8 best hotels near Duval Street in Key West

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That you look for the best hotels near Duval Street means that you have done your homework. Brimming with energy, Duval Street is the center of attention in Key West. Check in at one of the best Duval Street hotels to be close to all that the island has to offer, from those historic sights to the buzzing entertainment scene.

In north to south order, this guide reveals 8 gorgeous hotels near Duval Street. If you want to dig deeper, also check out our ultimate guide on where to stay in Key West.

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A north to south stroll on Duval Street

Stretching from north to south, Duval Street is 1.25 miles (2 km) of quirky gift shops, tasty restaurants, fun watering holes and an in general lively ambience. It’s the action-packed main drag of Key West’s Old Town.

But, which is the best location on Duval Street?

Duval Street’s northern part, the Gulf of Mexico end, is always busy. This side is where you find the iconic Sloppy Joe’s, always ready to pour you a drink, and Mallory Square, hosting the nightly Sunset Celebration.

The central slice of Duval Street is as full of energy. Enjoy something cooling at Willie T’s; then top off Duval’s liveliness with historic sights of the highest standard on the next street, Whitehead, including the engaging Hemingway Home and rising Key West Lighthouse.

As you get further south on Duval Street, the establishments and crowds start to thin out. The southern third of Duval Street, the Atlantic end, is much quieter than its northern counterpart.

However, don’t think that the show is over quite yet. Key West’s Old Town, of course, has another ace in its sleeve.

This part of the island marks the southernmost end of the continental USA. Only a block from Duval Street’s conclusion, the most famous photo opportunity in Key West awaits — the vivid Southernmost Point Buoy.

A heads up: Most of these hotels near Duval Street are for adults only. If you travel with children, see our Key West neighborhood guide for more suggestions.

1. Ocean Key Resort

On Zero Duval Street // Oceanfront and Duval Street address is a rare combo. At the Ocean Key Resort, facing the Gulf of Mexico, it’s certainly easy to embrace it. The tropical drinks taste as good as ever at the oceanfront pool bar; the Sunset Pier restaurant might offer the most breathtaking dining location in all of Key West. Making the most of its seaside location, Ocean Key Resort is a luxury Duval Street hotel that sets a remarkable scene for a Key West vacation.

2. Simonton Court

700 feet from Duval Street // Picture artisans carefully rolling cigars under the Key West sun: Simonton Court once was as a cigar factory, with its 1880s cottages functioning as worker homes. Then dip your feet in one of Simonton Court’s swimming pools; there are not one but four of them — one for every mood (or drink).

3. Old Town Manor

100 feet from Duval Street // It’s not called Old Town for nothing: Many of the best hotels near Duval Street wow guests with their history. An outstanding example of past and present intersecting beautifully, Old Town Manor, where each room is unique, has played various roles throughout the years. Since the adorable Victorian house, complete with a blooming patio and signature porches, was built in 1886, it has been used as a grocery and butcher store, doctor’s office and boardinghouse.

4. The Gardens Hotel

300 feet from Duval Street // From the outside, you can’t see much of The Gardens Hotel: The property, once intended to become a public garden, is enclosed by vegetation. But if you enter this Key West secret, there’s no way back. Laced with brick pathways framed by plants and flowers, the lovely compound provides tropical privacy at its best. Sleep like a baby in a tranquil guestroom, or, if you want some extra space, bed down in a luxurious cottage or suit.

5. Almond Tree Inn

200 feet from Duval Street // The devil is in the details, but Almond Tree Inn nails those details brilliantly. Think spotless grounds, tasteful decor and, to start your day in the best way, a complimentary continental breakfast prepared with love. This is a place to stay near Duval Street where the upscale resort and homey bed and breakfast meet.

6. Douglas House

100 feet from Duval Street // Douglas House has the recipe for a pleasant Key West stay in its DNA: It’s quiet (partiers, looks elsewhere), filled with greenery — the lush pool area is a fine Key West representative — and the best of Old Town is within steps. Yes, all about Douglas House radiates tropical coziness, making it one of the most popular hotels near Duval Street for couples.

7. Southernmost Point Guesthouse

On Duval Street // Southernmost Point Guesthouse was originally built across the street. However, the first owner, E.H. Gato senior, was a true perfectionist. He wanted a more favorable sun exposure on his beloved porches and moved the house to its current position with the help of logs and mules. Today, guests applaud the result as they enjoy one of the most unique Duval Street hotels. Ambience, charm, hospitality, views and, as a refreshing bonus, the attached Southernmost Point Bar in the USA — the Southernmost Point Guesthouse ticks all the right boxes.

8. Southernmost House Hotel

On Duval Street // The pastel-colored Victorian-style Southernmost House Hotel ends Duval Street with a bang. Facing the Atlantic Ocean, it enjoys stunning views and salty breezes, which are extra welcome those balmy Key West days. Add historical glamor: Celebrities swarmed the property during its 1940s nightclub years, then called Cafe Cayo Hueso, and dignities including five US presidents have stayed here. Completing the experience, the Seaside Cafe serves island classics — if you haven’t tried the lobster pizza, you’ve been missing out.

Best beaches near Duval Street

Now you know about the best hotels near Duval Street. But which are the best beaches near Duval Street?

  • South Beach – You don’t even need to leave Duval to find a beach. At Duval’s southern end, right at Southernmost Point Guest House and Southernmost House Hotel, South Beach is a small beach that is appreciated for its convenience.
  • Simonton Beach – Though it’s hidden and of humble size, there’s a beach up north too. One street from Duval’s northern end, the short and narrow Simonton Beach invites you to some lazy island time.
  • Higgs Beach – On the southern coast of Key West, a mile east of the Southernmost Point, Higgs Beach stands out as the best free beach near Duval Street. Savor 17 sandy acres and all the facilities you need for a full beach day.
  • Fort Zachary Taylor – Key West’s most complete beach, tranquil Fort Zachary Taylor Beach is as great for lounging as for snorkeling — its water is both clear and blue. Although only 20 minutes by foot away, the buzz of Duval Street feels distant here. Have in mind: As a protected state park, there’s a small fee to enter.

Pro tip: Fort Zachary Taylor is a beautiful spot for sunset too.

Best hotels near Duval Street FAQ

Is Duval Street in Old Town?

Duval Street cuts through Key West’s Old Town from north to south. It connects the Gulf of Mexico with the Atlantic Ocean, resulting in that quirky locals call Duval Street, 1.25 miles (2 km) short, the longest road in the world.

What is special about Duval Street in Key West?

Duval Street presents one of the most renowned nightlife scenes in the USA. Every night around the year, visitors come to the bar-lined Duval Street to let loose.

Which are the best cheap hotels near Duval Street?

While Key West and affordability rarely fit in the same sentence, Douglas House offers appreciated value just 100 feet from the iconic Duval Street. For even more budget-friendly rates, consider the low-key Blue Marlin Motel, set not far from the Southernmost Point.

Is Duval Street family friendly?

Mornings and midday are good times for families to get a glimpse of Duval Street. After Sunset Celebration, Duval Street gets livelier and families may prefer to retreat to quieter venues.

How far is Duval Street from the beach?

A small public beach, South Beach is located directly at the southern end of Duval Street. One street from Duval’s northern end, Simonton Beach is also tiny by Florida standards. For a bigger beach, consider Higgs Beach, Smather’s Beach or Fort Zachary Taylor Beach.

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