Chokoloskee Island Vacations from $325

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The Latest Chokoloskee Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites

Stay Inn & Suites

Winkler
Save 100% on your flight
$325
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
5/10 (1,001 reviews)
The place is good for the price

Reviewed on Jul 31, 2026

Manasota Key Resort

Manasota Key Resort

Save 100% on your flight
$624
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop 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
$1,086
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)
Front desk staff-awesome Valet staff- great Roof top manager and waitress. RUDE. Everyone else was terrific and property was clean, etc.

Reviewed on Aug 7, 2026

Shell Island Beach Club

Shell Island Beach Club

East End
Save 100% on your flight
$993
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

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$1,184
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
Everything excellent Excellent

Reviewed on Aug 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.