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.
Avalon Hotel

Avalon Hotel

3.5 out of 5
South Beach
Price was CA $779, price is now CA $375 per person
CA $375
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.2/10 Wonderful! (1,018 reviews)
Cross street to the beach. Very popular and busy area. Staffs are nice.

Reviewed on Aug. 25, 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was CA $1,422, price is now CA $630 per person
CA $630
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (2,500 reviews)
Excellent corner room overlooking the river, great stay.

Reviewed on Aug. 25, 2025

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 $1,319, price is now CA $599 per person
CA $599
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,171, price is now CA $555 per person
CA $555
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
I appreciated the close location to the beach. We were literally a walk across the street to the beach. Everything was walkable. The staff were attentive & present. Very helpful and friendly & accommodating. The lobby area always was clean smelling. I liked they provided complimentary bikes to ride, beach chairs & bottled water. What I did not like were the little bit of channels available on the tv. The stations they did have did not have service so it did not work. Would also recommend a full length mirror.

Reviewed on Aug. 23, 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 $22,347, price is now CA $11,054 per person
CA $11,054
per person
Nov 6 - Nov 9
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)

Ready to book your vacation to Cow Key?

 

Choose your dates

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 Aug 26 to Aug 27
CA $173
CA $265 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,474 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on Aug. 20, 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 2 to Sep 3
CA $232
CA $341 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,726 reviews)
"This property was wonderful! Absolutely gorgeous!"

Reviewed on Aug. 23, 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 $140 per night from Sep 1 to Sep 2
CA $140
CA $196 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,070 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on Aug. 18, 2025

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 $375 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.