Key West Holiday Rentals

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Holiday Rentals in Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is AU$439
includes taxes & fees
2 Dec - 3 Dec
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is AU$462
includes taxes & fees
16 Dec - 17 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West
9.6 out of 10, Exceptional, (410)
"Everything was excellent!"
United States
Susan L.
The price is AU$457
includes taxes & fees
8 Dec - 9 Dec
Steps from Duval, Pool on Site & Bikes Included!

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

Old Town Key West
10.0 out of 10, Exceptional, (25)
"Will stay here again "
United States
Matt O.
The price is AU$646
includes taxes & fees
10 Dec - 11 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
Key West
8.2 out of 10, Very good, (820)
"Great place really nice rooms"
United States
Eric
Coconut Mallory Resort And Marina By Kees Vacations

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

Old Town Key West
10.0 out of 10, Exceptional, (24)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
The price is AU$646
includes taxes & fees
17 Dec - 18 Dec
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!

Key West Historic District
9.4 out of 10, Exceptional, (87)
"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: Stayed here multiple times and it has been great every time!"
United States
Tyler R.
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!

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 AU$5,760
includes taxes & fees
15 Dec - 16 Dec
Private Heated Pool & Near Duval - The Curry House

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"The room was excellent, no complaints at all."
United States
Tonya
The price is AU$701
includes taxes & fees
3 Dec - 4 Dec
Island View 1BR Residence With Balcony

King Suite with Balcony - The James House

Key West Historic District
9.8 out of 10, Exceptional, (8)
"This property and room where great . It had everything you needed and was clean The location was absolutely great. Near to all restaurants and shopping. You can park your car and walk to it all or rent a scooter next door and get around town with no worries of parking. We will be back again and would recommend to anyone that wants to visit key west . Thank you for a great place"
United States
david q.
The price is AU$495
includes taxes & fees
15 Dec - 16 Dec
King Suite with Balcony - The James House

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

Old Town Key West
9.6 out of 10, Exceptional, (14)
"Great place with great service!"
United States
Mills T.
The price is AU$2,330
includes taxes & fees
3 Dec - 4 Dec
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

Wahoo Way | Charming Hideaway On Duval Street!

Old Town Key West
9.0 out of 10, Wonderful, (18)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Easy walks to everything!"
United States
Don N.
The price is AU$598
includes taxes & fees
17 Dec - 18 Dec
Wahoo Way | Charming Hideaway On Duval Street!

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 AU$781
includes taxes & fees
2 Dec - 3 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

Beachside
9.8 out of 10, Exceptional, (216)
"Lovely property with great amenities! We enjoyed our stay, thank you!! "
United States
Jamie S.
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

Heart of Downtown Key West Cottage With Off-Street Parking

Key West Historic District
10.0 out of 10, Exceptional, (142)
"Perfect location! Cute cottage had the best time. "
United States
jamie r.
Heart of Downtown Key West Cottage With Off-Street Parking

Luxury Waterfront at Galion Resort in Old Town

Key West Historic District
9.6 out of 10, Exceptional, (93)
"Enjoyed our stay at Galleon"
United States
Kay c.
The price is AU$1,165
includes taxes & fees
23 Dec - 24 Dec
Luxury Waterfront at Galion Resort in Old Town

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

Old Town Key West
9.8 out of 10, Exceptional, (25)
"Loved this little place "
United States
Charles N.
The price is AU$642
includes taxes & fees
14 Dec - 15 Dec
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Key West
8.6 out of 10, Excellent, (140)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is AU$571
includes taxes & fees
2 Dec - 3 Dec
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Conch Republic Consul General's Cottage.-Historic District

Old Town Key West
9.4 out of 10, Exceptional, (164)
"We really enjoyed our stay and plan to book again next time we visit the FL Keys. The cottage was clean and comfortable, and close to everything we wanted to do. My family also really enjoyed the pool, it was a perfect way to cool down after outdoor activities."
United States
Christine L.
Conch Republic Consul General's Cottage.-Historic District

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

Old Town Key West
8.6 out of 10, Excellent, (32)
"Clean, safe, accommodating, great value, good location, special attention when arriving and Transportation, reliable host, great communication, and friendliness."
United States
Nora Lee S.
The price is AU$469
includes taxes & fees
2 Dec - 3 Dec
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.

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Find out more about Key West

Everything you need to know about Key West holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Key West holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Key West holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Key West holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Key West holiday rentals we have selected for you start as low as AU$439 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Key West high marks for its great live music and lively festivals. While you're in the area, you can also enjoy the scenic seaside and entertainment choices.

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

Private Heated Pool & Near Duval - The Curry House: This highly rated holiday home rental in Key West is located in the city centre, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities such as a microwave and a coffee maker can make your holiday run smoothly. Some other homes for rent in Key West include CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! and New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis.

How many holiday rentals will I find in Key West?

With 1116 Expedia holiday rentals, you're guaranteed to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of the family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

What are holiday rentals like in Key West?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Key West. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.