Chokoloskee Island Vacation Packages 2026 from $573

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The Latest Chokoloskee Island vacation packages

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

The Perry Hotel Naples

$573

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Windward Passage Resort

Save 100% on your flight

$856

per person

Jan 3 - Jan 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.4/10 Very Good! (19 reviews)

Resort Harbour Properties

Punta Rassa

$1,344

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (372 reviews)

A+ experience

Reviewed on Oct 19, 2026

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$685

per person

Jan 16 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (31 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

$678

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (3,419 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

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

Chokoloskee FL

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Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL

10/10 Exceptional! (55 reviews)

"We had a great stay; the host was very helpful and nice, and we would definitely stay again."

Reviewed on Oct 7, 2026

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Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL

9.6/10 Exceptional! (136 reviews)

"Everything was awesome! It was the perfect place for our Everglades adventures!"

Reviewed on Aug 10, 2026

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See all 193 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.