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.
Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $2,062, price is now CA $1,218 per person
CA $1,218
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (481 reviews)
Property has a very cozy feel Very nice lobby area breakfast was cute and fun. Parking is very limited. Flash flooding made it a tad bit difficult to reach out room.

Reviewed on Aug 24, 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 $3,520, price is now CA $1,737 per person
CA $1,737
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This property is absolutely adorable! Room was clean and spacious. Front desk person was very nice and personable. The breakfast baskets that are delivered to your room are top notch! Will definitely be staying here again!

Reviewed on Aug 31, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $3,366, price is now CA $1,680 per person
CA $1,680
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The staff were wonderful and we loved the breakfast and sangria hour and how walkable the area was! We walked everywhere during our stay. The only downsides were it is very noisy, since you can hear everything outside from in the room, and the AC in our room took about 2 days to cool down enough to be comfortable after the previous guests apparently had left the AC off and the windows open during their stay.

Reviewed on Sep 3, 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 $2,796, price is now CA $1,454 per person
CA $1,454
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (781 reviews)
Pros: We loved the location. It's so easy to walk to any downtown place via Duval Street with tons of restaurant options. Since this is a hotel and no AirBnB, you gotta go eat somewhere. You can also rent a golf cart or take an Uber to Fort Zachary Taylor Historic State Park Beach (best beach in Key West, except for overpriced bad food options). A golf cart is the best mode of transportation with 2 kids in tow. Walking 30+min in this humid heat, including beach gear, snacks and etc..., is just no fun. Parking around your hotel may be tricky and make sure you know the rules. We went off-season, so it was easy, but during high season-we have been told-it can be a challenge. If you book a sunset, snorkeling, sandbar or fishing trip on a boat, which I highly recommend, it only takes 20min to walk to the harbor or you simply book a cab/Uber/Lyft. The housekeepers were amazing and always made sure that we had enough clean towels. Beach towels are never in shortage and available to pick up by the pool area 24/7. Cons: The pool is very small, but then we didn't go to Key West to spend time at a pool. We prefer the beach and what nature has to offer. The marine life is just too amazing to dwell in a pool for us.

Reviewed on Sep 8, 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was CA $3,153, price is now CA $1,659 per person
CA $1,659
per person
Oct 12 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,017 reviews)
Wonderful stay wonderful staff wonderful time

Reviewed on Sep 8, 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

Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St, Key West, FL
The price is CA $147 per night from Sep 17 to Sep 18
CA $147
CA $211 total
Sep 17 - Sep 18
includes taxes & fees
Heron House - Adult Only
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
The price is CA $137 per night from Sep 11 to Sep 12
CA $137
CA $183 total
Sep 11 - Sep 12
includes taxes & fees
Duval House
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 $124 per night from Sep 15 to Sep 16
CA $124
CA $202 total
Sep 15 - Sep 16
includes taxes & fees
The Cabana Inn Key West - Adults Only
See all 2,784 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 $1,218. 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

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
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 to Key West Day Trip with Activities

Miami to Key West Day Trip with Activity Options

CA $54
per adult
82% of travellers recommend
Miami to Key West Day Trip with Activity Options
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.