Where to stay in Key West, FL

  • Post last modified:July 29, 2023
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Key West marks the southernmost point of the continental US. Boasting endless summer and a unique quirky vibe, this Florida Keys destination attracts visitors from wide and far. But where to stay in Key West for the best experience?

Old Town is the best place to stay in Key West for access to attractions and the famous quirky vibe. Neighborhoods here include the Historic Seaport, Mallory Square, Heart of Old Town, Southernmost Point, Truman Annex and Bahama Village.

Other options for where to stay when visiting Key West are New Town and the neighboring Stock Island.

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Old Town of Key West

Old Town of Key West, also called the Historic District, holds most of the sights you come to enjoy. Occupying the western portion of Key West, this is for good reason the most popular option for where to stay in Key West.

Thanks to the compact size of Old Town, it’s effortless to take in the points of interest. At an average pace, it only takes 30 minutes to stroll from the northern to southern end of Old Town.

So, with your own two feet, discover the best things to do in Key West including the Hemingway House, Key West Lighthouse, Mallory Square and Southernmost Point.

A street and attraction in one, the 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 place to stay in Key West.

But, there are several charming Old Town neighborhoods to choose from. Should you stay in the Historic Seaport, Mallory Square, Heart of Old Town, Southernmost Point, Truman Annex or Bahama Village?

Let’s dig deeper into the best areas to stay in Old Town Key West.

Secure your hotel. Key West hotels in Old Town tend to book up early in advance. In particular, Key West hotels near Duval Street are extremely popular. Therefore make sure to book your Key West lodging as early as possible if you want Old Town as your base.

View over Old Town — one of the best places to stay in Key West
Old Town in Key West.

Historic Seaport

Once known as Key West Bight, Key West Historic Seaport is located at the northern end of Old Town. Here, a natural bight, or bend, has provided a sanctuary for seafarers for hundreds of years.

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.

In short, Key West Historic Seaport is an option for where to stay in Key West that stands out for its multifaceted mix of seaside offerings. As a bonus, it’s just a few blocks to Duval Street for even more distractions.

Pick Historic Seaport for: Salty marina views.

Recommended 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 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.

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 do that in roughly 30 minutes.

Mallory Square

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.

To sum up, Mallory Square is the best place to stay in Key West for Sunset Celebration. However, this is an overall great option for where to stay in Key West to be close to the best of the island’s nightlife scene.

Pick Mallory Square for: Sunset Celebration.

Recommended 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 Key West 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.

Performing artist on Mallory Square, Key West, during the colorful Sunset Celebration
Sunset Celebration on Mallory Square.

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.

This sounds pretty sweet, right?

But, 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, walk in 10 minutes to Southernmost Point and 20 minutes to Mallory Square.

In conclusion, the Heart of Old Town is the area to stay in Key West that gives you the ultimate vantage point for sightseeing. When staying at a Key West hotel here, you effortlessly walk to any Old Town attraction.

Pick Heart of Old Town for: Most convenient Key West hotels.

Recommended 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

Standing out for its green landscaping, Douglas House is a great place to stay in Key West near Duval Street. 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.

View of Old Town Key West, FL, dotted with green palm trees and surrounded by blue water
Old Town view from the lighthouse.

Southernmost Point

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.

At Key West hotels here, you really bed down at America’s conclusion.

The quietness of Old Town’s southern portion is a treasured feature too. Compared to the northern part of Duval Street, it’s significantly calmer down at Duval’s southern end.

Many visitors just come to the southern slice of Old Town 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.

All in all, the Southernmost Point is a unique option for where to stay in Old Town Key West. At America’s tropical end, this area stands out as a superb place to stay in Key West for visitors who prefer it quieter.

Pick Southernmost Point for: Quieter Old Town hotels.

Recommended hotels at Southernmost Point

Blue Marlin Motel

Sitting in Old Town near both Duval Street and the Southernmost Point, the 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 Key West hotels or motels, you don’t need to look further.

Concrete structure in form of a buoy at the ocean.
Southernmost Point, the end of the continental USA.

Need more inspiration? See the best hotels near Duval Street.

Truman Annex

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 touch, 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.

In short, the Truman Annex provides Old Town Key West lodging in a unique gated community setting. This is, although only blocks from Mallory Square and Duval Street, a sheltered place to stay in Key West.

Pick Truman Annex for: Gated community lodging.

Bahama Village

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 about 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.

In conclusion, Bahama Village is the best place to stay in Key West to enjoy the island’s Caribbean roots. However, the places to stay in Bahama Village are few, which means that a day visit is a strong option too.

Pick Bahama Village for: Caribbean vibe.

New Town

The area of Key West that is called New Town is the part of the island that is located east of Old Town. Unlike if you stay in the Historic District, you don’t have most attractions on your front step if you stay at Key West hotels in New Town.

There are a few popular restaurants in New Town that have appeal to both locals and visitors. But with that said, most of the priorities when you visit Key West are located on the western end of the island.

Because of that New Town is not the best area to stay in Key West if you want to be close to things to do. Then the Key West hotels in Old Town are much more convenient.

Still it’s just a few miles from Key West hotels in New Town to the island’s Old Town attractions. So you have decent access to most things to do when you stay in the New Town area as well.

Further from Duval Street also tends to mean cheaper Key West hotel rates. So you often find lower rates in New Town than at Key West hotels in Old Town. Therefore the New Town area is a very good alternative if you look for a more inexpensive place to stay in Key West.

In short, New Town is not as convenient as an Old Town stay when it comes to access to Key West entertainment. Still New Town is a great option for where to stay in Key West if you don’t need the very best access to the island’s sights. Away from Duval Street also means that New Town is an option for where to stay in Key West on a budget.

Pick New Town for: Key West hotels on a budget.

Recommended hotels in New Town

Margaritaville Beach House Key West

Margaritaville Beach House, formerly Barbary Beach House, offers easy beach access. The New Town resort is located just steps away from Smather’s Beach on the southern end of the island. Does it get better than a beach house in Key West? In addition it’s just 1.6 miles (2.6 km) to Southernmost Point in Old Town from the Key West resort.

Parrot Key Hotel & Villas

On the northern shore of Key West in New Town you find Parrot Key Hotel & Villas. The Key West hotel is surrounded by its impressive lush gardens. Parrot Key Hotel & Villas feels secluded and is one of the best place to stay in Key West if you look for a tranquil atmosphere by the ocean.

Palm tree in Key West, FL
A Key West palm tree.

Stock Island

Stock Island is the island next to Key West. If you drive the Overseas Highway from the mainland, Stock Island is the last island you pass before you enter the final key. So Stock Island is the most convenient option for where to stay near Key West.

The island prouds itself on its full 18 hole golf course and several good places to eat. Stock Island is certainly a great place to spend some relaxing time in the tropical Key West sun.

On the downside, when you stay at a Stock Island hotel you will need to think about and spend time on transportation to reach the main attractions in the Historic Disctrict of Key West. To get the 5 miles (8 km) one way from Stock Island lodging to Old Town takes about 15 minutes by car.

In conclusion, Stock Island is a great option for where to stay near Key West if you want a quiet vacation in the sunny weather. The hotels near Key West on Stock Island offer an appealing contrast to the traditional Key West stay. But Stock Island is too far away to be optimal if you plan to frequently go to Old Town in Key West.

Pick Stock Island for: The best place to stay near Key West.

Recommended 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. The stunning views, convenient location and appreciated amenities make Oceans Edge one of the best places to stay near Key West.

Orange sunset in Fort Zachary Taylor State Park, easily reached from Key West hotels in Old Town
Sunset in Key West.

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

Here you find the answers to some frequently asked questions about where to stay in Key West, Florida.

What is the best location to stay in Key West?

The best place to stay in Key West is in Old Town on or near Duval Street. From Key West hotels in Old Town you have walking distance to a majority of the best attractions, restaurants, bars and shops.

Should you stay in Old Town or New Town of Key West?

To stay in Old Town is the best option for a traditional Key West vacation with all the quirky things to do nearby. New Town in Key West is further away from the Duval Street liveliness but also a great option if you don’t mind the longer distance to most things to do on the island.

Which are the best places to stay in Key West for couples?

The best places to stay in Key West for couples include Almond Tree Inn and Douglas House. These romantic Key West 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.

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