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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
The price is NZ$458 per night from 13 Oct to 14 Oct
NZ$458
13 Oct - 14 Oct
includes taxes & fees
8.6/10 Excellent! (1,790 reviews)
"We went during off peak season and it was amazing and quiet, relaxing."

Reviewed on 23 Sept 2025

Margaritaville Beach House Key West
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 NZ$467 per night from 29 Sept to 30 Sept
NZ$467
29 Sept - 30 Sept
includes taxes & fees
8.8/10 Excellent! (1,735 reviews)
"This was a nice hotel complex. Not really a resort in that there was only one restaurant on the property. And it was extremely limited in the menu selections and very expensive for the portion served. The complex needs to have a small cafe with coffee, appetizers or snacks. Also they should not book ..."

Reviewed on 24 Sept 2025

Oceans Edge Key West Resort, Hotel & Marina
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$447 per night from 29 Oct to 30 Oct
NZ$447
29 Oct - 30 Oct
includes taxes & fees
8.6/10 Excellent! (2,777 reviews)
"Our concierge was amazing! Very attentive and accommodating."

Reviewed on 25 Sept 2025

Southernmost Beach Resort and Guesthouses
See all 2,807 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.