Downtown Key West Vacations

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Where to stay in Downtown Key West

Find the best Downtown Key West areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Key West
Old Town Key West

Old Town Key West

3 out of top 10 points of interest in this area
4.5/5(229 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Downtown Key West Hotel Deals

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Fully refundableReserve now, pay when you stay
The price is ₩249,899 per night from May 27 to May 28
₩249,899
₩346,888 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
Before we arrived, we called to verify our reservations. Morgan at the reception office was very helpful and friendly. Our room was small, but it was fine for the two of us. We were barely there anyway. The room was clean and every member of the staff was so nice. The breakfast was adequate and the ...

Reviewed on May 8, 2026

The Cabana Inn Key West - Adults Only
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is ₩254,511 per night from May 21 to May 22
₩254,511
₩337,155 total
May 21 - May 22
includes taxes & fees
9.2/10 Wonderful! (1,152 reviews)
Everything was absolutely perfect! It was absolutely beautiful, everyone was wonderful, it was exactly what I needed! I can’t wait to be back!!

Reviewed on May 8, 2026

Heron House - Adult Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
The price is ₩229,807 per night from May 20 to May 21
₩229,807
₩332,223 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
With being right on Duvall Street it is very loud! The bathrooms are old and very tiny, but the room and bathrooms were very clean. They have a small continental breakfast, which was nice with wanting to get out of town early the morning we left.

Reviewed on May 8, 2026

Pegasus International Hotel
See all 2,736 properties in Downtown Key West
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 a Downtown Key West vacation package cost?
Chart your own course with our Downtown Key West vacation packages, which start from a low . Handpick the hotels and flights that fit your travel plans. Then, add on one or two enriching experiences to round off your unique getaway.
How do I get a cheap travel package to Downtown Key West?
Our Downtown Key West vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and activities into a convenient package. But impressive bargains are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotel options all over the world to pick from. Whatever your style or budget, there's a vacation package here just for you.
Where should I stay in Downtown Key West?
A trip to Downtown Key West has to include Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel right nearby for quick access to these impressive sights.
What are the top hotels in Downtown Key West?
If it's your first visit to Downtown Key West, reserve a room at Maya's Secret Treasure @ Duval Private Pool And Balcony Over Duval + Last Key or Southernmost Retreat: 2 Blocks From Duval In Old Town. Both hotels offer comfy beds and are favorites with lots of travelers.
How far in advance should I book my Downtown Key West vacation?
Savvy travelers will likely want to book as early as possible. You can normally browse through international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't worry. Cheap prices occasionally become available just weeks before departure dates.
What does an Expedia Downtown Key West travel package include?
Choose from a combination of hotels, rental cars and flights. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to putting together your ideal Downtown Key West escape.
What should I know before booking a Downtown Key West travel package?
Whether it's relaxation or adventure you're seeking, a Downtown Key West vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Downtown Key West Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Downtown Key West vacation package?
It's hard to predict what the future holds, so it's good to know that you can change or cancel your Downtown Key West vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.