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.
Beach Place Hotel

Beach Place Hotel

2 out of 5
North Beach
Price was CA $1,046, price is now CA $597 per person
CA $597
per person
Oct 19 - Oct 25
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,000 reviews)
Good location. Super old. Very dated carpet, furniture, bedding. Clean though. Doing the best they can. Feels like most units are for residents.

Reviewed on Aug. 10, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $22,327, price is now CA $11,034 per person
CA $11,034
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $2,897, price is now CA $1,634 per person
CA $1,634
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
I thoroughly enjoyed my seaside suite. Gorgeous view. Loved that the property is located on the beach. The outdoor beach service is immaculate. John provides wonderful service with a smile. Throughout the property, I found the staff to be kind and attentive. I also enjoyed the pool area and the rooftop spa- it’s small but the service was quality. All in all- I enjoyed my respite at The Pelican.

Reviewed on Aug. 24, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Price was CA $3,479, price is now CA $1,977 per person
CA $1,977
per person
Nov 4 - Nov 9
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (73 reviews)
This place is very beautiful, greats views with great customer service. This place just makes you feel very comfortable like your at home

Reviewed on Aug. 20, 2025

Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Price was CA $1,927, price is now CA $1,098 per person
CA $1,098
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (95 reviews)
Such a great place to stay. Mins from the beach, dining and shopping! Very safe neighborhood!

Reviewed on May 26, 2025

Ready to book your vacation to Cow Key?

 

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Cow Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Sep 2 to Sep 3
CA $173
CA $265 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,480 reviews)
"The property was excellent, located in the heart of everything!! 😍"

Reviewed on Aug. 23, 2025

Beachside Resort & Residences
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Sep 1 to Sep 2
CA $232
CA $341 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,729 reviews)
"Excellent service"

Reviewed on Aug. 25, 2025

Oceans Edge Key West Resort, Hotel & Marina
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 3 to Sep 4
CA $148
CA $206 total
Sep 3 - Sep 4
includes taxes & fees
Hilton Garden Inn Key West / The Keys Collection
See all 3,114 properties in Cow Key
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cow Key vacation package cost?
You'll find cheap prices from CA $597 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.