Key West Holiday Rentals

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Holiday Rentals in Key West

View from Quality Hill overlooking historic district, quick walk to downtown
10.0 out of 10, Exceptional, (142)
"Gorgeous view, pretty home. It was fully of charm and had everything you need. The owners were easy to reach out to with any questions and were super friendly and helpful!"
View from Quality Hill overlooking historic district, quick walk to downtown
The Cottage on Lake Galena
9.8 out of 10, Exceptional, (228)
"Although house is great, the real draw is the patio on the lake."
The Cottage on Lake Galena
Close 2 Town ~ Dog Friendly ~ Private ~ Wildlife all around ~ EV Car Charger
9.8 out of 10, Exceptional, (125)
"We thought we would be closer to Main Street. We couldn’t walk. Overall very good experience."
Close 2 Town ~ Dog Friendly ~ Private ~ Wildlife all around ~ EV Car Charger
"The Original" Galena Coach House * Fireplace * Private Parking * WIFI*
9.8 out of 10, Exceptional, (188)
"Clean and comfortable stay in Galena. Great place to visit."
"The Original" Galena Coach House * Fireplace * Private Parking * WIFI*
Steps 2 Main St & Turner Hall 3 BR Historical Beauty-We are a GUEST FAVORITE!
10.0 out of 10, Exceptional, (117)
"Great time !!!!"
Steps 2 Main St & Turner Hall 3 BR Historical Beauty-We are a GUEST FAVORITE!
2 BR, 2 BA Galena Townhouse Near Downtown Shopping, Golf, Skiing, Hiking Trails!
10.0 out of 10, Exceptional, (317)
"things went well for our stay. Only hiccup was burnt out lights in the bathroom that the owner promptly resolved. "
2 BR, 2 BA Galena Townhouse Near Downtown Shopping, Golf, Skiing, Hiking Trails!
Rustic Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
9.4 out of 10, Exceptional, (13)
"Our stay was cut short due to the weather. The location was good for going to Galena and around Dubuque. Were allowed to drop off our personal items early which was nice. Sad the hot tub had leak we were looking forward to using. The bed main floor was comfortable. My daughter stated upstairs was not and she didnt get a lot of sleep."
The price is NZ$361
includes taxes & fees
23 June - 24 June
Rustic Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Linen&Stone Inn Unit 1, Charming, Historic, 1.5 Blocks to Main St.
9.8 out of 10, Exceptional, (23)
"The room my wife and I chose to reserve was the exact room we reviewed on the website. The room was gorgeous,, the bed comfortable, and check in the easiest I have EVER experienced. In fact, neither my wife nor me ever met the owner/manager. All communication is completed via email."
The price is NZ$327
includes taxes & fees
9 July - 10 July
Linen&Stone Inn Unit 1, Charming, Historic, 1.5 Blocks to Main St.
Outstanding Location, Beautifully Updated, Warm, Inviting and Dog Friendly!
10.0 out of 10, Exceptional, (71)
"Beautiful and very comfortable home! Will always try to book it for our yearly trip!"
Outstanding Location, Beautifully Updated, Warm, Inviting and Dog Friendly!
Welcome to your Galena Get Away!!!
10.0 out of 10, Exceptional, (231)
"We needed a place to stay for a wedding and were very happy to find this gem! I felt a bit needy before our stay, but the hosts were very communicative and accomodating. The weather did not cooperate with our outdoor plans for the remainder of the weekend but we were set with board games, movies, and some quick hiking trails nearby."
Welcome to your Galena Get Away!!!
At the Edge of the Woods ~ Dog Friendly & Family Friendly
10.0 out of 10, Exceptional, (56)
"It couldn't have done my health any better. You have to go there and see how peaceful and beautiful it is. Just wish check in was maybe 2 hour's earlier. Otherwise perfect."
At the Edge of the Woods ~ Dog Friendly & Family Friendly
Mississippi River waterfront cabin just steps from the beach and boat launch
9.8 out of 10, Exceptional, (176)
"It is a property that is ideal for boating, fishing and beach loving people. It’s a great location for all of the above mentioned"
Mississippi River waterfront cabin just steps from the beach and boat launch
Popular 2-story End Unit Townhome with Awesome Views. One bedroom per level.
9.2 out of 10, Wonderful, (135)
"We had an enjoyable stay"
Popular 2-story End Unit Townhome with Awesome Views. One bedroom per level.
Beautiful Golf Villa!
10.0 out of 10, Exceptional, (129)
"Clean property in a nice quiet location. Big enough for 5 of us on a weekend trip. Take advantage of the Owners Club, great amenities for kids and adults!"
Beautiful Golf Villa!
2 Bedroom, 2 bath townhouse in The Galena Territory.
9.8 out of 10, Exceptional, (124)
"My Wife and I enjoyed our stay. We found the location conveniently located to all amenities of the Galena Territory, and close enough to the town of Galena and Main Street. Everything is as advertised and was clean. Would definitely stay again."
2 Bedroom, 2 bath townhouse in The Galena Territory.
Spacious! Private Hot Tub and Fire Pit, Great Games! Close to Shopping and Food!
10.0 out of 10, Exceptional, (25)
"Good communication, nice property, close to downtown Galena. Wonderful stay"
Spacious! Private Hot Tub and Fire Pit, Great Games! Close to Shopping and Food!
Getaway Galena Home walking distance to downtown
9.4 out of 10, Exceptional, (8)
"We had a very peaceful & enjoyable weekend. You can walk down to town to get a GREAT lower body workout as downhill there & uphill back!! Back yard is nice to sit, relax, have a drink and talk!!"
Getaway Galena Home walking distance to downtown
Driftless Get Away
10.0 out of 10, Exceptional, (62)
"Historic property next to another historic property in an historic town. So much easily accessible by walking or by car. Practically on the Galena River Trail."
Driftless Get Away
Galena Luxury Penthouse Downtown Parking New
10.0 out of 10, Exceptional, (10)
"Was able to walk to everything. Unit has one parking spot with additional free parking one block away. Everything was very clean. Would highly recommend."
Galena Luxury Penthouse Downtown Parking New
Mississippi River House with unobstructed views!
10.0 out of 10, Exceptional, (32)
"Quick response to our question when we got there. Quiet and peaceful, I never heard the barges go by. Easy to find. Short drive to town for groceries and to Maquoketa Cave State Park. Daughters thought their beds upstairs were a little hard (personal preference), but the one downstairs was very comfortable. Well stocked kitchen. Best set of skillets I have seen in a rental."
Mississippi River House with unobstructed views!
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See all available properties 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.

Other types of properties in Key West you may be interested in

Wyndham Garden Galena Hotel & Day Spa
4.0 star property
9.4 out of 10, Exceptional, (288)
"This hotel was clean and had such a beautiful design! Much better than the standard bland, cookie-cutter hotels you usually see. The view of the pond from the back deck was beautiful. I always appreciate a hot breakfast, the only downside was that the dining area was really crowded and hard to navigate/find somewhere to sit, but it was a busy weekend. Overall, a great experience and good value for the money."
The price is NZ$184
includes taxes & fees
21 July - 22 July
Wyndham Garden Galena Hotel & Day Spa
Stoney Creek Inn Galena
2.0 star property
9.2 out of 10, Wonderful, (1014)
"Friendly place"
The price is NZ$185
includes taxes & fees
1 July - 2 July
Stoney Creek Inn Galena
Days Inn by Wyndham Dubuque
2.0 star property
7.0 out of 10, Good, (1003)
"Rooms clean the doors on rooms are flimsy "
The price is NZ$93
includes taxes & fees
3 July - 4 July
Days Inn by Wyndham Dubuque
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Key West holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Key West. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Key West. Seeing all the best attractions is bound to make you fall in love with Key West. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Key West short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Key West?

Yes, there are holiday rentals close to the most popular sights in Key West, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Key West?

While exploring the area, visit family-friendly sights like National Mississippi River Museum and Aquarium, or get outside and enjoy nature at Crystal Lake Cave. In the wider area, you’ll find University of Dubuque and Five Flags Center.

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 provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.

Recent reviews of Key West properties
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