Chokoloskee Island Vacation Packages 2026 from $665

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The Latest Chokoloskee Island vacation packages

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

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$665

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,004 reviews)

Este lugar es maravilloso

Reviewed on Sep 2, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$806

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

Resort Harbour Properties

Punta Rassa

Save 100% on your flight

$1,007

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (372 reviews)

The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.

Reviewed on Aug 11, 2026

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$820

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Pleasant stay. Staff friendly and attentive. Very relaxing stay. The view of the beach is a plus.

Reviewed on Aug 5, 2026

Windward Passage Resort

Save 100% on your flight

$729

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (9 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 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.