Midtown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Debbie McLay

  • Plan, book, travel with confidence

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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

3 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Our pick of the best 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 NZ$339 per night from 13 Aug to 14 Aug
NZ$339
13 Aug - 14 Aug
includes taxes & fees
8.4/10 Very Good! (1,444 reviews)
"Very beautiful place."

Reviewed on 11 Aug. 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 NZ$319 per night from 10 Sept to 11 Sept
NZ$319
10 Sept - 11 Sept
includes taxes & fees
7.6/10 Good! (1,541 reviews)
"Perfect"

Reviewed on 11 Aug. 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 NZ$449 per night from 25 Aug to 26 Aug
NZ$449
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (2,665 reviews)
"We really enjoyed our stay. We loved the location, as it was close to the action but also being at the end of the street, felt private still. There were a couple things broken in our room, like the blinds and a light in our room and the water pressure was awful, otherwise I would have given it 5 ..."

Reviewed on 8 Aug. 2025

Southernmost Beach Resort and Guesthouses
See all 2,804 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 1 000 000 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.