
Cow Key Vacations from $470
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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.



Cavalier Hotel South Beach
South Beach
Price was $1,114, price is now $520 per person
$520
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.
Reviewed on Aug 16, 2025


Hotel Riu Plaza Miami Beach
Mid Beach
Price was $1,572, price is now $807 per person
$807
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Honestly the staff made the stay so pleasant. They were very accommodating, kind, friendly, helpful and respectful. The “breakfast included” option was wonderful, great selection, I have a milk allergy and there was milk alternative (almond/soy, etc), and I was able to have fresh fruit & have the cook make my egg with no milk. If I can make a recommendation it would be to list milk allergies on all foods. I didn’t eat anything else because I feared it may have butter or milk in it. The mimosa on 1 of the days was delightful . The pool was a nice size. The pool area did not feel overcrowded, the staff took great care. The Maid service, valet parking, pool towel person, food service staff were really great! If I could make 1 more recommendation is -in order to be truly environmentally friendly, I did not have my towels washed daily. However, more towel racks in the bathroom (for 3-4 towels) and in the shower (for 3-4 wash cloths) are needed. There was no where to hang towels and that’s probably why most people have to turn them in to get washed daily. Again. Thank you for everything! It was a great stay.
Reviewed on Aug 8, 2025
Cow Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Aug 25 to Aug 26
$207 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,471 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"
Reviewed on Aug 20, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,716 reviews)
"I loved everything about this resort. So clean and easy to navigate our way around. Transportation offered worked well for us."
Reviewed on Aug 18, 2025

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Sep 1 to Sep 2
$142 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."
Reviewed on Aug 18, 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.
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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.