Cow Key Vacations from $446
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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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$14,328
per person
Dec 17 - Dec 23
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
Miami Vacation Rentals - Downtown
Downtown Miami
$1,055
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (92 reviews)
Beware! The parking is not as advertised and cost a fortune. The room was noisy at night making sleep difficult due to noisy air conditioner. The staff at the hotel was quite unfriendly and was quite unhelpful. And most of all getting in touch with Expedia was impossible to achieve, even as I write this review they have not responded to my claims.
Reviewed on Oct 4, 2026
The Local House
South Beach
$1,471
per person
Dec 1 - Dec 6
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient
Reviewed on Oct 5, 2026
Cow Key Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
$265 nightly
$298 total
Oct 7 - Oct 8
Total with taxes and fees
8.8/10 Excellent! (1,788 reviews)
"The staff were friendly and extremely helpful. The shuttle provided an excellent means for transportation to Duval Street as well as the ferry. The beaches in Key West are not the greatest so if your decision is based on proximity to the beach, it may not be worthwhile. The pool at the resort was ..."
Reviewed on Oct 5, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$168 nightly
$189 total
Oct 7 - Oct 8
Total with taxes and fees
8.6/10 Excellent! (2,714 reviews)
"Hot water in showers, bed comfort was okay, food was decent at the bars/restaurants, staff was friendly, pool clean and open until 11pm. Lots of fun games to play outside. The property and rooms were clean and the shuttle service to town was easy and very helpful!"
Reviewed on Oct 5, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$185 nightly
$208 total
Oct 7 - Oct 8
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 $446 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.
