Key West Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, 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?

 

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Key West Hotel Deals

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 CA $101 per night from Dec 13 to Dec 14
CA $101
CA $152 total
Dec 13 - Dec 14
includes taxes & fees
9.4/10 Exceptional! (1,531 reviews)
"Loved the theme and the entire property. Dinner at Frank O'Dowd's was also amazing."

Reviewed on Nov 11, 2026

Irish Cottage Inn & Suites
American Inn and Suites

American Inn and Suites

2.5 out of 5
100 Peosta St Peosta IA
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Dec 8 to Dec 9
CA $88
CA $93 total
Dec 8 - Dec 9
includes taxes & fees
American Inn and Suites
Wyndham Garden Galena Hotel & Day Spa

Wyndham Garden Galena Hotel & Day Spa

4 out of 5
11383 US Highway 20 Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Nov 18 to Nov 19
CA $120
CA $133 total
Nov 18 - Nov 19
includes taxes & fees
9.4/10 Exceptional! (1,342 reviews)
"4 star"

Reviewed on Nov 11, 2026

Wyndham Garden Galena Hotel & Day Spa
See all 686 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.
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What to do in Key West

Downtown Galena Food and Drink Tour

Downtown Galena Food and Drink Tour

CA $121
per adult
100% of travellers recommend
Downtown Galena Food and Drink Tour
Cocktail Adventure Tour 21+

Cocktail Adventure Tour 21+

CA $100
per adult
100% of travellers recommend
Cocktail Adventure Tour 21+
See all activities in Key West

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.