Cow Key Vacations from $300

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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.
Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
North Beach
Price was $655, price is now $300 per person
$300
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
11.2/10 Exceptional! (389 reviews)
La ubicacion es muy buena. La gente que trabaja en el hotel es de primera. El hotel es muy viejo, no limpiaron la habitacion en lps 5 dias que estuve.

Reviewed on Nov 17, 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 $1,594, price is now $679 per person
$679
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on Nov 16, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $1,500, price is now $639 per person
$639
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.4/10 Exceptional! (172 reviews)
The amenities were great. The balcony and the balcony view made every penny worth it - on top of that, the fully stocked kitchen and super comfy living space were relaxing. It would be cool if there was a tv in the bedroom, though…

Reviewed on Nov 9, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,198, price is now $548 per person
$548
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16.8/10 Exceptional! (1,001 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on Nov 4, 2025

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was $1,530, price is now $709 per person
$709
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16.4/10 Exceptional! (996 reviews)
Very nice staff. Very accommodating.

Reviewed on Oct 28, 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
$187 nightly
The price is $210 total per night from Nov 20 to Nov 21
$210 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (1,680 reviews)
Staff was horrible on directions to room. We had to give directions to 4 different sets of new guests as well as getting lost ourselves. Place was great. Nice location.

Reviewed on Nov 13, 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
$157 nightly
The price is $177 total per night from Dec 3 to Dec 4
$177 total
Dec 3 - Dec 4
Total with taxes and fees
7.8/10 Good! (1,693 reviews)
What a fun little resort. The amenities are fabulous! They have live music. We heard Ike Kanakanaui. He was REALLY good!

Reviewed on Nov 14, 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
$217 nightly
The price is $244 total per night from Nov 30 to Dec 1
$244 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,736 reviews)
If you book Oceans Edge through hotels.com or Expedia expect a resort fee & parking fee before booking. These extra costs are not included with your online booking which is misleading to hotel guests. The staff at Oceans Edge worked through this misleading situation which caused a lengthy check in ...

Reviewed on Nov 15, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,168 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 $300 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.