Cow Key Vacations from $380

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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.
Bahama Beach Club Pompano

Bahama Beach Club Pompano

4 out of 5
Price was $732, price is now $380 per person
$380
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (12 reviews)
This place was awesome. When we arrived there was a welcome basket with all kinds of goodies and info about surrounding restaurants and fun things to do. The beach was a short walk and was beautiful. They had everything you needed and someone was there within minutes if something needed to be done. I will be staying here again when I return to Florida.

Reviewed on Jul 10, 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 $12,696, price is now $5,738 per person
$5,738
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $1,687, price is now $821 per person
$821
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
The room was amazing with ocean view, the staff super friendly and the breakfast included really good, memorable experience.

Reviewed on Aug 17, 2025

President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was $846, price is now $422 per person
$422
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on Aug 8, 2025

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $963, price is now $488 per person
$488
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
5.8/10 (309 reviews)
It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.

Reviewed on Jun 21, 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
$184 nightly
The price is $207 total per night from Aug 25 to Aug 26
$207 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,471 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on Aug 20, 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 Sep 1 to Sep 2
$142 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on Aug 18, 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
$169 nightly
The price is $190 total per night from Sep 21 to Sep 22
$190 total
Sep 21 - Sep 22
Total with taxes and fees
7.8/10 Good! (1,548 reviews)
"Good for the price! Cleanliness can improve, when we complained about the cleaning our room we were promptly moved rooms and were very satisfied. Breakfast situation is a bit off, way overpriced for the portion, prepaid breakfast for the room but only offered one complimentary plate? Literally the ..."

Reviewed on Aug 19, 2025

Blue Flamingo Resort Key West
See all 3,114 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 $380 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.