Chokoloskee Island Vacation Packages

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Top Chokoloskee Island vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
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

Tween Waters Island Resort & Spa
3.0-star property

Tween Waters Island Resort & Spa

8.6/10 Excellent! (1,005 reviews)

Dec 7 - Dec 14

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,516, price is now $976 per person
$976
per person
found 1 day ago

Mariners Boathouse by Coolvacay
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

Landing Apartments Fort Myers near Eastwood Village
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

Windward Passage Resort
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

Waterfront 2 bedroom 1 bath with boat slip

Chokoloskee FL
0.25 mi from city center
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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

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

Chokoloskee FL
0.14 mi from city center
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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
Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands

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

Chokoloskee FL
0.15 mi from city center
Get rates
At Everglades Chokoloskee 3 bdrm Home w/ dock, marina, National Park,10,000 Islands, guests have access to features like laundry facilities.
Kitchen
Washer
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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.
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