Get Me There. Oakland to Key West
2,537 mi · 2 stops The cheapest round trip from Oakland to Key West right now is $647 — Nov 14 → 17, 3 nights, 2 stops.
Best fare
Key West Nov 14 → 17 · 3 nights · 2 stops
Above typical for this route ($557–$593) — it usually dips lower.
Prices checked on Oct 20
By month
October 2026 $747
November 2026cheapest $647
December 2026 $678
January 2027 $778
February 2027 $915
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Price history
12 weeks tracked · weekly lows↓13% vs 4 wks ago
All dates (379 priced)
Nov 14 → 17 3 nights · 2 stops
Dec 4 → 8 4 nights · 2 stops
Oct 29 → Nov 2 4 nights · 2 stops
Oct 30 → Nov 2 3 nights · 2 stops
Dec 5 → 8 3 nights · 2 stops
Dec 12 → 16 4 nights · 2 stops
Oct 30 → Nov 4 5 nights · 2 stops
Nov 27 → Dec 2 5 nights · 2 stops
Jan 9 → 14 5 nights · 2 stops
Nov 14 → 19 5 nights · 2 stops
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