Chokoloskee Island Vacation Packages 2026 from $837

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The Latest Chokoloskee Island vacation packages

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

The Perry Hotel Naples

Save 100% on your flight

$837

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

$919

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (123 reviews)

Staff were very polite and helpful other than when promotional items were attempted to be redeemed. Water stations were not available as stated. Very nice accommodations.

Reviewed on Oct 14, 2026

Southseas

Save 100% on your flight

$2,650

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

No reviews

Manasota Key Resort

Save 100% on your flight

$1,648

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (333 reviews)

We LOVED our stay at Manasota Key Resort! The pool was nice, refreshing and clean and so was the property. Being right on the beach was so convenient. It was a beautiful experience for us! We couldn't have been more pleased! The staff was very helpful when we had questions. Having Stumpy's stop right there at the resort was GREAT! Can't WAIT to go back!

Reviewed on Oct 14, 2026

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$1,062

per person

Dec 22 - Dec 28

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

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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! (55 reviews)

"We had a great stay; the host was very helpful and nice, and we would definitely stay again."

Reviewed on Oct 7, 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 194 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.