Midtown Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Midtown

Price found within the past 48 hours. Click for updated prices.
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 $1,470, price is now CA $1,036 per person
CA $1,036
per person
Jul 30 - Aug 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,267 reviews)
Great stay. Little gem that feels like home. Casual accommodations that fit perfectly for a trip to paradise. Two free drinks when you check in, SOLD. Will definitely return.

Reviewed on May 12, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $4,677, price is now CA $3,136 per person
CA $3,136
per person
Jul 25 - Aug 1
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (552 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $1,853, price is now CA $1,356 per person
CA $1,356
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The property staff wasn’t as attentive as I would have hoped at a resort like this. The rooms were spacious and clean.

Reviewed on May 12, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was CA $1,495, price is now CA $1,153 per person
CA $1,153
per person
Jul 30 - Aug 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,272 reviews)
Loved our stay with Southern most! It was safe, clean, quiet, roomy, and stylish. The staff were all friendly and knowledgeable.

Reviewed on May 13, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Price was CA $3,277, price is now CA $2,530 per person
CA $2,530
per person
Jul 25 - Aug 1
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
We enjoyed our stay at the Marker. It was clean and well maintained, the breakfast and bar food were good. My only issue is that we requested a specific area well in advance and they put us in the complete opposite of what we asked for.

Reviewed on May 9, 2026

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

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

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Key West FL
9.8/10 Exceptional! (315 reviews)
The condo is worth every star! The unit was beautifully decorated and had everything we needed. Communication was exceptional before and during our stay. Having access to bikes and beach chairs was a nice bonus and the warm heated pool and hot tub were perfect for a day of relaxing. Everyone we encountered ...

Reviewed on Apr 22, 2026

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Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
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 $208 per night from Jun 3 to Jun 4
CA $208
CA $311 total
Jun 3 - Jun 4
includes taxes & fees
8.4/10 Very Good! (2,216 reviews)
It was a fun hotel

Reviewed on May 13, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
The price is CA $285 per night from Jun 8 to Jun 9
CA $285
CA $407 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,818 reviews)
The view from our toom was obsteucted, parking area only. The beach is across the street from the resort, but they do have a fresh water shower at the front to rinse off. The beach area was nice, soft sand when we went for evening walks. They had lounge chairs with umbrellas for guests, not sure ...

Reviewed on May 12, 2026

Margaritaville Beach House Key West
See all 2,754 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 $1,036. 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.