Downtown Key West Holidays

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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
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Southernmost Point.

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 S$213 per night from 3 Jun to 4 Jun
S$213
3 Jun - 4 Jun
includes taxes & fees
9.2/10 Wonderful! (1,148 reviews)
"While the hotel feels dated, it had friendly employees. The location was great. Everything is tops 1-2 miles walk away. No parking however, be prepared to walk."

Reviewed on 31 May, 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 S$248 per night from 2 Jun to 3 Jun
S$248
2 Jun - 3 Jun
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Not good"

Reviewed on 31 May, 2026

Pegasus International Hotel
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
The price is S$283 per night from 3 Jun to 4 Jun
S$283
3 Jun - 4 Jun
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"All good"

Reviewed on 30 May, 2026

Wicker Guesthouse
See all 2,720 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 1,000,000 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.

Things to do

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

S$35
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

S$57
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

S$71
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Key West

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.