Key West Holiday Rentals

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Check prices for these dates

Tonight
25 Nov - 26 Nov
Tomorrow
26 Nov - 27 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Key West

Restaurant
Aqua Lodges at Hurricane Hole Marina

Houseboat in Stock Island

2.0 star property
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is HK$825
HK$2,233 total
includes taxes & fees
30 Nov - 1 Dec
Aqua Lodges at Hurricane Hole Marina
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Apartment in Old Town Key West

3.5 star property
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 HK$1,841
HK$2,334 total
includes taxes & fees
16 Dec - 17 Dec
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior
Steps from Duval, Pool on Site & Bikes Included!

Apartment in Old Town Key West

9.6 out of 10, Exceptional, (409)
"I had a great time at this property and while in Key West. It was a perfect retreat and exactly what I needed. The place was clean and having access to the bikes was a plus! Also, Ken was an excellent host and very responsive."
United States
Danielle J.
The price is HK$1,114
HK$2,251 total
includes taxes & fees
30 Nov - 1 Dec
Steps from Duval, Pool on Site & Bikes Included!
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Cottage in Old Town Key West

10.0 out of 10, Exceptional, (23)
"Will stay here again "
United States
Matt O.
The price is HK$1,074
HK$3,040 total
includes taxes & fees
9 Dec - 10 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Meeting facility
Coconut Mallory Resort And Marina By Kees Vacations

Condo in Key West

3.0 star property
8.2 out of 10, Very good, (820)
"Great place really nice rooms"
United States
Eric
Coconut Mallory Resort And Marina By Kees Vacations
Property grounds
Private Heated Pool & Near Duval - The Curry House

Holiday Home in Old Town Key West

10.0 out of 10, Exceptional, (6)
"Great property! "
United States
Austin C.
The price is HK$10,873
HK$25,612 total
includes taxes & fees
1 Dec - 2 Dec
Private Heated Pool & Near Duval - The Curry House
1 bedroom, free WiFi, bed sheets
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Cottage in 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 HK$1,074
HK$3,001 total
includes taxes & fees
17 Dec - 18 Dec
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1 bedroom
Island View 1BR Residence With Balcony

Aparthotel in Key West

2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is HK$2,203
HK$3,141 total
includes taxes & fees
1 Dec - 2 Dec
Island View 1BR Residence With Balcony
Terrace/patio
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

Holiday Home in Old Town Key West

9.8 out of 10, Exceptional, (12)
"Great place with great service!"
United States
Mills T.
The price is HK$5,089
HK$10,793 total
includes taxes & fees
9 Dec - 10 Dec
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Beach
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Condo in 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 HK$1,066
HK$2,881 total
includes taxes & fees
1 Dec - 2 Dec
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Terrace/patio
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Cottage in Old Town Key West

9.8 out of 10, Exceptional, (25)
"Loved this little place "
United States
Charles N.
The price is HK$1,074
HK$3,040 total
includes taxes & fees
9 Dec - 10 Dec
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
A heated pool
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Holiday Home in Old Town Key West

9.6 out of 10, Exceptional, (193)
"Perfect stay, awesome communication with the property manager at all times 5"
United States
Devotion808 g.
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Exterior
Heart of Downtown Key West Cottage With Off-Street Parking

Cottage in 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
1 bedroom, free WiFi, bed sheets
Wahoo Way | Charming Hideaway On Duval Street!

Holiday Home in 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 HK$708
HK$2,032 total
includes taxes & fees
30 Nov - 1 Dec
Wahoo Way | Charming Hideaway On Duval Street!
A heated pool
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

Holiday Home in Beachside

2.0 star property
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis
Outdoor pool
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Houseboat in 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 HK$1,946
HK$3,922 total
includes taxes & fees
26 Nov - 27 Nov
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Outdoor dining
King Suite with Balcony - The James House

Apartment in Key West Historic District

9.8 out of 10, Exceptional, (7)
"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 HK$1,268
HK$2,391 total
includes taxes & fees
8 Dec - 9 Dec
King Suite with Balcony - The James House
Fridge, microwave, oven, stovetop
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!

Condo in 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!
Outdoor pool, a heated pool
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Condo in Old Town Key West

2.0 star property
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Terrace/patio
Luxury Waterfront at Galion Resort in Old Town

Condo in Key West Historic District

9.6 out of 10, Exceptional, (93)
"Enjoyed our stay at Galleon"
United States
Kay c.
The price is HK$5,408
HK$6,855 total
includes taxes & fees
23 Dec - 24 Dec
Luxury Waterfront at Galion Resort in Old Town
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 Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The property has beach access. They have multiple pools. We had breakfast looking at the water that was nice. The only negative I have to say is that the property has a lot of roosters and they start making noise very early in the morning and it wakes you up and doesn’t let you go back to sleep. Not all rooms have this problem. Our room was facing the street. "
Nelson 1-night trip
Posted 2 days ago
Southernmost Beach Resort and Guesthouses

Find out more about Key West

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

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

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

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.