Old Town Key West Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Old Town Key West

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $2,576, price is now CA $1,868 per person
CA $1,868
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,020 reviews)
Everything was clean in the room just a bit outdated, the rooms probably could use some updating. However, the pool area and grounds were absolutely beautiful. I would stay again just for the grounds and pool. It is next to the airport so during the day there are a lot of planes going out with some flight noise.

Reviewed on Mar 24, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $3,238, price is now CA $2,201 per person
CA $2,201
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (536 reviews)
Love this place! Perfect location, nice rooms and cool bar with live music every night on site!

Reviewed on Mar 17, 2026

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $2,691, price is now CA $1,876 per person
CA $1,876
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (575 reviews)
Great location, friendly staff, and plenty of amenities.

Reviewed on Mar 23, 2026

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 $3,485, price is now CA $2,517 per person
CA $2,517
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,194 reviews)
Property was immaculate, staff is so friendly and goes out of their way to make sure you have everything you need. Walking distance to Duval, Southernmost point and Sunset Pier. Amenities are top notch. Can't say enough about how much we enjoyed our stay! 20 out of 10!

Reviewed on Mar 24, 2026

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $3,917, price is now CA $2,837 per person
CA $2,837
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (886 reviews)
This is one of those places that you hate to tell people was so good because it will be harder to make reservations later down the road

Reviewed on Mar 22, 2026

Where to stay in Old Town Key West

Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West
Audubon House and Tropical Gardens featuring a house

Key West Historic District

2 out of top 10 points of interest in this area
4.5/5(157 area reviews)

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Find hotels in Key West Historic District

Old Town Key West Hotel Deals

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $735 per night from Apr 15 to Apr 16
CA $735
CA $920 total
Apr 15 - Apr 16
includes taxes & fees
8.4/10 Very Good! (586 reviews)
Outside building was great. Could improve with room maintenace. Our room was ocean view, but toilet fil valve was broken, and takes 30 minutes wait to flush. Window frame paint was peeling. Otherwise its a great place.

Reviewed on Mar 20, 2026

Casa Marina Key West, Curio Collection by Hilton
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $520 per night from Apr 19 to Apr 20
CA $520
CA $639 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (1,069 reviews)
TV selections were poor. Did not have ABC which is a basic cable channel. Other channels very limited too. Realize you are not coming to watch TV but if you have a few days of bad weather or retire to the room early evening, nothing much to watch, no variety.

Reviewed on Mar 24, 2026

Opal Key Resort & Marina, Key West
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $529 per night from Apr 5 to Apr 6
CA $529
CA $688 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
We had a great stay and experience. Access to sister resort was great. Beach was perfect.

Reviewed on Mar 21, 2026

The Reach Key West, Curio Collection by Hilton
See all 1,300 properties in Old Town 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 an Old Town Key West vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Old Town Key West from just CA $1,868. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Old Town Key West?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Select a combination that best suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options around the globe, which lets you customize your Old Town Key West getaway.
Where should I stay in Old Town Key West?
A trip to Old Town Key West isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel as close as possible for quick access to these awesome attractions.
What are the top hotels in Old Town Key West?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of this area's most in-demand properties. Another top-rated option in Old Town Key West is Curry House.
How far in advance should I book my Old Town Key West vacation?
Smart travelers often book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing tickets last minute, don't despair. Budget prices occasionally become available just weeks prior to departure.
What does an Expedia Old Town Key West travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to create an awesome Old Town Key West vacation.
What should I know before booking an Old Town Key West travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever your vacation goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Town Key West vacation package?
You can. We realize life doesn't always go to plan, so we're here to help if you have to make changes to your Old Town Key West vacation package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Old Town Key West

Southernmost Point featuring signage as well as a large group of people

Southernmost Point

4/5(161 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
South Beach featuring a sandy beach and general coastal views as well as a small group of people

South Beach

4/5(54 reviews)

The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

South Beach
Higgs Beach which includes a beach and tropical scenes as well as a large group of people

Clarence S. Higgs Memorial Beach Park

4/5(26 reviews)

Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.

Clarence S. Higgs Memorial Beach Park

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $62
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 $83
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

CA $75
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
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.