Midtown Vacations from $787
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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.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,934, price is now $1,731 per person
$1,731
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Absolutely amazing hidden gem in Key West. Chris, Renee and the rest of the staff are incredible. Beautiful rooms and bathrooms. Backyard is an oasis with a full service tiki bar and stage for live music. It’s a tropical oasis of beauty! Always clean and awesome. Can’t wait to come back!
Reviewed on Feb 28, 2026
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,570, price is now $969 per person
$969
per person
May 4 - May 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
The staff was amazing and it was a quick uber from everything! Beautiful view, beautiful room! We will be back!
Reviewed on Feb 25, 2026
Oceans Edge Key West Resort, Hotel & Marina
Price was $1,917, price is now $1,311 per person
$1,311
per person
Mar 30 - Apr 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The room was spotless, the employees all courteous, friendly and helpful. The food was delicious and overall it was an exceptional experience.
Reviewed on Feb 27, 2026
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $2,577, price is now $1,785 per person
$1,785
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Staff was excellent.. Best breakfast we have ever had at a hotel
Reviewed on Feb 25, 2026
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
4 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
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Key West FL
9.8/10 Exceptional! (308 reviews)
Sherri was amazing to work with! And to say her place is nice is an understatement. From the island decor, the well stocked kitchen, the comfortable bedding, and the amazing partial view of the ocean , Attitudes is a gem! We loved having access to bikes for our morning exercise. The pool is so nice, ...
Reviewed on Feb 9, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$529 nightly
The price is $595 total per night from Mar 30 to Mar 31
$595 total
Mar 30 - Mar 31
Total with taxes and fees
8.8/10 Excellent! (3,097 reviews)
Location was great! Breakfast, pools, friendly attentive staff.
Reviewed on Feb 27, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$374 nightly
The price is $420 total per night from Mar 1 to Mar 2
$420 total
Mar 1 - Mar 2
Total with taxes and fees
8/10 Very Good! (2,114 reviews)
The rooms need a refresh
Reviewed on Feb 28, 2026
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.