Old Town Key West Holidays

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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
Smathers Beach which includes windsurfing, tropical scenes and a sandy beach

Beachside

1 out of top 10 points of interest in this area

If you're spending some time in Beachside, Smathers Beach and Florida Keys Beaches are top sights worth seeing.

Find hotels in Beachside

Top hotels in Old Town Key West

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 S$344 per night from 26 Oct to 27 Oct
S$344
26 Oct - 27 Oct
includes taxes & fees
8.6/10 Excellent! (2,777 reviews)
"Our concierge was amazing! Very attentive and accommodating."

Reviewed on 25 Sept, 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 S$339 per night from 14 Oct to 15 Oct
S$339
14 Oct - 15 Oct
includes taxes & fees
8.2/10 Very Good! (364 reviews)
"This was a wonderful property. Staff was incredibly gracious, grounds were beautiful and the room was very nice!"

Reviewed on 24 Sept, 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 S$374 per night from 5 Oct to 6 Oct
S$374
5 Oct - 6 Oct
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"Everything was good, good location, private beach good food at marlins good service with the waiter filip"

Reviewed on 22 Sept, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,328 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 holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Old Town Key West from just . And the more you bundle, the more money you save. The holiday 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 holiday?
Smart travellers 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 favourite 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 holiday.
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 holiday goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia holiday 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 holiday package?
You can. We realise 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 holiday 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.

Popular places to visit

Southernmost Point

Southernmost Point

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

Southernmost Point
Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Harry S. Truman Little White House

Simonton Beach

Why not spend a care-free afternoon at Simonton Beach during your travels in Key West? While you're in the area, stroll along the seaside.

Simonton Beach

Things to do

Snorkler waving underwater in Key West

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

S$71
per adult
84% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

S$127
per adult
MIAMI: Key West Day Trip with Boating Options
Miami to Key West Day Trip with Activities

Miami to Key West Day Trip with Activity Options

S$50
per adult
82% of travellers recommend
Miami to Key West Day Trip with Activity Options
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.