Cow Key Vacation Packages
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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.
Top Cow Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
North Beach
Price was CA $9,343, price is now CA $4,430 per person
CA $4,430
per person
Aug 9 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
The W - Bayshore Unit 1003
East Fort Lauderdale
Price was CA $1,653, price is now CA $1,000 per person
CA $1,000
per person
Aug 16 - Aug 20
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.4/10 Good! (3 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.
Reviewed on May 20, 2026
Cow Key Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jun 7 to Jun 8
CA $174
CA $274 total
Jun 7 - Jun 8
includes taxes & fees
8.4/10 Very Good! (2,329 reviews)
"What a lovely place to stay. The staff were so friendly and helpful. It was our 40th wedding anniversary and unbeknown to us, our daughter contacted the hotel to let them know. They had left a bottle of wine with a red heart balloon attached and a lovely card in our room. It was such a sweet and ..."
Reviewed on Jun 5, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Jun 29 to Jun 30
CA $281
CA $417 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (3,360 reviews)
"Look, we had a nice time. I put "OK" for your survey questions which may seem like we didn't enjoy. But, it would be hard to put "Good" for your survey answers. The beach was unusable due to dead, smelly seaweed that permeated the main pool, overall exterior (stairs, pool area, etc.) rooster poop, ..."
Reviewed on Jun 5, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $346 per night from Jul 6 to Jul 7
CA $346
CA $478 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,817 reviews)
"We loved our first time stay at the Margaritaville Beach House Key West"
Reviewed on Jun 4, 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.
