Chokoloskee Island Vacation Packages 2026 from $701

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The Latest Chokoloskee Island vacation packages

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

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$701

per person

Nov 12 - Nov 17

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

The Perry Hotel Naples

Save 100% on your flight

$1,282

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Windward Passage Resort

Save 100% on your flight

$858

per person

Nov 12 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (11 reviews)

The rooms are very comfortable and clean

Reviewed on Sep 8, 2026

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,001

per person

Nov 9 - Nov 16

found 19 hours ago

Roundtrip non-stop flight included

New York (JFK) to Fort Myers (RSW)

9.6/10 Exceptional! (11 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$886

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 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

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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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! (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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See all 197 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.