Midtown Holidays from £925

Book a Hotel + Flight or Car together to unlock savings

Photo by Debbie McLay

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Your Midtown Holiday

Take in everything this neighbourhood has to offer with a tailor-made Midtown holiday package. However you see yourself spending your time here, you'll find endless opportunities for fun, relaxation and adventure. Your trip to Midtown wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia is here to put your plans into action. Book your perfect Midtown holiday today.

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
9/10 Wonderful! (1,700 reviews)
There was scum along the waterline of the pool. Our “Ocean View” was a swamp mess and at closing there was a bunch of $600 charges on top of the $400 upon arrival and 2k prior.

Reviewed on 5 Aug 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
9.4/10 Exceptional! (1,044 reviews)
Great experience overall! Clean hotel and pool, great local food and convenient shuttle service to downtown Key West. We did on site laundry… were told one price for a bag of clothing and were charged another, even though all items fit into their laundry bag and closed. We had the mimosa package special upon booking and it was never delivered upon, they stated we would get that refunded to us. Those were our only two complaints!

Reviewed on 5 Aug 2025

Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Key West Historic District
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
8.8/10 Excellent! (469 reviews)
Convenient location to Key West Express, and restaurants, bars shopping. Duval Street. Quiet.

Reviewed on 6 Aug 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
9.4/10 Exceptional! (356 reviews)
Great place to stay! Staff was amazing. We will definitely stay here again. A little paradise off of Duval!

Reviewed on 4 Aug 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (1,019 reviews)
Great stay with a group of friends. We all loved it!

Reviewed on 6 Aug 2025

Where to stay in Midtown

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

Old Town Key West

3 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Top hotels in Midtown

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 £151 per night from 19 Aug to 20 Aug
£151
19 Aug - 20 Aug
includes taxes & fees
8.4/10 Very Good! (1,425 reviews)
"Great property. Clean. Great pool."

Reviewed on 4 Aug 2025

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 £138 per night from 7 Sept to 8 Sept
£138
7 Sept - 8 Sept
includes taxes & fees
7.6/10 Good! (1,529 reviews)
"THE SHOWER WAS NOT THAT CLEAN"

Reviewed on 4 Aug 2025

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 refundable
The price is £199 per night from 20 Aug to 21 Aug
£199
20 Aug - 21 Aug
includes taxes & fees
8.6/10 Excellent! (2,659 reviews)
"Very nice e property! Quiet area, but very convenient to local bus stop to Duval Street and other attractions. We would definitely stay here again. Be sure to try Frenchie’s Cafe across the street. Great brunch!"

Reviewed on 5 Aug 2025

Southernmost Beach Resort and Guesthouses
See all 2,801 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Midtown travel package cost?
Starting from an incredible £925, you can handcraft your own Midtown package. Simply bundle hotels, flights and rental cars and be rewarded with discounts.
If I'm not able to travel, can I cancel my Midtown travel package?
If your travel plans in Midtown have been upended, it's good to know that you can cancel your booking. If you made your booking in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. For more information, check our Customer Service Portal.
How do I get a cheap travel package to Midtown?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Midtown travel package to save a ton of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your own way. We offer over 550 partner airlines and 1,000,000 hotel options throughout the world, so that everyone has a chance to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Midtown holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If making bite-sized repayments each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan from Klarna.

Where should I stay in Midtown?
Urban adventurers come from near and far to see Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in Midtown. Book a hotel near these awesome attractions and visit them whenever you want.
What are the top hotels in Midtown?
The Gates Hotel Key West and Crowne Plaza Key West-La Concha are a couple of the most popular properties in Midtown. Why not check out the facilities and rates at each and then decide?
How far in advance should I book my Midtown holiday?
It's difficult to pick the perfect time for airfares, but we normally say the earlier, the better. Most international flights on Expedia become available to compare up to a year in advance. If you're booking at the last minute, don't worry. Low prices occasionally appear just weeks before departure dates.
What does an Expedia Midtown travel package include?
Rental cars, flights and hotels, or any combination of the three — it's up to you! Whether you're exploring Midtown with the family or travelling solo, there's a package to fit every style and budget. Once you've made your booking, why not add on one or two tours or activities?
What should I know before booking a Midtown travel package?
So many places to visit, so many things to see. With a package, you'll be able to check more of them off your list. Bundle your hotels, flights and rental cars and score big savings.
Can I choose my airline with a Midtown Expedia travel package?
Yes, you sure can. We have more than 550 partner airlines around the world, so select the carrier that fits your budget and travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.