Where to Stay in Key West | Best Areas & Hotels

With a population of just over 26,000, Key West definitely isn’t one of the biggest cities in the US, but that doesn’t mean that it’s not worth visiting.

The Florida Keys are a tourist hotspot all year round, but in this article, we’ll tell you exactly where to stay in Key West so that you can get the most out of your visit to the southernmost point in the continental United States.

Where to Stay in Key West

Key West is known for its connection to both Ernest Hemingway and Harry Truman. As both of these historical figures have at some point in the past lived or at least spent a significant time in this city, both of their homes have since been turned into museums where people can go and just learn a bit more about the lives of these individuals.

There are several residential areas located all over the city, but there are even more hotels, restaurants, and tourist locations. This means that a lot of the businesses in this city are heavily reliant on the tourism industry, so hotels are incredibly easy to find.

There’s no shortage of bars, restaurants, and everything else that comes with the territory of a popular tourist spot like Key West.

Key West doesn’t really have any notable stadiums or sports teams with diehard fans, and while saying that might anger some Cubs or Padres fans, the truth is that there really aren’t many sports events that take place here. 

You should always plan your trip based on what sort of fun you’re looking to have while in Key West. As the City of Key West constitutes several islands, getting around to the best parts of town might be a bit cumbersome.

That’s why we’ve pointed out where to stay in Key West based on what you hope to see and which area you should stay in to be as close to your favorite attractions.

Key West’s Best Parts of Town

Key West is a relatively small city, but it still holds a lot of historic significance and it has a lot of sights to see.

If you’re interested in getting to know more about this city and the most notable attractions that it holds, then we’d recommend starting with the following locations:

1. Duval Street: Full of nightclubs, restaurants, and shops
2. Truman Annex: The go-to place for history buffs
3. Casa Marina: Ideal for anyone that wants to spend some time on the beach
4. Old Town: The center of the entire city
5. Bahama Village: The best place to get some food and just relax

Key West’s Best Areas and Hotels

There are hotels and lodgings all over the place, and it’s going to be incredibly easy to find a hotel in any section of the city. We’ve gone ahead and outlined what we consider to be some of the best hotels in each section of the city and divided them based on their price range and the sorts of amenities they have.

We’ve also mentioned what every area of the city is famous for, and where you can get some decent grub regardless of where you’re staying. With all of that, we’re pretty confident that you should be able to easily find where to stay in Key West and have a nice visit.

1. Duval Street

There is no better place to be in Key West if you want to have a fun night out than Duval Street. Here you’ll find most of the bigger nightclubs and the fancier restaurants, and if you want to party until dawn, you’ll have quite a selection to choose from. If you don’t like the drinks or the music in a particular pub, you can just go next door.

There’s always something going on here, there’s always a party somewhere, and there’s always a live band or a concert happening at any time of the day. It’s as easy as keeping an ear open while taking a walk in order to find the party.

If you’re more in the mood for shopping while on a trip, then Duval street has got you covered as well. This section of the city has the more notable brand shops and the larger boutiques and malls in Key West, so if you can’t find it here, you won’t find it anywhere else in the city.

Having a party all day long can sound fun, but it might get a bit tiring if you’re trying to sleep. You should be fine as long as you go for a hotel that’s a bit further away from the nightclub scene. While that would mean that you’ll need to walk a bit more towards the fun, it’s worth it if you want to have a good night’s sleep.

Things to Do

• Visit a place called “Rick’s” and you’ll be able to go to a nightclub, strip club, rock bar, or five other types of entertainment venues all housed on different floors of the building.
• You can go and enjoy one of the many LGBTQ clubs that are open in this area of the city and try out their large assortment of cocktails.
• Go to the green parrot if you’re tired of partying and just want to chill out and relax with a drink in a jazz joint with a very chill atmosphere to it.
• Catch a play at the Red Barn Theatre, or maybe go to the Tropic Cinema if you’re more in the mood for a movie.

Where to Eat

• Onlywood Pizzeria is a great place to go for a nice slice of pizza and pick out any toppings that you want.
• First Flight Island Restaurant & Brewery is for people that just want to take a load off and enjoy a drink with their friends and maybe a quick bite as well.
• Southernmost Beach Cafe has a decently large fish-focused menu, as well as a pretty big list of cocktails that you can get as well.

Duval Street Budget Hotels

• Kimpton Ridley House has a pool that you can use at any time, and it’s located close to a lot of fun nightclubs and restaurants that you can get to in minutes.
• Almond Tree Inn offers rooms with satellite TV, a microwave, as well as a patio, tea and coffee making facilities, and even a hot tub and a free continental breakfast each morning.

Duval Street Mid-Range Hotels

• The Cabana Inn comes with a daily continental breakfast, a free parking spot and a business center located in the hotel.
• Orchid Key Inn is located right in the heart of Key West, and it provides you with one complimentary cocktail of choice every day.

Duval Street Luxury Hotels

• Paradise Inn has an outdoor pool, a sitting area inside the hotel, a complimentary breakfast and a glass of wine a day, and even a small Koi pond where you can sit and enjoy your drink at night.
• The Gardens Hotel has two outdoor pools that the guests can use, rooms fully-equipped with a flat-screen TV and free wifi, and the hotel itself is just a short walk away from the Key West Aquarium and the Shipwreck museum.

2. Truman Annex

The Truman Annex is home to what is called the “Truman Little White House”, which used to be the winter home of the 33rd president of the US, Harry Truman.

This residence has been turned into a presidential museum that holds tours several times a day that allow you to see the home and the possessions within in their entirety, along with a lot more information about the man himself.

On the residence, you’ll also find several gift shops, and if you’re lucky, you might time your visit with one of the many events that are regularly organized in the backyard of the Little White House. These events range from art exhibitions to charity events, and they’re usually well advertised so you’ll find a flyer in the city if you’re interested.

Most of the locations and even restaurants in this section carry the Truman name in honor of the president that this section of the city was named after. That said, the museum and the historical significance that it carries aren’t actually the only attractions in this part of town.

You can visit the historic seaport and maritime museum, both of which hold as much history as the presidential residence, and you can also simply spend a fun afternoon exploring the aquarium. If you’d like to take a breather from all the information, a calm walk in one of the parks will do you wonders.

It’s undeniable that history buffs will have a lot of fun in this part of Key West, but people that aren’t all that interested in the history of the city or the president might want to skip this particular location while on vacation.

Things to Do

• Take a guided tour of the presidential home and learn a bit more about the history of one of the more noteworthy presidents of the US.
• The Maritime Museum has a very interesting exhibit that displays several interesting and massive galleons that you can explore.
• Try and catch one of the interesting shows that are usually organized on a weekly basis in the Key West amphitheater.
• The Truman Waterfront Park is the best place to go if you want to go down a few slides, splash around a bit, and maybe just have a swim.

Where to Eat

• Kermit’s is your local one-stop shop for cookies, pies, cake, and virtually anything edible that’s key lime flavored.
• Sloppy Joe’s is where you go when you want a good old-fashioned American burger and some fries to go along with it.
• Sandbar Sports Grill has some of the best BBQ this side of Key West, and they generally have a live band play most nights for some entertainment.

Truman Annex Budget Hotels

• Hyatt Residence Club comes with a room that has a TV and DVD player, as well as access to an on-site spa and even a laundrette.

Truman Annex Mid-Range Hotels

• Weatherstation Inn provides you with an outside pool, and a private parking spot, and it’s located really close to the Ernest Hemingway museum.
• Admirals Gold is a spacious and fully-equipped holiday home that can be rented and is located remarkably close to the beach whenever you want to go for a swim.

Truman Annex Luxury Hotels

• The Saint Hotel comes with a restaurant in the hotel with a pretty large menu and a bar with an equally impressive list of drinks and different cocktails that you can try out if you just want to relax and chat without even going out on the town.
• Opal Key Resort & Marina comes with everything from a heated pool and hot tub, to a business and fitness center inside the hotel, and even an on-site restaurant and bar that guests can visit.

3. Casa Marina

This place is the home of the Edward B. Knight Pier, which might not mean anything to you, but it’s the southernmost point of the continental United States. While this is an interesting tidbit, it’s not really much of a reason to visit this place, so it’s a good thing that Casa Marina is also home to some incredibly beautiful beaches as well.

Smathers Beach is the biggest one, and it has a lot of fun cocktail bars that you can visit and lounge areas that you can relax in. Higgs Beach is a bit smaller, but the water here is no less clear and the sun is no less pleasant, making it a close #2 when it comes to Key West beaches.

Pet owners will also be happy to know that there’s a pet-friendly beach as well, which means that you can walk your dog while sipping Mimosas and chatting with other animal lovers.

There are also quite a few hotels that allow you to keep your pet in your room as well, so you don’t need to leave them in a kennel overnight. This section of the city is either hotels or residential houses, and the beachfront hotels are usually full during high season, a bit on the expensive side, or both.

You’ll either need to book a room in this section of the city pretty early on, or you’ll need to find a hotel a bit further away from the beach and walk each day, which isn’t necessarily bad if you ask us.

Things to Do

• Rent a lounge chair, sit on the beach all day, enjoy a drink, and either read a book or soak in some Vitamin D.
• Visit the Key West Butterfly and Nature Conservatory if you want to see some breathtaking flora and fauna.
• Grab a pole and try to catch something on the hook that would be impressive to take a picture of and frame when you get back home.
• If you want to stretch your legs, you can go for a walk in the nature preserve and get a bit of fresh air in your lungs.

Where to Eat

• Louie’s Backyard offers Caribbean-American cuisine, an ocean view, and a fully stocked wine bar.
• Salute! On The Beach is a great place where you can just sit down and get out of the sun for a bit while enjoying a nice cold drink.
• Sun Sun Beach Bar & Grill is another place where you can grab a drink on the beach, but now you can also get some BBQ to go along with it as well.

Casa Marina Budget Hotels

• El Patio Motel is a pretty simple accommodation, but it provides the guests with a cable TV, a refrigerator, and an AC unit in every room.
• Blue Marlin Motel offers you a TV, microwave, and coffee-making facilities at a very reasonable price.

Casa Marina Mid-Range Hotels

• Tropical Village provides the guests with a unit that’s equipped with an AC, TV, and microwave, and some of the units also come with a dishwasher and oven.
• Alexander Palms Court is a modest property that’s right next to the beach and that comes with an outside pool and free wifi.

Casa Marina Luxury Hotels

• Casa Marina Key West is located right next to a private beach that guests can use, the hotel comes with a fitness center, and you also have a spa that offers massages, facials, and aromatherapy.
• Santa Maria Suites Resort is less than a 10-minute walk away from the beach, it comes with a pretty large outdoor seasonal pool, and it has an on-site restaurant called Ambrosia that has a large selection of items on the menu.

4. Old Town

Old Town is actually divided into a north and south section, but there honestly aren’t too many meaningful distinctions between both of these to draw a clear line, so it’s just better to think of them as just one part of the city. Here you’ll find the most hotels and restaurants that you can find in any one place in the city.

While there might not be quite as many nightclubs or cafes as on Duval Street, Old Town actually borders all of the other notable sections of Key West, which means that getting a hotel here puts you within walking distance of any attraction that you might be interested in.

As you might have guessed by the name, this section is also home to some of the oldest buildings in the entire city and the place where you can go to if you’re partial to interesting architecture from different periods.

Old Town is also the former home of Ernest Hemingway, including his residence, while some of the gargantuan churches in this part of the city are also a sight to behold.

While this section is probably the center of Key West, it doesn’t really have any one specific thing that you’d stay here for. While it’s great for the many hotels that you can find, looking at buildings gets old after a while and you want to go do something a bit more exciting.

Things to Do

• Get some exercise and see the sights on one of the bicycle tours that are organized on a daily basis.
• Visit the Papa’s Pillar distillery and buy yourself a cocktail, or a bottle, or just visit one of Ernest Hemingways favorite drinking spots.
• Catch a trolley tour that actually takes you through the entirety of Key West and tells you everything you need to know about the history of the city in just a few hours.
• While it may seem strange, you can also take a guided tour of the Key West Cemetary and see all of the noteworthy monuments that are housed here.

Where to Eat

• Azur is a great place for some Mediterranean food and it has a large list of exotic foods on the menu that are available.
• Old Town Bakery is just a small place where you can stop by, get something to eat, and keep exploring the city with a pastry in your hands.
• Harpoon Harry’s is the place to be for fish lovers since they get a fresh supply each and every day.

Old Town Budget Hotels

• Eden House comes with a sundeck for sunbathing, hammocks where you can enjoy a book and a drink in the sun, and a heated pool that’s great for a nighttime swim.
• Pegasus International Hotel is located just 10-minutes away from the beach if you walk, and it comes with free wifi, a heated pool, and a hot tub.

Old Town Mid-Range Hotels

• Silver Palms Inn has an outdoor pool, a flat-screen TV in every room, free wifi, and a complimentary breakfast each morning.
• Old Town Manor is a pet-friendly hotel that provides you with a complimentary breakfast each morning that comes with pastries, an assortment of fruit, and dessert cakes.

Old Town Luxury Hotels

• The Palms Hotel comes with a heated pool that the guests can use at any time of the day, as well as a daily continental breakfast that can be served to you poolside while you enjoy a dip.
• The Mermaid & The Alligator Provides its guests with a shared lounge and a beautiful garden to sit in, an à la carte breakfast each morning, and a hot tub that all of the guests can enjoy.

5. Bahama Village

Bahama Village is one of the smaller neighborhoods of Key West in general. While the size might be the main reason why so many tourists seem to overlook Bahama Village, there are still plenty of reasons why you should pay this location a visit.

Bahama Village might not have as many restaurants as Old Town, but the variety between them more than makes up for it. This is where you go if you want to get some authentic Cuban cuisine. If you prefer to go for a bit more fish in your diet or even some BBQ, Bahama Village has you covered.

This quaint location also has a lot of natural beauty in the form of parks where you can just stroll around, while the many playgrounds make it a family-friendly place as well. While this may be one of the calmest sections of the city that you can visit, a lot of people don’t really go on vacation or on a trip just to sip coffee while sitting on a park bench.

If you’re looking for something a bit more fun or exciting, Duval Street or Casa Marina might fit you better. Nevertheless, families can book their lodgings here, and use Bahama Village as an exploration base.

Things to Do

• If you’re in the mood for some peace and tranquility, then you can rent out a boat and go do some fishing off the coast.
• Visit the Bahama Village market and shop for everything from fresh produce to a nice straw hat that can help you beat the heat.
• Go to one of the many sports courts and play a few games of basketball or tennis to work up a bit of a sweat.
• Take a tour of the historic Key West Lighthouse that can be found in this area.

Where to Eat

• Blue Heaven is probably one of the best restaurants where you can get yourself some breakfast with a good selection of different pies.
• Santiago’s Bodega is where you go when you’re in the mood for some classic Cuban food or something that’s a bit on the spicy side.
• La Crêperie French Café is where you go if you’ve had enough of Cuban and want to go for some French food instead.

Bahama Village Budget Hotels

• Howe Street Hideaway has a TV with cable, two bedrooms, a fully equipped kitchen, and all of this at a reasonable price.

Bahama Village Mid-Range Hotels

• Papa’s Hideaway comes with an outdoor pool, a sun terrace with lounge chairs, and you can even hire a bicycle on the property if you want to explore the city a bit.

Bahama Village Luxury Hotels

• Kimpton Lighthouse Hotel is located near the Ernest Hemingway and Keeper’s Quarters museums and comes with a swimming pool, free parking, pet-friendly rooms, and a bar where you can grab a drink.
• Douglas House is just a five-minute walk from the beach, each room comes with a microwave, refrigerator, and coffee-making facilities, and you can access the free wifi from anywhere, including the pool.

So, Where Should You Stay in Key West?

When searching for the best part of Key West to say, we think you should pick the location based on what sort of attractions it holds and how interested you are in them. In terms of hotels, there are a few that we believe you should pay a bit more attention to.

• Old Town Manor is one of the more famous hotels in this city and it provides you with all of the amenities that you might need on your vacation, and at a reasonable price to boot.
• The Paradise Inn is a bit more spacious as accommodations go, and if you’re willing to spend a few more dollars, then you can spend your vacation in a bit more luxury.
• The Blue Marlin Motel is a great budget option for anyone that wants to save a bit of money on the room itself, but still wants to stay in a decent hotel.

The best hotels are the ones that provide you with the essentials that you need but don’t charge too much money, so you should be just fine with any of the hotels that we’ve put on our list as long as you know your budget and you stick to it.