Old Town Key West Vacation Packages

Name: The Southernmost Inn - Adults Only
Price range: CA $241
Rating: 8.4

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Top Holiday Package Deals in Old Town Key West

Price found within the past 48 hours. Click for updated prices.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

CA $3,562

per person

Jan 23 - Jan 30

found 22 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Key West (EYW)

10/10 Exceptional! (1 review)

Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!

Reviewed on Jul 26, 2026

The Key West Hotel

Key West Historic District

CA $4,894

per person

Jan 29 - Feb 1

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Key West (EYW)

9.2/10 Wonderful! (564 reviews)

Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!

Reviewed on Oct 29, 2026

Sky Suite on Duval by Brightwild Condo w Balcony

Old Town Key West

CA $7,253

per person

Jan 23 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

No reviews

Mesa House Dos by Brightwild Unreal Location

Key West Historic District

CA $6,424

per person

Jan 23 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

No reviews

NEW The Rigby House - Pvt Pool Amazing Location

Key West Historic District

CA $13,298

per person

Jan 28 - Jan 31

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

No reviews

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

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

CA $299

CA $445 total

Nov 30 - Dec 1

includes taxes & fees

8.6/10 Excellent! (3,660 reviews)

"Staff were not the most pleasant especially the bartenders and attendant at the beach"

Reviewed on Nov 11, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

CA $322

CA $457 total

Nov 23 - Nov 24

includes taxes & fees

The Southernmost Inn - Adults Only

525 United Street Key West FL

Fully refundableReserve now, pay when you stay

CA $241

CA $335 total

Nov 29 - Nov 30

includes taxes & fees

8.4/10 Very good! (1,462 reviews)

"The rooms were small, but totally usable for our needs. We had one of the better rooms with a back porch next to the pool. We enjoyed coffee there every morning. Our friends' room was across the hall, a little smaller, without the porch. The beds were very comfortable. Location was excellent, everything ..."

Reviewed on Nov 11, 2026

See all 1,267 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.

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 $3,562. 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.