Chokoloskee Island Vacation Packages 2026 from $363

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The Latest Chokoloskee Island vacation packages

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

Quality Inn Fort Myers Cape Coral

Save 100% on your flight

$363

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

7.6/10 Good! (431 reviews)

The Perry Hotel Naples

$1,220

per person

Dec 10 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight

$545

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,001 reviews)

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$869

per person

Nov 27 - Dec 2

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,077

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Reviewed on Sep 17, 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

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL

10/10 Exceptional! (54 reviews)

"Place was spotless and nicely decorated. Great location for fishing. Great hospitality. Thanks for a great stay"

Reviewed on May 24, 2026

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

Chokoloskee FL

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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 198 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.