Cow Key Vacations from $411
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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.
Casablanca Miami Beach
North Beach
Price was $5,979, price is now $2,554 per person
$2,554
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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
President Hotel
South Beach
Save 100% on your flight
Price was $1,178, price is now $590 per person
$590
per person
Jul 9 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (2,390 reviews)
Very nice boutique hotel in a great location. Near beach and many restaurants within walking distance. Would stay here again!
Reviewed on Jun 3, 2026
Cow Key Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Jun 7 to Jun 8
$197 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (2,322 reviews)
"The outdoor pool and atmosphere were amazing ! I enjoyed my stay there snd would highly recommend it."
Reviewed on Jun 3, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $290 total per night from Jun 29 to Jun 30
$290 total
Jun 29 - Jun 30
Total with taxes and fees
8.8/10 Excellent! (3,356 reviews)
"Proximity to things, walkability, friendly bartenders at Pineapple Pool. Great conceriage."
Reviewed on Jun 3, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $347 total per night from Jul 1 to Jul 2
$347 total
Jul 1 - Jul 2
Total with taxes and fees
8.8/10 Excellent! (1,813 reviews)
"Room was very clean , pool bar area was excellent."
Reviewed on Jun 3, 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.