Cow Key Vacations from $494
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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.
Miami Downtown Condos
Downtown Miami
Price was $1,763, price is now $494 per person
$494
per person
Jul 13 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (161 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
The W - Bayshore Unit 1003
East Fort Lauderdale
Price was $1,467, price is now $573 per person
$573
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
6/10 (2 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.
Reviewed on May 20, 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 May 28 to May 29
$207 total
May 28 - May 29
Total with taxes and fees
8.4/10 Very Good! (2,285 reviews)
"Excellent hotel"
Reviewed on May 27, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$261 nightly
The price is $294 total per night from Jun 8 to Jun 9
$294 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (3,338 reviews)
"Staff were all amazing, easy check in, with a wrist band that we really liked. No searching for room card. Easy walking through the main streets. There was a lot of sargassum in the ocean front but, Mother Nature, nothing they can do about that at the resort. I like to take a dip in the ocean but, ..."
Reviewed on May 26, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$268 nightly
The price is $302 total per night from Jun 10 to Jun 11
$302 total
Jun 10 - Jun 11
Total with taxes and fees
8.8/10 Excellent! (1,807 reviews)
"The room was a large King Suite for 2-4 people. King Bed, convertible sofa bed. Very clean, fresh smell, included a good small refrigerator, microwave, Keurig coffee maker, supply of coffee and some bottles of water. Wide bathroom counter and single sink with plenty of room for 2 people to get ready ..."
Reviewed on May 26, 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.
