Midtown Vacations from $757

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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.
Hyatt Vacation Club at Beach House, Key West
Kona Kai Oasis
Oceans Edge Key West Resort, Hotel & Marina
The Key West Hotel
Hyatt Vacation Club at Windward Pointe, Key West

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown

Midtown Hotel Deals

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
$145 nightly
The price is $164 total per night from Nov 30 to Dec 1
$164 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.

Reviewed on Nov 25, 2025

Blue Flamingo Resort Key West
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
$188 nightly
The price is $211 total per night from Dec 2 to Dec 3
$211 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!

Reviewed on Nov 26, 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $161 total per night from Dec 14 to Dec 15
$161 total
Dec 14 - Dec 15
Total with taxes and fees
7.8/10 Good! (1,134 reviews)
Great pool and exercise/weight room area!

Reviewed on Nov 23, 2025

Hilton Garden Inn Key West / The Keys Collection
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.