Cow Key Vacations from $418

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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.
Iberostar Waves Miami Beach

Iberostar Waves Miami Beach

4 out of 5
South Beach
Price was $973, price is now $418 per person
$418
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (825 reviews)
Great property access to two sunbeds included on the beach!

Reviewed on Nov 25, 2025

Hollywood by the Sea Hotel

Hollywood by the Sea Hotel

3 out of 5
Hollywood Beach
Price was $1,502, price is now $555 per person
$555
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (349 reviews)
Pictures were a bit deceiving. Floors were sticky and felt a little unclean. We arrived at night and it felt a little unsafe. And we were charged extra $19 that we are refuting. But the proximity to the beach can’t be beat! The sunrise was beautiful!

Reviewed on Oct 25, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $3,145, price is now $1,169 per person
$1,169
per person
Feb 21 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
Amazing for young families! Heading back again!

Reviewed on Nov 29, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,361, price is now $592 per person
$592
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Wonderful stay for it being our first time in Miami. The hotel was clean and perfectly sized for a nice short trip. Location was incredible being on Ocean drive. Pricing was extremely fair for it being a holiday week and the service was incredible. Thank you for a good time and a pleasant stay!

Reviewed on Nov 28, 2025

Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
South Beach
Price was $1,679, price is now $733 per person
$733
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,449 reviews)
Is a very good hotel. Location is excellent and the staff is very kind. Recommended.

Reviewed on Dec 2, 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
$202 nightly
The price is $228 total per night from Dec 16 to Dec 17
$228 total
Dec 16 - Dec 17
Total with taxes and fees
8.6/10 Excellent! (1,734 reviews)
Staff very courteous! We arrived very early- hoping we could at least chk our bags before going to lunch ( 2 couples- booking two rooms). Our friends' room was already available .We were told ours would be ready soon. We had a lovely, long, leisurely lunch at Chicken Walk. Our room still wasnt ready ...

Reviewed on Dec 3, 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
$175 nightly
The price is $197 total per night from Dec 4 to Dec 5
$197 total
Dec 4 - Dec 5
Total with taxes and fees
8/10 Very Good! (1,750 reviews)
Yes

Reviewed on Dec 1, 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
$194 nightly
The price is $218 total per night from Dec 4 to Dec 5
$218 total
Dec 4 - Dec 5
Total with taxes and fees
8.8/10 Excellent! (1,760 reviews)
My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed.

Reviewed on Dec 1, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,166 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 $418 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.