Chokoloskee Island Vacation Packages 2026 from $626

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The Latest Chokoloskee Island vacation packages

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

Casa Ybel Resort

Mid Island

Save 100% on your flight

$626

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (417 reviews)

Brand new place ! Beautiful and right on the beach ! The restaurant its excellent !

Reviewed on Sep 9, 2026

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,150

per person

Dec 2 - Dec 9

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (11 reviews)

The Perry Hotel Naples

Save 100% on your flight

$880

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

All great, we will return.

Reviewed on Sep 10, 2026

GreenLinks Golf Villas at Lely Resort

Save 100% on your flight

$798

per person

Dec 2 - Dec 9

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (578 reviews)

It was a great experience to stay in there we loved it

Reviewed on Sep 8, 2026

Park Shore Resort

Park Shore

Save 100% on your flight

$933

per person

Dec 2 - Dec 9

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (730 reviews)

Todo bien organizado. No todo funcionaba en la habitacion pero no clasifico a todas igual solo la q mw toco

Reviewed on Sep 8, 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.