Cow Key Holidays from £551

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Your Cow Key Holiday

When you book a holiday 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 neighbourhood 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 holiday 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 Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Very friendly and helpful staff.

Reviewed on 27 Jun 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
15 Sept - 21 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on 31 May 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
18 Sept - 25 Sept
found 14 hours ago
Return flight included
London (LGW) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Very relaxing, & private. Loved it! Very easy to get ahold of management for any needs.

Reviewed on 22 Jun 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Save 100% on your flight
per person
18 Sept - 25 Sept
found 14 hours ago
Return flight included
London (LGW) to Miami (MIA)
9/10 Wonderful! (125 reviews)
Great place and good value. Only complain, they should put black out at the bedroom! To bright in the morning.

Reviewed on 19 Jun 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
18 Sept - 25 Sept
found 14 hours ago
Return flight included
London (LGW) to Miami (MIA)
9/10 Wonderful! (63 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on 23 May 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
18 Sept - 25 Sept
found 14 hours ago
Return flight included
London (LGW) to Miami (MIA)
9.2/10 Wonderful! (3,178 reviews)
Beautiful hotel right in heart of brickell action. Rooms are fantastic with balconies and restaurants are fantastic. A go to spot in downtown Miami to stay.

Reviewed on 29 Jun 2025

Cow Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach

Our pick of the best Cow Key Hotel Deals

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Stay at this 3.5-star beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very Good! (1,258 reviews)
Beachside Resort - Awesome in June!
"Very nice for the price. Very friendly and accommodating staff. Decent location away from town and crowd, but the shuttle service to the tourist area is great! They have two 15 passenger, air conditioned vans that leave and pickup on time as scheduled on a first come first serviced basis, so you ..."

Reviewed on 29 Jun 2025

Beachside Resort & Residences
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the pool and the restaurant ...
8.6/10 Excellent! (1,733 reviews)
"Outstanding stay!!! Extremely welcoming staff!! Very accommodating. Food was great. Drinks were flowing. Very laid back relaxing vibe. Jimmy would be proud!!"

Reviewed on 26 Jun 2025

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses
4 out of 5
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the bar in their reviews. ...
8.6/10 Excellent! (2,564 reviews)
"The front desk was great. We had a couple set backs as far our room. And we were over charged."

Reviewed on 27 Jun 2025

Southernmost Beach Resort and Guesthouses
See all 3,153 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Cow Key holiday with Expedia?
With exceptional-value airfares, car hire and accommodation choices all in one place, Expedia makes arranging your Cow Key getaway easy. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Choose from amazing retreats, add flights and/or a hire car (and maybe also some exciting tours and activities!) and land incredible prices. Need to change your plans? Expedia has a flexible cancellation policy for many bookings. To find out more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Cow Key?
Peak season falls in January, February and March and is a thrilling time to visit --- if you don't mind the crowds. August, September and October are usually quieter times of the year. Arrange your escape to Cow Key based on what kind of holiday you want. January is the coolest month, when daytime temperatures average 21ºC. In August, the warmest period, you will experience temperatures of around 29ºC during the day.
What is the top hotel for my holiday in Cow Key?
Offering plenty of amenities and a cosy place to relax between adventures, The Gates Hotel Key West will make an ideal base for your Cow Key getaway.
How do I get a cheap holiday to Cow Key?
Booking a Cow Key holiday with Expedia is a smart way to save. We have access to more than 400 air carriers and 321,000 hotel options across the globe. With such an amazing range to pick from, you'll have no trouble creating your dream escape. Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Cow Key holiday?
There's an almost endless list of things to see and do while on a holiday in Cow Key. Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens, Mallory Square and Smathers Beach are among this destination's most popular attractions.
Do I need a visa for my Cow Key holiday?
Visa requirements for Cow Key vary depending on your nationality and the purpose of your visit. It's best to check official government websites to determine if you need a visa for your trip. This is also a good place to find the most up-to-date information, including details about application procedures or supporting documentation that may be necessary. Enquire about your visa requirements well in advance to ensure a smooth travel experience. Finally, double-check to see that your passport is valid for at least six months from your return date.
What should I wear on my Cow Key holiday?
Do a little research into the types of clothing people in Cow Key wear, and consider browsing style blogs for some fashion tips. Aim to create a versatile wardrobe with pieces that work for your destination and showcase your personal style. Take a look at the weather forecast so you can pack appropriately. The warmest month in Cow Key is August, with average daily temperatures of 29ºC. If you're on holiday during the coolest month of January, the mercury hovers around 21ºC during the day.
What does an Expedia Cow Key holiday include?
With Expedia, you can select any combination of hotels, flights and car hires to create your ideal Cow Key travel package. Once you've made your booking, simply add on the fun stuff like sightseeing tours and activities. Remember --- the more you bundle, the more you'll save! Customise your dream escape with Expedia's flexible and varied options.
Does Expedia offer Book Now, Pay Later Cow Key holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply select the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers payments in multiple transactions that fit all budgets, so you can book that well-deserved holiday sooner.
  • No-deposit holidays: Clicking on the "book now" button is easier with this payment option. With no deposit required for your holiday, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Cow Key Expedia holiday?
You certainly can. We have more than 400 partner airlines worldwide, so opt for the carrier that's a good fit for your budget and travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.