Note: All travel is subject to frequently-changing governmental restrictions—please check federal, state, and local advisories before scheduling trips.
Sometimes, where you unpack your bags on vacation is as important as the destination itself. And fortunately for those traveling to Key West, the tropical escape’s quirky and quaint island charm fully comes through in its accommodations, with historic conch-house inns and charming B&Bs galore. But the flip side to the Conch Republic’s lack of sprawling high-rise resorts is that accommodations come at a premium. If you’re headed to this highly sought after locale, you can still find charming and convenient places to park your suitcase that, while not always cheap, are a great value, and include plenty of amenities. Here are a few of them.
RELATED: Which Florida beach a re you? (QUIZ)
Tucked away on Angela Street, The Gardens Hotel stands within walking distance of Duval Street and the heart of the action, but you’d never know it. This tranquil, lush garden oasis offers a peaceful respite from all the activity outside. The main building, formerly the Gardens Mansion built in the 1800s, is listed on the National Register of Historic Places. Botanicals collected by former owner Peggy Mills frame the winding pathways, secluded seating areas, and two heated pools. Guests (including kids ages 16 and up) can select from five cottages, guest rooms, and suites all with private entrances and access to outdoor verandas. Bahamian plantation-style furnishings and locally crafted artwork adorn the rooms. Upon check in, guests receive a card to purchase wine at the D’Vine Wine Gallery on site, in 1-, 3- or 6-ounce pours. Sip from the 36-wine assortment while listening to nightly live piano music in the evenings from 5–7pm and live Jazz on Sundays from 5–8pm. Rates include complimentary WiFi and breakfast served poolside. The property also offers a business center, bicycle rentals, valet laundry service, concierge services, on-site parking ($30 per night), and a pool bar.
Just 15 minutes by car from downtown Key West, Stock Island provides an alternative locale that is a bit more tranquil and less congested, but with great dining options and a beautiful marina. The Oceans Edge Key West, which opened in 2017, is one of the area’s larger resorts with 175 rooms. It’s situated adjacent to the 165-slip marina, with full-service resort amenities. The daily $45 resort fee covers shuttle service to and from Key West; two hours of paddleboard, kayak and bicycle use per guest, per day; 24-hour gym access; resort activities such as yoga, SUP classes, poolside movies, and lawn games (like giant chess, Connect Four and ping pong); and high speed WiFi. Check the weekly schedule for a complimentary one-hour marine science eco experience, pairing live animal guests with lively topics and led by marine scientists. All guestrooms feature contemporary furnishings as well as a furnished balcony, mini fridge, and coffee maker. The property offers six saltwater, temperature-controlled pools with poolside service and towels. The Yellowfin Bar & Kitchen is open for breakfast, lunch and dinner, with happy hour at the bar 3–6pm daily and live music Thursdays through Sundays 6–9pm. The Oceans Edge Café is the perfect place to grab a coffee, smoothie, or quick bite 7–11am.
Also on Stock Island, The Perry Hotel is situated on a more than 40-acre campus, steps from an onsite 288-slip marina, the largest deep-water marina in all of the Florida Keys. Check in to the 100-room boutique property with a complimentary glass of champagne. Guestrooms feature contemporary furnishings and balconies (some with open-air showers) from which to soak up serene island views. Hotel amenities include complimentary WiFi, parking, and shuttle to and from Old Town Key West; two waterfront pools; golf cart, bike, scooter and 3-wheel Key West Arcimoto (all-electric utility vehicle) rentals; access to the Salute the Sole Yoga on the event lawn, a fully equipped F45 Training Gym, and boot camps on the event lawn. On-site restaurants include Matt’s Stock Island Kitchen & Bar, Salty Oyster Dockside Bar & Grill, and Sloppy Joe’s Dockside. The latter two host a daily happy hour with discounted drinks. Sloppy Joe’s features live music every Friday and Saturday 6–9pm. The Great Lakes Coffee Roasting Company serves farmer-direct coffees, smoothies and baked goods with indoor/outdoor seating.
Located in the heart of Old Town Key West on Truman Street, several blocks from Duval, Kimpton Winslow’s Bungalows boasts three private pools, a pool bar, and tropical gardens. Eighty-five comfortably appointed guest rooms, including two deluxe suites, are situated over several blocks and in several Key West architectural styles. The $35 daily guest amenities fee includes parking, loaner bikes on a first come, first served basis, continental breakfast, WiFi, a boozy welcome beverage, use of a snorkel kit off property, and access to Press Reader on your smart device (choose from more than 7,000 newspapers and magazines). Though many Key West properties are pet friendly, Winslow’s Bungalows allows pets regardless of size, weight, or breed at no extra charge, no damage deposit required.
Situated in three separate structures on both sides of Caroline Street in the heart of Old Town, Amsterdam’s Curry Mansion offers 28 air-conditioned guestrooms, each uniquely decorated, and a pool and a deck area, where breakfast and cocktails are served. The original mansion was built in 1869, home to William Curry, considered the first self-made Florida millionaire. His son demolished and reconstructed much of the home in 1901 to the Georgian Revival mansion that stands today. Many reports concur that in this kitchen “Aunt Sally” invented Key Lime Pie, a dessert served throughout Key West. Guest rates include free parking; a full breakfast with made-to-order omelets; a two-hour cocktail party each evening with an open liquor bar, beer, wine, snacks and live music; concierge service; use of a computer and printer; WiFi; use of a washer, dryer and laundry supplies, and a self-guided tour of the mansion, including historic treasures in the attic, leading up to the Widow’s Walk affording panoramic views of Key West.
Alexander’s, an adults-only LGBTQ-oriented guesthouse, welcomes guests in a safe, inclusive space that’s listed in the National Register of Historic Places. This three-story Key West conch house on Fleming Street was built in 1902 and still retains original pine wood floors. Guests may select from 17 well appointed, tropically decorated guestrooms spread across three renovated homes (1902-1904). Rates include an expanded continental breakfast, including eggs, muffins and fruit served poolside; local newspapers; daily poolside happy hour from 4:30–5:30pm; WiFi; full concierge services; a lending library of books in the lobby; a pool and Jacuzzi; and two clothing optional pool decks.
A short drive from Old Town on Roosevelt Road, Havana Cabana exudes the charm and character of Cuba, with classic cars out front and Cuban influenced artwork throughout. Many of the contemporary rooms feature views of the pool or ocean, some with bunk beds to accommodate families. The hotel boasts the largest pool in Key West and the action here is focused at weekly pool parties featuring a DJ, pool games, and food and drink specials (1–4pm every Saturday and Sunday). On Sundays at 4:30pm, join a traditional game of Loteria (a Latin game similar to bingo) where the winning teams get special prizes. Mojito’s Pool Bar hosts a daily happy hour from 10am to noon with discounted Bloody Marys and draft beer. Throughout the day order more than 15 types of mojitos and other Cuban-inspired drinks. Guests can enjoy complimentary smoothies at noon, popsicles at 2pm and churros at 4pm. The Floridita Food Truck serves up Cuban fare throughout the day in an open-air setting. A complimentary shuttle takes guests to and from Old Town.
Note: Orbitz compensates authors for their writings appearing on this site.