Chokoloskee Island Vacation Packages 2026 from $548

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The Latest Chokoloskee Island vacation packages

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

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$548

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

The Perry Hotel Naples

Save 100% on your flight

$1,100

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,759

per person

Dec 19 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

Landing Apartments Fort Myers near Eastwood Village

$602

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (31 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$693

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,013 reviews)

This was an amazing place to stay. The staff was amazing. The rooms were clean and the amenities were great. we will definitely be returning.

Reviewed on Oct 6, 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

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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Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

Chokoloskee FL

9.6/10 Exceptional! (136 reviews)

"Everything was awesome! It was the perfect place for our Everglades adventures!"

Reviewed on Aug 10, 2026

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See all 195 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.