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!
- Where to Stay in Key West
- Key West Neighborhood Guide
- Top 4 Areas to Stay in Key West
- 1. Old Town – Best Place to Stay in Key West for your First Time
- 2. New Town – Where to Stay in Key West on a Budget
- 3. Lower Duval – Best Area in Key West for Nightlife
- 4. Smathers Beach – Best Area in Key West for Families
- Final Thoughts on Where To Stay in Key West
Private Houseboat in Key West – Key West Yacht
Everyone that visits the Florida Keys dreams of having their own yacht – and this Airbnb will turn those dreams into reality. It’s officially moored in New Town, but you’ll also be within walking distance of Smathers Beach. Of course, being a boat and all, you can take it anywhere you want along the coast of Key West.
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 sits in the peaceful Smathers Beach neighbourhood. The décor is somewhat minimalist but comfortable, with a balcony offering views across the Keys. We also love the sports and pool facilities on offer within the complex.
Serene Hotel in Key West – H2O Suites
Kick back and relax in the heart of the Historic District in this peaceful hotel. It’s adult-only, so you won’t need to worry about noisy kids running around the place. Rooms are beautifully decorated to create a bright and airy vibe. The Key West Butterfly and Nature Conservatory is only a stone’s throw away, and most of the city centre attractions can be accessed on foot.
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 neighbourhood 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.
The Historic District, also known as the Old Town, is the beating heart of Key West. 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 this neighbourhood.
Lying to the east of Old Town, New Town is a more modern neighbourhood 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 traveling on a budget.
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.
Finally, Smathers Beach is 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, 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.
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.
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. 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! 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.
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 stylish hotel is designed with budget travellers in mind. 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.
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 favorites 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 Key West Butterfly and Nature Conservatory has a huge selection of native insect life – perfect for a family day out on the odd bad weather day.
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.
Modern Home in New Town – Sea Glass Cay
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.
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.
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 sat 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.
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!
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.
Things to See and Do in Lower Duval:
- Discover the hippest bars and quirkiest cocktails in this fantastic 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.
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.
Peaceful Apartment in Smathers Beach – Moondance at La Brisa
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. La Brisa Condominium Complex is known as one of the best in Key West, with more sports and dining facilities than you’ll have time to get through.
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 condo. 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.
- Scooters Direct mostly sell scooters, but you can also hire them (or e-bikes) for a unique way to explore the city.
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. With something for everyone on offer, it’s no wonder Florida’s coast is such a popular destination among travelers in the USA.
The neighbourhood 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\1 Whether you’re looking for interesting historic attractions, peaceful beaches, 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!
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