Chokoloskee Island Vacation Packages 2026 from $667

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The Latest Chokoloskee Island vacation packages

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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$667

per person

Oct 31 - Nov 7

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (87 reviews)

The Perry Hotel Naples

Save 100% on your flight

$770

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (970 reviews)

Casa Tiki

Hancock

Save 100% on your flight

$734

per person

Oct 23 - Oct 30

found 9 hours ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

No reviews

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

Manasota Key Resort

Save 100% on your flight

$795

per person

Sep 20 - Sep 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (304 reviews)

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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

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

Chokoloskee FL

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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.