Key West is the final stop along the Florida Keys, and is considered the Southernmost Point of the Continental United States. This stunning destination attracts sun-seekers from across the country every year. Hundreds of thousands of tourists flock to enjoy the Caribbean climate, chilled out nightlife, and pristine beaches of Key West.
This island might be small, but is so full of things to do that it’s impossible to fit it all in on one trip. For this reason, it’s really important to plan your itinerary in advance. Each neighbourhood offers something unique to travellers, so it’s a good idea to know exactly what to expect.
That’s where we come in! We’ve combined our personal experience with hints and tips from locals and tour guides to bring you this guide to the four best places to stay in Key West. Whether you’re looking for bustling nightlife, peaceful coastal escapes or simply somewhere cheap to enjoy the sunshine, we’ve got you covered.
So, let’s dive right in!
With something for everyone on offer, it’s no wonder Florida’s coast is such a popular destination among travellers in the USA. It’s the perfect spot for a family holiday, a wild weekend with your besties or a relaxing break by the coast!
So, you’re wondering where to stay in Key West for the perfect trip, well, let’s get down to business and find out!
Whether you’re looking for a stunning historic hotel with an outdoor pool or a stylish boutique hotel with a complimentary breakfast. We’ve got you covered with the best hotels and airbnbs in town!
Private Houseboat in Key West – Key West Yacht
Everyone that visits the Florida Keys dreams of having their own yacht – and this bed and breakfast in Florida will turn those dreams into reality. It’s officially moored in New Town, but you’ll also be just a short walk from Smathers Beach and Key West’s historic seaport. Of course, being a boat and all, you can take it anywhere you want along the coast of Key West including sailing around the southernmost point of the USA!
Family Condo in Key West – Driftwood Dreams
Condos are popular accommodation options across America – and the Florida Keys are home to some of the best. This particular condo is popular with families and is just a short walk from Smathers Beach as well as the southernmost point of the USA. With a balcony offering views across the Keys, and the sports and outdoor pool facilities it beats most of the best hotels in the region.
Serene Hotel in Key West – H2O Suites
Kick back and relax in the heart of the Historic District in of the best Key West hotels on offer. It’s adult-only, so you won’t need to worry about noisy kids running around the place. The rooms are beautifully decorated to create a bright and airy vibe and the outdoor pool is surrounded by palm trees. Most of the main downtown Key West attractions can be accessed on foot including the historic seaport and Key West lighthouse.
Key West Historic District, also known locally as the Old Town, is where the city first began. This is where you will find the most iconic architecture in the city, as well as the bulk of local attractions.
To the east of the Old Town lies the New Town! As you can probably gather from the name, this is the more modern part of the city. It was built to be a mostly residential neighbourhood, and whilst it still is, there are some great accommodation options popping up along the coast.
The entirety of Duval Street is within the Historic District, but in many ways, it is a neighbourhood in its own right. Upper Duval, on the south end, is pretty peaceful, but Lower Duval, on the north side of the city, is where you will find the best nightlife in town.
Just south of the airport, Smathers Beach is the largest in the city. Despite the size and nearby transit hub, it’s actually a super peaceful neighbourhood. This makes it an excellent spot for families looking to kick back and relax.
Top 4 Areas to Stay in Key West
Key West might be small, but it is an incredibly diverse destination when you scratch beneath the surface. Each of Key West’s neighbourhoods offers something different from the rest, and where you stay can really make or break your trip. Thankfully, getting around is super easy even for those that don’t have a car. It’s even easy to get to Key west international airport with the shuttle service.
Old Town: The Key West historic district, also known as the Old Town, is the beating heart of the area. For first-time visitors, the Old Town is a great place to get a sense of what Key West is all about, with loads of attractions concentrated in the centre. You’ll also find most tour operators are based in Key West’s old town.
New Town: Lying to the east of Old Town, New Town is a more modern neighbourhood that is growing in popularity with visitors. Previously a residential area, it’s one of the cheapest places to stay on the Keys and is ideal for anyone travelling on a budget as you’ll find some of Key West’s best hotels at a reasonable rate here.
Upper Duval and Lower Duval: Key West is arguably the best place to stay in the Florida Keys for nightlife, thanks to vibrant Duval Street. It cuts right through the Old Town, with Upper Duval and Lower Duval forming two popular neighbourhoods. You’ll find bustling parties, chilled-out bars, and everything in between in this neighbourhood. During the day, it’s a popular shopping area as well as being close to the Key West historic seaport.
Smathers Beach: Finally, Smathers Beach offers a completely different vibe. Laid-back condos and holiday rentals line the coast here, offering your own little secluded paradise in this tourist hotspot. For families visiting Key West, Smathers Beach is close enough to the city centre that you’ll have plenty to explore but distant enough for some peace and quiet in the evenings. If you’re looking for a Key West resort then this is a great spot too.
Still undecided? We’ve got some more information about each neighbourhood below, as well as our top accommodation picks and things to do in each area.
5 Best Areas to Stay in Key West
There are many interesting experiences to be found all around Key West, but where should you stay? Each neighbourhood has its own vibe. I’ve rated the top neighbourhoods to stay in when you visit Key West below.
1. Old Town – Best Place to Stay in Key West for your First Time
Key West Historic District, also known locally as the Old Town, is where the city first began. This is where you will find the most iconic architecture in the city, as well as the bulk of local attractions. First-time visitors will get a good understanding of everything on offer, as well as a vast selection of excursions to take them elsewhere along the Keys.
The Old Town is also the best-connected part of the city. It sits literally in the centre of Key West, so you can easily reach all of the other neighbourhoods mentioned in this guide on foot as well as Key West international airport. This is perfect for those that don’t have access to a car.
Romantic Nest in Old Town – Hidden Beach
This love nest is located right on the coast and includes an outdoor pool! It’s actually on the only natural beach in Key West and comes with stunning Caribbean views. There is a small decked area where you can sit back, relax and enjoy a couple of cocktails with the sunset. Sleeping up to two people, this is our top pick for couples heading to the city. It’s one of the most romantic Airbnbs in Florida!
Hip Hotel in Old Town – Not Your Average Hotel
Key West is a pricey destination, especially the Historic Old Town. There aren’t any hostels in the city, but backpackers don’t need to feel left out! This boutique hotel is designed with budget travellers in mind and comes with a complimentary breakfast. Rooms are simple but well priced – but that doesn’t mean you miss out on small splashes of luxury. It also has some great communal areas as well as a pool making it one of the best hotels in Key West for the price.
Calm Hotel in Old Town – H2O Suites
Straddling the boundary between the Historic District and Casa Marina, this is a fantastic choice if you want to stay close to the action whilst still enjoying a calm atmosphere. This four-star hotel is a little bit of a splurge, but the luxury extras make it worth every penny. Rooms incorporate modern technology and stylish fittings to create an upscale vibe, and some even have their own private pool!
Things to See and Do in Old Town:
- Duval Street isn’t the only nightlife in the city. Hit up some local favourites in this tour of Key West’s alternative bars and clubs.
- Key West is home to the Southernmost Point in the Continental United States – you can take a guided tour of the best attractions in the area on this experience.
- Famous writer Ernest Hemingway spent his late years in the Caribbean. Check out his Key West residence and learn more about his work at his former house.
- The Green Parrot Bar is over 100 years old and offers incredible live music and a laid back local vibe for a night out.
We’ve tested countless backpacks over the years, but there’s one that has always been the best and remains the best buy for adventurers: the broke backpacker-approved Osprey Aether and Ariel series.
Want more deetz on why these packs are so damn perfect? Then read our comprehensive review for the inside scoop!View on Osprey View on REI
2. New Town – Where to Stay in Key West on a Budget
As you can probably gather from the name, this is the more modern part of the city. It was built mostly as a residential neighbourhood, and whilst it still is, there are some great accommodation options popping up along the coast. These are often far more affordable than those in the city centre, ideal for anyone visiting Florida on a budget.
New Town is also a major shopping destination, housing the largest mall in the city. North Roosevelt Boulevard is the beating heart of the neighbourhood. This is where you will find some of the best shopping bargains and cheapest restaurants in the city. It’s also super close to the Key West nature preserve where you’ll find the southernmost point of the USA.
Cute Houseboat in New Town – Key West Yacht
It doesn’t get any more Florida Keys than this! This boat is moored in New Town but you can take it anywhere you want around the city. Want to travel further afield? You can also hire an experienced Captain to take you on day trips around other Keys. It’s powered mostly using solar energy, making it a great choice for more environmentally-conscious travellers.
Affordable Hotel in New Town – The Capitana Key West
This hotel is a more affordable option for couples and solo travellers. You’ll also get to enjoy all the additional services and convenience associated with staying in a hotel. Located right on North Roosevelt Boulevard, you’ll be within walking distance of some of the most budget-friendly shops and restaurants in Key West.
Modern Home in New Town – Paradise villa with pool
This Florida Keys Airbnb sits on the boundary between Old Town and New Town, so you’re actually within walking distance of both areas. The home itself has a calm oceanic vibe to it, with enough space for up to eight people. The huge pool area is surrounded by luscious plant life, and there is a breakfast bar nearby where you can take in the morning air.
Paradise villa with pool is one of our favourites in Key West but they’re not taking guests right now. We’re not sure if they’re closed for good but we hope they’ll come back soon.
Things to See and Do in New Town:
- Soak up the gorgeous coastal scenery in this laid-back kayak tour taking in the mangrove mazes surrounding the Keys.
- The Meadows is an up-and-coming neighbourhood sitting between New Town and Old Town. Head on over for this upbeat party boat experience.
- Key Plaza is the largest mall in the city, housing local boutiques, international brands and a large food court to suit all budgets.
- Take a trip over to Dredgers Key – it’s mostly a residential island, but it’s a popular spot for fishing in the city.
3. Lower Duval – Best Area in Key West for Nightlife
Key West is the best place to stay in the Florida Keys for nightlife, and Lower Duval is where you’ll find it! The entirety of Duval Street is within the Historic District, but in many ways, it is a neighbourhood in its own right. Upper Duval provides a more peaceful location that’s still close to the action.
Lower Duval is also home to some of the best shopping boutiques on the Keys. You’ll also find some great restaurants and cafés dotted around the area. In many ways, this is the city’s entertainment district.
Traditional Apartment in Lower Duval – Historic Caroline
This apartment is a little more basic, but with prices this cheap, we’ll take it! It only has one bedroom, making it a great choice for couples and solo travellers planning to hit up the local nightlife. It’s only one street over from Duval Street and about a one-minute walk from the boardwalk area. Guests also have access to a shared pool deck.
Quirky Inn in Lower Duval – Simonton Court Historic Inn & Cottages
This four-star hotel has a unique atmosphere that will make you not want to leave. Built within a historic home, this inn has thoughtful extras to enhance your comfort throughout your stay. The outdoor pool deck is a little cosy, with plenty of plant life to add a laid-back vibe to the whole affair.
Charming Townhouse in Lower Duval – The Foundry
We can’t get enough of the gorgeous interiors of this historic townhouse! Located in the Truman Annex part of town, this is actually a super quiet neighbourhood despite only being a stone’s throw from the main nightlife area. Perfect for when you need a good night of sleep after days spent partying!
The Foundry is one of our favourites in Key West but they’re not taking guests right now. We’re not sure if they’re closed for good but we hope they’ll come back soon.
Things to See and Do in Lower Duval:
- Discover the hippest bars and quirkiest cocktails on a pub crawl through Duval Street and Historic Key West.
- Take to the seas in this epic excursion into the Caribbean to spot dolphins, turtles, and other marine life on a guided snorkel with a local biologist.
- Truman Annex is a great spot to kick back and relax. It’s also where you can look into booking a cruise of the Caribbean if that takes your fancy.
- Visit the southernmost point of the continental USA as well as the Key West lighthouse and Key West’s historic seaport.
A new country, a new contract, a new piece of plastic – booooring. Instead, buy an eSIM!
An eSIM works just like an app: you buy it, you download it, and BOOM! You’re connected the minute you land. It’s that easy.Grab an eSIM!
4. Smathers Beach – Best Area in Key West for Families
Just south of the airport, Smathers Beach is the largest beach in the city. Despite the size and nearby transit hub, it’s actually a super peaceful neighbourhood. This makes it an excellent spot for families looking to kick back and relax.
There’s not much to do in the area itself, but this is part of the charm! If you want to find something to keep the kids entertained, neighbouring Casa Marina is also an excellent spot. It’s also where you’ll find many quirky and affordable VRBOS in Florida Keys.
Peaceful Apartment in Smathers Beach – Seaside condo with pool
If you have a little more money to spend, check out this luxurious condo. The spacious interiors are complemented with thoughtful interior design, creating a bright and breezy vibe. This Condominium Complex comes with two pools, private parking, a tennis court and a shuffleboard area.
Roomy Condo in Smathers Beach – Driftwood Dreams
This cool little condo is our top pick for families heading to Key West! It can sleep up to six people, and larger families can also rent out their neighbouring condos. The interiors have recently been renovated, with a super modern kitchen and bathroom to maximize your comfort.
Laid-Back Hotel in Smathers Beach – Barbary Beach House
Soak up those beachy vibes in this hotel located right on Smathers Beach. It’s within walking distance of the airport, making it a good choice for those that don’t have a car. A continental breakfast is included within the rate, and other perks include an onsite pool and bar.
Things to See and Do in Smathers Beach:
- The Artisan Market in Casa Marina is a must-visit attraction where you can pick up local cuisine and souvenirs.
- Smathers Beach itself offers a peaceful spot to soak up the sun, snorkel and enjoy the Caribbean breeze. It’s the perfect way to spend a day in Key West.
- Scooters Direct mostly sell scooters, but you can also hire them (or e-bikes) for a unique way to explore the surrounding areas, especially some that are more off the beaten track.
- Wanna see something weird!? Check out the Robert the Doll at the Fort East Martello Museum and he’ll haunt your dreams forever!
Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.
It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)Hide Yo’ Money!
What To Pack For Key West
Pants, socks, underwear, soap?! Take it from me, packing for a hostel stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.
Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.
Hanging Laundry Bag
Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.
Sea To Summit Micro Towel
Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.
Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.
Grayl Geopress Water Bottle
Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!
Check out my definitive Hotel Packing list for even more top packing tips!
Don’t Forget Travel Insurance for Key West
ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.
They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.
SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!
Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.
Final Thoughts on Where To Stay in Key West
Sun, sea, and sand are only one half of the story when it comes to Key West. The city is also home to some great nightlife options, fascinating historic attractions, and epic adventure activities.
The neighborhood that really stands out to us is Lower Duval! It’s home to the best nightlife in the city, and is also a major hub for the culinary and shopping scenes in Key West. Everywhere else mentioned in this guide is within walking distance, so it’s also super convenient for getting around.
That being said, the best place for you really depends on what you want to get out of your trip. Whether you’re looking for interesting historic attractions, peaceful beaches, things to do in Key West with kids, or a Florida road trip stopover, we hope this guide has helped you narrow down your options.
Did we miss anything? Let us know in the comments!
And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!