Downtown Key West Vacation Packages

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Top Holiday Package Deals in Downtown Key West

Price found within the past 48 hours. Click for updated prices.
Heron House Court - Adult Only

Heron House Court - Adult Only

3 out of 5
Key West Historic District
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
9/10 Wonderful! (1,004 reviews)
Roman was a wonderful host. We loved our accommodations.

Reviewed on Mar. 6, 2025

Douglas House

Douglas House

3 out of 5
Old Town Key West
Save 100% on your flight
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
9.6/10 Exceptional! (44 reviews)
Very nice. No negatives.

Reviewed on Mar. 27, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
9.8/10 Exceptional! (1,002 reviews)
A lovely, quaint motel in the heart of it all. The staff was OUTSTANDING. Super clean rooms and pool area. Will definitely stay again!

Reviewed on Mar. 27, 2025

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
per person
May 17 - May 24
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Key West (EYW)
8.8/10 Excellent! (421 reviews)
Fitch Lodge is a great property somewhat away from the crowds and noise of Key West but still close enough to be easily accessible to most of the city’s attractions, shopping and dining. The pool is small but we didn’t even use it other than to relax by with our complimentary afternoon cocktail. Very relaxing visit to KW!

Reviewed on Mar. 25, 2025

Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays

Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays

3 out of 5
Old Town Key West
Save 100% on your flight
per person
May 1 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
No reviews

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
Key West Historic District

Old Town Key West

4 out of top 10 points of interest in this area

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

Duval House
Duval House
3 out of 5
815 Duval St, Key West, FL
The price is CA $312 per night from Apr. 2 to Apr. 3
CA $312
CA $382 total
includes taxes & fees
Apr 2 - Apr 3
9.2/10 Wonderful! (1,001 reviews)
"It was very cool"

Reviewed on Mar. 26, 2025

Duval House
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is CA $242 per night from Apr. 3 to Apr. 4
CA $242
CA $315 total
includes taxes & fees
Apr 3 - Apr 4
9/10 Wonderful! (1,065 reviews)
"The location is perfect."

Reviewed on Mar. 26, 2025

Heron House - Adult Only
Paradise Inn Key West - Adults Only
Paradise Inn Key West - Adults Only
3.5 out of 5
819 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $457 per night from Mar. 31 to Apr. 1
CA $457
CA $578 total
includes taxes & fees
Mar 31 - Apr 1
9/10 Wonderful! (1,002 reviews)
"The Paradise Inn is an absolutely wonderful place to stay. It is very conveniently located in the center of old town Key West making walking to all events and locations very easy. The staff are very friendly and the morning breakfast buffet is fantastic. The pool and hot tub are just the right size ..."

Reviewed on Mar. 26, 2025

Paradise Inn Key West - Adults Only
See all 2,807 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 CA $1,873. 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.

Discover the most popular places to visit in Downtown Key West

Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4.5/5(77 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum
Jackson Square showing an administrative building and heritage architecture

Jackson Square

4.5/5(4 reviews)

You can learn about the history of Key West with a stop at Jackson Square. Stroll along the beautiful beaches or discover the area's beautiful sunsets.

Jackson Square

Things to do

MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

CA $111
per adult
MIAMI: Key West Day Trip with Boating Options
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

CA $142
per adult
76% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
The Dark Side of Key West Adults Only Walking Tour

The Dark Side of Key West Adults Only Walking Tour

CA $50
per adult
100% of travellers recommend
The Dark Side of Key West Adults Only Walking 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.