Chokoloskee Island Vacation Packages 2026 from $614

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The Latest Chokoloskee Island vacation packages

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

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$614

per person

Dec 11 - Dec 15

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

The Perry Hotel Naples

Save 100% on your flight

$959

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$1,273

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,005 reviews)

Olde Marco Island Inn and Suites

Olde Marco

Save 100% on your flight

$625

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,002 reviews)

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$710

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (15 reviews)

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

Reviewed on Sep 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

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 195 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.