Old Town Key West Vacation Packages

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Top Holiday Package Deals in Old Town Key West

Price found within the past 48 hours. Click for updated prices.
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 $2,773, price is now CA $1,795 per person
CA $1,795
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on Aug. 18, 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 $2,671, price is now CA $1,809 per person
CA $1,809
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (775 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!

Reviewed on Aug. 19, 2025

Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Old Town Key West
Price was CA $3,102, price is now CA $2,207 per person
CA $2,207
per person
Oct 28 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (220 reviews)
Love the pool and bar area.

Reviewed on Aug. 22, 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 $2,938, price is now CA $2,119 per person
CA $2,119
per person
Oct 28 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (811 reviews)
Good breakfast wish it had more of a meat selection.....and climbing the stairs to the room was a little bit exhausting at times.

Reviewed on Aug. 20, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Price was CA $3,983, price is now CA $2,904 per person
CA $2,904
per person
Oct 28 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1,005 reviews)
Very nice place with great little touches and extremely friendly staff.

Reviewed on Aug. 21, 2025

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
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Key West Historic District

2 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 hotels in Key West Historic District

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $236 per night from Sep 7 to Sep 8
CA $236
CA $359 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (2,697 reviews)
Great location and fun vibe
"This resort has the perfect location, located at the southern most tip and end of Duval. Check in was easy and our room overlooked the Pineapple pool and bar, which made for fun evenings sitting on our balcony. The only downside to this resort was I felt the room was a little outdated and the bathroom ..."

Reviewed on Aug. 20, 2025

Southernmost Beach Resort and Guesthouses
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 $307 per night from Sep 2 to Sep 3
CA $307
CA $429 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (304 reviews)
"The staff and service is exemplary. Ask for Nicole and Marsha at the Dorada beach bar. Both are awesome bartenders and great people!!!"

Reviewed on Aug. 19, 2025

Casa Marina Key West, Curio Collection by Hilton
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 $312 per night from Sep 15 to Sep 16
CA $312
CA $434 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Tropical paradise within your Reach
"Staff friendly and so accommodating! My wife somewhat particular about view from room; Phiwe and her colleague guided us to the perfect room overlooking pool and, a few feet beyond, the sandy beach. Lots of extras and you are able to walk over to sister property Casa Marina and hang out there too. ..."

Reviewed on Aug. 10, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,326 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 $1,795. 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

Southernmost Point

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

Southernmost Point
South Beach

South Beach

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

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

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: 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
Snorkler waving underwater in Key West

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

CA $76
per adult
84% 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.