Chokoloskee Island Vacation Packages 2026 from $664

Photo by Noel Benadom

The Latest Chokoloskee Island vacation packages

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

Landing Fort Myers Near Highland Pines

Daniels Corridor

Save 100% on your flight

$664

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (13 reviews)

Great place to stay with kids.

Reviewed on Aug 18, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,195

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,074 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$929

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

So nice to have the benefit of being able to enjoy both the beach side and bay side.

Reviewed on Aug 31, 2026

Wiggins Pass Chalet

Save 100% on your flight

$718

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (284 reviews)

I would especially like to highlight the wonderful service we received from Alyssa. She was incredibly sweet, attentive, and kind throughout our experience. She made us feel very welcomed and well taken care of. Alyssa truly went above and beyond, and her excellent service made our experience even more enjoyable. Thank you, Alyssa!

Reviewed on Aug 30, 2026

Lani Kai Beachfront Resort

Save 100% on your flight

$724

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (1,947 reviews)

El hotel muy cómodo. Habitaciones limpias y camas cómodas. Acceso a la playa súper fácil. Personal súper amable y siempre dispuesto a ayudar. Comida excelente.

Reviewed on Sep 1, 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

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.