Cow Key Vacations from $222
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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.
Henrosa Hotel
South Beach
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (795 reviews)
Everyone is extremely nice. They allowed me to check in early. The rooms are clean but not sure of the vibe trying to give off. The beds are immaculate but everything else around that looks suspicious. There are stains on the walls and what looks to be mold on some places. There are some sugar ants ( to be expected in Florida). It’s a great hotel but if they can clean up the aesthetic of the room, I would’ve gave 5 starts.
Reviewed on Jun 8, 2025
The Shelborne By Proper
South Beach
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
10/10 Exceptional! (3 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.
Reviewed on May 31, 2025
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (1,002 reviews)
Beautiful property!!! We really enjoyed it and the staff was so friendly. Walking distance or the beach and beach chairs available as well
Reviewed on Jun 11, 2025
Pelican Hotel
South Beach
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (341 reviews)
A historic and ideally located property right by the beach with a helpful and very accommodating staff. Beautiful renovations highlight the retro-design which creates a relaxing environment of quality and sophistication without feeling too pretentious or haughty. Highly recommended.
Reviewed on Jun 23, 2025
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $218 total per night from Jun 26 to Jun 27
$218 total
Jun 26 - Jun 27
Total includes taxes and fees
8.4/10 Very Good! (1,231 reviews)
"My trip was nice and for my bday I got a champagne bottle and that was so nice! Thanks guys!"
Reviewed on Jun 22, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$289 nightly
The price is $325 total per night from Jul 14 to Jul 15
$325 total
Jul 14 - Jul 15
Total includes taxes and fees
8.6/10 Excellent! (2,537 reviews)
"Friendly staff clean rooms"
Reviewed on Jun 22, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$303 nightly
The price is $341 total per night from Jul 13 to Jul 14
$341 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,735 reviews)
June Trip
"It was a very pleasant stay, nice staff, close and clean beach."
Reviewed on Jun 23, 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.