Midtown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Abbas Ali

Where to stay in Midtown

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

5 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Find hotels in Old Town Key West

Top hotels in Midtown

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 6.659.072 ₫ per night from 14 Jan to 15 Jan
6.659.072 ₫
8.821.324 ₫ total
14 Jan - 15 Jan
includes taxes & fees
8.6/10 Excellent! (1,879 reviews)
Front desk staff was excellent as was the breakfast staff. Only had breakfast and it was excellent. Room could’ve been cleaner because that was disappointing. Two out of three soaps didn’t work in the shower. Overall a nice stay.

Reviewed on 7 Jan 2026

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 7.777.363 ₫ per night from 15 Jan to 16 Jan
7.777.363 ₫
10.226.997 ₫ total
15 Jan - 16 Jan
includes taxes & fees
8/10 Very Good! (1,828 reviews)
The Blue Flamingo is amazing and the service is spotless! Very clean room and very nice resort. We has little problem (on our end not theirs) and we needed to switch room at the last second, in the middle of our stay and they accommodated us in a heartbeat. Sincerely, thank you!

Reviewed on 7 Jan 2026

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 12.203.264 ₫ per night from 26 Jan to 27 Jan
12.203.264 ₫
15.649.757 ₫ total
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (2,994 reviews)
The room were clean and well appointed. Support staff was very friendly and ready to assist when asked for help. The views were amazing, pools clean and lots of activities each day. The food at the cafe was excellent. Everything you need all in one location, while being in the heart of Duvall ...

Reviewed on 9 Jan 2026

Southernmost Beach Resort and Guesthouses
See all 2,844 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 holiday package cost?
We make it easy to travel somewhere new, with Midtown holiday 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 1null000null000 properties around the globe, your Midtown holiday 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 holiday 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 holiday?
Savvy travellers 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 holiday package is the most convenient way to organise 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 holiday package?
It's hard to predict what tomorrow might bring, so it's good to know that you can change or cancel your Midtown holiday 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.