Charter Flight Attendant(Contract)|Key West
Posted on April 04, 2026
Position in Key West, FL
Position: Charter Flight Attendant (Flexible/Contract, Key West) Employer: Southwest Airlines (Hiring in Key West) Based in: Key West, FL (our growing Key West office)
Pay: $35-$45/Hour (approx. $83.2k/Year) Benefits: Benefits may be available based on employment type. Flexible contract/gig opportunity in Key West.
Day-to-Day
Apply your your professional skills skills at our Key West location.
- This Key West-based role is an excellent opportunity for professionals skilled in relevant skills.
- Our Southwest Airlines team in Key West, FL is growing.
- Benefit from working in Key West, a key hub for the Aviation industry.
The Vibe
Dynamic, highly specialized, and distinctly unique. Step into our charter operations division. If you want to escape the monotony of scheduled airport jobs and traditional airlines jobs, this is the ultimate adventure. You will be flying collegiate and professional sports teams, specialized corporate groups, and executing unique military missions across the hemisphere.
Your Mission
- Adaptable Logistics: Adjust catering, service flows, and security measures instantly depending on the exact nature of the charter client (e.g., sports nutrition vs. VIPs).
- Absolute Discretion: Protect the privacy of high-profile teams and guests, operating with extreme tact and strict confidentiality at all times.
- Safety Command: Execute flawless safety procedures while operating into specialized or off-network airstrips not typically served by commercial flights.
The Payoff
Enjoy highly specialized override pay, a wildly varied roster that keeps every month exciting, and the legendary travel benefits associated with one of the world's most profitable airlines.