Chokoloskee Island Vacation Packages 2026 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

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

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

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

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

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

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.