The first settlers arrived in Key West in 1521 and a fishing village and garrison were established as Florida was becoming a Spanish territory. The original Spanish word for the area is Cayo Hueso, which means “bone cay.” The island earned the nickname due to the littered bones of the previous inhabitants who had been using Key West as a communal graveyard. Despite the island's grisly history, it's now cherished as one of the premier vacation destinations in Florida, offering a Caribbean-style getaway without the need for a passport.
Today, you can wander around Key West and discover prime shopping opportunities on Duval Street, street performances in Mallory Square, and a variety of historic museums and nature conservatories to keep you busy for the duration of your stay. Whatever your reason for traveling to Key West, it's important to find the right accommodation that allows you to enjoy everything the island has to offer.
When to Visit Key West, FL
In terms of weather, there isn't a bad time to visit Key West. Temperatures are pleasant year-round, although summer is the island's rainy season. If you're willing to bring an umbrella and brave the showers, you can take advantage of discounted room rates from June to August. Expect temperatures to hover around the high 80s and low 90s.
Bargain hunters may also want to consider visiting from September to November. Fall is Key West's hurricane season, but most tourists simply head for higher ground if a storm approaches. Hotel rates are slashed due to the increased chances of hurricanes, but you can snag some unbelievable deals if you're up for the adventure. You'll also be here for popular fall events, including Key West Brewfest and Fantasy Fest Carnival.
Peak tourist season in Key West is in the wintertime from December to February. This is when travelers are trading northern snow showers for an ocean view and mid-70-degree temps. Winter is also a popular time because hurricane season is over, and several popular events take place, such as the Key West Food & Wine Festival. If you're looking to save money on your room, however, winter is the worst time to travel. Hotel rates are high and Key West is crowded, especially during the holidays.
Overall, the best time to visit Key West is in the early spring between March and May. Key West enjoys climbing temperatures and clear skies that make it the perfect time of year for an ocean getaway. Hotel rates are low and the island itself is too isolated for spring breakers. Plus, you'll get a chance to experience several festivals, including ConchFest, Conch Republic Independence Celebration, and Taste of Key West.
Below is a chart of the current pricing seasonality of hotels and motels in Key West, FL:
Key West, FL: Prices by Star Rating Class
Below are 3 charts illustrating avg. nightly cost trends by star rating class in Key West, FL. Browse these illustrations to calculate the cheapest months to book a room in Key West for upcoming travels.
Luxury Hotel Options in Key West, FL
4 Star Average Prices: $279.62
Upscale accommodations abound in Key West. Ocean Key Resort & Spa overlooking Sunset Pier at Duval Street is among the island's most prestigious hotels. This classic island-inspired resort is within walking distance of shops, the Ernest Hemingway Home and Museum, the historic Sloppy Joe's bar, and the Harry S. Truman Little White House. Guest rooms are brightly decorated and boast whirlpool tubs, flat-screen televisions, free WiFi, and balconies. In addition to a full-service spa, the property also features a poolside lounge, hot tub, outdoor pool, valet parking, and an on-site boutique and restaurant.
Pier House Resort & Spa is another great option for anyone wanting to splurge on Duval Street accommodations. Located a minute's walk from Mallory Square, Pier House Resort & Spa is an elegant resort that extends over the water on wooden piles. Its refined rooms offer coffee makers, complimentary WiFi, rainfall showers, and fridges. Upgrading to a suite will get you a wet bar, and some suites offer a whirlpool bath and kitchen. One of the best things about this luxury resort is the private beach, which also boasts a hot tub and heated outdoor pool. You won't even have to go far for some great eats, as there is a beachside bar and grill and Caribbean-style café on-site.
If you're hoping to score the private beach perk, you'll also want to consider Casa Marina, A Waldorf Astoria Resort. This upscale accommodation is within walking distance of Duval Street and boasts Mediterranean-style rooms with ocean or city views. All rooms feature mini-fridges, Nespresso machines, and iPod docking stations. Enjoy upscale amenities like an on-site spa, steakhouse, two oceanfront pools, water activities, a casual beachside restaurant, and a kids' club.
Affordable Hotel Options in Key West, FL
3 Star Average Prices: $228.38
Finding an affordable hotel option in Key West can be difficult, but you just need to know where to look. Seashell Motel & Key West Hostel is a smart dorm-style option in the heart of Old Town. Here you can experience the laid-back atmosphere of Key West surrounded by island-inspired charm and hospitality that won't break the bank. Plus, the hostel's convenient downtown location is just three blocks from Duval Street. If you don't feel comfortable bunking with strangers, Seashell Motel & Key West Hostel offers private motel rooms that provide you with up to two double beds, mini-fridges, cable TV, en suite bathrooms, free WiFi, free limited parking, and coin-operated laundry facilities.
If you're willing to pay a little more, another budget-friendly option is The Inn at Key West. Overlooking the gulf, this tropically furnished three-star accommodation is located a short drive from Key West Golf Club and Smathers Beach. Rooms feature patios or balconies, coffee makers, premium channels, complimentary WiFi, and blackout drapes. There's even an outdoor pool with a waterfall, hot tub, poolside tiki bar, and lush gardens.