Downtown Key West Holidays

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Our guide on 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

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

Our pick of the best Downtown Key West Hotel Deals

Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is NZ$302 per night from 28 May to 29 May
NZ$302
28 May - 29 May
includes taxes & fees
9.2/10 Wonderful! (1,143 reviews)
"This is a gem of a property that is reasonably priced, has the Key West charm, nice pool area, and amazing staff! I can't say enough about Trent and Greg up front as well as the wonderful lady in charge of the breakfast (I'm so sorry I didn't get her name but she was absolutely the sweetest!). Highly ..."

Reviewed on 19 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 NZ$403 per night from 31 May to 1 June
NZ$403
31 May - 1 June
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"It’s a great place to stay. You can walk to every thing. Park your car and forget about it. It’s safe there. I would go back again!!!!"

Reviewed on 21 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 NZ$423 per night from 27 May to 28 May
NZ$423
27 May - 28 May
includes taxes & fees
8.2/10 Very Good! (1,025 reviews)
"Breakfast fresh nice clean room"

Reviewed on 19 May 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 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.

Activities

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$75
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12 hours Day at Key West With Boat Tour and Snorkeling

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

NZ$46
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aboard the trolley in Key West

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

NZ$93
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.