Cow Key Vacations from $349

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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.
Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was $760, price is now $349 per person
$349
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay.

Reviewed on Dec 8, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $2,980, price is now $1,266 per person
$1,266
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
Beautiful balcony and porch views.

Reviewed on Dec 8, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,588, price is now $683 per person
$683
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Everything was clean and well maintained

Reviewed on Dec 12, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $28,148, price is now $12,898 per person
$12,898
per person
Jan 19 - Jan 26
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $2,770, price is now $1,359 per person
$1,359
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Nice staff, great area

Reviewed on Dec 9, 2025

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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
$226 nightly
The price is $254 total per night from Dec 17 to Dec 18
$254 total
Dec 17 - Dec 18
Total with taxes and fees
8.6/10 Excellent! (1,757 reviews)
Staff was very polite and amazing ,grounds well taken care of .the suite was top notch ,George the bartender and Keith front desk were top notch

Reviewed on Dec 7, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Dec 14 to Dec 15
$197 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (1,758 reviews)
This was really great! It was quiet, peaceful and everything about this place was just so accommodating. My family and I slept very good, we were very comfortable and the staff was very welcoming and catered to us the entire time of our stay. If we visit again, we will be back!

Reviewed on Dec 12, 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $245 total per night from Dec 14 to Dec 15
$245 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,746 reviews)
Rooms were beautiful

Reviewed on Dec 9, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,206 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.

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 $349 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.