Get Me There. Oakland to Key West
2,537 mi · 2 stops The cheapest round trip from Oakland to Key West right now is $818 — Mar 24 → 29, 5 nights, 2 stops.
Best fare
Key West Mar 24 → 29 · 5 nights · 2 stops
Above typical for this route ($557–$588) — it usually dips lower.
Prices checked on Oct 6
By month
February 2027 $838
March 2027cheapest $818
April 2027 $940
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Price history
10 weeks tracked · weekly lows
All dates (239 priced)
Mar 24 → 29 5 nights · 2 stops
Feb 6 → 9 3 nights · 2 stops
Feb 7 → 9 2 nights · 2 stops
Mar 16 → 18 2 nights · 2 stops
Mar 22 → 24 2 nights · 2 stops
Mar 22 → 25 3 nights · 2 stops
Mar 23 → 25 2 nights · 2 stops
Feb 28 → Mar 3 3 nights · 2 stops
Mar 1 → 3 2 nights · 2 stops
Mar 9 → 11 2 nights · 2 stops
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