Cow Key Vacations from $622
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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
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,308, price is now $646 per person
$646
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
The Cavalier is a quirky, fun hotel in the art deco district. It’s near the quieter end, so it’s perfect for adults, they provide beach access and free chairs, the restaurant is great- a mix of American and Italian. The employees are nice, Philip checked us in and Lester was our wonderful bar tender and server and had our drinks waiting! We should be back in six months for our bi annual girls trip! The rooms are quirky and cute and really loved the stylized feel with the older touches they preserved! Room was super clean, breakfast cost less than Starbucks and was so much better! Loved the original elevator- a must try- and just the whole vibe! This is old Miami at its best!
Reviewed on Mar 5, 2026
Cow Key Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$551 nightly
The price is $620 total per night from Mar 24 to Mar 25
$620 total
Mar 24 - Mar 25
Total with taxes and fees
8.8/10 Excellent! (3,121 reviews)
Great location at the end of Duval Street, but between the outdated grounds and one issue after another from check-in to checkout, the experience simply didn’t justify the price. We stayed four nights and chose this property because the pricing suggested a level of service comparable to resorts we ...
Reviewed on Mar 7, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$366 nightly
The price is $412 total per night from Mar 8 to Mar 9
$412 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (2,052 reviews)
We were celebrating my husband’s 80th birthday. The property failed to notify us that their elevators had not been working for over a month. They would not move us and so using canes my husband, our friends, and I were limited to how many times we could climb to the 4th floor room. We have email, ...
Reviewed on Mar 6, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$389 nightly
The price is $437 total per night from Mar 24 to Mar 25
$437 total
Mar 24 - Mar 25
Total with taxes and fees
8/10 Very Good! (2,134 reviews)
I read a few reviews after I booked this place and it had me kinda worried, After my experience I realized I made the best choice I could have made. Great hotel with the whole beach vibe. Loved my whole stay and all the staff. Everyone was helpful and friendly. Thank you for everything Joseph ...
Reviewed on Mar 7, 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.