If you’re planning a visit to the Florida Keys, a long strip of islands south of Miami and the Everglades that can be driven over on the exhilarating Overseas Highway – you don’t want to miss out on the southernmost city in mainland America, Key West, which was once the haunt of Spanish and Cuban sailors and the feared pirates of the Caribbean and, for lovers of literature, a place of great inspiration for the writer Ernest Hemingway, who lived here and also wrote (among others) his masterpiece A Farewell to Arms here.
As easy as it is to get around the length and breadth of this little island, it is important to point out that – despite its size – there are plenty of attractions to visit in Key West, so it is highly recommended to stay at least one night in town. If you’ve already started reading up on it, you’ll certainly have noticed that Key West offers a wide choice of traditional hotels, more or less luxurious resorts, nice b&b’s and historic hotels, all at prices that are generally above average. But before going into details, it is necessary to understand which is the most suitable area where to stay: in this article, therefore, I will give you some tips to choose the best area where to stay in Key West, and some advice on the most beautiful and fascinating structures.
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Where to stay in Key West: the Old Town
If unfortunately you arrive in Key West without having booked a hotel, but especially without the slightest idea of where to stay, and you ask someone for advice, they will not hesitate to say: “Old Town“! We are talking about the north-western area of the small island, the historic heart of Key West, gathered around the legendary Duval Street.
Here you will find all the major attractions of Key West: museums, historic houses, gardens, the fabulous view of Mallory Square, Fort Zachar Taylor, the Truman Annex, Bahama Village and, of course, Duval Street, the lively and picturesque shopping street that is the beating heart of this small island in the Atlantic.
Find a hotel near Duval Street
Here are a few hotels in the area we’ve chosen that might be right for you.
Courtney’s Place Historic Cottages & Inns
Far enough away from the triumph of sounds and lights of Duval Street, there is Courtney’s Place, a beautiful historic hotel in colonial style with prices a bit below the average of the city for this type of structure. We are in a quiet street, yet 5-10 minutes from the historic center: the structure offers a rather small number of spacious family cottages with kitchen, but for those who do not require one there are some delightfully furnished rooms, equipped with all amenities.
All accommodations face around the courtyard with a pool, shaded by palm trees and equipped with a barbecue in the back. It should be mentioned that the wifi works better on the porch around the courtyard than in the room, and breakfast is nothing exceptional. Parking is free, but not guaranteed (first come, first served): if you can’t find one, it’s because someone has seen fit to occupy it with more than one vehicle. However, you can park in the surrounding streets: it’s free.
The Gardens Hotel
Just a minute’s walk from Duval Street, you’ll find this elegant, historic colonial-style guesthouse. Although it is in the heart of the city, it is quiet and peaceful, away from the busy streets. The outdoor pool is fascinating and characteristic, set amidst the gardens full of palm trees, in a perfect tropical environment.
The hotel is a short walk from Ernest Hemingway’s house-museum and the Key West Lighthouse, and Keeper’s Quarters Museum.
The Margaritaville Key West Resort & Marina
Located right on the waterfront and a stone’s throw from the most vital and touristy heart of Key West, this Key West resort could be a nice choice for those who want to enjoy a relaxing vacation, as a guest of a facility that offers all the amenities you could want: pool, spa, gym, lounge bar, a restaurant and more.
As much as the experience may be a little less authentic than the establishments mentioned so far, it’s also worth booking a room here because of its proximity to Mallory Square. It doesn’t even matter if you descend into the crowds during the Sunset Celebration: you get the same, unforgettable sunset from the resort’s terrace.
Amsterdam’s Curry Mansion Inn
When I first walked into this beautiful and flashy historic building on Caroline Street, I thought I had the wrong address. In fact, what appeared to be a bizarre museum overflowing with collectible antiques, nineteenth-century furnishings and dusty memorabilia was just the hotel lobby! The aristocratic appearance of this old colonial-style mansion that once belonged to William Curry – an eccentric millionaire businessman from Key West – may intimidate or raise eyebrows for those accustomed to more modest, modern accommodations, but it’s a once-in-a-lifetime experience in my opinion.
There’s convenient parking and an outdoor pool available for guests, who sleep upstairs in precious suites with four-poster beds. Both in the communal areas and in the private accommodations, the risk of kitsch is averted because, by crossing the threshold of this hotel, you agree to take a real trip back in time.
If you feel like it, you can venture onto the tiny terrace at the top of the building, reached by an uncomfortable wooden staircase: the view is not exceptional, but legend has it that from up there wives used to look at the sea on the horizon, hoping for the return of their sailor husbands. The name of the terrace (“Widow’s Walk”) makes us understand how often, alas, those hopes were unfounded.
Smallest Bar Inn
In the center of town you can’t get any more downtown than this, there is a curious, tiny, traditional hotel: apart from the disadvantages (Duval Street is a bit chaotic), the Smallest Bar Inn – also known as the Old Custom House Inn – is perfect for those who are looking for a room in Key West and don’t want to spend too much. In addition to the location, the best feature of this very white colonial-style hotel is its fairly low price, at least by city standards.
Being in the mid-range, the structure lacks some comfort, but it is ideal and strategic for those who want to immediately immerse themselves in the joyful climate of the island. A fun fact: Right next to the guesthouse is the bar of the same name, baptized as the smallest in Key West: as you can see with your eyes, it is not a just words!
Where to stay in Key West: hotels near Southernmost Point
If you prefer to take a break and get away from the center of Key West, you could choose the southern area, near the city beaches and the Southernmost Point buoy, a panoramic point that indicates to tourists one of the most southern places in the United States. Actually, to be precise, this area is also located within the Old Town, but a bit further away from the liveliness of Mallory Square and its surroundings, with the possibility of enjoying a nice view of the expanse of the ocean.
Southernmost House Hotel (Casa Cayo Hueso)
Walking around these parts, it is curious to note how the owners of the various buildings compete to see who owns the southernmost house in Key West, and therefore in the continental United States. There are many plaques posted at the entrances to the houses proudly announcing this record, but there is no denying that Casa Cayo Hueso (“Key West” in Spanish) – first the residence of jurist Harris, then of the Ramos Lopez family of merchants – has a decided advantage.
Located right at the far end of Duval Street, this grand historical building in pastel colors surrounded by a tropical garden stands out from the surrounding houses for its magnificence and magniloquence: this colorful showiness certainly attracts at first glance, but sometimes the most demanding guests have complained about the quality-price ratio, more like a b&b than a hotel. Worth mentioning are the swimming pool, the breakfast and the excellent location, far from the noisiest part of Duval Street. A small fun fact: the sign in front of the hotel reads:“No ballroom on second floor – Never was and never will be“. Who knows what stories this notice hides!
Blue Marlin Motel
I finally recommend a motel (strange to say, eh? After all these historic houses!). Located in a favorable area for both the south and the historic center, this structure offers good rooms and a pool where you can cool off in the hottest hours, since the sea is not always clean. The price, although a bit lower than average, is not really an American motel but it is also true that in Key West finding low cost rates is not at all easy.
Obviously, these are just some of the hotels available in Key West. Clicking below you will find the complete list of all accommodations available on the island:
On the other hand, if you want to discover the best hotels that overlook the sea, I recommend you to read our section in the article dedicated to the best beaches in Key West.
Where to Stay between Miami and Key West
One of the most common routes in Florida’s road trip itineraries is definitely the one that connects Miami to Key West; it takes about 3 and a half hours and, although it can be undertaken without overnight stays, an intermediate stop between the two is advisable, especially to enjoy the many attractions of the Keys along the way. Where can you stop for the night?
If you are looking for a stop closer to Miami, the best choice is Key Largo, the largest island of the archipelago, with many accommodations, services and an unforgettable coral reef. Here are our tips on where to stay in Key Largo.
A valid alternative is represented by Islamorada, only 20 minutes away from Key Largo, a group of islands that extends for about 20 miles, creating one of the most enchanting corners of all the keys. Here are our tips for stay in Islamorada.
An interesting alternative is to plan a stop in Marathon, in the Middle Keys, not only to visit its natural parks, but also not to miss the beautiful beaches of Bahia Honda State Park. Also in this case we suggest you read our advice on where to stay in Marathon.
