Chokoloskee Island Vacation Packages 2026 from $347

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The Latest Chokoloskee Island vacation packages

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

Quality Inn Fort Myers Cape Coral

Save 100% on your flight

$347

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

7.6/10 Good! (417 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,050

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Great location for get unique island travel experience . Beautiful ocean view on Restaurant to see incredible sunset. Food was delicious also. Property needs to be maintained . Total price includes resort fee is a bit higher for current property conditions.

Reviewed on Sep 4, 2026

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$840

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Very short line for check in. The checking in was extremely smooth and the agent was efficient and friendly, extremely helpful!

Reviewed on Sep 6, 2026

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,014

per person

Nov 28 - Dec 5

found 4 hours ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

9.4/10 Exceptional! (9 reviews)

Landing Furnished Apartments minutes from Downtown Fort Myers

Hancock

Save 100% on your flight

$856

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

No 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.