to other families and would love to come back again. ⭐️⭐️⭐️⭐️⭐️
Reviewed on Sep 21, 2026

Tween Waters Island Resort & Spa
$940
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining.
Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes.
The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove.
All staff we encountered were very friendly and helpful.
We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded.
The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva.
Overall I would recommend and would stay here again.
Reviewed on Sep 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

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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















