Downtown Key West Holidays

Book a Hotel + Flight or Car together to unlock savings

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
5/5(6 area reviews)

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

Find hotels in Old Town Key West

Top hotels in Downtown Key West

Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is 3.579.919 ₫ per night from 27 May to 28 May
3.579.919 ₫
4.918.897 ₫ total
27 May - 28 May
includes taxes & fees
9.2/10 Wonderful! (1,150 reviews)
"We moved from a tropical king to a king suite. This room did not have any seating however, our room faced the pool which I loved and enjoyed. The suite was larger with seating inside and on the porch. Will definitely come back. A shout out to Greg and Larry for their great hospitality!"

Reviewed on 17 May 2026

Heron House - Adult Only
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 4.505.954 ₫ per night from 26 May to 27 May
4.505.954 ₫
6.254.773 ₫ total
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"We enjoy our stay and tge staff was very nice."

Reviewed on 16 May 2026

The Cabana Inn Key West - Adults Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
The price is 4.625.250 ₫ per night from 25 May to 26 May
4.625.250 ₫
6.537.476 ₫ total
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (1,019 reviews)
"Very clean room. Great location!"

Reviewed on 17 May 2026

Pegasus International Hotel
See all 2,738 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 holiday package cost?
Chart your own course with our Downtown Key West holiday 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 holiday 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 1null000null000 hotel options all over the world to pick from. Whatever your style or budget, there's a holiday 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 favourites with lots of travellers.
How far in advance should I book my Downtown Key West holiday?
Savvy travellers 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 holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation 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 holiday 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 holiday 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 holiday 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.

Popular places to visit

Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

You can spend time studying the exhibits at Ernest Hemingway Home and Museum during your trip to Key West. Wander the area's seaside or simply enjoy one of its lively bars.

Ernest Hemingway Home and Museum
KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"

San Carlos Institute - Casa Cuba

You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.

San Carlos Institute - Casa Cuba
Jackson Square

Jackson Square

You can learn about the history of Key West with a trip to Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.

Jackson Square