Midtown Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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 Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $1,781, price is now CA $1,327 per person
CA $1,327
per person
Sep 10 - Sep 14
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,150 reviews)
We had a wonderful stay! The room was very clean, comfortable, and well maintained. The staff was friendly, welcoming, and always ready to help with any questions we had. The outdoor pool was clean and a great place to relax after a day of exploring. Parking was convenient and easy, which made our trip even more enjoyable. Overall, it was a great experience, and I would definitely stay here again and recommend it to other travelers.

Reviewed on Jul 7, 2026

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was CA $1,999, price is now CA $1,444 per person
CA $1,444
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8/10 Very good! (2,299 reviews)
Shower didn't get hot, the rooms are outdated and the showers are very small. The A/C is outdated and doesn’t get the room cold. The only pro was the pool area.

Reviewed on Jul 7, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $3,693, price is now CA $2,679 per person
CA $2,679
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Northside Resort
Price was CA $1,885, price is now CA $1,481 per person
CA $1,481
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Key West (EYW)
9/10 Wonderful! (1,417 reviews)
Wonderful place to stay, great location. The staff was amazing! The pools were clean and the room was extremely clean as well. We really enjoyed our stay!

Reviewed on Jul 7, 2026

Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $3,086, price is now CA $2,452 per person
CA $2,452
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (203 reviews)
The floors in the condo had not been cleaned in quite some time as the bottoms of our feet got nasty just by walking around the condo. Be aware that if you stay on any floor except the first floor, you are having to walking up and down all flight of stairs as there aren’t any elevators. Also, the older white lady that was at check in was telling me how awful it was to stay there. In actuality, it wasn’t except for the inconvenience of no elevator and the floors not being clean. Oh and the internet/tv connection is terrible.

Reviewed on Jul 6, 2026

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 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 $195 per night from Jul 15 to Jul 16
CA $195
CA $356 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (2,332 reviews)
"The rooms were very large and comfortable. Having the shuttle to downtown saved driving and very convenient. The pool and hot tub was enjoyed by all."

Reviewed on Jul 8, 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 13 to Jul 14
CA $178
CA $280 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very good! (2,507 reviews)
"TThis place is pet friendly. the staff is really nice and I can only say that the hotel was so much more then we expected. We will definitely be staying there when we go back to the Keys."

Reviewed on Jul 8, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Jul 15 to Jul 16
CA $237
CA $371 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (3,432 reviews)
"Very expensive property. Need investment in maintenance."

Reviewed on Jul 7, 2026

Southernmost Beach Resort and Guesthouses
See all 2,728 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
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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 $1,327. 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.