Cow Key Vacations

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Find the Best Cow Key Vacation Packages

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 ₩185,724 per night from Aug 11 to Aug 12
₩185,724
₩279,071 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very Good! (1,416 reviews)
"The unit was very spacious which was perfect for a family. The view from our unit was spectacular."

Reviewed on Aug 2, 2025

Beachside Resort & Residences
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 ₩157,865 per night from Sep 4 to Sep 5
₩157,865
₩255,503 total
Sep 4 - Sep 5
includes taxes & fees
7.6/10 Good! (1,533 reviews)
"The staff and the manager are so nice I had a small issue with my room after the first night and the manager was so kind to move us to a new and gave us a 50.00 bar credit for the inconvenience he was very understanding about the issue and took care of it right away this property is family friendly ..."

Reviewed on Aug 4, 2025

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is ₩255,195 per night from Aug 25 to Aug 26
₩255,195
₩380,579 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,651 reviews)
"Great place, my wife and I love it!"

Reviewed on Aug 2, 2025

Southernmost Beach Resort and Guesthouses
See all 3,145 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.

Frequently asked questions

How much does a Cow Key vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 vacation. 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 vacation package as early as possible.
Is it cheaper to book a Cow Key vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customize 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 vacation 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 accommodations 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 customized Cow Key vacation package.

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