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Top Holiday Package Deals in Midtown
Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
per person
Dec. 2 - Dec. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8/10 Very Good! (1,627 reviews)
I liked the location. It was close enough to attractions and shuttle made it convenient enough. Free breakfast was good the first day then went downhill. Restaurant closed last 2 days without notice and no toasters even available last day. The rooms were adequate and pretty clean. The outside would have been great if it did not have such a terrible odor. Most front desk people OK but one was very poor customer service. We rented a scooter one day which was fun but almost double the price of rentals downtown.
Reviewed on Sep. 25, 2024
Ella's Cottages - Key West Historic Inns
Key West Historic District
Save 100% on your flight
per person
Nov. 17 - Nov. 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Key West (EYW)
9.2/10 Wonderful! (204 reviews)
Ella’s was absolutely amazing. Quiet and quaint. Close to downtown. Rooms were very clean and comfortable.
Reviewed on Sep. 24, 2024
The Southernmost Inn - Adults Only
Key West Historic District
Save 100% on your flight
per person
Dec. 2 - Dec. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
8/10 Very Good! (1,002 reviews)
We stayed for one night and loved it! Such a cute inn, bigger than I thought for sure. Breakfast was simple and delicious, they also had a wine happy hour from 5-7pm which was great too! Few feet away from Duval Street and the area was beautiful and safe to walk around.
Reviewed on Sep. 26, 2024
Almond Tree Inn Hotel - Adults Only
Key West Historic District
Save 100% on your flight
per person
Dec. 2 - Dec. 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
10/10 Exceptional! (1,000 reviews)
The detaill to service, personality of staff, and tropical landscape of the property are unique and memorable. It was a perfect place to stay for our individual Wedding Day and Honeymoon! Thank you Almond Tree Inn
Reviewed on Sep. 26, 2024
Where to stay in Midtown
Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
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.
Midtown Hotel Deals
Southernmost Beach Resort
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $362 per night from Sep. 29 to Sep. 30
CA $362
CA $493 total
includes taxes & fees
Sep 29 - Sep 30
8.4/10 Very Good! (2,125 reviews)
"Excellent property in a beautiful area. Attentive and knowledgeable staff. Very clean and well maintained"
Reviewed on Sep. 25, 2024
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from Oct. 10 to Oct. 11
CA $286
CA $406 total
includes taxes & fees
Oct 10 - Oct 11
8.4/10 Very Good! (1,797 reviews)
"Amayzing place to stay we really had a great time. Freindly staff very clean"
Reviewed on Sep. 26, 2024
Havana Cabana at Key West
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep. 29 to Sep. 30
CA $186
CA $294 total
includes taxes & fees
Sep 29 - Sep 30
8.6/10 Excellent! (1,584 reviews)
"I Loved everything about it"
Reviewed on Sep. 24, 2024
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.
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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.