A sunset over a beach with a wooden pier and a small structure on it.

Cow Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Cow Key holiday rentals

Exterior

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is HK$2,315
HK$3,309 total
includes taxes & fees
8 Jul - 9 Jul
Resort View 1BR Suite With Direct Pool Access
Premium bedding, individually decorated, individually furnished

Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is HK$3,661
HK$9,005 total
includes taxes & fees
12 Jul - 13 Jul
Lighthouse Suites Collection
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (190 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is HK$699
HK$2,100 total
includes taxes & fees
30 Jun - 1 Jul
Aqua Lodges at Hurricane Hole Marina
Interior

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is HK$2,172
HK$4,683 total
includes taxes & fees
28 Jun - 29 Jun
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Living area

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is HK$7,755
HK$10,292 total
includes taxes & fees
10 Jul - 11 Jul
Coconut Mallory Marina and Resort Condo
Exterior

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is HK$6,468
HK$10,413 total
includes taxes & fees
29 Jun - 30 Jun
Contra House Key West
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$5,116
HK$8,842 total
includes taxes & fees
27 Jul - 28 Jul
Atlantic View Luxury Villa with Pool
Exterior

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is HK$2,502
HK$3,494 total
includes taxes & fees
29 Jun - 30 Jun
Ocean Front One Bedroom Residence
Terrace/patio

Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is HK$3,322
HK$6,000 total
includes taxes & fees
13 Jul - 14 Jul
Poolside Suite by Brightwild Pvt Pool Parking
Terrace/patio

Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is HK$1,709
HK$3,582 total
includes taxes & fees
29 Jun - 30 Jun
Banana Split by Brightwild Pool Grill
1 bedroom, Internet

New Coastal Rose - Bright Loft With High Ceilings

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
Key West Historic District
The price is HK$2,930
HK$5,810 total
includes taxes & fees
2 Jul - 3 Jul
New Coastal Rose - Bright Loft With High Ceilings
2 bedrooms

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is HK$2,998
HK$5,022 total
includes taxes & fees
1 Jul - 2 Jul
Resort View 2BR Residence
Exterior

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is HK$3,384
HK$3,807 total
includes taxes & fees
28 Jun - 29 Jun
Ocean Front 2BR Residence
2 bedrooms, Internet

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is HK$3,294
HK$6,371 total
includes taxes & fees
8 Jul - 9 Jul
Sea Breeze by Brightwild Off-street Parking
Interior

Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
The price is HK$3,793
HK$7,033 total
includes taxes & fees
13 Jul - 14 Jul
Sky Suite on Duval by Brightwild Condo w Balcony
1 bedroom, Internet

Poolside Retreat by Brightwild Cottage w Pool

Poolside Retreat by Brightwild Cottage w Pool
2.5 star property
Old Town Key West
2.0 out of 10, (1 review)
"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...
United States
Julia
The price is HK$2,093
HK$3,863 total
includes taxes & fees
13 Jul - 14 Jul
Poolside Retreat by Brightwild Cottage w Pool
2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is HK$2,616
HK$5,708 total
includes taxes & fees
7 Jul - 8 Jul
Starlight Serenity - Hideaway w Stunning Views
2 bedrooms, Internet

Mesa House Dos by Brightwild Unreal Location

Mesa House Dos by Brightwild Unreal Location
2.0 star property
Key West Historic District
The price is HK$3,165
HK$7,382 total
includes taxes & fees
29 Jun - 30 Jun
Mesa House Dos by Brightwild Unreal Location
2 bedrooms, Internet

The Collins on Duval by Brightwild

The Collins on Duval by Brightwild
2.0 star property
Old Town Key West
The price is HK$4,282
HK$7,582 total
includes taxes & fees
29 Jun - 30 Jun
The Collins on Duval by Brightwild
Exterior

Sky Loft by Brightwild Penthouse in Prime Spot

Sky Loft by Brightwild Penthouse in Prime Spot
2.0 star property
Old Town Key West
The price is HK$3,000
HK$4,883 total
includes taxes & fees
13 Jul - 14 Jul
Sky Loft by Brightwild Penthouse in Prime Spot
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cow Key Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"The hotel was perfect and clean. The beach and pool were lovely and there were plenty of options for food and drink. The staff were super friendly and responsive. And the location was amazing for exploring Key West."
Jennifer 4-night trip
Posted less than an hour ago
Pier House Resort & Spa

Find out more about Cow Key

Search for holiday rentals in Cow Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Cow Key using one of the methods below:

  • View our selection of featured holiday rentals in Cow Key
  • Use the map to find apartments and other holiday homes in the Cow Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cow Key while they last

Look no further and take a look at our great range of rental properties in Cow Key!

Frequently asked questions

Are there holiday rentals in Cow Key?

Yes, there are holiday rentals close to the most popular sights in Cow Key, or you can select a more secluded option if you're looking for a relaxing stay. Cow Key is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best holiday rentals that Cow Key has to offer?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Cow Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Key West Shipwreck Museum, or get out into nature at a spot like Florida Keys Beaches. While in the area, you can also visit popular places such as Duval Street and Southernmost Point.

What are holiday rentals like in Cow Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cow Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.