Accommodations

$50–100

Budget accommodation during high season is next to impossible to come by, but Olivia by Duval (511 Olivia St., 305/296-5169, from $89 d) is a pleasant basic guesthouse in a central location, with a pool and a quiet courtyard. The guest rooms are mainly efficiency suites, but they also have a two-bedroom and a one-bedroom unit; all guest rooms have ceiling fans, air-conditioning, TVs, and private baths.

The Blue Lagoon Resort (3101 N. Roosevelt Blvd., 305/296-1043, from $69 d) is another cheap stay, but unlike the value-oriented Olivia, it’s really just cheap; the property is in pretty rough condition, the guest rooms are fairly grungy, and even though it’s on the waterfront, its location is far from convenient to any of Key West’s sights.

$100–200

Stepping up into the midrange category, there are considerably more options. A great place for one-stop shopping for some of Key West [1]’s most unique—and affordable—accommodations is Key West Historic Inns (www.keywesthistoricinns.com [3], 305/294-5229). The company operates six historic bed-and-breakfasts on the island, all of which are located in charming, mostly residential neighborhoods.

Each property has its own individual personality and offers surprisingly decent rates, ranging from the large Chelsea House Pool & Gardens (709 Truman Ave., 33 guest rooms, from $169 d) and the spacious, quiet, and romantic Key Lime Inn (725 Truman Ave., 37 guest rooms, from $179 d) to the aptly named but quite nice Budget Key West (1031 Eaton St., 17 guest rooms, from $139 d) and the rustic minimalism of the Merlin Guesthouse (811 Simonton St., 20 guest rooms, from $159 d). All of the properties are rented hotel-style via a central reservations system, but each accommodation is unique.

Historic accommodations are abundant on Key West, and the history of the Speakeasy Inn (1117 Duval St., 305/296-2680, from $129 d)—it was the 19th-century home of Raul Vasquez, a noted rumrunner—is evident both in its classic architecture and the downstairs rum bar. The one-, two-, and three-bedroom units are open and spacious, with hardwood floors and ceiling fans. Nearby is the Avalon Bed & Breakfast (1317 Duval St., 305/294-8233, from $169 d).

Southernmost on the Beach (508 South St., 305/296-6577, http://southernmostresorts.com [4], from $189 d) recently completed a massive expansion that not only tripled their guest room count but also added a much-needed dose of contemporary luxury—at marginally accessible prices—to the less-crowded southern end of the island. The nicest and newest guest rooms can run as much as $600 during high season, but the renovations have added a touch of class to the entire property. Across the street—and thus lacking the excellent ocean views—is a sister property, the Southernmost Hotel (1319 Duval St., from $119 d), which offers 127 standard modern hotel rooms, two swimming pools (with tiki bars), in-room Wi-Fi, and beach access at the neighboring property.

Duval Gardens (1012 Duval St., 305/292-3379, from $149 d) is a pet-friendly B&B with regular hotel accommodations (king, queen, and double queen) as well as one kitchenette-equipped guest room with a mini-fridge, a stove-oven combo, a coffeemaker, and a microwave. Tiled bathrooms and four-poster canopy beds accent the beautiful tropical setting.

The Caribbean colonial-styled Conch House (625 Truman Ave., 305/293-0020, from $168 d) is a complex composed of four separate buildings. The nicest guest rooms are located in the two-story main building and the shotgun-style Delaney House, but the tiny Casa Cabana room is the most private; regardless of your needs, all the accommodations are classic Key West [1]. The wraparound porches and green shutters of the main house evoke Conch House’s century-plus past—yes, there’s a Hemingway story; no, it’s not very good—but the owners have managed to combine historic charm with modern convenience and value.

Both New Orleans House (724 Duval St., 305/293-9800, from $165 d) and Pearl’s Rainbow (525 United St., 305/292-1450, from $179 d) have very specific audiences in mind; gay men in the case of the former, lesbians in the case of the latter. The quiet, classy atmosphere at Pearl’s extends to its three cottages and two hotel buildings, which are decorated in a light tropical style; all the guest rooms are spacious, with free Wi-Fi and private baths, and lodging rates include a hot breakfast. New Orleans House, on the other hand, is all about the party. Although there are two buildings separate from the main facility, the booming nightclub activity at the downstairs Bourbon Street Pub goes until 4 a.m., and the activity keeps the whole place hopping. The pool area is clothing-optional. The guest rooms are basic and a bit worn, but sleeping seems to be the last thing on most guests’ minds.

Over $200

Although Azul (907 Truman Ave., 305/296-5152, $159–319 d) offers adults-only accommodation, the atmosphere is decidedly upscale. The historic Queen Anne house is located a few blocks away from the activity along Duval Street [5], but on traffic-heavy Truman Avenue; nonetheless, the vibe is quiet, and the views from the wraparound porches are gorgeous, especially those that look out over the pool area. Inside there are only nine guest rooms and two suites, all with flat-screen TVs, Wi-Fi, marble-floored bathrooms, and fashionable contemporary furnishings.

Unlike most of the historic properties on Key West [1], the Orchid Key Inn (1004 Duval St., 305/296-9915, from $229 d) doesn’t evoke 18th-century opulence; the newly opened hotel is a modern stylish version of a ’50s motel. From the neon sign to the crisp white paint and open layout, it looks as if it were transported from a Miami Beach [6] feverish dream. The four-star facility only has 24 guest rooms and suites, all of which have free Wi-Fi, plasma-screen TVs, plush beds, surround-sound audio, and other luxury touches. The property is lushly decorated with tropical plants and water features throughout, and the hip Orchid Bar is popular among guests and nonguests alike.