Midtown Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
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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
Old Town Key West
4 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 Florida Keys Beaches.
Downtown Key West
While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.
Key West Historic District
2 out of top 10 points of interest in this area
Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.
New Town
While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Fort East Martello Museum and Gallery.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Our pick of the best Midtown Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
NZ$336
4 Oct - 5 Oct
includes taxes & fees
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
NZ$522
7 Oct - 8 Oct
includes taxes & fees
8.6/10 Excellent! (3,640 reviews)
"We were looking for good value- we got it! Staff was friendly from start to finish. Rooms provided everything we wanted from a comfortable bed to a scenic ocean view."
Reviewed on 1 Oct 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
NZ$529
4 Oct - 5 Oct
includes taxes & fees
8.8/10 Excellent! (1,806 reviews)
"My overall experience was good. I wasn’t overly impressed, but was content. I don’t have many complaints besides the food. We ate twice at the resort and had issues both times. We decided to eat elsewhere after that."
Reviewed on 30 Sept 2026
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.
Activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
NZ$74
per adult
94% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$57
per adult
82% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$97
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.