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Hollywood Gateway Inn

Hollywood Gateway Inn

2 out of 5
North Central Hollywood
Price was $487, price is now $232 per person
$232
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
An outdoor pool is featured at this motel, along with free self parking. Free continental breakfast is served. WiFi in public areas is provided and the front desk is staffed around-the-clock.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,685, price is now $725 per person
$725
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
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 $16,861, price is now $7,593 per person
$7,593
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was $872, price is now $447 per person
$447
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $1,307, price is now $669 per person
$669
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
This historic resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

Top Cow Key hotels deals

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
$206 nightly
The price is $232 total per night
$232 total
Nov 16 - Nov 17
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
$157 nightly
The price is $177 total per night
$177 total
Nov 18 - Nov 19
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 onsite laundry facilities. 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
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $217 total per night
$217 total
Nov 12 - Nov 13
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Free Cancellation
$242 nightly
The price is $272 total per night
$272 total
Nov 30 - Dec 1
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 for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
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
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $126 total per night
$126 total
Dec 1 - Dec 2
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.
Pool
Hot Tub
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$221 nightly
The price is $249 total per night
$249 total
Dec 3 - Dec 4
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly
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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 $232. 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.

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