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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $584, price is now CA $391 per person
CA $391
per person
Sep 23 - Sep 26
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
This property was beautiful and everyone was very friendly it’s an amazing option !!!

Reviewed on Aug. 23, 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 $857, price is now CA $505 per person
CA $505
per person
Sep 23 - Sep 26
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (775 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!

Reviewed on Aug. 23, 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 $2,966, price is now CA $1,867 per person
CA $1,867
per person
Nov 16 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on Aug. 18, 2025

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was CA $3,192, price is now CA $2,107 per person
CA $2,107
per person
Nov 16 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,014 reviews)
The bathroom was very nice. The rest of the room was just ok. The common hallway had trash on the floor for the entire weekend. Nobody swept the floor at all. For the money you pay there are better hotels.

Reviewed on Aug. 18, 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 $2,288, price is now CA $1,516 per person
CA $1,516
per person
Nov 16 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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

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 $234 per night from Sep 7 to Sep 8
CA $234
CA $357 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (2,697 reviews)
"Its very clean and the staff was friendly. They charge $60 a day extra for "amenities" which is ridiculous because paying $300ish a night for a hotel should include the use of pools and whatever anyway. Plus another $50 to park if you have a vehicle, so keep that in mind when booking. The restaurant ..."

Reviewed on Aug. 23, 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 $305 per night from Sep 2 to Sep 3
CA $305
CA $426 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 $310 per night from Sep 15 to Sep 16
CA $310
CA $432 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Great time. Thank you"

Reviewed on Aug. 23, 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.
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All Inclusive Vacations
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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 $391. 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.