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. 20 - Aug. 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
6.6/10 (1,003 reviews)
It was a very nice "old school property". The staff was kind and attentive. Really the only challenging piece was the dining. Breakfast was in the ballroom, and quite good, but for lunch and dinner, it was difficult as the only formal dining area was outside by the beach. The food was great, just not an indoor option for lunch and dinner.

Reviewed on Jun. 23, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Aug. 20 - Aug. 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
7.8/10 Good! (1,578 reviews)
Place was perfect. Very friendly staff upon arrival and throughout the stay. The rooms were comfortable and even had their own personal terraces with hammocks. The hotel had its own private beach area (although the water isn’t great to get it in as it is very rocky and muddy) it had an amazing view and setting. Hammocks and beach chairs. The restaurant was very cute & had some good food

Reviewed on Jun. 23, 2024

The Gardens Hotel

The Gardens Hotel

4 out of 5
Key West Historic District
per person
Aug. 20 - Aug. 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.6/10 Exceptional! (933 reviews)
Located just off Duval street but once inside the property it is was like an oasis in the middle of the desert.

Reviewed on Jun. 24, 2024

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
per person
Aug. 20 - Aug. 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (1,003 reviews)
Pier House Resort is a great place to stay! Close to all the fun on Duval, private clean beach, restaurant and bars at the property, and great views of the water. Staff is friendly and very helpful.

Reviewed on Jun. 23, 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. 20 - Aug. 23
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,001 reviews)
Fantastic place with best location. Beautiful room, superb breakfast, highly recommend.

Reviewed on Jun. 22, 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 $228 per night from Jul. 9 to Jul. 10
CA $228
CA $336 total
includes taxes & fees
Jul 9 - Jul 10
8.8/10 Excellent! (1,533 reviews)
"Amazing hotel"

Reviewed on Jun. 23, 2024

Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $309 per night from Jul. 10 to Jul. 11
CA $309
CA $434 total
includes taxes & fees
Jul 10 - Jul 11
8.2/10 Very Good! (1,914 reviews)
"Room was comfortable. Walkable to all attractions Food was delicious Drinks were really good. The service was excellent Beach was small but nice"

Reviewed on Jun. 23, 2024

Southernmost Beach Resort
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 $382 per night from Jul. 16 to Jul. 17
CA $382
CA $517 total
includes taxes & fees
Jul 16 - Jul 17
8.4/10 Very Good! (1,767 reviews)
"Overall chill vibe. Pool and pool bar relaxing. Excellent food (and drinks)."

Reviewed on Jun. 20, 2024

Margaritaville Beach House Key West
See all 2,726 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

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 $1,078. 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.