Key West Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Key West Vacation
The hassle-free way to experience this interesting city is with a customized Key West vacation package. Base yourself in the neighborhood of Downtown Dubuque, which is good for bars and pubs, culture and cafes or choose someplace else — our package deals are all about you. Diamond Jo Casino, National Mississippi River Museum and Aquarium and Q Casino are just some of the attractions you'll want to check out during your trip to Key West. Your dream Key West vacation is only clicks away. Search flights, accommodations and more on Expedia for a getaway that's tailored to suit your style.
Ready to book your vacation to Key West?
Key West Hotel Deals
Irish Cottage Inn & Suites
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
CA $123
CA $174 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (1,463 reviews)
"Great breakfast!!"
Reviewed on Aug 31, 2026
Days Inn by Wyndham Dubuque
1111 Dodge St Dubuque IA
Fully refundableReserve now, pay when you stay
CA $75
CA $84 total
Sep 27 - Sep 28
includes taxes & fees
7.4/10 Good! (1,174 reviews)
"It was a nice stay good place to be"
Reviewed on Aug 31, 2026
Wyndham Garden Galena Hotel & Day Spa
11383 US Highway 20 Galena IL
Fully refundableReserve now, pay when you stay
CA $138
CA $153 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,308 reviews)
"Overall very pleased with the hotel, we utilized the bar, game room, breakfast, gym, and wrap around deck. My only complaint is the floors seem to be thin. We could hear heavy walking constantly in our first floor room. We kept the A/C fan blowing all night long to try and drain out the noise."
Reviewed on Aug 31, 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
CA $120
per adult
100% of travellers recommend
Frequently asked questions
How much does a Key West vacation package cost?
You'll find cheap prices on Expedia for your Key West break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Key West costs.
What are the cheapest months to go to Key West?
You can generally find lower rates and greater availability in January, February and November. Browse our cheap Key West vacation packages and you could get some excellent off-season deals.
How many days is enough for Key West?
For a Key West vacation, a handful of days will be enough to see all the highlights. Make sure to check out Five Flags Centre — it's one of the top sights in this destination. If you're looking for more activities, consider basing yourself here and setting off on some day trips from Key West.
How to find the best Key West package deals?
Use Expedia's filters to help you find some great Key West package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Key West package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Key West vacation as a package?
You can enjoy significant savings on your next Key West retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Key West?
Secure incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Key West break.
How to plan a trip to Key West?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Key West.
- Set a budget: Factor in costs like flights, transportation and food when calculating how much to save for your trip to Key West. Then, pick a hotel that fits your budget, whether that's an economical stay or a swankier retreat.
- Determine how many days away: Start by listing all the activities and attractions you'd like to get to in Key West. Then, estimate how long you'll need at each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Key West vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
