Fly Southwest: IAH to Key West, Florida

If you're a discerning traveler keen on making the most of your journey from Houston to Key West, then flying Southwest is definitely an option worth considering. It’s not just about the convenience of multiple flights but also about an experience that amalgamates comfort, affordability, and reliability.

For those unfamiliar, Southwest offers both Direct flights and Connecting flights to Key West. If you're in a hurry, Direct flights have the advantage avoiding Layovers, and can result in a shorter Flight duration. On the other hand, Connecting flights often cost less, offering Cheap flights for those whose primary concern is the Airfare. Furthermore, Southwest’s user-friendly cancellation policy can come to your rescue in case of any sudden change in travel plans.

Southwest tends to be particularly generous with their Baggage allowance — a serious point of consideration for those who travel heavy. Offering two free checked bags, Southwest's Baggage allowance can truly be a boon to travelers who need that extra suitcase or two. It's a stark contrast to the usual practice of nickel-and-diming passengers for every piece of checked luggage.

Let's focus on the finer details for a moment. When considering Southwest, it's not all about saving money. The in-flight experience can also make a significant difference. Southwest does not categorize its seats into First-class or Business class. Instead, offering a single class that's comparably spacious and comfortable. The lack of Business class might dissuade some, but the reality is, you're getting more legroom than most Economy class in other airlines. Helps when you have an hour or more to be airborne, doesn't it?

Did I mention Southwest's in-flight services? Irrespective of whether you've booked a One-way or Round-trip, you can bank on the cheerful and energetic flight attendants to make your journey enjoyable. They provide complimentary drinks and snacks, and the airline is known for its entertaining cabin crew, some of whom have been known to perform funny songs or jokes over the PA system.

As a frequent flyer on Southwest, taking advantage of their Mileage program is almost a must. Accumulating points not only becomes a ticket to free flights but also allows priority check-in, boarding, and extra baggage. Plus, there's nothing like being acknowledged and appreciated for brand loyalty, isn't it?

The ‘Best time to book’ varies significantly by your flexibility and schedule. Generally speaking, mid-week, especially Tuesday and Wednesday, is when you are likely to catch the best Flight deals. For the Last-minute flights seekers, subscribing to Southwest's Click 'N Save program could help you snag some great deals.

Just remember, every traveler's preferences differ, and what works best for you may not work for someone else. Whether you desire an uninterrupted, Non-stop journey or one with Layovers, domestic or International flights, early morning or Red-eye flight, Southwest has got your flying needs covered. So, the next time you plan that trip from Houston to Key West, why not give joining the Southwest flyers a shot?

Before I forget, it’s worth taking a quick look at Airline reviews. Time and again, Southwest’s commitment to customer satisfaction and value-for-money services have won them high praise from their customers, ensuring you're making the right choice.

So, here's to an informative insight into flying Southwest, ensuring your journey from Houston to Key West is about more than arriving at your destination. It's about making the journey as enjoyable as the destination. Safe travels!