Chokoloskee Island Vacation Packages 2026 from $555

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The Latest Chokoloskee Island vacation packages

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

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight

$555

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

La limpieza excelente y el anfitrión muy atento cuando teníamos dudas nos ayudó

Reviewed on Aug 17, 2026

The Perry Hotel Naples

Save 100% on your flight

$927

per person

Nov 9 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Staff was understanding and accommodating.

Reviewed on Aug 19, 2026

Manasota Key Resort

Save 100% on your flight

$1,474

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (307 reviews)

The property need update!!

Reviewed on Aug 16, 2026

Innovation Hotel

Save 100% on your flight

$919

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (632 reviews)

All was excellent..!!

Reviewed on Aug 18, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

$675

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.8/10 Exceptional! (1,283 reviews)

They have a sunset cruise and a very nice mall. It's a great place.

Reviewed on Aug 18, 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.