Midtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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Top Holiday Package Deals in Midtown

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,117, price is now CA $1,411 per person
CA $1,411
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (768 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!

Reviewed on Aug. 19, 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was CA $2,399, price is now CA $1,557 per person
CA $1,557
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (802 reviews)
Do not stay on 3rd floor, stairs are terrible and you can feel the rising

Reviewed on Aug. 12, 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was CA $2,135, price is now CA $1,539 per person
CA $1,539
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (1,007 reviews)
property was clean and quiet and staff was super friendly

Reviewed on Aug. 19, 2025

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
Price was CA $2,295, price is now CA $1,654 per person
CA $1,654
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
8.4/10 Very Good! (269 reviews)
The staff and service is exemplary. Ask for Nicole and Marsha at the Dorada beach bar. Both are awesome bartenders and great people!!!

Reviewed on Aug. 19, 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $5,225, price is now CA $3,802 per person
CA $3,802
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (491 reviews)
Excellent location right in the heart of town super friendly staff and very nice property

Reviewed on Aug. 3, 2025

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
3.5/5(8 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

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 CA $176 per night from Aug 26 to Aug 27
CA $176
CA $268 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,468 reviews)
gorgeous view
"It was so nice—we ended up with a gorgeous view."

Reviewed on Aug. 18, 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 27 to Aug 28
CA $140
CA $196 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,066 reviews)
"Nice hotel"

Reviewed on Aug. 14, 2025

Hilton Garden Inn Key West / The Keys Collection
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 CA $164 per night from Sep 18 to Sep 19
CA $164
CA $262 total
Sep 18 - Sep 19
includes taxes & fees
7.6/10 Good! (1,545 reviews)
Pretty good for budget
"Was clean and friendly staff, shuttle driver were also nice, the pool was awesome and so was the bar. Only thing is I thought there was a balcony but it is more of a motel set up. But the rooms are comfy and very coast home inspired"

Reviewed on Aug. 17, 2025

Blue Flamingo Resort Key West
See all 2,791 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.
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Frequently asked questions

How much does a Midtown vacation package cost?
We make it easy to travel somewhere new, with Midtown vacation packages starting from as little as CA $1,411. 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 vacation 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 vacation 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 vacation?
Savvy travelers 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 vacation package is the most convenient way to organize 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 vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can change or cancel your Midtown vacation 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.