Tourism on Anguilla is a relatively recent phenomenon—most development didn't begin until the early 1980s. The lack of native topography and, indeed, vegetation, and the blindingly white expanses of beach have inspired building designs of some interest; architecture buffs might have fun trying to name some of the most surprising examples. Inspiration largely comes from the Mediterranean: the Greek Islands, Morocco, and Spain, with some Miami-style art deco thrown into the mixture.
Anguilla accommodations basically fall into two categories: grand resorts and luxury resort-villas, or low-key, simple, locally owned apartments and small beachfront complexes. The former can be surprisingly expensive, the latter surprisingly reasonable. In the middle are some condo-type options, with full kitchens and multiple bedrooms, which are great for families or for longer stays. Private villa rentals are becoming more common and are increasing in number and quality of design and upkeep every season as development on the island accelerates.
A good phone chat or email exchange with the management of any property is a good idea, as units within the same complex can vary greatly in layout, accessibility, distance to the beach, and view. When calling to reserve a room, ask about special discount packages, especially in spring and summer. Most hotels include Continental breakfast in the price, and many have meal-plan options. But keep in mind that Anguilla is home to dozens of excellent restaurants before you lock yourself into an expensive meal plan that you may not be able to change. All hotels charge a 10% tax, a $1 per room/per day tourism marketing levy, and—in most cases—an additional 10% service charge. A few properties include these charges in the published rates, so check carefully when you are evaluating prices.