Cow Key Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Cow Key

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 3.504.167 ₫ per night from 24 Jun to 25 Jun
3.504.167 ₫
5.265.070 ₫ total
24 Jun - 25 Jun
includes taxes & fees
8.4/10 Very Good! (1,234 reviews)
"Great places to shop and eat in town only about 5 minutes away. The on site bar and restaurant were great as well! Rooms are beautiful, clean and comfy (and I’m picky about bed comfort). The pool looked great too!"

Reviewed on 23 Jun 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 5.975.114 ₫ per night from 14 Jul to 15 Jul
5.975.114 ₫
8.485.846 ₫ total
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (2,525 reviews)
"Great, quiet resort on the southern point of Old Town in Key West."

Reviewed on 20 Jun 2025

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
The price is 6.297.571 ₫ per night from 8 Jul to 9 Jul
6.297.571 ₫
8.743.073 ₫ total
8 Jul - 9 Jul
includes taxes & fees
8.6/10 Excellent! (1,726 reviews)
"Great staff"

Reviewed on 19 Jun 2025

Margaritaville Beach House Key West
See all 3,153 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 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.