Uptown - Upper Duval Holidays & Package Deals

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Our guide on where to stay in Uptown - Upper Duval

Find the best Uptown - Upper Duval areas and neighborhoods for the activities you enjoy most. Learn more about Uptown - Upper Duval

A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.

A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.

Historic Seaport

If you're spending some time in Historic Seaport, Duval Street and Florida Keys Beaches are top sights worth seeing.

Our pick of the best Uptown - Upper Duval Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

NZ$443

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (3,606 reviews)

"A little annoyed at the gate that got locked (leading us to our room), and that the gate was not repaired during our stay, but that was the only real issue out of the entire stay."

Reviewed on 21 Sept 2026

Southwinds Motel

1321 Simonton Street Key West FL

NZ$304

23 Sept - 24 Sept

includes taxes & fees

8.6/10 Excellent! (1,382 reviews)

"The room was clean and the staff very helpful"

Reviewed on 21 Sept 2026

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Fully refundableReserve now, pay when you stay

NZ$451

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (1,029 reviews)

"The facility was clean and well Maintained. The personnel were helpful and kind. I would recommend this resort to all friends and family."

Reviewed on 20 Sept 2026

See all 2,700 properties in Uptown - Upper Duval

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does an Uptown - Upper Duval holiday package cost?

Explore the best of Uptown - Upper Duval from just . Choose from a great selection of flights, hotels and rental cars to suit your budget. Land even more discounts when you add a few tours or activities to your holiday package.

How do I get a cheap travel package to Uptown - Upper Duval?

Bundling your flight and hotel with Expedia won't just save precious time — it'll save you a nice amount too. An Uptown - Upper Duval holiday package makes it easy to organise the perfect trip. With more than 550 airlines worldwide to pick from, finding convenient flights that fit your schedule will be no sweat. In addition to that, we've got over 1 000 000 hotel options globally to pick from. Now that's what we call choice. No matter who you are, Expedia can show you the world.

Where should I stay in Uptown - Upper Duval?

A trip to Uptown - Upper Duval isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Reserve a room close by so you can easily access these fantastic sights.

What are the top hotels in Uptown - Upper Duval?

Sea Breeze - Walking Distance And Off and Casa Key West - Rooftop Pool Access And Free Parking are two of the most popular properties in Uptown - Upper Duval. Why not look up the rates and facilities at each and then decide?

How far in advance should I book my Uptown - Upper Duval holiday?

While prices change from time to time, we generally suggest booking your spot as early as possible. Most international fares can be compared on Expedia up to 12 months in advance. If circumstances have left you booking late, you may still get lucky. Cheaper tickets to Uptown - Upper Duval sometimes emerge only weeks before departure.

What does an Expedia Uptown - Upper Duval travel package include?

It depends on what kind of trip you have in the works. Uptown - Upper Duval travel deals can include car rentals, hotels and flights. You can mix and match to create the bundle that fits your needs. You can also add on experiences and activities after you've booked to land even bigger discounts.

What should I know before booking an Uptown - Upper Duval travel package?

When you book your flights, hotels and car rentals together, you'll nab awesome discounts. Whether you're planning a beach escape in a villa or prefer to stay in a cosy apartment in the city, Expedia can help make it happen.

Can I choose my airline with an Uptown - Upper Duval Expedia holiday package?

Definitely. Expedia has over 550 airline partners to choose from all over the world. With such a huge range of choice, finding the ideal carrier to whisk you away to Uptown - Upper Duval won't be difficult.

If I'm not able to travel, can I cancel my Uptown - Upper Duval holiday package?

Don't stress if you're rethinking your Uptown - Upper Duval holiday package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can throw the occasional spanner in the works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.