Cow Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jun. 1 - Jun. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.4/10 Exceptional! (1,349 reviews)
This is a hidden jewel among the many overrated and over priced hotels/motels nearby. It was very clean and the staff are remarkable.

Reviewed on Apr. 28, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 3 - Jun. 10
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
It was a great family resort

Reviewed on Apr. 23, 2025

Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,216 reviews)
Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down.

Reviewed on Apr. 30, 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
per person
May 30 - Jun. 2
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1 review)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.

Reviewed on Mar. 17, 2025

Ready to book your vacation to Cow Key?

 

Choose your dates

Cow Key Hotel Deals

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $377 per night from May 11 to May 12
CA $377
CA $517 total
includes taxes & fees
May 11 - May 12
8.6/10 Excellent! (2,452 reviews)
"Great place to stay. Has it all. 3 pools, beach and more."

Reviewed on Apr. 29, 2025

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $332 per night from May 18 to May 19
CA $332
CA $461 total
includes taxes & fees
May 18 - May 19
8.6/10 Excellent! (1,709 reviews)
"Had a great time thanks"

Reviewed on Apr. 29, 2025

Margaritaville Beach House Key West
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from May 26 to May 27
CA $256
CA $327 total
includes taxes & fees
May 26 - May 27
7.8/10 Good! (1,095 reviews)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping ..."

Reviewed on Apr. 20, 2025

Fairfield Inn and Suites by Marriott Key West
See all 3,252 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 $427 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.