Cow Key Holidays from NZ$1,147
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The Latest Cow Key Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel
South Beach
Save 100% on your flight
Price was NZ$1,866, price is now NZ$1,147 per person
NZ$1,147
per person
5 Mar - 8 Mar
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
pool across street in other hotel. Breakfast disaster .elevator out of order. no drinks at bar in hotel
Reviewed on 13 Dec 2025
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was NZ$5,157, price is now NZ$2,995 per person
NZ$2,995
per person
5 Mar - 8 Mar
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
We love the 1 hotel! Staff are friendly and helpful and the facilities are immaculate. Room was gorgeous and the food on property was phenomenal. We loved being on the beach and having access to lounge chairs and towels- also so nice to have waiter service on the beach and at the pools!
Reviewed on 13 Dec 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was NZ$3,735, price is now NZ$2,196 per person
NZ$2,196
per person
5 Mar - 8 Mar
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Really great spot. Love the low key aesthetic and cool design. The tiles in the bar area are great. Nice breakfast spot by pool, and beach club is outstanding.
Only small issue is there were a bunch of loud little kids shouting and cannon-balling into the pool. Super disruptive to the peaceful setting and zero was done to ask the kids to chill just a bit.
Overall - super spot and renovation has made it a gem again.
Reviewed on 14 Dec 2025
Cow Key Holiday
Our pick of the best Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$427 per night from 18 Dec to 19 Dec
NZ$427
18 Dec - 19 Dec
includes taxes & fees
8.6/10 Excellent! (1,780 reviews)
It was overall great but one night at 2 am the fire alarm went off for Like 25mins and no body give reasons not even a single staff member was there to provide guidance or shutdown the alarms
Reviewed on 14 Dec 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$339 per night from 16 Dec to 17 Dec
NZ$339
16 Dec - 17 Dec
includes taxes & fees
8/10 Very Good! (1,763 reviews)
Clean, friendly, great pool and game areas, free shuttle was a bonus. Away from the crowded tourist area. Motel has bikes which we rented for two days. Will stay here again.
Reviewed on 14 Dec 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is NZ$490 per night from 18 Dec to 19 Dec
NZ$490
18 Dec - 19 Dec
includes taxes & fees
8.6/10 Excellent! (2,934 reviews)
The room was very clean. The staff were very pleasant. Constantine, the bartender at the Pineapple pool was amazing!!!
Reviewed on 15 Dec 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
