Old Town Key West Vacation Packages

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Top Holiday Package Deals in Old Town Key West

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
May 24 - May 31
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (667 reviews)
The fact there was only one elevator was a bummer. We didnt find the luggage carrrier until well after we climbed all 52 stairs several times to bring all our belongings up. Our room was amazing and the view was so nice. I would definitely recommend staying here

Reviewed on Mar. 25, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Jun. 8 - Jun. 11
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
7.8/10 Good! (1,614 reviews)
Really nice place to stay in Key West but was highly disappointed for having to pay a $50 resort fee in addition to the total Expedia payment .. still not sure I didn't get ripped off 😕

Reviewed on Apr. 18, 2024

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
per person
Jun. 8 - Jun. 11
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
It was very nice place to stay! Very clean and everyone was nice.

Reviewed on Apr. 16, 2024

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Jun. 8 - Jun. 11
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (1,551 reviews)
Great place, will stay much longer nex t time

Reviewed on Apr. 17, 2024

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
May 24 - May 31
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (784 reviews)
Great place with lots to do!

Reviewed on Apr. 8, 2024

Prices and availability subject to change. Additional terms may apply.

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

4 out of top 10 points of interest in this area
4.5/5(156 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 hotel + flight trips in Key West Historic District

Old Town Key West Hotel Deals

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $516 per night from May 5 to May 6
CA $516
CA $668 total
includes taxes & fees
May 5 - May 6
8/10 Very Good! (1,786 reviews)
Set your dial to “relax”
"We had a lovely time here due to the delightful staff and lovely setting BUT(and this is a substantial BUT) the management should do a better job explaining that the “ocean view Balcony king” has a communal balcony on the other side of the walkway- there is no view from the room because you have ..."

Reviewed on Apr. 16, 2024

Southernmost Beach Resort
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is CA $317 per night from May 5 to May 6
CA $317
CA $384 total
includes taxes & fees
May 5 - May 6
9/10 Wonderful! (1,038 reviews)
"Excellent hotel! Lovely room upgrade! Nice breakfast. Pool temp was perfect. Excellent location. Very walkable area with some wonderful restaurants nearby. Only downside was no parking. Limited free street parking on select streets."

Reviewed on Apr. 17, 2024

Heron House - Adult Only
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $510 per night from May 12 to May 13
CA $510
CA $631 total
includes taxes & fees
May 12 - May 13
8.8/10 Excellent! (656 reviews)
"Everything was beautiful. The only thing we could’ve wished for was to have a chair in our room. There was a bench, but there was no luggage rack and no chair to sit on the bench was small. We asked for a luggage rack and a small chair and they gave them to us."

Reviewed on Apr. 18, 2024

Winslow's Bungalows - Key West Historic Inns
See all 1,315 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.

Explore other types of vacation packages

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 $1,298. 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

Image for Southernmost Point

Southernmost Point

4/5(160 reviews)

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

Southernmost Point
Image for Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4.5/5(77 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum
Image for South Beach

South Beach

4/5(52 reviews)

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

South Beach

Things to do

Image for Snorkel Adventure at Coral Reef

Snorkel Adventure at Coral Reef

CA $80
Per adult
86% of travellers recommend
Snorkel Adventure at Coral Reef
Image for Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

CA $221
Per adult
84% of travellers recommend
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Image for Guided Jet Ski Tour in Key West

Guided Jet Ski Tour in Key West

CA $247
Per adult
94% of travellers recommend
Guided Jet Ski Tour in Key West
See all activities in Key West

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.