Midtown Holidays from £762

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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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
per person
17 Sept - 21 Sept
found 1 hour ago
Return direct flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Great place, huge rooms, 2 bathrooms, washer and dryer, screened in porch. Covered parking. Pool and games for lids. We had a great time.

Reviewed on 29 Jul 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
per person
17 Sept - 21 Sept
found 1 hour ago
Return direct flight included
London (LON) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
Beautiful with excellent customer service. I very much enjoyed being here and didnt want to leave

Reviewed on 27 Jul 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
17 Sept - 21 Sept
found 1 hour ago
Return direct flight included
London (LON) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
We have fallen in love with this place !!! Never had been here, came to Orchid Key for our anniversary weekend and are hooked. Local motel, quaint, clean, retro, friendly and amazing location. We have already rebooked ♥️

Reviewed on 28 Jul 2025

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
per person
17 Sept - 21 Sept
found 1 hour ago
Return direct flight included
London (LON) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Beautiful place ,the price incredible ,but the view from my balcony is the best , I fall in love with my apt/room .

Reviewed on 30 Jul 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
per person
17 Sept - 21 Sept
found 1 hour ago
Return direct flight included
London (LON) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Location was perfect.

Reviewed on 31 Jul 2025

Where to stay in Midtown

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

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 18 Aug to 19 Aug
£151
18 Aug - 19 Aug
includes taxes & fees
8.4/10 Very Good! (1,399 reviews)
"Loved the room! So big and spacious. The room we had 123 had stainless steel pans and not many, basically impossible to cook with and not burn. Everything else was awesome. Call in plenty of time if you need ice. Pool was awesome and opened 24/7."

Reviewed on 28 Jul 2025

Beachside Resort & Residences
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 £206 per night from 25 Aug to 26 Aug
£206
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (2,650 reviews)
"Stay was good but we expected the private beach and it was not clean due to seaweeds so we couldn't use at all. The only reason we booked that hotel due to private beach access which was not available. Otberwise everything was good."

Reviewed on 27 Jul 2025

Southernmost Beach Resort and Guesthouses
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 £149 per night from 5 Aug to 6 Aug
£149
5 Aug - 6 Aug
includes taxes & fees
7.6/10 Good! (1,487 reviews)
"Good value for your money, convenient location and a friendly, welcoming staff. As a pet friendly resort, perhaps in the future have a couple of dog friendly entertainment areas on the resort so owners and their fur babies can spend time together."

Reviewed on 29 Jul 2025

Blue Flamingo Resort Key West
See all 2,794 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
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Family Friendly Holidays

Frequently asked questions

How much does a Midtown travel package cost?
Starting from an incredible £762, 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.