Cow Key Vacations from $200
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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
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (795 reviews)
Good location and friendly staff, Lois recently remodeled. My room door had plenty of sand in the floor.
Reviewed on Jun 28, 2025
The Shelborne By Proper
South Beach
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.6/10 Exceptional! (4 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
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.
Reviewed on Jul 1, 2025
B Ocean Resort Fort Lauderdale Beach
East Fort Lauderdale
Save 100% on your flight
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
7.6/10 Good! (2,919 reviews)
I love the private beach and activities on the sand they have for the kids and the free beach chairs, umbrellas etc. 2 great pools! Family friendly
Reviewed on Jul 1, 2025
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $219 total per night from Jul 7 to Jul 8
$219 total
Jul 7 - Jul 8
Total includes taxes and fees
8.4/10 Very Good! (1,278 reviews)
"Great property. Clean and spacious rooms!"
Reviewed on Jul 1, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $343 total per night from Jul 15 to Jul 16
$343 total
Jul 15 - Jul 16
Total includes taxes and fees
8.6/10 Excellent! (1,735 reviews)
"Amazing!"
Reviewed on Jun 27, 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 15 to Jul 16
$325 total
Jul 15 - Jul 16
Total includes taxes and fees
8.6/10 Excellent! (2,596 reviews)
"The amenities on the property were great! We enjoyed the shores pool and pool bar during our stay. However, we did not enjoy the pigeons and roosters roaming everywhere or their waste all over the property. There was pigeon poop all outside our room and down the steps leading to the pool area. We ..."
Reviewed on Jul 1, 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.