Cow Key Vacations from $360

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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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was $712, price is now $360 per person
$360
per person
Oct 23 - Oct 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on Aug 16, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was $1,039, price is now $469 per person
$469
per person
Oct 23 - Oct 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
What a great experience, the whole staff was amazing I very recommend this place to stay

Reviewed on Aug 19, 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 $16,467, price is now $7,607 per person
$7,607
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Barnacle Resort

Barnacle Resort

3 out of 5
Long Beach Estates
Price was $813, price is now $388 per person
$388
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (39 reviews)
Perfect place for a quiet getaway.

Reviewed on May 24, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $962, price is now $468 per person
$468
per person
Oct 23 - Oct 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
Had a great stay here . Very nice clean place . Would definitely recommend. Thanks Eric ( Day Manager )

Reviewed on Aug 20, 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
$186 nightly
The price is $209 total per night from Aug 26 to Aug 27
$209 total
Aug 26 - Aug 27
Total includes taxes and fees
8.4/10 Very Good! (1,465 reviews)
"Food options was great, the bed comfort was a little to firm, but the linens was awesome, the suite was very equipped and beautifully updated. Did not get in the pool because the water was not circulating clean and maintenance at night, very nice pool area, but felt the pool water was not clean."

Reviewed on Aug 17, 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Aug 27 to Aug 28
$142 total
Aug 27 - Aug 28
Total includes taxes and fees
7.8/10 Good! (1,069 reviews)
"Loved the pool and convince of hotel. Staff was Excellent!!"

Reviewed on Aug 17, 2025

Hilton Garden Inn Key West / The Keys Collection
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
$173 nightly
The price is $195 total per night from Aug 25 to Aug 26
$195 total
Aug 25 - Aug 26
Total includes taxes and fees
7.6/10 Good! (1,553 reviews)
"Super clean quiet friendly staff and great atmosphere all around"

Reviewed on Aug 18, 2025

Blue Flamingo Resort Key West
See all 3,132 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.

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Frequently asked questions

How much does a Cow Key vacation package cost?
Offering great value package deals from $360 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.