Midtown Vacation Packages

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Top Holiday Package Deals in Midtown

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Property was resort like with a small beach area, pool and tiki bar that served good food and beverages

Reviewed on Jul. 27, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Excellent property! We very much enjoyed the location (right off of Duval but not loud at all), pool, Happy Hour and Breakfast. Our room was very nicely appointed and although the elevator was not working, that did not hinder us at all. The property is well taken care of and the staff was top notch, we particularly appreciated Cary and Catherine (I hope I got her name right, she was awesome) as the front desk and HH and Breakfast attendants. Would certainly stay here again and highly recommend.

Reviewed on Jul. 26, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Clean, beautful and very comfortable

Reviewed on Jul. 24, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Had a great time place was awesome. Can’t wait to return

Reviewed on Jul. 26, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Beautiful hotel..we stayed at Duval gardens guesthouse on duval street about 5 mins walk from the lobby..bellmen are available for transport..breakfast was nice and pool area was well kept..staff is attentive and made sure we had everything we need

Reviewed on Jul. 26, 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

4 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 $177 per night from Aug 20 to Aug 21
CA $177
CA $268 total
Aug 20 - Aug 21
includes taxes & fees
8.4/10 Very Good! (1,386 reviews)
"I liked everything except the parking fee of $25.00 each night. I loved the towels and bed. I wished there’s a microwave and a bigger refrigerator."

Reviewed on Jul. 27, 2025

Beachside Resort & Residences
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 CA $252 per night from Aug 25 to Aug 26
CA $252
CA $377 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,641 reviews)
"Very nice resort and great staff!!! Julie at concierge was the best ever!!!!"

Reviewed on Jul. 24, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Aug 26 to Aug 27
CA $167
CA $265 total
Aug 26 - Aug 27
includes taxes & fees
7.6/10 Good! (1,494 reviews)
"This property is amazing and has everything you need. We will be back."

Reviewed on Jul. 25, 2025

Blue Flamingo Resort Key West
See all 2,781 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 Vacations
All Inclusive Vacations
Beach Vacations
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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 $1,353. 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.