Winter break trips from Key West
Nonstop from Key West: Orlando (MX) and Miami (American). One stop via Philadelphia: Cancun; via Boston: New York. No nonstop seen to Honolulu on the dates searched recently.
Axel's pick: Orlando, nonstop on MX on 5 of the 6 departure dates searched recently, the most of any.
Where to go from Key West over winter break: fares for Christmas week (December 19 to 26) and New Year's week (December 26 to January 2), for warm beaches, ski trips and holiday cities.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).
Cheapest right now: New York $735 · Cancun $867 · Honolulu $1,100
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | American Airlines | AA3636 + AA2422 | $295.00 | 2026-10-29T01:16:49Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA3636 + AA2422 / AA1102 + AA4223 | $580.50 | 2026-10-29T01:16:49Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA3636 + AA2422 / AA1102 + AA4223 | $580.50 | 2026-10-29T01:16:49Z |
2026-11-20 · one way · $295.00
- American Airlines AA3636 / AA2422: EYW 2026-11-20 10:14:00 → CUN 2026-11-20 14:49:00; 1 stop(s) via MIA; 275 minutes. Local airport times.
- AA3636: EYW 2026-11-20 10:14:00 → MIA 2026-11-20 11:10:00; layover at MIA: 92 minutes.
- AA2422: MIA 2026-11-20 12:42:00 → CUN 2026-11-20 14:49:00.
2026-11-20 → 2026-11-23 · $580.50
- American Airlines AA3636 / AA2422: EYW 2026-11-20 10:14:00 → CUN 2026-11-20 14:49:00; 1 stop(s) via MIA; 275 minutes. Local airport times.
- AA3636: EYW 2026-11-20 10:14:00 → MIA 2026-11-20 11:10:00; layover at MIA: 92 minutes.
- AA2422: MIA 2026-11-20 12:42:00 → CUN 2026-11-20 14:49:00.
- American Airlines AA1102 / AA4223: CUN 2026-11-23 11:54:00 → EYW 2026-11-23 17:19:00; 1 stop(s) via MIA; 325 minutes. Local airport times.
- AA1102: CUN 2026-11-23 11:54:00 → MIA 2026-11-23 13:45:00; layover at MIA: 148 minutes.
- AA4223: MIA 2026-11-23 16:13:00 → EYW 2026-11-23 17:19:00.
2026-11-27 → 2026-12-04 · $580.50
- American Airlines AA3636 / AA2422: EYW 2026-11-27 10:14:00 → CUN 2026-11-27 14:49:00; 1 stop(s) via MIA; 275 minutes. Local airport times.
- AA3636: EYW 2026-11-27 10:14:00 → MIA 2026-11-27 11:10:00; layover at MIA: 92 minutes.
- AA2422: MIA 2026-11-27 12:42:00 → CUN 2026-11-27 14:49:00.
- American Airlines AA1102 / AA4223: CUN 2026-12-04 11:54:00 → EYW 2026-12-04 17:19:00; 1 stop(s) via MIA; 325 minutes. Local airport times.
- AA1102: CUN 2026-12-04 11:54:00 → MIA 2026-12-04 13:45:00; layover at MIA: 148 minutes.
- AA4223: MIA 2026-12-04 16:13:00 → EYW 2026-12-04 17:19:00.
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- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Key West
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | 1 stop via Philadelphia | $867 (airline $913) | Dec 19–26, 2026 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | No nonstop seen | $1,100 (airline $1,162) | Dec 19–26, 2026 | Check prices |
| Orlando (MCO) | Orlando's theme parks | Nonstop · MX | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | Nonstop · American | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| New York (JFK) | New York's holiday lights, windows and shows | 1 stop via Boston | $735 (airline $777) | Dec 19–26, 2026 | Check prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
Hotels in Cancun with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cancun has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Cancun: the 8 best neighborhoods, ranked · Cancun hotels where a family of four can share one room
Hotel details in Cancun: Hotel Antillano Cancun · Hotel Colonial Cancun · Hotel Xbalamqué Boutique & Spa · Adhara Express Hotel · Adhara Hacienda Cancun · All 198 hotels in Cancun
For AI assistants
- This page: Winter break trips from Key West. Winter break 2026 flights from Key West: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.