Cow Key Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Brickell Arch High Floor Free Parking by Palermo Home Miami
Brickell
CA $1,396
per person
Dec 3 - Dec 9
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (9 reviews)
A spacious large condo set within the AKA hotel in the financial district of Miami,it is well situated for public transport and has numerous restaurants within walking distance. The condo is well appointed but a number of light fittings are not working and the broken kettle mentioned in a post in November 2025 is still inoperable. Although not specifically mentioned, the pictures show a balcony which is correct but it is an internal one overlooking the hotel dining room. Communication with the managing agents is good with precise detailed joining and leaving instructions, which are vital as arriving by car is a complicated and time critical process overseen by the hotel valeting staff.
Overall, an enjoyable stay and value for money given its location
Reviewed on Apr 22, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,387
per person
Dec 7 - Dec 14
found 21 hours ago
Roundtrip flight included
Ottawa (YOW) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Ready to book your vacation to Cow Key?
Cow Key Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $156
CA $255 total
Oct 1 - Oct 2
includes taxes & fees
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $268
CA $406 total
Oct 6 - Oct 7
includes taxes & fees
8.6/10 Excellent! (3,637 reviews)
"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."
Reviewed on Sep 29, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $296
CA $423 total
Oct 6 - Oct 7
includes taxes & fees
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.
Frequently asked questions
How much does a Cow Key vacation package cost?
You'll find cheap prices from CA $1,396 on Expedia for your Cow Key break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Cow Key costs.
What are the cheapest months to go to Cow Key?
January, February and August are the best times to search for cheap Cow Key vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Cow Key?
To fully enjoy your Cow Key vacation, we recommend staying for 3 days. Split your time between discovering Southernmost Point, Ernest Hemingway Home and Museum and other well-known attractions, in addition to experiencing neighbourhoods like Key West Historic District and Old Town Key West. If you've got some time to spare, include a day trip in your Cow Key vacation itinerary.
How to find the best Cow Key package deals?
Use Expedia's handy filters to help you find some unbeatable Cow Key package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Cow Key package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Cow Key vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Cow Key trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
How to plan a trip to Cow Key?
- Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Cow Key.
- Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Cow Key.
- Work out your trip length: Think about how much time you want to spend discovering Cow Key. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Cow Key vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
