Old Town Key West Holidays

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Your Old Town Key West Holiday

Organising your next exciting getaway just got a whole lot easier with a holiday package to Old Town Key West. Take in the best this neighbourhood has to offer while making precious memories you'll replay for years. Some leading nearby attractions to check out during your trip to Old Town Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help put your plans into action. Book your ideal Old Town Key West holiday now.

Price found within the past 48 hours. Click for updated prices.
  • 2 outdoor pools, open 7:00 AM to 10:00 PM, pool cabanas (surcharge)
    Jul 21 - Jul 31

    Blue Flamingo Resort Key West + Flight

    New Town
    10 nights
    4.0 star property
    8.4/10 - Very good (2,315 reviews)
    "Enjoying fun outdoor games, lounging in a mini cabana by the sparkling pool, with a refreshing frozen Miami Vice in hand, and you all set to relax in Key West. We enjoyed this as a staycation and will definitely do so again. Thanks for the memories!"
    Reviewed May 31, 2026
    Return • Sydney (SYD) - Miami (MIA)
    SYD - MIA • 1 stop MIA - SYD • 1 stop
    AU$4,105
    AU$3,397
    per traveller
    found 15 hours ago
    Blue Flamingo Resort Key West
  • Property grounds
    Jul 21 - Jul 31

    Hyatt Vacation Club at Windward Pointe, Key West + Flight

    Key West
    10 nights
    3.5 star property
    9.4/10 - Exceptional (1,100 reviews)
    "The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."
    Reviewed May 28, 2026
    Return • Sydney (SYD) - Miami (MIA)
    SYD - MIA • 1 stop MIA - SYD • 1 stop
    AU$6,837
    AU$4,903
    per traveller
    found 15 hours ago
    Hyatt Vacation Club at Windward Pointe, Key West

Our guide on where to stay in Old Town Key West

Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West
Key West Historic District

Key West Historic District

2 out of top 10 points of interest in this area
4.5/5(10 area reviews)

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

Find hotels in Key West Historic District

Our pick of the best Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$409 per night from 8 June to 9 June
AU$409
8 June - 9 June
includes taxes & fees
8.8/10 Excellent! (3,341 reviews)
"The property we stayed at was nice. They got us into the room right away and it was conveniently located to Duvall Street. However, the room attendant did not come every day and our shower door would not close all the way which we told them the first day we got there and they never came to fix it. ..."

Reviewed on 30 May 2026

Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$465 per night from 27 June to 28 June
AU$465
27 June - 28 June
includes taxes & fees
8.4/10 Very Good! (685 reviews)
"We were really disappointed by the beach. It’s rocky and was covered in seaweed (during our visit). The pools are beautiful, staff was lovely. The room was enormous and well maintained. I just wish we had more transparency regarding the condition of the beach."

Reviewed on 30 May 2026

Casa Marina Key West, Curio Collection by Hilton
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$460 per night from 11 June to 12 June
AU$460
11 June - 12 June
includes taxes & fees
9.2/10 Wonderful! (1,116 reviews)
"The property was very nice the only complaint is that with paid for an ocean view room and on 2 of our 4 days a cruise ship docked and obscured the view from 8am to 5pm."

Reviewed on 29 May 2026

Opal Key Resort & Marina, Key West
See all 1,289 properties in Old Town Key West
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.
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Frequently asked questions

How much does an Old Town Key West holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Old Town Key West from just . And the more you bundle, the more money you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Old Town Key West?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Select a combination that best suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1 000 000 hotel options around the globe, which lets you customize your Old Town Key West getaway.
Where should I stay in Old Town Key West?
A trip to Old Town Key West isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel as close as possible for quick access to these awesome attractions.
What are the top hotels in Old Town Key West?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of this area's most in-demand properties. Another top-rated option in Old Town Key West is Curry House.
How far in advance should I book my Old Town Key West holiday?
Smart travellers often book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing tickets last minute, don't despair. Budget prices occasionally become available just weeks prior to departure.
What does an Expedia Old Town Key West travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is pick and choose your favourite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to create an awesome Old Town Key West holiday.
What should I know before booking an Old Town Key West travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever your holiday goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Town Key West holiday package?
You can. We realise life doesn't always go to plan, so we're here to help if you have to make changes to your Old Town Key West holiday package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Old Town Key West

Southernmost Point

Southernmost Point

4/5(5 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4/5(5 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum
Key West Butterfly and Nature Conservatory

Key West Butterfly and Nature Conservatory

4/5(1 review)

Encounter hundreds of butterflies in a tropical rainforest setting, butterfly-friendly birds and an indoor waterfall at this popular Key West attraction.

Key West Butterfly and Nature Conservatory

Activities

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

AU$62
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

AU$77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

AU$38
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.