Cow Key Vacations from $200

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Your Cow Key Vacation

When you book a vacation package to Cow Key, you can relax and enjoy your escape knowing that all your travel arrangements have been worked out ahead of time. Uncover the wonders of this lively city from your base in a neighborhood like Sunset Key, which is good for coastal beaches. If your trip to Cow Key includes some sightseeing, check out famous attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Your ideal Cow Key vacation is only clicks away. Explore hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Cow Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
The Shelborne By Proper
Cavalier Hotel South Beach
B Ocean Resort Fort Lauderdale Beach
Flow Miami Hotel
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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
$195 nightly
The price is $219 total per night from Jul 7 to Jul 8
$219 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (1,278 reviews)
"Great property. Clean and spacious rooms!"

Reviewed on Jul 1, 2025

Beachside Resort & Residences
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
$305 nightly
The price is $343 total per night from Jul 15 to Jul 16
$343 total
Jul 15 - Jul 16
Total includes taxes and fees
8.6/10 Excellent! (1,735 reviews)
"Amazing!"

Reviewed on Jun 27, 2025

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
$289 nightly
The price is $325 total per night from Jul 15 to Jul 16
$325 total
Jul 15 - Jul 16
Total includes taxes and fees
8.6/10 Excellent! (2,596 reviews)
"The amenities on the property were great! We enjoyed the shores pool and pool bar during our stay. However, we did not enjoy the pigeons and roosters roaming everywhere or their waste all over the property. There was pigeon poop all outside our room and down the steps leading to the pool area. We ..."

Reviewed on Jul 1, 2025

Southernmost Beach Resort and Guesthouses
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.

Find the Best Cow Key Vacation Packages

Cow Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach

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Frequently asked questions

How much does a Cow Key vacation package cost?
Offering great value package deals from $200 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 can typically find lower prices and better availability in August, September and October. Take a look at our cheap Cow Key vacation packages and you could get some excellent off-season deals.
How many days is enough for Cow Key?
The ideal duration of your Cow Key vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to go to all the top attractions and explore some hidden treasures along the way.
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.
Does Expedia offer Book Now, Pay Later Cow Key vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Cow Key trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.