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 Bay Inn at Lani Kai
3.0-star property

The Bay Inn at Lani Kai

7.8/10 Good! (502 reviews)

Nov 19 - Nov 25

6 night stay

Cedar Rapids (CID) to Fort Myers (RSW)

American Airlines • Non-stop roundtrip • Coach
Price was $1,079, price is now $742 per person
$742
per person
found 1 day ago
the beach is very close .the room has been recently renovated

Reviewed on Sep 24, 2026

The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

9.6/10 Exceptional! (1,099 reviews)

Nov 4 - Nov 8

4 night stay

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,958, price is now $1,228 per person
$1,228
per person
found 1 day ago
The hotel is new. Rooms are very spacious. Hotel pool is cute, although small. The boat ride to the beach is a nice touch but keep in mind you must reserve ahead of time. Having the coffee shop in the lobby was convenient. The location is a bit weird behind a small shopping center.

Reviewed on Sep 26, 2026

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 24 hours 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.
Everglades Adventures Hotel Suites by Ivey House

Everglades Adventures Hotel Suites by Ivey House

2.5 out of 5
107 Camellia St E Everglades City FL
Free Cancellation
Reserve now, pay when you stay
4.03 mi from city center
$76 nightly
The price is $84 total per night
$84 total
Sep 27 - Sep 28
Total with taxes and fees
Guests of Everglades Adventures Hotel Suites by Ivey House enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. A stay here includes free parking. Front-desk staff can assist with tours/tickets and luggage storage.
Pool
Parking included
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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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