Chokoloskee Island Vacation Packages 2026 from $675

Photo by Noel Benadom

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Chokoloskee Island vacation packages

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

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)

Tween Waters Island Resort & Spa

Save 100% on your flight

$796

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Was able to watch the dolphins in the morning from the balcony. Short walk across the street to the beach and they have umbrellas and chairs to rent. Would definitely come back.

Reviewed on Aug 13, 2026

The Perry Hotel Naples

Save 100% on your flight

$818

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$720

per person

Sep 23 - Sep 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$796

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (87 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chokoloskee Island

View all trips

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.

See properties

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

Get rates

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool

Chokoloskee FL

Get rates

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

Get rates

See all 199 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.