Cow Key Holidays
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Cow Key Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Price was S$1,704, price is now S$1,370 per person
S$1,370
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Good... The carpet needs deep cleaned. Stayed here before and room was newer/cleaner.
Reviewed on 26 Jan, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was S$2,984, price is now S$2,038 per person
S$2,038
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on 28 Jan, 2026
Ella's Cottages - Key West Historic Inns
Old Town Key West
Price was S$2,306, price is now S$1,812 per person
S$1,812
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
The room was good but very small. It wasn’t a major thing because we were not in it most of the day. Everything was clean and cleaning services were provided daily. The breakfast wasn’t what I was expecting, but it was a true continental breakfast I guess. Front desk help was great. We didn’t use the pool because it was cold weather when we were there.
Reviewed on 26 Jan, 2026
Havana Cabana at Key West
New Town
Price was S$1,714, price is now S$1,383 per person
S$1,383
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Great room and bathroom. Loved the amenities.The shuttle was awesome. Wish we could have stayed longer.
Reviewed on 29 Jan, 2026
The Perry Hotel & Marina Key West
Price was S$1,716, price is now S$1,403 per person
S$1,403
per person
10 Mar - 13 Mar
found 1 day ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Loved the hotel, the balcony over the marina, the restaurants. However, having to pay a premium (much higher than any other hotel) for our dog for a dirty dog run without cleanup bags was not acceptable.
Reviewed on 29 Jan, 2026
Top hotels in Cow Key
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is S$859 per night from 3 Feb to 4 Feb
S$859
3 Feb - 4 Feb
includes taxes & fees
8.6/10 Excellent! (3,032 reviews)
Nice clean resort! Great fun time!
Reviewed on 26 Jan, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is S$560 per night from 1 Feb to 2 Feb
S$560
1 Feb - 2 Feb
includes taxes & fees
8/10 Very Good! (2,062 reviews)
It seemed clean. Hotel is dated and bathrooms could use some updating.
Reviewed on 24 Jan, 2026
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is S$655 per night from 1 Feb to 2 Feb
S$655
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (1,783 reviews)
Good... The carpet needs deep cleaned. Stayed here before and room was newer/cleaner.
Reviewed on 26 Jan, 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.
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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
