Get Me There. Oakland to Key West
2,537 mi · 2 stops The cheapest round trip from Oakland to Key West right now is $587 — Oct 24 → 29, 5 nights, 2 stops.
Best fare
Key West Oct 24 → 29 · 5 nights · 2 stops
Above typical for this route ($557–$582) — it usually dips lower.
Prices checked on Sep 16
By month
September 2026 $728
October 2026cheapest $587
November 2026 $627
December 2026 $798
February 2027 $809
March 2027 $896
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Price history
7 weeks tracked · weekly lows
All dates (464 priced)
Oct 24 → 29 5 nights · 2 stops
Nov 6 → 11 5 nights · 2 stops
Nov 7 → 11 4 nights · 2 stops
Oct 26 → 31 5 nights · 2 stops
Oct 3 → 6 3 nights · 2 stops
Sep 28 → Oct 3 5 nights · 2 stops
Sep 29 → Oct 3 4 nights · 2 stops
Oct 29 → 31 2 nights · 2 stops
Oct 24 → 28 4 nights · 2 stops
Sep 26 → 28 2 nights · 2 stops
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