Boasting endless summer and a unique quirky vibe, Key West marks the southernmost point of the continental US. This sun-kissed island sets the perfect scene for a relaxed vacation. But where to stay in Key West for the best experience?
Old Town is the best area to stay in Key West for access to attractions: Choose from an array of colorful neighborhoods including the Historic Seaport, Mallory Square, Heart of Old Town, Southernmost Point, Truman Annex and Bahama Village.
Disclosure: This guide contains carefully selected affiliate links through which we may earn commission when you make a purchase. Learn more ›
Old Town of Key West
Occupying the island’s western portion, Old Town of Key West — also known as the Historic District — holds most of the sights you come to enjoy. Staying here, you have the best of Key West at your fingertips.
Thanks to Old Town’s compact size, it’s effortless to take in the main points of interest. At an average pace, it only takes 30 minutes to stroll from the northern to southern end of Old Town.
A street and attraction in one, buzzing Duval Street ties Old Town together, connecting the Gulf and Atlantic sides. Prepare for a myriad of eye-popping shops, tasty restaurants and refreshing watering holes.
Overall, for sightseeing and nightlife, Old Town is the best area to stay in Key West.
But there’re several charming Old Town neighborhoods: Should you stay in the Historic Seaport, Mallory Square, Heart of Old Town, Southernmost Point, Truman Annex or Bahama Village?
At the northern end of Old Town, a natural bight — Key West Bight — has provided a sanctuary for seafarers for hundreds of years. Today, Key West Historic Seaport continues to thrive.
The seaport is comfortably strolled thanks to the Historic Seaport Harbor Walk. Lined by anchored boats, inviting grills and bars always ready to serve you a drink, the half-a-mile boardwalk is a true pleasure to explore.
For an adventure on the water, a wide range of boating excursions depart from Key West Historic Seaport.
A grand choice is the ferry ride to Dry Tortugas National Park, home to an isolated group of Caribbean islands and historic Fort Jefferson. Other popular excursions include fun-filled dolphin tours and romantic sunset cruises.
Back on dry land, just follow Duval Street south to see more of Old Town. Especially, the northern and central parts of this one-of-a-kind street are lively, offering all the nighttime entertainment you crave for.
Pick Historic Seaport for: Salty marina views.
Best hotels at Historic Seaport
- Hyatt Centric – Perched on Old Town’s northern edge, the oceanfront Hyatt Centric is a tranquil escape from your everyday life. Stroll the adjacent Historic Seaport Harbor Walk, take a boat tour or live your best life on Duval Street. Then, return back to the Key West resort to kick back on your balcony — can’t you feel that warm Gulf breeze in your hair?
- Seaport Inn – For a small-scale take on Key West, check in at the cozy Seaport Inn, framed by tropical vegetation. Having just six units, across three levels, this is a home-away-from-home place to stay in Key West.
Secure your hotel. Hotels in Old Town tend to book up early in advance. In particular, those near Duval Street are extremely popular — make sure to book your lodging as early as possible if you want Old Town as your base.
A stone’s throw west of the Historic Seaport, Mallory Square is a unique meeting point for locals and visitors alike. Every late afternoon, when the sun starts to set over the Gulf of Mexico, people gather on Mallory Square to celebrate.
The Sunset Celebration on Mallory Square is one of the things that makes Key West so special. Watch street performers, savor snacks and drinks — or just enjoy the sunset along with hundreds of fellow visitors.
This is a nightly (and free) Key West show for visitors of all ages.
When the Sunset Celebration is over, the night continues on Duval Street. It’s just minutes by foot from Mallory Square to the most iconic watering hole in Key West, Sloppy Joe’s.
Sloppy Joe’s is the bar where Ernest Hemingway himself, one of America’s biggest writers of all time, used to wet his throat. Reflect on that as you cool down with a drink yourself in the balmy Key West evening.
Pick Mallory Square for: Sunset Celebration.
Best hotels at Mallory Square
- Ocean Key Resort – On the island’s coolest address, Zero Duval Street, it starts with the view: Ocean Key Resort faces both the Gulf of Mexico and Mallory Square. Add to that remarkable waterfront dining and an elegant pool area (cocktails, anyone?) — this is one of the most luxurious resorts in Key West.
- Opal Key Resort – Next to Mallory Square, Opal Key Resort makes it easy to enjoy the iconic Sunset Celebration. Yet this upscale resort’s own Sunset Deck, overlooking the Mexican Gulf, is an as sweet spot to savor those last daylight moments. Here, the vibe is relaxed, beverages thirst quenching and sunsets, of course, jaw-dropping.
Get around. Luckily, getting around Key West is painless. As it’s only 1.25 miles (2 km) from the northernmost Historic Seaport to Southernmost Point, visitors who want to traverse the entire island by foot can do that in roughly 30 minutes.
Heart of Old Town
The walkability is one of the many reasons to visit Key West. If you pick the Heart of Old Town for where to stay in Key West, you get the best of the best when it comes to accessibility.
For liveliness, the core of Duval Street is on your doorstep. This undulating attraction, packed with eateries, watering holes and gift shops, is as entertaining no matter when you visit Key West.
The parallel thoroughfare, Whitehead Street, is significantly quieter but, at least, as charming.
Ernest Hemingway, who lived on Whitehead for a majority of the 1930s, took full advantage of its inspirational setting. Visit the Hemingway Home and see for yourself where he wrote many of his most celebrated books.
Across the street, climb the 88 steps to the top of Key West Lighthouse. From the crown, enjoy panoramic views of the entire Old Town area.
It certainly doesn’t stop there. In the Heart of Old Town, all those other quirky Old Town attractions are at your fingertips too — you’re literally surrounded by rewarding Key West sights.
For example, from the lovely Almond Tree Inn, you can walk to Southernmost Point in 10 minutes and Mallory Square in 20 minutes.
Pick Heart of Old Town for: Convenience.
Best hotels in Heart of Old Town
- Almond Tree Inn – Almond Tree Inn sits on Truman Avenue, offering easy access to the Duval action. Still the property is extremely neat and quiet with all you need for a relaxing stay, including a reviving, palm-fringed pool. For a peaceful stay in the heart of Key West, you can’t beat Almond Tree Inn.
- Douglas House – Although this Old Town inn has Duval Street literally around the corner, it feels secluded. With a lush courtyard and comfy rooms, Douglas House is a fantastic place to stay in Key West for couples — love is in the air.
Sure, it’s not the most central option for where to stay in Key West. It’s also across Old Town from the famous Sunset Celebration on Mallory Square. However, the Southernmost Point area has its own drawcard.
Anchored where Whitehead and White streets meet, the Southernmost Point buoy represents the end of the continental USA. No other connected point of the contiguous USA is located further south.
The quietness of Old Town’s southern portion is a treasured feature too. It’s significantly calmer here, compared to the northern part of Duval Street.
Many visitors just come to this Old Town slice to tick off the Southernmost Point, and possibly the Butterfly Garden, before they head back to the more activity-dense northern streets of Key West.
Thanks to its tucked-away location, the Southernmost Point offers possibilities for budget travelers. Although it’s never easy to find cheap hotels in Old Town Key West, your dollars last slightly longer down south.
Pick Southernmost Point for: Quietness.
Best hotels at Southernmost Point
- Blue Marlin Motel – Sitting in Old Town near both Duval Street and the Southernmost Point, relaxed Blue Marlin Motel isn’t the fanciest among the places to stay in Key West. However, the motel certainly has comfy rooms and a quirky charm. If you look for more inexpensive Old Town hotel or motel, you don’t need to look further.
Need more inspiration? See the best hotels near Duval Street.
Two unique Key West enclaves, the Truman Annex and Bahama Village neighborhoods expand to the west of Whitehead Street. The northern of the pair, the Truman Annex, is an upscale option for where to stay in Key West.
Passing by the Truman Annex area — originally a military base but brilliantly redesigned and renovated in the 1990s — you might think that the area is out of touch: This is a carefully manicured gated community.
However, these gates are different, inviting pedestrians and bicyclists to visit during daytime. Therefore, the Truman Annex still, although with a high-end aura, flows nicely with the rest of Old Town Key West.
The Truman Annex, in fact, holds one of the best Key West sights, Harry Truman’s Little White House. Come and see where President Harry S. Tuman spent 175 days of his presidency, making it his Florida white house.
Even if you don’t stay in the Truman Annex — lodging options are fewer here — the area is well worth a visit. Boasting stunning landscaping and architecture, the district is like made for memorable walks and bicycle rides.
Pick Truman Annex for: Gated community lodging.
South of the Truman Annex and west of Whitehead Street, the smells of Bahama Village lure you in. Many of Key West’s most appreciated ingredients can be traced to this tranquil neighborhood, which too many visitors yet miss out on.
Bahama Village, settled by Bahamians in the 1800s, is defined by Caribbean attributes. Wander past houses in shades of Caribbean blue, listen to tones of calypso, raggae and junkanoo — and embrace exciting island flavors.
The main hub of activity, Petronia Street, boasts a unique dining scene.
Blue Heaven is a Bahama Village institution, serving breakfast with the roosters, lunch in the shade and dinner under the stars. Expect a delicious fusion of Florida and the Caribbean.
Then there’s the nostalgia: In what today makes up Blue Heaven’s dining room, Ernest Hemingway (who else?) used to referee boxing matches during the 1930s. Reflect on that while you have another bite of that delicious banana bread or key lime pie.
Further down on Petronia Street, away from Whitehead Street, Santiago’s Bodega is a fantastic spot for tapas and sangria.
Pick Bahama Village for: Caribbean vibe.
Want to dodge the crowds? Then consider New Town, the under-the-radar part of Key West located east of Old Town.
Here, the intense Duval Street liveliness feels distant. Yet when you need some more stimulation, those popular Old Town sights are just a short ride away — think 5 to 15 minutes depending on your location.
While it’s never easy to find inexpensive hotel rates in Key West, New Town stands out as an option for where to stay on a budget: The further you go from Duval Street, the better value you tend to find.
Pick New Town for: Hotels on a budget.
Best hotels in New Town
- Margaritaville Beach House Key West – Formerly Barbary Beach House, this resort sits just steps from Smathers Beach, on the south shore. Does it get better than a beach house in Key West?
- Parrot Key Hotel & Villas – On the north shore, Parrot Key Hotel & Villas is surrounded by impressive lush gardens. Enter to embrace a tranquil atmosphere and an oceanfront lifestyle.
Stock Island is the eastern neighbor of Key West. It prides itself on its full 18 hole golf course and several good places to eat. This is certainly a great place to spend some relaxing time in the tropical Key West sun.
But when staying on Stock Island, you need to think about transportation to the sights in the Historic District of Key West; getting the 5 miles (8 km) from Stock Island to Old Town takes about 15 minutes by car.
Pick Stock Island for: The next key.
Best hotels on Stock Island
- Oceans Edge Key West – Oceans Edge on Stock Island offers panoramic water views just an island away from Key West. Its marina setting is beautiful, and the Stock Island hotel has a nice pool area that is perfect for lazy days.
Final words about where to stay in Key West
Key West is a tropical island city full of things to do. To make the most of a visit, there are also gorgeous places to stay in Key West — think lush inns and resorts where the attention to detail is immaculate.
Stay in Old Town for that convenient access to everything that the island has to offer. Within steps you reach sights such as the captivating Ernest Hemingway Home, iconic Southernmost Point and vibrating Duval Street.
Only stay in New Town, or on Stock Island, if you’re sure that you don’t mind being a ride away from those appreciated Key West attractions.
Where to stay in Key West FAQ
The best place to stay in Key West is in Old Town on or near Duval Street. From hotels in Old Town, you have walking distance to a majority of the best attractions, restaurants, bars and shops.
Staying in Old Town is the best option for a traditional Key West vacation with all the quirky things to do nearby. To the east, New Town is also a great option if you don’t mind the longer distance to most of the big-ticket items on the island.
The best places to stay in Key West for couples include Almond Tree Inn and Douglas House. These romantic inns offer both peacefulness and easy access to popular island attractions. With its cozy setting Key West is the perfect scene for a romantic USA trip.
Best of Florida Keys
Key West is the most vibrating among the areas to stay in Florida Keys. However, also consider the other portions of the sun-drenched island chain.
- Lower Keys – This slice of the Florida Keys includes the quiet islands closest to Key West. To kick back with a view, head to Bahia Honda Beach, brilliantly overlooking Bahia Honda Rail Bridge.
- Marathon – How about a relaxed escape to the heart of Florida Keys? Get sand between your toes on the soft Sombrero Beach and learn about local wildlife at the educational Florida Keys Turtle Hospital.
- Islamorada – The resorts in Islamorada are famous. Picture palm-dotted beachfront properties, many with their own fishing piers shooting out into the surrounding ocean — this is vacation.
- Key Largo – Discover clear waters full of exciting marine creatures. Marking the start of the Overseas Highway, Key Largo boasts America’s first underwater park, John Pennekamp State Park.
Make the most of every trip with our newsletter delivered to your inbox.