Deals on vacations and trips to Cow Key

Save when you book Cow Key package deals

Choose two or more items and save on your trip:

Cow Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Silver Spray Motel

Silver Spray Motel

3 out of 5
Hollywood Beach
Save 100% on your flight
Price was $671, price is now $368 per person
$368
per person
Apr 24 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This aparthotel features free WiFi in public areas, laundry facilities, and self parking. Enjoy the 5 outdoor pools and free continental breakfast each morning. A terrace, a picnic area, and concierge services are also on offer.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,206, price is now $523 per person
$523
per person
Mar 23 - Mar 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,237, price is now $590 per person
$590
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
Ilios Rentals

Ilios Rentals

2 out of 5
Downtown Miami
Price was $2,052, price is now $1,040 per person
$1,040
per person
Apr 9 - Apr 14
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
This apartment features an outdoor pool and a 24-hour gym. There's a hot tub on site, and a 24-hour front desk and a terrace are also provided.
AKA Brickell Sea View by Palermo Home

AKA Brickell Sea View by Palermo Home

2 out of 5
Downtown Miami
Price was $1,097, price is now $588 per person
$588
per person
Apr 9 - Apr 14
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
An outdoor pool is available at this apartment.

Top Cow Key hotels deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
$530 nightly
The price is $596 total per night
$596 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pool
Spa
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
$389 nightly
The price is $437 total per night
$437 total
Mar 8 - Mar 9
Total with taxes and fees
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$418 nightly
The price is $471 total per night
$471 total
Feb 9 - Feb 10
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$436 nightly
The price is $491 total per night
$491 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$426 nightly
The price is $479 total per night
$479 total
Feb 8 - Feb 9
Total with taxes and fees
This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.
Pool
Pet friendly
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$391 nightly
The price is $439 total per night
$439 total
Feb 8 - Feb 9
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.
Pool
Free airport shuttle
Don't see what you're looking for?
See all available properties in Cow Key
View all properties
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.

Frequently asked questions

How much are vacation packages to Cow Key?
You'll find an excellent flight and hotel bundle from just $368. With one of our Travelocity vacation packages, an escape to Cow Key has never looked more enticing! Save your time and cash and then get a start on packing those bags.
Where can I get the best vacation package deals for Cow Key?
With at least 400 partner airlines and 1,000,000 properties around the world, it's hard to top Travelocity. Look through our impressive range and score an incredible Cow Key vacation package. Don't you love it when trip planning is that easy?
Why should I book my Cow Key vacation bundle with Travelocity?
We make traveling the world easy. Whether you're after a new destination to wander around or want to ensure you get the best deal around, we're here to help. Our 24/7 support, high-quality service and Price Match Guarantee mean you can book with confidence.
Will I save money on my Cow Key car rental if I book it with my hotel or flight?
Absolutely — bundle your car, flight and hotel into a Cow Key vacation package and you'll save a ton. With so many things to do in and around Cow Key, having your own set of wheels will more than come in handy. Once you're behind the wheel, get out on the wide open road and make your way to Zoo Miami, a renowned attraction around 110 mi from Cow Key.
What is the best time of year to go to Cow Key?
January, February and March are the months when most travelers visit, while August, September and October are typically less busy. If you've got a limited budget, you'd be better off visiting during . is generally regarded as the costliest time of year to drop by.
Which airport is best for Cow Key?
The major airport for Cow Key is Key West Intl. Airport (EYW). It's situated 1 mi northeast of downtown.

Photos of local treasures

Browse Cow Key vacation photos for more inspiration

Explore More Ways to Travel with Travelocity