Old Town Key West Vacations

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Your Old Town Key West Vacation

Take the stress and hassle out of organizing your next adventure by booking an Old Town Key West vacation package. Take in the sights and sounds of this captivating neighborhood and enjoy what it has to offer. Wondering what to see and do during your trip to Old Town Key West? Nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are good places to begin. No matter your travel plans or the size of your budget, booking your dream Old Town Key West vacation is quick and easy with Expedia.

The Latest Old Town Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
location location.. perfect

Reviewed on Apr 25, 2024

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
10/10 Exceptional! (1,001 reviews)
Wonderful hotel and staff! Location is perfect to walk to restaurants/shopping/excursions. We will be back!

Reviewed on Apr 22, 2024

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
I honestly had no idea what to expect but this place is amazing . The people, the room , the location to literally everything just was awesome. We will be back!!

Reviewed on Apr 28, 2024

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
8.8/10 Excellent! (1,551 reviews)
Very clean Great food at the Yellow Finn Trolley to downtown Six pools

Reviewed on Apr 28, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
7.8/10 Good! (1,614 reviews)
Clean and nice place.. the AC didn't work that great.

Reviewed on Apr 28, 2024

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
Audubon House and Tropical Gardens featuring a house

Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(4,033 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 hotel + flight trips in Key West Historic District

Old Town Key West Hotel Deals

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $359 per night from Apr 29 to Apr 30
$359
$467 total
includes taxes & fees
Apr 29 - Apr 30
8.2/10 Very Good! (1,827 reviews)
"Awesome property, great views of the ocean, will be back!"

Reviewed on Apr 27, 2024

Southernmost Beach Resort
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is $199 per night from May 5 to May 6
$199
$244 total
includes taxes & fees
May 5 - May 6
9/10 Wonderful! (1,045 reviews)
"Wonderful location"

Reviewed on Apr 28, 2024

Heron House - Adult Only
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $380 per night from May 7 to May 8
$380
$469 total
includes taxes & fees
May 7 - May 8
8.8/10 Excellent! (670 reviews)
"It was a lovely property and the staff was amazing"

Reviewed on Apr 26, 2024

Winslow's Bungalows - Key West Historic Inns
See all 1,304 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly 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 $639. 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

Image for Southernmost Point

Southernmost Point

4.5/5(3,182 reviews)

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

Southernmost Point
Image for South Beach

South Beach

4/5(980 reviews)

Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.

South Beach
Image for Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4.5/5(1,707 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum

Things to do

Image for Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

$163
Per adult
84% of travellers recommend
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Image for Guided Jet Ski Tour in Key West

Guided Jet Ski Tour in Key West

$183
Per adult
94% of travellers recommend
Guided Jet Ski Tour in Key West
Image for Rum & Reggae: Snorkel & Sunset Sail Combo

Rum & Reggae: Snorkel & Sunset Sail Combo

$64
Per adult
88% of travellers recommend
Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Key West

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.