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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was CA $2,318, price is now CA $1,571 per person
CA $1,571
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Nice rooms. Pool water needs attention due to some algae growth on bottom.

Reviewed on Aug. 21, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $3,299, price is now CA $2,241 per person
CA $2,241
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
easy access to fishing, shuttle to key west, great rooms

Reviewed on Aug. 20, 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,903, price is now CA $1,988 per person
CA $1,988
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on Aug. 18, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was CA $2,789, price is now CA $1,972 per person
CA $1,972
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (2,697 reviews)
Great stay awesome staff we will definitely stay here again.

Reviewed on Aug. 20, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,359, price is now CA $1,675 per person
CA $1,675
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (775 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!

Reviewed on Aug. 19, 2025

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
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Old Town Key West

3 out of top 10 points of interest in this area
3.5/5(8 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 CA $153 per night from Aug 24 to Aug 25
CA $153
CA $235 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"I enjoyed the cocktails and appetizers in the evening. The place was centrally located. Parking was awesome. I enjoyed our huge room."

Reviewed on Aug. 18, 2025

The Cabana Inn Key West - Adults Only
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
The price is CA $123 per night from Aug 26 to Aug 27
CA $123
CA $168 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (1,014 reviews)
"Great place, friendly staff and nice atmosphere."

Reviewed on Aug. 20, 2025

Duval House
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
512 Truman Ave, Key West, FL
The price is CA $286 per night from Sep 14 to Sep 15
CA $286
CA $322 total
Sep 14 - Sep 15
includes taxes & fees
9.8/10 Exceptional! (1,005 reviews)
"The management and staff go above and beyond! The rooms are comfortable and updated. The hotel is small and quiet given its proximity to Duval St. great hotel!"

Reviewed on Aug. 18, 2025

Almond Tree Inn Hotel - Adults Only
See all 2,763 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.
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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 $1,571. 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.

Things to do

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 $136
per adult
74% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

CA $136
per adult
MIAMI: Key West Day Trip with Boating Options
The Dark Side of Key West Adults Only Walking Tour

The Dark Side of Key West Adults Only Walking Tour

CA $48
per adult
80% 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.