Midtown Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Graciela Arena
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Midtown Vacation

Take in everything this neighborhood has to offer with a tailor-made Midtown vacation package. However you see yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. Your trip to Midtown wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia is here to put your plans into action. Book your perfect Midtown vacation today.

The Latest Midtown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
per person
Aug 8 - Aug 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
8.8/10 Excellent! (447 reviews)
The staff were amazing. Everyone was very helpful and kind. Area was quiet and perfectly located in between everything.

Reviewed on Jun 2, 2024

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug 8 - Aug 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
8.8/10 Excellent! (1,004 reviews)
Location, service, the property in general, a first class experience.

Reviewed on Jun 3, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Aug 8 - Aug 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
7.8/10 Good! (1,609 reviews)
Awesome for our nine day stay for our 5yr anniversary!

Reviewed on Jun 2, 2024

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Old Town Key West
per person
Aug 8 - Aug 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
6.6/10 (1,004 reviews)
Great property, communication and service!

Reviewed on Jun 2, 2024

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
8.4/10 Very Good! (618 reviews)
Staff were friendly & helpful. Property was beautiful & close to everything

Reviewed on Jun 1, 2024

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
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

Midtown Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $167 per night from Jun 5 to Jun 6
$167
$246 total
includes taxes & fees
Jun 5 - Jun 6
8.8/10 Excellent! (1,517 reviews)
"I paid for ocean view but was assigned a view of the pool and harbor. This problem was corrected and I was reassigned an ocean view."

Reviewed on May 30, 2024

Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $251 per night from Jun 4 to Jun 5
$251
$347 total
includes taxes & fees
Jun 4 - Jun 5
8.4/10 Very Good! (1,775 reviews)
"This is a great place to stay, next time we decide to visit Key West we will fly. This property has shuttle service to and from the airport, they also have shuttle services to the main attraction area, you do not need a vehicle visiting Key West. The beach is directly across the street from the resort ..."

Reviewed on Jun 2, 2024

Margaritaville Beach House Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is $272 per night from Jun 19 to Jun 20
$272
$369 total
includes taxes & fees
Jun 19 - Jun 20
8.2/10 Very Good! (1,899 reviews)
"We loved the location of our room with real close access to the pool and beach. We loved the morning breakfast and afternoon snacks. Everybody was extremely friendly."

Reviewed on Jun 2, 2024

Southernmost Beach Resort
See all 2,684 properties in Midtown
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 a Midtown vacation package cost?
We make it easy to travel somewhere new, with Midtown vacation packages starting from as little as $715. You’ll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate escape, why not add a couple of tours and experiences to your itinerary?
How do I get a cheap travel package to Midtown?
Bundle your flights and hotels with Expedia to save big bucks on your next big adventure. With over 550 air carriers and 1,000,000 properties around the globe, your Midtown vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or more interesting activities and tours? It’s an easy way to unlock even more bargains. Your dream vacation in Midtown is much closer than you thought!
Where should I stay in Midtown?
Most visitors who travel to Midtown include both Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens on their must-see lists. Why not book a hotel within walking distance of these main attractions?
What are the top hotels in Midtown?
Get your trip off to a fantastic start by booking a room at Southernmost Swim And Social Club. It’s one of most sought-after hotels in Midtown. Another comfortable option is Luxury High End, 2 Bikes, Highspeed Wi.
How far in advance should I book my Midtown vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can generally browse through international airfares on Expedia up to 12 months before your intended flight. If you’ve left things to the last minute, don’t stress. Cheap prices sometimes occur just weeks before departure dates.
What does an Expedia Midtown travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your ideal Midtown getaway. You can also add on experiences and activities once you’ve made your booking. You’re the boss! When you bundle your bookings with Expedia, you’ll score discounts you won’t find elsewhere.
What should I know before booking a Midtown travel package?
Bundling your bookings into a Midtown vacation package is the most convenient way to organize your trip. Not only that, you’ll save just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Midtown Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You get to decide. We have more than 550 airline partners worldwide, so you have options galore when putting together your Midtown adventure.
If I'm not able to travel, can I cancel my Midtown vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Midtown vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Other vacations you might like

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