Cow Key Vacations from $491
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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.
Iberostar Waves Berkeley Shore
South Beach
Price was $1,407, price is now $549 per person
$549
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,449 reviews)
I absolutely loved my stay at the Iberostar Waves Berkeley Shore! From the moment we arrived, the service exceeded all expectations. The hotel is modern, clean, and perfectly located near the beach, restaurants, and all the best parts of South Beach.
A special shoutout to Abdullah—he was truly amazing. He was warm, welcoming, and went above and beyond to make us feel at home. Every interaction with him was genuine, and he made our stay feel extra comfortable and memorable.
The rooftop pool was peaceful, the rooms were spotless, and the beach service was a huge bonus. Overall, our experience was lovely, and I would absolutely stay here again. Highly recommended for anyone visiting Miami!
Reviewed on Nov 27, 2025
Cavalier Hotel South Beach
South Beach
Price was $1,345, price is now $560 per person
$560
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Wonderful stay for it being our first time in Miami. The hotel was clean and perfectly sized for a nice short trip. Location was incredible being on Ocean drive. Pricing was extremely fair for it being a holiday week and the service was incredible. Thank you for a good time and a pleasant stay!
Reviewed on Nov 28, 2025
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $228 total per night from Dec 15 to Dec 16
$228 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!
Reviewed on Nov 26, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $170 total per night from Dec 4 to Dec 5
$170 total
Dec 4 - Dec 5
Total with taxes and fees
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.
Reviewed on Nov 25, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Dec 2 to Dec 3
$228 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (1,748 reviews)
The property was beautiful. The staff was welcoming and helpful. The room and accommodations were wonderful. Enjoyed the convenience of the concierge services as well as the shuttle. Everyone from the bellmen Sam to the shuttle drivers were friendly and made the time spent on property a joy.
Reviewed on Nov 25, 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.