Get Me There. Oakland to Key West
The cheapest round trip from Oakland to Key West right now is $557 — Dec 5 → 9, 4 nights, 2 stops.
Best fare
Key West Dec 5 → 9 · 4 nights · 2 stops
In the typical range for this route ($557–$565).
Prices checked on Aug 27
By month
August 2026 $822
September 2026 $738
October 2026 $738
November 2026 $607
December 2026cheapest $557
Get the best Oakland deals by email — most Fridays, free.
Price history
4 weeks tracked · weekly lows↓5% vs 3 wks ago
All dates (356 priced)
Dec 5 → 9 4 nights · 2 stops
Dec 12 → 16 4 nights · 2 stops
Nov 14 → 17 3 nights · 2 stops
Sep 6 → 11 5 nights · 2 stops
Oct 27 → 31 4 nights · 2 stops
Oct 26 → 31 5 nights · 2 stops
Nov 14 → 18 4 nights · 2 stops
Dec 5 → 10 5 nights · 2 stops
Nov 14 → 19 5 nights · 2 stops
Sep 5 → 10 5 nights · 2 stops
The Friday Deal Sheet
The week's best deals from Oakland, most Fridays — free.