Cow Key Vacations from $686

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $2,119, price is now $686 per person
$686
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6/10 (2 reviews)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was $3,092, price is now $903 per person
$903
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
No reviews
Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was $2,397, price is now $739 per person
$739
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
No reviews
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was $2,793, price is now $882 per person
$882
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
No reviews
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $2,216, price is now $710 per person
$710
per person
Jun 12 - Jun 17
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
2/10 (2 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Cow Key
View all trips

Cow Key Hotel Deals

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
$211 nightly
The price is $237 total per night from May 10 to May 11
$237 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (2,203 reviews)
This place is trying really hard to be hip. It was a little too much of a party vibe for me, but for those who are into live music and avocado toast and lawn games and a couple of onsite bar options, you all would really like this place. Two pools (one was full of kids, the other had more adults), ...

Reviewed on May 7, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $256 total per night from Jun 8 to Jun 9
$256 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (1,809 reviews)
Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.

Reviewed on May 7, 2026

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$283 nightly
The price is $319 total per night from May 25 to May 26
$319 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (3,289 reviews)
Check in was a long line. Front desk gave me wrong information

Reviewed on May 7, 2026

Southernmost Beach Resort and Guesthouses
See all 3,100 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cow Key vacation package cost?
Offering great value package deals from $686 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.