Cow Key Vacations from $302

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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.
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $602, price is now $302 per person
$302
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (2,544 reviews)

Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Price was $703, price is now $310 per person
$310
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.4/10 Exceptional! (228 reviews)
Your staying here for the location. Very old Florida. The a/c was very loud and hard to sleep through and the bed was flimsey and uncomfortable. All the toiletries are in the lobby which if you dont know that can be annoying. There are two cats that roam around very cute. And an adorable area in the back perfect for reading or having a glass of wine.

Reviewed on Jul 13, 2026

The Marlin Hotel

The Marlin Hotel

4 out of 5
South Beach
Price was $1,006, price is now $478 per person
$478
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Perfect location for South Beach. One block off Ocean Drive with bars, restaurants, clubs, etc. all within walking distance & a great Italian restaurant on-property too.

Reviewed on Jul 13, 2026

The Local House

The Local House

3.5 out of 5
South Beach
Save 100% on your flight
Price was $757, price is now $381 per person
$381
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
We only stayed for one night before driving down to the keys for my birthday but we really enjoyed our stay at The Local House. All of the staff were incredibly kind and they even blew up balloons and decorated our room for my birthday. Considering how busy the area was, the rooms were incredibly quiet and the bed was super comfortable. The only complaint we would have is that the bathrooms are slightly outdated in comparison to the bedrooms but other than that, we really enjoyed our stay and would recommend The Local House to anyone looking to stay in South Beach.

Reviewed on Jul 5, 2026

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Save 100% on your flight
Price was $956, price is now $482 per person
$482
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (227 reviews)
Debería haber una atención al huesped más directa y dar facilidades a entregas como Amazon, FedEx, UPS, et.

Reviewed on Jul 10, 2026

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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
$223 nightly
The price is $250 total per night from Jul 16 to Jul 17
$250 total
Jul 16 - Jul 17
Total with taxes and fees
8.6/10 Excellent! (2,344 reviews)
"Great location, great service and very clean."

Reviewed on Jul 14, 2026

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Aug 10 to Aug 11
$253 total
Aug 10 - Aug 11
Total with taxes and fees
8.8/10 Excellent! (3,462 reviews)
"No fault of the hotel/resort, but the seaweed on the beach was gross. It is not always like that, I know. Great place to spend time in Key West."

Reviewed on Jul 15, 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$184 nightly
The price is $207 total per night from Aug 9 to Aug 10
$207 total
Aug 9 - Aug 10
Total with taxes and fees
Blue Flamingo Resort Key West
See all 3,079 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 $302 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.