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
Price was CA $1,500, price is now CA $983 per person
CA $983
per person
Nov 15 - Nov 19
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,008 reviews)
Convenient closer to shop market. Staff friendly property clean.

Reviewed on Aug. 24, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was CA $2,260, price is now CA $1,376 per person
CA $1,376
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Fantastic staff, always smiling. Great amenities, super clean, fantastic location.

Reviewed on Aug. 25, 2025

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was CA $3,627, price is now CA $2,327 per person
CA $2,327
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,014 reviews)
It was fabulous. The staff was amazing and we enjoyed the pool, beach and restaurant. My only suggestion is they add a pet walking area with turf. There is no grass on the property for pet relief.

Reviewed on Aug. 24, 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $3,422, price is now CA $2,237 per person
CA $2,237
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (366 reviews)
everything was easy and staff was very helpful!

Reviewed on Aug. 18, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $2,468, price is now CA $1,649 per person
CA $1,649
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
It's a really nice property next to a marina. Quiet at night much livelier during the day. There is a shuttle from property to get to down town if you don't have a rental car. Rental car is needed and necessary in my opinion. The pool was great and there are three places to eat in the immediate area. Our first time here and we will be returning in the future.

Reviewed on Aug. 25, 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 $173 per night from Aug 26 to Aug 27
CA $173
CA $265 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,480 reviews)
"The property was excellent, located in the heart of everything!! 😍"

Reviewed on Aug. 23, 2025

Beachside Resort & Residences
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Sep 2 to Sep 3
CA $232
CA $341 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,726 reviews)
"This property was wonderful! Absolutely gorgeous!"

Reviewed on Aug. 23, 2025

Oceans Edge Key West Resort, Hotel & Marina
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 Sep 1 to Sep 2
CA $140
CA $196 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,070 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on Aug. 18, 2025

Hilton Garden Inn Key West / The Keys Collection
See all 2,779 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
Beach Vacations
Family Vacations
Family Vacations

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 $983. 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.