Cow Key Vacations from $410
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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
South Beach
Save 100% on your flight
Price was $818, price is now $410 per person
$410
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
Super cute and great location. Waiting staff was great and front was nice but a little lack of communication. Our room air wasn’t working really well so they switched our room and comp our breakfast the rest of the stay.
Reviewed on Jun 3, 2026
Miami Downtown Condos
Downtown Miami
Price was $1,654, price is now $431 per person
$431
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (171 reviews)
We booked this option as a place to begin a cruise. It's conveniently located close to cruise port, Bayside and bus route to the beach. The unit was clean and modern with a view of the city. We loved the option to cook and be able to do some last minute laundry before heading for our cruise. We didn't appreciate the wopping 300 deposit requested nor did we enjoy the smell of cannabis wafting from the elevators or hallways. There are no smoking signs posted but they're obviously being ignored. Everyone deserves fresh and clean air!! The other negative was the blind in the main room was broken and so we couldn't view the city from that area. Overall, the condo served our purpose but we wouldn't make it a choice for future travels.
Reviewed on May 26, 2026
Casablanca Miami Beach
North Beach
Price was $5,537, price is now $2,432 per person
$2,432
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
Cow Key Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Jun 14 to Jun 15
$207 total
Jun 14 - Jun 15
Total with taxes and fees
8.4/10 Very Good! (2,378 reviews)
"The hotel itself is beautiful, the staff is friendly and helpful. The pools were great. The only cons was that there were some roaches in the bathroom and hair from the previous guests in the shower. The food is delicious but quite pricey and it includes an automatic gratuity fee which adds up quite ..."
Reviewed on Jun 13, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$269 nightly
The price is $302 total per night from Jun 22 to Jun 23
$302 total
Jun 22 - Jun 23
Total with taxes and fees
8.8/10 Excellent! (3,390 reviews)
"Very pleasantly surprised by the facilities. Staff was great, amenities and the very nice room were top notch."
Reviewed on Jun 13, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Jun 21 to Jun 22
$149 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (1,237 reviews)
"easy check-in good vibe, efficient, clean enjoyed my stay… thank you. Enjoyed the pool. The hot tub wasn’t working so that was a bummer.. overall good experience"
Reviewed on Jun 12, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
