Old Town Key West Vacations from ￥151,625

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The Latest Old Town Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was ￥153,694, price is now ￥151,625 per person
￥151,625
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
9.2/10 Wonderful! (1,461 reviews)

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was ￥211,391, price is now ￥175,186 per person
￥175,186
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
9.8/10 Exceptional! (1,001 reviews)
We loved this motel. The pool area is secluded and private. The staff are amazing. The room was so nice. We will be back.

Reviewed on Oct 29, 2026

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
Key West Historic District
Price was ￥181,257, price is now ￥166,926 per person
￥166,926
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
8.8/10 Excellent! (500 reviews)
Perfeito

Reviewed on Nov 2, 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
A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

Find hotels in Downtown Key West

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 refundableReserve now, pay when you stay
The price is ￥32,090 per night from Nov 15 to Nov 16
￥32,090
￥48,154 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (3,632 reviews)
"A mixed bag. Good: - location. - quiet (apart from the Roosters and party goers). - beach cafe food. - pool. - beds. - balcony room (part ocean view). Bad: - parking charges. - bad hotel management putting our family in the middle of an obvious group of party people. - grumpy and rude pool bar staff. ..."

Reviewed on Nov 1, 2026

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 ￥38,445 per night from Nov 4 to Nov 5
￥38,445
￥53,886 total
Nov 4 - Nov 5
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"First off do not go through Expedia; the hotel supposedly could not tell me how much the nightly rate was when I called because it was booked through a “third party” and then the hotel charged me an additional 500$ (nightly Resort Charge + tax) when we checked out after I paid for the resort and ..."

Reviewed on Nov 1, 2026

Casa Marina Key West, Curio Collection by Hilton
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
Fully refundableReserve now, pay when you stay
The price is ￥25,383 per night from Nov 3 to Nov 4
￥25,383
￥35,646 total
Nov 3 - Nov 4
includes taxes & fees
The Southernmost Inn - Adults Only
See all 1,269 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 ￥151,625. 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.

Stay near popular Old Town Key West attractions

A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
See properties

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

￥7,046
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

￥10,963
per adult
76% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

￥8,714
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
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.