Midtown Vacation Packages

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Top Holiday Package Deals in Midtown

Price found within the past 48 hours. Click for updated prices.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Old Town Key West
per person
Aug. 26 - Aug. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
6.6/10 (1,006 reviews)
Great property, communication and service!

Reviewed on Jun. 2, 2024

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Aug. 26 - Aug. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (1,007 reviews)
Location, service, the property in general, a first class experience.

Reviewed on Jun. 3, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Jul. 8 - Jul. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
7.8/10 Good! (1,572 reviews)
Beautiful setting the room AC could be updated but very clean

Reviewed on Jun. 4, 2024

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
per person
Jul. 8 - Jul. 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (454 reviews)
Nice, cozy and quaint property steps away from Duval St and all the happening places. Great staff.

Reviewed on Jun. 5, 2024

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
per person
Aug. 26 - Aug. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,001 reviews)
It’s a great spot to stay. Very large rooms compared to most places in Key West. Would definitely stay there again.

Reviewed on Jun. 4, 2024

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
Audubon House and Tropical Gardens featuring a house

Key West Historic District

4 out of top 10 points of interest in this area
4.5/5(156 area reviews)

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Find hotel + flight trips in Key West Historic District

Midtown Hotel Deals

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 $229 per night from Jun. 9 to Jun. 10
CA $229
CA $337 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (1,527 reviews)
"We enjoy the area, out of the way, yet convenient to most of keys. Relaxing spot and property is always well maintained. Great pool service staff."

Reviewed on Jun. 3, 2024

Oceans Edge Key West Resort, Hotel & Marina
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 $326 per night from Jun. 27 to Jun. 28
CA $326
CA $453 total
includes taxes & fees
Jun 27 - Jun 28
8.4/10 Very Good! (1,776 reviews)
"This is a great place to stay, next time we decide to visit Key West we will fly. This property has shuttle service to and from the airport, they also have shuttle services to the main attraction area, you do not need a vehicle visiting Key West. The beach is directly across the street from the resort ..."

Reviewed on Jun. 2, 2024

Margaritaville Beach House Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $328 per night from Jun. 19 to Jun. 20
CA $328
CA $455 total
includes taxes & fees
Jun 19 - Jun 20
8.2/10 Very Good! (1,911 reviews)
"All the people were very friendly and helpful. It was close to all the hot spots in old town. Would definitely stay again."

Reviewed on Jun. 5, 2024

Southernmost Beach Resort
See all 2,684 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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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 $1,143. 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.

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