Cow Key Holidays from £762
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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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
£11,277
per person
20 Nov - 27 Nov
found 20 hours ago
Return flight included
London (LON) 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
The Penguin Hotel
South Beach
£770
per person
10 Dec - 17 Dec
found 13 hours ago
Return flight included
London (LHR) to Miami (MIA)
8.4/10 Very good! (1,979 reviews)
Everything was great only thing I didn’t like was there’s no headboard attached to the bed just. Blank wall elevators extremely small only holds 3 people
Reviewed on 29 Sept 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
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
£136
1 Oct - 2 Oct
includes taxes & fees
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
£222
7 Oct - 8 Oct
includes taxes & fees
8.6/10 Excellent! (3,637 reviews)
"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."
Reviewed on 29 Sept 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
£225
1 Oct - 2 Oct
includes taxes & fees
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
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
- Flights to Key West
- Flights from Key West Intl.
- British Airways London (LHR) to Key West (EYW) flights
- Delta London (LCY) to Key West (EYW) flights
- Delta Miami (MIA) to Key West (EYW) flights
- United Seattle (SEA) to Key West (EYW) flights
- Flights from Naples (APF) to Key West (EYW)
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- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Melbourne (MEL) to Key West (EYW)
- Flights from Memphis (MEM) to Key West (EYW)
- Flights from Manchester (MHT) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Melbourne (MLB) to Key West (EYW)
- Flights from Marco Island (MRK) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Nassau (NAS) to Key West (EYW)
- Flights from Newcastle (NCL) to Key West (EYW)
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- Flights from Palm Springs (PSP) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Savannah (SAV) to Key West (EYW)
- Flights from Orlando (SFB) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Tulsa (TUL) to Key West (EYW)
- Flights from Tucson (TUS) to Key West (EYW)
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Big Pine Key Holidays
- Calusa Beach
- Clarence S. Higgs Memorial Beach Park
- Visit Cow Key
- Curry Hammock State Park
- Duval Street
- Ernest Hemingway Home and Museum
- Fort East Martello Museum and Gallery
- Fort Zachary Taylor Historic State Park
- Key West Holidays
- Visit Key West
- All inclusive Holiday Packages Key West
- Mallory Square
- Marathon Holidays
- Smathers Beach
- Sombrero Beach
- South Beach
- Vaca Key
* 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.
