Midtown Vacations from $693
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Your Midtown Vacation
Your next escape is calling out to you with a vacation package to Midtown. Fun, food and good times — you're bound to find it in this neighborhood. Not sure what to do and see during your trip to Midtown? Nearby attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are excellent places to start. No matter what your dream Midtown vacation may look like, you can make it a reality with Expedia.
The Latest Midtown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
8.2/10 Very Good! (193 reviews)
beautiful property. grounds well maintained. staff super friendly and accommodating. room very clean and comfortable. nice bed and linens. housekeeping very friendly and kept our coffee and water stocked. The Canary Room excellent cocktails. The Dorada restaurant was excellent. Will stay again. rent the golf cart you won’t regret it!!!
Reviewed on Jul 10, 2025
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
This is my second stay at Almond Tree and since it was so nice the first time I’ll just keep going back. The hotel is great and the location can’t be beat.
Reviewed on Jul 9, 2025
Where to stay in Midtown
Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 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.
Midtown Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from Jul 21 to Jul 22
$234 total
Jul 21 - Jul 22
Total includes taxes and fees
8.4/10 Very Good! (1,302 reviews)
"Expensive compared to a “real resort”"
Reviewed on Jul 6, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$259 nightly
The price is $291 total per night from Aug 4 to Aug 5
$291 total
Aug 4 - Aug 5
Total includes taxes and fees
8.6/10 Excellent! (2,608 reviews)
"Very close to the Hot Spot of Duval St. yet far enough away to not hear the late night shenanigans! It looked as though there was plenty of pool space, unfortunately due to time constraints, we were not able to partake ."
Reviewed on Jul 7, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $199 total per night from Jul 13 to Jul 14
$199 total
Jul 13 - Jul 14
Total includes taxes and fees
7.6/10 Good! (1,459 reviews)
"Excellent place and location, the outdoor area is beautiful, and the pools are too."
Reviewed on Jul 7, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.