
Midtown Vacation Packages
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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
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
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
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
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
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
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.
Midtown Hotel Deals

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

Blue Flamingo Resort Key West
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

Margaritaville Beach House Key West
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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.










