Cow Key Vacations from $445

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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.

The Latest Cow Key vacation packages

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was $887, price is now $445 per person
$445
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Good stay for a night

Reviewed on Nov 3, 2026

Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was $2,216, price is now $978 per person
$978
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $21,549, price is now $10,089 per person
$10,089
per person
Jan 28 - Feb 2
found 1 hour ago
Roundtrip flight included
Boston (BOS) 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

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $1,083, price is now $525 per person
$525
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (952 reviews)

72 Park Miami Beach Boutique Residences by IliosRentals

72 Park Miami Beach Boutique Residences by IliosRentals

4.5 out of 5
North Beach
Price was $2,289, price is now $1,141 per person
$1,141
per person
Jan 28 - Feb 2
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (18 reviews)
We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!

Reviewed on Oct 17, 2026

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Cow Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,814 reviews)
"Nice property"

Reviewed on Nov 4, 2026

Margaritaville Beach House Key West
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
$200 nightly
The price is $225 total per night from Nov 19 to Nov 20
$225 total
Nov 19 - Nov 20
Total with taxes and fees
9/10 Wonderful! (1,893 reviews)
"I wish we didn’t have a room Right beside the road and have to wake up The employees loud cleaning with machines by the window both days at 8 am. The food should be a lot better, but it wasn’t. Service was kind and helpful."

Reviewed on Nov 3, 2026

Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Nov 15 to Nov 16
$207 total
Nov 15 - Nov 16
Total with taxes and fees
8.6/10 Excellent! (2,771 reviews)
"Very relaxed vibe day and night. Both bars were well staffed and quick to serve. Everything was kept immaculately clean."

Reviewed on Nov 4, 2026

Blue Flamingo Resort Key West
See all 3,074 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.

Find the Best Cow Key Vacation Packages

Cow Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach

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Frequently asked questions

Is Cow Key better suited for a beach vacation or a cultural trip?
Cow Key is a central urban destination known for family-friendly attractions, offering a blend of beach relaxation and cultural exploration. For beach lovers, Smathers Beach (about 4 miles away) and Clarence S. Higgs Memorial Beach Park (about 5 miles away) provide sandy shores and water activities.

For those interested in culture and entertainment, Duval Street and Mallory Square, both about 7 miles from central Cow Key, offer vibrant nightlife, shops, and historic sites. A Cow Key vacation can easily combine both interests, making it versatile for different travel styles.
How can I save money on a Cow Key vacation package?
When you bundle, you can save up to 30%*. To save money on a Cow Key package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Cow Key?
A Cow Key vacation offers a variety of attractions, from golf to beaches and vibrant streets:

Browse and book things to do in Cow Key on Expedia.
Are there vacation package hotels in Cow Key within walking distance of restaurants and shops?
Cow Key vacation package hotels can indeed place you within easy walking distance of restaurants and shops, particularly around the vibrant Duval Street area.

For example, Artist House Key West, a 3.5-star property rated 9.4 out of 10, is about a 5-minute walk from Duval Street. Similarly, H2O Suites - Adults Only, also 3.5-star and rated 9.3 out of 10, is just about a 5-minute walk away. L'Habitation Guest House - Adults Only, rated 9.2 out of 10, also sits about a 5-minute walk from this popular area. Actual walking routes may differ from straight-line distances, so it's always a good idea to check the map for your selected hotel.
Can I change or cancel my Cow Key vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Cow Key vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Cow Key vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Cow Key vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Cow Key?
To find last-minute vacation packages to Cow Key, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Cow Key vacation packages?
Free cancellation on a Cow Key vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Cow Key vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Cow Key getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Cow Key vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.