
Chokoloskee Island Vacations from $465
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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 $1,574, price is now $862 per person
$862
per person
Oct 10 - Oct 16
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
If you are disabled or handicapped DO NOT stay here. The management was rude and hurtful. We have stay there almost 30 years. Something bad is going on there.
Reviewed on Aug 4, 2026

Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $935, price is now $622 per person
$622
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.8/10 Excellent! (391 reviews)
Great place to stay. Always check your invoice because they had extra charges on my bill and place a huge hold on CC for deposit and takes time for return. It could be the bank too. They also charged me by error and refunded but still haven’t received after few days.the amenities were great and the beach! Also entrance with wood little bridge really scared us. I believe they fixed while we were there. Lots of bugs !! Maybe property should clean up trees and fumigate because we were bit by noseeums
Reviewed on Aug 5, 2026

Shell Island Beach Club
East End
Save 100% on your flight
Price was $1,506, price is now $1,022 per person
$1,022
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
New York (JFK) 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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $754, price is now $523 per person
$523
per person
Oct 19 - Oct 23
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.6/10 Exceptional! (75 reviews)
We enjoyed our stay very much. Checkin outside and at front desk was fast. We felt bad for the attendants outside as we were staying in the villas and we had a few heavy items. We felt it could have been an easier checkin ( shorter distance) for everyone at the valet entrance farther down closer to where sunsuites were. We had forgotten about this area. All our family used valet for their vehicles at that entrance.
We had the 3-bedroom villa which was spotless clean and so nicely decorated. The appliances were top notch ( it took a little time to learn how to operate everything). One suggestion might be a lil card with simple instructions on operation of ice maker, oven, and dishwasher. Also WiFi instructions somewhere would have saved us asking the bell hop about an access number which we didn't need.
The beds were so comfortable as well as bedding and pillows. All window coverings worked beautifully. We had a magnificent view of the peace harbor and loved the massive deck on both sides.
We had 5 people staying and 2 dogs. We did have to circulate the dinnerware as there are only 4 of everything except coffee cups & glasses. Please add a silicone flexible turner for cooking. If we'd known in advance what we had to bring along, it would have helped us. We had breakfast in the apt each morning.
The layout of the whole resort is a little complicated. The promenade is nice but it is long in terms of a walk to reflections pool. On the road side it is more complicated and no
Reviewed on Aug 4, 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.



















