Key West Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Key West

Grand Harbor Resort and Waterpark

Grand Harbor Resort and Waterpark

3.5 out of 5
350 Bell St, Dubuque, IA
The price is 4.971.834 ₫ per night from 27 Aug to 28 Aug
4.971.834 ₫
6.363.948 ₫ total
27 Aug - 28 Aug
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Close to the river. I liked the walking area. I wish it was longer for my run and walk, but it's lovely and well maintained. It would be a great place to bring our grandchildren!"

Reviewed on 24 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! (1,211 reviews)
"Loved this Inn! Super rustic feel and clean!"

Reviewed on 18 Aug 2025

Get rates
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 2.817.373 ₫ per night from 23 Sept to 24 Sept
2.817.373 ₫
3.856.712 ₫ total
23 Sept - 24 Sept
includes taxes & fees
9.4/10 Exceptional! (1,175 reviews)
"Loved this hotel ! Very clean and cute plus the pool area was great! Wonderful breakfast as well ! Will definitely recommend this hotel!"

Reviewed on 23 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.

Popular places to visit

Crystal Lake Cave showing caves

Crystal Lake Cave

Explore the great outdoors at Crystal Lake Cave, a lovely green space in Dubuque. Visit the casinos and top-notch restaurants in this family-friendly area.

Crystal Lake Cave
Eagle Point Park featuring a garden

Eagle Point Park

Explore the great outdoors at Eagle Point Park, a lovely green space in Dubuque. Make time to visit the area's casinos or simply enjoy its top-notch restaurants.

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

Dubuque Arboretum and Botanical Gardens

Explore the great outdoors at Dubuque Arboretum and Botanical Gardens, a lovely green space in Dubuque. Stroll along the riverfront or visit the casinos in the area.

Dubuque Arboretum and Botanical Gardens

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.