Cow Key Holidays from £991

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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.

Top Cow Key Flight + Hotel 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
Save 100% on your flight
Price was £1,738, price is now £991 per person
£991
per person
22 Jan - 29 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)

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 £27,058, price is now £14,434 per person
£14,434
per person
7 Jan - 14 Jan
found 12 hours ago
Return flight included
London (LHR) 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 22 Jun 2016

Eurostars Winter Haven

Eurostars Winter Haven

4 out of 5
South Beach
Save 100% on your flight
Price was £2,521, price is now £1,408 per person
£1,408
per person
22 Jan - 29 Jan
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.8/10 Excellent! (275 reviews)
It is a nice little boutique hotel. We enjoyed the complimentary breakfast option and the proximity to South Beach. The only real drawback is that they have one very small elevator.

Reviewed on 4 Nov 2026

EAST Miami

EAST Miami

5 out of 5
Brickell
Price was £4,281, price is now £2,425 per person
£2,425
per person
8 Feb - 12 Feb
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
9.2/10 Wonderful! (4,218 reviews)

Plunge Beach Resort

Plunge Beach Resort

3.5 out of 5
Price was £3,194, price is now £1,825 per person
£1,825
per person
8 Feb - 12 Feb
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
8.8/10 Excellent! (1,582 reviews)
Have no microwave nor fridge in the rooms. Need to disclose parking cost at Expedia website. I had a phone in my room that didn’t work. Parking gate QR code issue to me to access the parking lot didn’t work the 3 nights I stayed. A buzzer at the door entrance of the building that came on every time the door was opened. I was waking us up very late at night.

Reviewed on 15 Nov 2026

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

Top hotels in Cow Key

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is £243 per night from 18 Nov to 19 Nov
£243
18 Nov - 19 Nov
includes taxes & fees
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
The price is £151 per night from 30 Nov to 1 Dec
£151
30 Nov - 1 Dec
includes taxes & fees
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
The price is £149 per night from 16 Nov to 17 Nov
£149
16 Nov - 17 Nov
includes taxes & fees
8.6/10 Excellent! (2,797 reviews)
"Todo estaba en buenas condiciones y limpio. Valoración precio calidad ."

Reviewed on 14 Nov 2026

Blue Flamingo Resort Key West
See all 3,044 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.

Explore a world of travel with Expedia

* 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.