Cow Key Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Cow Key vacation rentals

Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is ￥17,796
￥46,138 total
includes taxes & fees
Dec 17 - Dec 18
Aqua Lodges at Hurricane Hole Marina
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.4 out of 10, Very Good, (320)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is ￥39,134
￥49,286 total
includes taxes & fees
Dec 18 - Dec 19
Hyatt Vacation Club at Sunset Harbor, Key West
Apartment | 1 bedroom
Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
Ocean Front One Bedroom Residence
Apartment | 1 bedroom
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is ￥46,776
￥65,875 total
includes taxes & fees
Dec 18 - Dec 19
Island View 1BR Residence With Balcony
Apartment | 1 bedroom
Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is ￥64,561
￥85,883 total
includes taxes & fees
Dec 17 - Dec 18
Ocean Front 1BR Suite With Direct Beach Access
Exterior
Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (413)
"Everything was excellent!"
United States
Susan L.
The price is ￥33,515
￥60,338 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Steps from Duval, Pool on Site & Bikes Included!
Meeting facility
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
Key West
8.2 out of 10, Very Good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (27)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is ￥20,567
￥59,727 total
includes taxes & fees
Dec 16 - Dec 17
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Exterior
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking
Key West Historic District
10.0 out of 10, Exceptional, (142)
"As always, the host and house provided a great experience in KW. We have stayed there multiple times and will continue coming back!"
United States
Tom H.
Heart of Downtown Key West Cottage With Off-Street Parking
Outdoor pool
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is ￥38,953
￥78,061 total
includes taxes & fees
Dec 20 - Dec 21
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
2 bedrooms, iron/ironing board, WiFi, bed sheets
Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
8.6 out of 10, Excellent, (20)
"It is definitely an historic property with some cracks in the floor boards and bathrooms but it has its charms and the location is excellent! I would stay there again!"
United States
Martha B.
The price is ￥62,947
￥128,037 total
includes taxes & fees
Dec 21 - Dec 22
Private Parking, Heated Pool - Sweet Caroline
Property grounds
Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!
2.0 star property
Stock Island
Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!
1 bedroom, free WiFi, bed sheets
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25)
"Wonderful clean place. It was an enjoyable experiance. "
United States
Chels J.
The price is ￥20,567
￥59,727 total
includes taxes & fees
Dec 17 - Dec 18
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Sport court
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
The price is ￥59,208
￥87,858 total
includes taxes & fees
Dec 16 - Dec 17
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Outdoor pool, a heated pool
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
2.0 star property
Old Town Key West
8.0 out of 10, Very Good, (1)
"We had 3 people in the space. While there is sleeping for 6, there is not comfortable seating for 6 (not at table or in general area). Note that there is no couch, only a trundle day bed in general area. Kitchen was sparse - don’t expect to do much beyond boil water or use the toaster. Thought we wouldn’t mind bring off the beaten path, but this was too far out."
United States
Michelle J.
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
TV, offices
Private Heated Pool & Near Duval - The Curry House

Private Heated Pool & Near Duval - The Curry House

Private Heated Pool & Near Duval - The Curry House
Old Town Key West
10.0 out of 10, Exceptional, (6)
"Great property! "
United States
Austin C.
The price is ￥430,191
￥782,030 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Private Heated Pool & Near Duval - The Curry House
Marina
Living the Dream Key West Style

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (36)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is ￥41,928
￥52,001 total
includes taxes & fees
Dec 16 - Dec 17
Living the Dream Key West Style
Pool
Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
10.0 out of 10, Exceptional, (17)
"Great location. Very clean and hospitable."
United States
Derrick H.
The price is ￥91,149
￥193,596 total
includes taxes & fees
Dec 18 - Dec 19
Keys Breeze - Walk to Duval, Private Pool
Outdoor pool, a heated pool
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
10.0 out of 10, Exceptional, (195)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is ￥233,715
￥403,802 total
includes taxes & fees
Dec 16 - Dec 17
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Fridge, stovetop, coffee/tea maker, toaster
Super-Cozy boat in Key West!

Super-Cozy boat in Key West!

Super-Cozy boat in Key West!
Key West
8.0 out of 10, Very Good, (1)
"Yes, Troy was very welcoming. Met me at the airport and gave me a ride to his boat. Very accomodating. 2 diff.options for sleeping and boat was very comfortable. Plenty of fresh towels.Picked up whatever I needed and brought it out to me. Thx!"
United States
rachael K.
The price is ￥38,797
￥48,633 total
includes taxes & fees
Dec 16 - Dec 17
Super-Cozy boat in Key West!
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.
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Top Cow Key Hotel Reviews

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Absolutely wonderful stay! The property and the room were beautiful! The staff was so helpful and welcoming. Highly recommend this property! "
Julianna 4-night trip
Posted 2 hours ago
Parrot Key Hotel & Villas

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:

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Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. 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 vacation rentals that Cow Key has to offer?

Spacious home with pool & balcony - 1 block from Duval Street: Visitors like this Cow Key vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Key West Tropical Forest and Botanical Garden. In the larger area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.