
Chokoloskee Island Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

4.5-star property
The Perry Hotel Naples
9.6/10 Exceptional! (1,099 reviews)
Dec 3 - Dec 7
4 night stay
Cleveland (CLE) to Fort Myers (RSW)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,320, price is now $804 per person
$804
per person
found 21 hours ago
Excelent instalation and services
Reviewed on Sep 26, 2026


3.0-star property
Mariners Boathouse by Coolvacay
South Island
9.8/10 Exceptional! (13 reviews)
Dec 5 - Dec 12
7 night stay
Cedar Rapids (CID) to Fort Myers (RSW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,617, price is now $1,057 per person
$1,057
per person
found 1 day ago
Very nice place, our 2nd time here and we still love it
Reviewed on Sep 7, 2026

3.0-star property
Landing Apartments Fort Myers near Eastwood Village
9.8/10 Exceptional! (31 reviews)
Dec 5 - Dec 12
7 night stay
Cedar Rapids (CID) to Fort Myers (RSW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,289, price is now $875 per person
$875
per person
found 1 day ago
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

2.0-star property
Windward Passage Resort
8.8/10 Excellent! (11 reviews)
Dec 5 - Dec 12
7 night stay
Cedar Rapids (CID) to Fort Myers (RSW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,515, price is now $1,031 per person
$1,031
per person
found 1 day ago
Wonderful view of the ocean
Reviewed on Sep 15, 2026
Top rated hotels for your Chokoloskee Island vacation package

Waterfront 2 bedroom 1 bath with boat slip
Chokoloskee FL
0.25 mi from city center
At Waterfront 2 bedroom 1 bath with boat slip, guests have access to features like laundry facilities.
Kitchen
Free WiFi

The Reel'em Inn, Chokoloskee Island Fisherman's Paradise with Pool
Chokoloskee FL
0.14 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Pool
Kitchen
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View all propertiesLowest 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.
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