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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Price found within the past 48 hours. Click for updated prices.
  • 6 outdoor pools, free cabanas, pool umbrellas
    Jul 29 - Aug 4

    Oceans Edge Key West Resort, Hotel & Marina + Flight

    Stock Island
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,865 reviews)
    "I was very impressed with how friendly the staff were. It was a fun place to eat, drink and stay. Fishing with the Captains located at their marina was great too."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - MIA • 1 stop FLL - YYZ • 1 stop
    CA $2,309
    CA $1,581
    per traveller
    found 19 hours ago
    Oceans Edge Key West Resort, Hotel & Marina
  • Exterior
    Jul 2 - Jul 7

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Beautiful property. Excellent service."
    Reviewed May 15, 2026
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $5,201
    CA $2,479
    per traveller
    found 1 day ago
    Southernmost House - Adult Exclusive
  • Property grounds
    Aug 9 - Aug 16

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    7 nights
    3.5 star property
    9.4/10 - Exceptional (1,096 reviews)
    "Beautiful property"
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Fort Lauderdale (FLL)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $3,423
    CA $2,099
    per traveller
    found 1 day ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Outdoor pool
    Jul 2 - Jul 7

    The Key West Hotel + Flight

    Key West Historic District
    5 nights
    3.0 star property
    9.2/10 - Wonderful (556 reviews)
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $4,108
    CA $2,713
    per traveller
    found 1 day ago
    The Key West Hotel
  • Terrace/patio
    Aug 1 - Aug 8

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    7 nights
    3.5 star property
    8.6/10 - Excellent (373 reviews)
    "Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"
    Reviewed May 18, 2026
    Roundtrip • Toronto (YYZ) - Key West (EYW)
    YYZ - EYW • 1 stop EYW - YYZ • 1 stop
    CA $4,082
    CA $2,738
    per traveller
    found 10 hours ago
    Hyatt Vacation Club at Sunset Harbor, Key West

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
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

Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
The price is CA $164 per night from May 31 to Jun 1
CA $164
CA $231 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,151 reviews)
"Fantastic place, clean and great location."

Reviewed on May 25, 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 CA $210 per night from May 27 to May 28
CA $210
CA $299 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"The location of this hotel is more than excellent- and for its age is maintained well! With a breakfast and a happy hour and and a pool and hot tub - awesome! Parking is always an issue in this area of key west (30 dollars for overnight at the hotel and 37 for overnight in city lot parking practically ..."

Reviewed on May 26, 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 CA $213 per night from May 28 to May 29
CA $213
CA $310 total
May 28 - May 29
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great place to stay off Duvall street We had an issue with a/c it’s was taken cared of . Parking is a plus ."

Reviewed on May 24, 2026

Pegasus International Hotel
See all 2,731 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 . 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

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $61
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 $76
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $75
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
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.