Cow Key Vacations from $721
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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.
1818 Meridian House Apartments and Suites by Eskape Collection
South Beach
Save 100% on your flight
Price was $1,409, price is now $721 per person
$721
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (664 reviews)
The location was great and walkable to the beach and shopping/dinning. The apartment was overall clean but looked old and had a smell. The kitchen has everything needed for cooking but the pots were in poor condition. After we have arrived and during the check-in, we have learned that all parking spots are reserved. This was not communicated to us. The person at the reception was rude, non-apologetic, and said that we signed the registration card which contained that information regarding potential unavailability of the parking. He also said that if we choose to cancel the reservation, there will be no refund.
Reviewed on Dec 31, 2025
Casablanca Miami Beach
North Beach
Price was $1,503, price is now $726 per person
$726
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly
Reviewed on Nov 12, 2025
President Hotel Villa
South Beach
Save 100% on your flight
Price was $1,498, price is now $767 per person
$767
per person
Mar 19 - Mar 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Breakfast was better than La Quinta, but not especially good. Balcony was worthless, no view and over a noisy alleyway.
Reviewed on Jan 7, 2026
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$317 nightly
The price is $357 total per night from Jan 11 to Jan 12
$357 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (1,871 reviews)
Very awesome and accommodating place!
Reviewed on Jan 5, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $318 total per night from Jan 11 to Jan 12
$318 total
Jan 11 - Jan 12
Total with taxes and fees
8/10 Very Good! (1,831 reviews)
Room was clean. Amenities were great.
Reviewed on Jan 6, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$427 nightly
The price is $480 total per night from Jan 26 to Jan 27
$480 total
Jan 26 - Jan 27
Total with taxes and fees
8.6/10 Excellent! (2,982 reviews)
Fun and safe
Reviewed on Jan 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.
