Cow Key Vacations from $465
Book a Hotel + Flight or Car together to unlock savings
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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$6,839
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
President Hotel Villa
South Beach
$692
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,004 reviews)
I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.
Reviewed on Sep 7, 2026
President Hotel
South Beach
$714
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,738 reviews)
The stay was good but we decided to take the Miami Double Deck Bus and it was awful. Rip off totally do not recommend at all. The rooms are clean and the staff was cordial and so attentive and helpful.
Reviewed on Sep 15, 2026
Cow Key Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
$269 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (3,604 reviews)
"Booked this place for the location and how many pools they had. Didn’t know until we got there that the largest pool was under renovation and completely out of service. Not the end of the world but this made the other 2 pools (combined they were the size of the 1 that was closed) more cramped. Then ..."
Reviewed on Sep 15, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$160 nightly
$180 total
Sep 17 - Sep 18
Total with taxes and fees
8.6/10 Excellent! (2,672 reviews)
"Clean room, clean pool. staff very helpful,"
Reviewed on Sep 15, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$234 nightly
$263 total
Sep 30 - Oct 1
Total with taxes and fees
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 $465 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.