Hotel Rex (562 Sutter St., 800/433-4434, www.jdvhotels.com, $235–275) has a classic feel, evoking a hotel in San Francisco early in the 1900s. Guest rooms are comfortable and spacious, decorated with the work of local artists and artisans. The dimly lit lobby bar is famous in the City for its literary bent—you may find yourself embroiled in a fascinating conversation as you enjoy your evening glass of wine. Amenities include a small elevator (not all boutique hotels in SF have them), access to a nearby gym, and valet parking packages for an additional fee. The attached Café Andre serves dinner each night; ask at the desk about reservations.

It might look small compared to the mammoth hotels on Union Square, but The Cartwright Hotel (524 Sutter St., 415/421-2865, www.cartwrighthotel.com, $175–285) has plenty of room for budget-minded guests. Guest rooms are freshly redecorated with antiques, and the small lobby has a light, airy feel. Enjoy a complimentary continental breakfast, a wine reception each evening, and free Wi-Fi access. Only about two blocks from Union Square and half a block from the Powell cable car line, this boutique hotel is perfectly located for both business and pleasure travelers.

Just off Union Square, the Handlery Hotel (351 Geary St., 800/995-4874, www.handlery.com, $175–330) offers a wide variety of rooms for all different price ranges. Value rooms in the historical section of the hotel tend to be small, and the appointments a bit sterile, but the amenities are as good as those in the newer, pricier Club section of the complex. For a serious splurge, rent the Rooftop Garden Suite, complete with an outdoor patio overlooking the City. A heated outdoor pool is available to all, and the Daily Grill restaurant serves up large portions of standard California cuisine all day long.

Only half a block down from the square, the Sir Francis Drake (450 Powell St., 800/795-7129, www.sirfrancisdrake.com, $190–250) has its own history beginning in the late 1920s. Here at the Drake you’ll find a bit less opulence in the lobby (compared to the St. Francis) and a bit more in the guest rooms. The Beefeater doorman (almost always available for a photo), the unique door overhang, and the red and gold interior all add to the character of this locals’ and tourists’ favorite.