Cow Key Vacations from $764
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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 $6,900, price is now $2,696 per person
$2,696
per person
Jun 3 - Jun 8
found 20 hours 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
Cow Key Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$399 nightly
The price is $449 total per night from Apr 13 to Apr 14
$449 total
Apr 13 - Apr 14
Total with taxes and fees
8.8/10 Excellent! (1,783 reviews)
We had a nice stay there.
Reviewed on Mar 13, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$357 nightly
The price is $402 total per night from Apr 13 to Apr 14
$402 total
Apr 13 - Apr 14
Total with taxes and fees
8.2/10 Very Good! (1,970 reviews)
If I came back I would book a room high up maybe that would help with the noise early morning from the chickens that roam the island. Shuttle drivers and service were amazing. Property is nice had a nice pool and lots of games around to play.
Reviewed on Mar 14, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $443 total per night from Apr 13 to Apr 14
$443 total
Apr 13 - Apr 14
Total with taxes and fees
8.6/10 Excellent! (2,069 reviews)
The hotel was adequate. There were no vending machines nor ice machines available to guests. We had rented a cart and at no time could we pull up to the bank of chargers to plug in. The same carts were in the same spots at all times. The pool definitely needs more chairs and towels.
Reviewed on Mar 13, 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.
