Chokoloskee Island Vacation Packages 2026 from $514

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The Latest Chokoloskee Island vacation packages

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

Landing Fort Myers - Eastwood Village

Eastwood Village

Save 100% on your flight

$514

per person

Oct 27 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

10/10 Exceptional! (2 reviews)

Nice place

Reviewed on Mar 25, 2026

The Perry Hotel Naples

Save 100% on your flight

$964

per person

Oct 21 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,295

per person

Dec 7 - Dec 14

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (11 reviews)

Mariners Boathouse by Coolvacay

South Island

$607

per person

Nov 17 - Nov 21

found 1 day 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

Bellasera Resort

Old Naples

Save 100% on your flight

$1,397

per person

Oct 21 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (2,328 reviews)

Great place , near to fifth ave .

Reviewed on Sep 11, 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.