Key West Holidays

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Key West Holiday

Our pick of the best Key West Hotel Deals

Grand Harbor Resort and Waterpark

Grand Harbor Resort and Waterpark

3.5 out of 5
350 Bell St, Dubuque, IA
The price is NZ$322 per night from 27 Aug to 28 Aug
NZ$322
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Rooms are nothing special but clean. Great location on the river."

Reviewed on 23 Aug. 2025

Grand Harbor Resort and Waterpark
Stoney Creek Inn Galena

Stoney Creek Inn Galena

2 out of 5
940 Galena Square Dr, Galena, IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,210 reviews)
"Loved this Inn! Super rustic feel and clean!"

Reviewed on 18 Aug. 2025

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Stoney Creek Inn Galena
Irish Cottage Inn & Suites

Irish Cottage Inn & Suites

3.5 out of 5
9853 US-20, Galena, IL
Fully refundableReserve now, pay when you stay
The price is NZ$224 per night from 25 Aug to 26 Aug
NZ$224
25 Aug - 26 Aug
includes taxes & fees
9.4/10 Exceptional! (1,173 reviews)
"We really enjoyed the whole vibe. The bar was a bit pricey, but has an amazing feel. It served us very well as a home base in our stay in Galena, and had us within short drives to all the places we wanted to visit. Potosi, Dubuque, Effegy Mounds and of course downtown Galena."

Reviewed on 21 Aug. 2025

Irish Cottage Inn & Suites
See all 557 properties in 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.

Discover the most popular places to visit in Key West

Dubuque Arboretum and Botanical Gardens featuring a pond and a park as well as an individual female

Dubuque Arboretum and Botanical Gardens

While nature puts on a show all year, this spot capitalizes on its natural beauty. Spend some time going through the serene and immaculately maintained grounds.

Dubuque Arboretum and Botanical Gardens

Diamond Jo Casino

Why not try your luck with a visit to Diamond Jo Casino during your time in Dubuque? Wander the area's riverfront or simply enjoy one of its top-notch restaurants.

Diamond Jo Casino

What to do in Key West

Downtown Galena Food and Drink Tour

Downtown Galena Food and Drink Tour

NZ$144
per adult
100% of travellers recommend
Downtown Galena Food and Drink Tour
See all activities in Key West

Frequently asked questions

How much does a Key West holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Key West costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Key West?
You're likely to find lower prices and better availability in January, February and November. Take a look at our cheap Key West holiday packages and you could score some great off-season discounts.
How many days is enough for Key West?
Generally, a handful of days is enough to go to the main sights during your Key West holiday. But if you want to have some time to relax or go on day tours, consider extending your trip.
How to find the best Key West package deals?
Use Expedia's handy filters to help you find some fabulous Key West package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Key West package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.
Is it cheaper to book a Key West holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a customised Key West holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Key West?
If you're considering an impromptu Key West adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Key West?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Key West.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodation will probably be the largest expense during your trip to Key West.
  3. Decide how long to go for: Now that you're up to speed on Key West, you can work out the ideal length of your holiday. Create a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Key West holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.