Cow Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Avi Lux Stay
East Fort Lauderdale
CA $1,498
per person
Nov 16 - Nov 23
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $25,652
per person
Dec 23 - Dec 28
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
The Penguin Hotel
South Beach
CA $1,587
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very good! (1,996 reviews)
There is a resort fee per day, on top of 150 they need for the room Just an fyi. The front desk ladies were very helpful and nice but the one of the over night men couldn’t have a worse attitude up front I wish I got his name. The pool closes at 7 and it’s not located at this hotel it’s at the building behind it and the bar is also located not actually at this hotel. Elevator worked but very loud so we heard it every time it went up or down. And the walls are paper thin so it didn’t help.They say it’s every 3 days they clean but knocked on our door every morning and the lady was very friendly. Wasn’t the worst hotel I’ve stayed in but I don’t think I’ll be back. Only plus is the location because the beach being across the street
Reviewed on Oct 15, 2026
Ready to book your vacation to Cow Key?
Cow Key Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $290
CA $415 total
Oct 30 - Oct 31
includes taxes & fees
8.8/10 Excellent! (1,794 reviews)
"Very nice and friendly staff. It was a great place."
Reviewed on Oct 16, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $178
CA $280 total
Oct 25 - Oct 26
includes taxes & fees
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $166
CA $322 total
Oct 27 - Oct 28
includes taxes & fees
8.6/10 Excellent! (2,618 reviews)
"Just not what we were expecting! Multiple elevators out, no ice machines, and our air quit. We were moved to a new room! Pool was nice but food was just okay. “Beach” area definitely needed some improvements."
Reviewed on Oct 16, 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.
Frequently asked questions
How much does a Cow Key vacation package cost?
You'll find cheap prices from CA $1,498 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.
