Midtown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Jun 24 - Jun 29

    Southernmost House - Adult Exclusive + Flight

    Old Town Key West
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "Beautiful property. Excellent service."
    Reviewed May 15, 2026
    Roundtrip Montreal (YUL) - Miami (MIA)
    YUL - MIANonstop MIA - YULNonstop
    CA $3,226
    CA $1,716
    per traveller
    found 1 day ago
    Southernmost House - Adult Exclusive
  • Aug 9 - Aug 15

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,092 reviews)
    "Great location and hotel!"
    Reviewed May 20, 2026
    Roundtrip Toronto (YYZ) - Fort Lauderdale (FLL)
    YYZ - FLLNonstop FLL - YYZNonstop
    CA $2,759
    CA $1,754
    per traveller
    found 22 hours ago
    Hyatt Vacation Club at Windward Pointe, Key West
  • Jul 31 - Aug 8

    Hyatt Vacation Club at Sunset Harbor, Key West + Flight

    Old Town Key West
    8 nights
    3.5 star property
    8.6/10 - Excellent (371 reviews)
    "Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"
    Reviewed May 18, 2026
    Roundtrip Montreal (YUL) - Key West (EYW)
    YUL - EYW1 stop EYW - YUL1 stop
    CA $4,847
    CA $3,165
    per traveller
    found 7 hours ago
    Hyatt Vacation Club at Sunset Harbor, Key West
  • Jun 24 - Jun 29

    The Key West Hotel + Flight

    Key West Historic District
    5 nights
    3.0 star property
    9.2/10 - Wonderful (555 reviews)
    Roundtrip Montreal (YUL) - Miami (MIA)
    YUL - MIANonstop MIA - YULNonstop
    CA $3,121
    CA $2,096
    per traveller
    found 1 day ago
    The Key West Hotel
  • Jun 24 - Jun 29

    Hyatt Vacation Club at Beach House, Key West + Flight

    Key West
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,062 reviews)
    "Nice clean room. one smoking area is not enough. no on site restaurant or snack bar of vending for snacks. "
    Reviewed May 19, 2026
    Roundtrip Montreal (YUL) - Miami (MIA)
    YUL - MIANonstop MIA - YULNonstop
    CA $2,800
    CA $1,894
    per traveller
    found 1 day ago
    Hyatt Vacation Club at Beach House, Key West

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown

Midtown Hotel Deals

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 $197 per night from Jun 1 to Jun 2
CA $197
CA $299 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (2,247 reviews)
"Staff waa really kind and helpful."

Reviewed on May 20, 2026

Blue Flamingo Resort Key West
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 $290 per night from Jun 21 to Jun 22
CA $290
CA $427 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (3,342 reviews)
"Good place"

Reviewed on May 20, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $287 per night from May 25 to May 26
CA $287
CA $410 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
"Excellent service, highly recommended"

Reviewed on May 19, 2026

Margaritaville Beach House Key West
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 vacation package cost?
We make it easy to travel somewhere new, with Midtown vacation 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 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.