Cow Key Vacations from $787
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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 $5,390, price is now $2,262 per person
$2,262
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (320 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
Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was $1,865, price is now $1,026 per person
$1,026
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,151 reviews)
Fresh coffee should be there in lobby at all tomes. All else was good friendly staff fresh breakfast cleanliness e.t.c.
Reviewed on Mar 5, 2026
Cow Key Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is $557 total per night from Apr 5 to Apr 6
$557 total
per night
Apr 5 - Apr 6
8.8/10 Excellent! (3,119 reviews)
Room was dirty and the garden view balcony looked at a poop covered roof. Staff was rude
Reviewed on Mar 6, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is $412 total per night from Mar 8 to Mar 9
$412 total
per night
Mar 8 - Mar 9
8.6/10 Excellent! (2,051 reviews)
Floors in room were very dirty. Bottoms of my feet were black from walking around barefoot in the room. Refrigerator could be on a stand and not the floor. Pool and bar close way too early! Leaves in pool and grounds need more upkeep and maintenance. Elevator was not working and front desk people ...
Reviewed on Mar 6, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is $470 total per night from Apr 5 to Apr 6
$470 total
per night
Apr 5 - Apr 6
8/10 Very Good! (2,133 reviews)
Greta expérience, Room clean and confortable
Reviewed on Mar 6, 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.