Downtown Key West Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Downtown Key West

Price found within the past 48 hours. Click for updated prices.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Price was CA $5,464, price is now CA $4,155 per person
CA $4,155
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (3 reviews)
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .

Reviewed on Mar 26, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $9,837, price is now CA $7,052 per person
CA $7,052
per person
Jan 10 - Jan 17
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $7,373, price is now CA $5,395 per person
CA $5,395
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Wonderful stay all around!

Reviewed on Oct 27, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $8,782, price is now CA $6,497 per person
CA $6,497
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (3 reviews)
Loved it

Reviewed on Mar 20, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $6,916, price is now CA $5,175 per person
CA $5,175
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Great place! Very peaceful and quiet. walking distance to duval street. Would definitely stay there again

Reviewed on Oct 26, 2026

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
A white building with shutters, palm trees, and a lawn.

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 $181 per night from Oct 29 to Oct 30
CA $181
CA $234 total
Oct 29 - Oct 30
includes taxes & fees
9.6/10 Exceptional! (1,128 reviews)
"Room was very clean and well maintained. Nice continental breakfast."

Reviewed on Oct 25, 2026

Duval House
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
819 Simonton Street Key West FL
The price is CA $205 per night from Oct 29 to Oct 30
CA $205
CA $300 total
Oct 29 - Oct 30
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"I am accustomed to additional fees, but Paradise takes it to new level. Expect to pay double the advertised priced for the most absurd items never offered or available. Rooms not available until after 4pm, bedroom door would not close due to warped floor."

Reviewed on Oct 27, 2026

Paradise Inn Key West - Adults Only
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is CA $177 per night from Oct 28 to Oct 29
CA $177
CA $246 total
Oct 28 - Oct 29
includes taxes & fees
Heron House - Adult Only
See all 2,715 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 $4,155. 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.

Stay near popular Downtown Key West attractions

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
See properties

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
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

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
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.