Cow Key Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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 S$272 per night from 7 Jul to 8 Jul
S$272
7 Jul - 8 Jul
includes taxes & fees
8.4/10 Very Good! (1,165 reviews)
"Outstanding suite. Clean, friendly and helpful staff. Will definitely be back next year."

Reviewed on 10 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 S$418 per night from 25 Jun to 26 Jun
S$418
25 Jun - 26 Jun
includes taxes & fees
8.6/10 Excellent! (2,508 reviews)
"Not our first time at this resort. Disappointed in some little noticeable differences – they discontinued the morning happy hour at the beach restaurant and no longer have cable. I know we weren’t there to watch television but it’s nice to have it on when you are back in the room winding down – only ..."

Reviewed on 10 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
Fully refundableReserve now, pay when you stay
The price is S$382 per night from 29 Jun to 30 Jun
S$382
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,714 reviews)
"The shuttle was nice, since the resort is not located near anything of interest. The bar and restaurant is way overpriced and there is no discounts or happy hour for guests."

Reviewed on 11 Jun, 2025

Margaritaville Beach House Key West
See all 3,161 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.