Key West Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Key West
Irish Cottage Inn & Suites
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
S$160
22 Sept - 23 Sept
includes taxes & fees
9.4/10 Exceptional! (1,464 reviews)
"Be aware there is a $25 per day "ameneties fee" that is added to your hotel bill...I find this a sneeky way of charging for things the hotel says is free...like the breakfast and shuttle service to the town's main street shopping area. The shuttle is ok if you truly need it...say on the weekends ..."
Reviewed on 12 Sept, 2026
Days Inn by Wyndham Dubuque
1111 Dodge St Dubuque IA
Fully refundableReserve now, pay when you stay
S$79
23 Sept - 24 Sept
includes taxes & fees
Hotel Julien Dubuque
200 Main Street Dubuque IA
Fully refundableReserve now, pay when you stay
S$151
20 Sept - 21 Sept
includes taxes & fees
9.2/10 Wonderful! (1,942 reviews)
"Great location. Great restaurant. Room did not have a microwave but everything else was fantastic."
Reviewed on 12 Sept, 2026
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.
What to do in Key West
Downtown Galena Food and Drink Tour
S$111
per adult
100% of travellers recommend
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?
- 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.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
