Midtown Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Abbas Ali

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Midtown

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

Old Town Key West

4 out of top 10 points of interest in this area
4.5/5(226 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Midtown Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ₩340,252 per night from Dec 19 to Dec 20
₩340,252
₩457,424 total
Dec 19 - Dec 20
includes taxes & fees
8.6/10 Excellent! (1,780 reviews)
It was overall great but one night at 2 am the fire alarm went off for Like 25mins and no body give reasons not even a single staff member was there to provide guidance or shutdown the alarms

Reviewed on Dec 14, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is ₩317,670 per night from Dec 21 to Dec 22
₩317,670
₩440,451 total
Dec 21 - Dec 22
includes taxes & fees
8/10 Very Good! (1,770 reviews)
Get together with other guest and tv sport.

Reviewed on Dec 18, 2025

Blue Flamingo Resort 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 ₩413,511 per night from Jan 13 to Jan 14
₩413,511
₩573,023 total
Jan 13 - Jan 14, 2026
includes taxes & fees
8.6/10 Excellent! (2,918 reviews)
Beautiful beach property. Great pools, fun activities, lovely pier to sun bask on. Clean rooms. Avalon house all decked out for Christmas. Second time here, highly recommend!

Reviewed on Dec 11, 2025

Southernmost Beach Resort and Guesthouses
See all 2,850 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.

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