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

Prices and availability subject to change. Additional terms may apply.
Icon Residences By Sunnyside Hotel and Resorts

Icon Residences By Sunnyside Hotel and Resorts

4 out of 5
Downtown Miami
per person
May 29 - Jun. 3
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (707 reviews)
Within a mile of Bay Front Park. We didn't have a car during our stay, but there were plenty of amenities close (the apartment offered a full kitchen), and a row of food trucks we could see from our room, coffee shop in lobby of W hotel, Whole Foods a short walking distance among a shopping mall. Apartment was very spacious with full amenities (washer/dryer, dishwasher), walk out balcony. Host was very responsive and we felt safe during our stay.

Reviewed on Apr. 1, 2024

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
Jul. 14 - Jul. 21
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
May 31 - Jun. 3
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
Staff is wonderful and the food and drinks were great. Highly recommend.

Reviewed on Apr. 24, 2024

Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
Save 100% on your flight
per person
Jun. 30 - Jul. 5
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (477 reviews)
Very nice property.

Reviewed on Apr. 23, 2024

Amazing Apartments at H Beach House

Amazing Apartments at H Beach House

3.5 out of 5
Hollywood Beach
Save 100% on your flight
per person
Jul. 13 - Jul. 20
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (8 reviews)
Beautiful views from the pool area. Well kept grounds, and updated beautiful units. The only downside we experienced is a lack of elevators for the size of the tower. The waits for elevators often exceeded 20 minutes especially trying to go down in the late morning (around checkout time).

Reviewed on Feb. 20, 2024

Cow Key Hotel Deals

Havana Cabana at Key West
Havana Cabana at Key West
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $396 per night from Apr. 29 to Apr. 30
CA $396
CA $535 total
includes taxes & fees
Apr 29 - Apr 30
8.6/10 Excellent! (1,434 reviews)
"This is an amazing place, I loved the vintage style of Cuba. Such an amazing experience"

Reviewed on Apr. 22, 2024

Havana Cabana at Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $441 per night from Apr. 29 to Apr. 30
CA $441
CA $583 total
includes taxes & fees
Apr 29 - Apr 30
8.2/10 Very Good! (1,807 reviews)
"Good experience. In walking distance to everything"

Reviewed on Apr. 23, 2024

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 $403 per night from May 13 to May 14
CA $403
CA $541 total
includes taxes & fees
May 13 - May 14
8.4/10 Very Good! (1,764 reviews)
"Can't wait to go back"

Reviewed on Apr. 22, 2024

Margaritaville Beach House Key West
See all 2,965 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.

Explore other types of vacation packages

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?
Maybe less than you imagined — from only CA $991, as a matter of fact! By bundling flights, hotels and car rentals into your own customized travel package, your trip to Cow Key is only clicks away.
How do I get a cheap travel package to Cow Key?
You’ll save loads of cash if you combine your flights, car rentals and hotels into a Cow Key travel package. Sometimes cheap packages mean fewer choices. But that’s not the case with Expedia. We offer over 550 air carriers and 1,000,000 properties throughout the world, so you’ll always have plenty of variety to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Cow Key?
With popular attractions like Smathers Beach and Key West Art and Historical Society in this neighborhood, try to find a hotel near either one. Key West Golf Club is another Cow Key hot spot that visitors flock to.
How far in advance should I book my Cow Key vacation?
It all depends on the airline, but you can generally look up international airfares on Expedia nearly a year in advance. While it’s generally recommended to book ahead of time, lucky customers will sometimes score a cheaper ticket just weeks before departure dates.
What does an Expedia Cow Key travel package include?
Expedia has everything you need to book your Cow Key trip, but how you structure your package is your call. Pick from any combination of hotels, flights and rental cars. Chasing a few activities to keep you entertained? Once you’ve made your booking, you can add them on too. Whatever your budget, there’s a deal to meet your needs.
What should I know before booking a Cow Key travel package?
You can look forward to saving with an Expedia travel package. Bundle your flights, rental cars and hotels and be rewarded with terrific discounts. Hotels aren’t your only choice, however. Book with us and choose from island resorts, chalets in the middle of mountains and even treehouses and ranches!
Can I choose my airline with a Cow Key Expedia vacation package?
The choice is all yours! We have access to over 550 partner airlines around the world, so you can tailor your Cow Key trip according to your travel preferences.
If I'm not able to travel, can I cancel my Cow Key vacation package?
You sure can, and we’ll help you every step of the way. You may be able to change or cancel your Cow Key vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, browse our Customer Service Portal for further information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.