Get Me There. Oakland to Key West
The cheapest round trip from Oakland to Key West right now is $668 — Oct 27 → 31, 4 nights, 2 stops.
Best fare
Key West Oct 27 → 31 · 4 nights · 2 stops
Prices checked on Aug 7
By month
October 2026cheapest $668
November 2026 $972
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Price history
1 week tracked · weekly lows
All dates (108 priced)
Oct 27 → 31 4 nights · 2 stops
Oct 24 → 28 4 nights · 2 stops
Oct 26 → 31 5 nights · 2 stops
Oct 28 → 31 3 nights · 2 stops
Oct 30 → Nov 4 5 nights · 2 stops
Oct 29 → 31 2 nights · 2 stops
Oct 25 → 28 3 nights · 2 stops
Oct 26 → 28 2 nights · 2 stops
Oct 20 → 22 2 nights · 2 stops
Oct 25 → 30 5 nights · 2 stops
The Friday Deal Sheet
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