Search Holiday Rentals in Cow Key

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top Holiday Rentals in Cow Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is £186
includes taxes & fees
17 Aug - 18 Aug
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (309)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is £219
includes taxes & fees
2 Sept - 3 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

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

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is £242
includes taxes & fees
19 Aug - 20 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (395)
"this was exactly as advertised and close to all the action"
The price is £171
includes taxes & fees
21 Aug - 22 Aug
Steps from Duval, Pool on Site & Bikes Included!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (139)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is £185
includes taxes & fees
20 Aug - 21 Aug
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is £609
includes taxes & fees
31 Aug - 1 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is £203
includes taxes & fees
19 Aug - 20 Aug
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (13)
"Great place to stay! Very clean and steps to Duval Ave."
The price is £298
includes taxes & fees
17 Aug - 18 Aug
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is £178
includes taxes & fees
17 Aug - 18 Aug
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (141)
"We had a great stay places is amazing"
The price is £181
includes taxes & fees
18 Aug - 19 Aug
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

Living the Dream Key West Style

10.0 out of 10, Exceptional, (21)
"Great hosts and great accommodations!"
The price is £256
includes taxes & fees
17 Aug - 18 Aug
Living the Dream Key West Style

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (179)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

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

9.8 out of 10, Exceptional, (20)
"Will stay here again "
The price is £237
includes taxes & fees
17 Aug - 18 Aug
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (296)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

8.4 out of 10, Very good, (9)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and very nice room"
The price is £242
includes taxes & fees
18 Aug - 19 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

8.4 out of 10, Very good, (25)
"Property as described in listing, enjoyed our stay! Would def stay again! "
The price is £190
includes taxes & fees
20 Aug - 21 Aug
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cow Key Hotel Reviews

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?

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!: This holiday home rental outside of Cow Key is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 Mel Fisher Maritime Museum, or get out into nature at a spot like Key West Tropical Forest and Botanical Garden. In the wider area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

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.