Midtown Holidays

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Your Midtown Holiday

Your next escape is calling out to you with a holiday package to Midtown. Fun, food and good times — you're bound to find it in this neighbourhood. Not sure what to do and see during your trip to Midtown? Nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are excellent places to start. No matter what your dream Midtown holiday may look like, you can make it a reality with Expedia.

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
A white building with shutters, palm trees, and a lawn.

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 Southernmost Point.

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 AU$343 per night from 14 July to 15 July
AU$343
14 July - 15 July
includes taxes & fees
8.6/10 Excellent! (2,340 reviews)
"Elevator was down. All of them. My dad is handicap and their only solution was to give him “waived parking fee”. Not really a solution… in the meantime, I’m Hauling everything up 4 flights of stairs. They should’ve waived the parking fee for everyone. We’ve stayed here before. And came back an again. ..."

Reviewed on 10 July 2026

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$364 per night from 10 Aug to 11 Aug
AU$364
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (3,446 reviews)
"My oceanfront room with a balcony was ocean view with a shared balcony! Do not pay for a balcony unless you verify it isn’t shared! The bathroom had mold around the top of the door and the room smelt of mildew. The sargassum smell right now is terrible, so be aware. We used the pool for a very short ..."

Reviewed on 11 July 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is AU$298 per night from 13 July to 14 July
AU$298
13 July - 14 July
includes taxes & fees
8.4/10 Very good! (2,527 reviews)
"We loved the amenities- the Backyard was super cool and to have multiple pools to use was nice as well. Only complaint was slow and broken elevators over half the days we were there"

Reviewed on 12 July 2026

Blue Flamingo Resort Key West
See all 2,723 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.
All Inclusive Holidays
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All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

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

Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

AU$116
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

AU$80
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

AU$115
per adult
96% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.