Chokoloskee Island Vacations from $921

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The Latest Chokoloskee Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Manasota Key Resort

Manasota Key Resort

Save 100% on your flight
$921
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (304 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$991
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Me gustó la limpieza la atención muy buena sobre todo Regina la del frente y la Sra Migdalia que nos ayudó mucho en conjunto todos muy amables volveremos

Reviewed on Aug 9, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$1,086
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Great location, excellent facilities and a short walk across the road to the beach to watch th sunset. Excellent and thoroughly recommend

Reviewed on Aug 8, 2026

Casa Ybel Resort

Casa Ybel Resort

Mid Island
Save 100% on your flight
$1,027
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (391 reviews)
I’ve been staying at Casaybel for 49 years! Everything was great! Rooms very clean. The pool was good. The only problem I had was the front desk with a package that was delivered by the post office through Amazon that showed delivered yet the girl said there was no package and she would check the mailbox. The next day no call. So when we came back from dinner I stopped at the mail box and it was packed with mail and my package! I wonder how often they check the mailbox? Also I paid for weekly chairs and umbrella at the beach. One day it rained in the morning. I called and left a message for my chairs after the sun was shining and no call and no chairs. I found people on the beach with chairs and asked if they were brought out for them and she told me she retrieved them herself. No compensation. I understand they have staff issues with the beach stuff but then they shouldn’t offer them when 2 chairs and 1 umbrella cost $150 per week when I could have ordered them from Billy’s. My family owns 6 weeks and we love it! I also rented this week in the 1 bedrooms through Expedia since my family is growing. Maybe they could do better with the problems I experienced. Thanks for listening. Oh and also we saw a coyote walking around between the beach and the building 😳

Reviewed on Aug 9, 2026

Shell Island Beach Club

Shell Island Beach Club

East End
Save 100% on your flight
$1,008
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

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Stay 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.
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Chokoloskee Island Hotel Deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

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

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Deep Water Access with a Panoramic View of Chokoloskee Bay
Waterfront Everglades basecamp with dock, trailer parking, and direct bay access

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

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Waterfront Everglades basecamp with dock, trailer parking, and direct bay access
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

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

Chokoloskee FL
The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
See all 199 properties in Chokoloskee Island
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.