Midtown Vacation Packages

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Top Holiday Package Deals in Midtown

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (433 reviews)
Beautiful historic Key West Inn one block off of Duval. Quiet, great location, small bar with an excellent breakfast. Eric the bartender had great recommendations for restaurants and Pilar Rum.

Reviewed on May 28, 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. 2 - Aug. 5
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (1,002 reviews)
Amazing! Will definitely be going back!

Reviewed on May 28, 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
Aug. 2 - Aug. 5
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
7.8/10 Good! (1,594 reviews)
Ibis Bay Resort was phenomenal. From the great hospitality from Claudine and the bartender to the peaceful room upgrade. Initially we weren’t sure what this place would entail. To our surprise everything met our expectation and more. We will be coming back. If you see a bad review on here take it lightly…because this place is great for rest and relaxation from high strung lifestyles.

Reviewed on May 28, 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. 2 - Aug. 5
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
The pool is was quiet and beautiful. Very relaxing. Our room was clean but the toilet kept not filling up with water. Also one staff member acted very annoyed by any request we had.

Reviewed on May 16, 2024

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. 2 - Aug. 5
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
6.6/10 (1,002 reviews)
The property is amazing! Beautiful area

Reviewed on May 27, 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 $260 per night from Jun. 10 to Jun. 11
CA $260
CA $372 total
includes taxes & fees
Jun 10 - Jun 11
8.8/10 Excellent! (1,509 reviews)
"Excellent resort"

Reviewed on May 27, 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 $303 per night from Jun. 5 to Jun. 6
CA $303
CA $428 total
includes taxes & fees
Jun 5 - Jun 6
8.4/10 Very Good! (1,763 reviews)
"Great hotel, I would come back anytime."

Reviewed on May 24, 2024

Margaritaville Beach House Key West
Havana Cabana at Key West - Adults Only
Havana Cabana at Key West - Adults Only
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Jun. 23 to Jun. 24
CA $250
CA $369 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (1,464 reviews)
"Good place"

Reviewed on May 29, 2024

Havana Cabana at Key West - Adults Only
See all 2,693 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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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 $845. 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.