Cow Key Holidays

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Your Cow Key Holiday

With everything planned before you go away, our Cow Key holiday packages mean you can simply focus on letting the good times roll. Whether you base yourself in the neighbourhood of Sunset Key, which is great for coastal beaches, or somewhere else in town, this interesting city offers a wealth of discoveries. Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are just some of the many attractions worth visiting during your trip to Cow Key. No matter your travel plans or the size of your budget, organising a tailored Cow Key holiday is a cinch with Expedia.

Cow Key Holiday

Cow Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park

Our pick of the best Cow Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 26 Aug to 27 Aug
AU$297
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (1,465 reviews)
"Food options was great, the bed comfort was a little to firm, but the linens was awesome, the suite was very equipped and beautifully updated. Did not get in the pool because the water was not circulating clean and maintenance at night, very nice pool area, but felt the pool water was not clean."

Reviewed on 17 Aug. 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 24 Aug to 25 Aug
AU$222
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,068 reviews)
"Loved the pool and convince of hotel. Staff was Excellent!!"

Reviewed on 17 Aug. 2025

Hilton Garden Inn Key West / The Keys Collection
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$291 per night from 16 Sept to 17 Sept
AU$291
16 Sept - 17 Sept
includes taxes & fees
7.6/10 Good! (1,545 reviews)
Pretty good for budget
"Was clean and friendly staff, shuttle driver were also nice, the pool was awesome and so was the bar. Only thing is I thought there was a balcony but it is more of a motel set up. But the rooms are comfy and very coast home inspired"

Reviewed on 17 Aug. 2025

Blue Flamingo Resort Key West
See all 3,132 properties in Cow Key
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Cow Key holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Cow Key costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cow Key?
You're likely to find reduced prices and greater availability in January, February and August. Take a look at our cheap Cow Key holiday packages and you could score some excellent off-season deals.
How many days is enough for Cow Key?
Generally, a handful of days is enough to tick off the major sights during your Cow Key holiday. But if you prefer to have some time to rest or take day tours, consider extending your itinerary.
How to find the best Cow Key package deals?
Use Expedia's filters to help you find some unbeatable Cow Key package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Cow Key package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Cow Key holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customise your Cow Key escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Cow Key?
If you've got your Cow Key travel dates confirmed, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Cow Key?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Cow Key.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Cow Key.
  3. Decide how long to go for: Now that you know more about Cow Key, you can work out the ideal length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customised Cow Key holiday package.

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