$213 Cheap flight deals from Madison (MSN) to Dredgers Key (EYW)

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This Weekend's Flight Deals from Madison to Dredgers Key

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 1 - Wed, Feb 18
MSN
Dane County Regional
EYW
Key West Intl.
$409 Roundtrip, found 3 days ago
$409
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Feb 1 from Dane County Regional to Key West Intl., returning Wed, Feb 18, priced at $409 found 3 days ago

Airfares from $213 One Way, $288 Round Trip from Madison to Dredgers Key

Prices starting at $288 for return flights and $213 for one-way flights to Dredgers Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 25 - Sat, May 2
MSN
Madison
EYW
Key West
$288 Roundtrip, found 19 hours ago
$288
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Key West, returning Sat, May 2, priced at $288 found 19 hours ago
Sat, Apr 25 - Sat, May 2
MSN
Madison
EYW
Key West
$336 Roundtrip, found 19 hours ago
$336
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Key West, returning Sat, May 2, priced at $336 found 19 hours ago
Wed, Apr 22 - Fri, May 1
MSN
Madison
EYW
Key West
$339 Roundtrip, found 19 hours ago
$339
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Apr 22 from Madison to Key West, returning Fri, May 1, priced at $339 found 19 hours ago
Sat, Apr 25 - Sat, May 2
MSN
Madison
EYW
Key West
$341 Roundtrip, found 19 hours ago
$341
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Madison to Key West, returning Sat, May 2, priced at $341 found 19 hours ago
Sat, Sep 19 - Sat, Sep 26
MSN
Madison
EYW
Key West
$343 Roundtrip, found 3 days ago
$343
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 19 from Madison to Key West, returning Sat, Sep 26, priced at $343 found 3 days ago

Dredgers Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
2.5-star property

Ibis Bay Beach Resort

8.2/10 Very Good! (2,000 reviews)

Mar 14 - Mar 21

7 night stay

Madison (MSN) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,115, price is now $1,524 per person
$1,524
per person
found 1 day ago
Room was very small. Window shade wouldn't block the light beaming in my window all night. Not that big of a deal though, i wasn't there for the room. The beach was pretty much rock, so that wasn't great. The facilities offer plenty for you. Bar, restaurant, boat rentals. Tours. My favorite was probably be the hammocks a plenty

Reviewed on Jul 15, 2025

Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Mar 14 - Mar 21

7 night stay

Madison (MSN) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,251, price is now $2,069 per person
$2,069
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful! Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy. Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you. The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was. Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor! Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am. Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side. Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.

Reviewed on Dec 28, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Mar 14 - Mar 21

7 night stay

Madison (MSN) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,824, price is now $3,150 per person
$3,150
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

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More About Flying To Dredgers Key from Madison

Route Information for Flights from Madison to Dredgers Key

Origin Airport IATA Code
MSN
Destination Airport IATA Code
EYW
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Madison to Dredgers Key

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.