Cow Key Vacations from $283
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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.
Hawks Cay Resort
Price was $2,885, price is now $1,099 per person
$1,099
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,011 reviews)
Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.
Reviewed on Nov 7, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,255, price is now $878 per person
$878
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Amenities are really clean, excellent quality ingredients, nice quality decor
Reviewed on Nov 9, 2025
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $217 total per night from Nov 20 to Nov 21
$217 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (1,669 reviews)
Clain for one of the nicest places in Key West
Reviewed on Nov 9, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $167 total per night from Nov 16 to Nov 17
$167 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,671 reviews)
The star was outstanding and the experience was overall great. Only caveat is the resort fees and taxes not being very crystal clear with Expedia pricing and what they hold at the resort and charge.
Reviewed on Nov 8, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from Nov 30 to Dec 1
$234 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,732 reviews)
Excellent
Reviewed on Nov 7, 2025
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.