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Key West Holiday Rentals

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Our top choices for Key West holiday rentals

1. 1129#3 / Ken’s place-cute / Free Parking

1129#3 / Ken’s place-cute / Free Parking
Downtown Dubuque
9.6 out of 10, Exceptional, (20 reviews)
"Very nice stay for a short while. It was great having off street parking. "
United States
elise h.
The price is NZ$283
includes taxes & fees
18 Oct - 19 Oct
1129#3 / Ken’s place-cute / Free Parking

2. 1129#1- Market view studio/steps Millwork district

1129#1- Market view studio/steps Millwork district
Downtown Dubuque
9.6 out of 10, Exceptional, (52 reviews)
"Clean rooms, comfortable bed, excellent location, communicative host."
United States
Berta Y.
The price is NZ$289
includes taxes & fees
25 Oct - 26 Oct
1129#1- Market view studio/steps Millwork district

3. 1157#5-Urban Oasis: Steps from Millwork district

1157#5-Urban Oasis: Steps from Millwork district
Downtown Dubuque
10.0 out of 10, Exceptional, (44 reviews)
"Great stay, safe and clean, responsive / great host."
United States
Richard D.
The price is NZ$307
includes taxes & fees
18 Oct - 19 Oct
1157#5-Urban Oasis: Steps from Millwork district

4. 1129 #2 / Charming 1-bedroom apartment with WiFi, AC, Free parking

1129 #2 / Charming 1-bedroom apartment with WiFi, AC, Free parking
Downtown Dubuque
9.0 out of 10, Wonderful, (4 reviews)
"Great place to stay. Conveniently located and clean. Comfortable bed and quiet."
United States
Kyle
1129 #2 / Charming 1-bedroom apartment with WiFi, AC, Free parking

5. 1127 / Downtown Dubuque, first floor, free parking

1127 / Downtown Dubuque, first floor, free parking
Downtown Dubuque
10.0 out of 10, Exceptional, (18 reviews)
"This place was super cute and cozy. We really enjoyed our stay here and would definitely recommend to others."
United States
Jennifer B.
The price is NZ$297
includes taxes & fees
18 Oct - 19 Oct
1127 / Downtown Dubuque, first floor, free parking

6. 1157#3 / Tiny studio, Great Location, Dubuque

1157#3 / Tiny studio, Great Location, Dubuque
Downtown Dubuque
9.2 out of 10, Wonderful, (15 reviews)
"Very nice property and very affordable. "
United States
Jennifer C.
The price is NZ$289
includes taxes & fees
16 Nov - 17 Nov
1157#3 / Tiny studio, Great Location, Dubuque

7. Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!
Dubuque
9.8 out of 10, Exceptional, (39 reviews)
"1 person staying 1 night... was perfect for me. Bed very comfy! Host very responsive! Would stay again. "
United States
Linda S.
The price is NZ$218
includes taxes & fees
18 Oct - 19 Oct
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

8. Check It Out! Great Location Large Priv w/Parking

Check It Out! Great Location Large Priv w/Parking
Dubuque
9.6 out of 10, Exceptional, (30 reviews)
"Perfect for visiting family "
United States
Kimberly D.
The price is NZ$329
includes taxes & fees
19 Oct - 20 Oct
Check It Out! Great Location Large Priv w/Parking

9. 1103#203 / Downtown Oasis: En-Suite Master

1103#203 / Downtown Oasis: En-Suite Master
Downtown Dubuque
9.8 out of 10, Exceptional, (36 reviews)
"Clean, pretty, convient. Loved it. Will stay again!"
United States
Shawna
The price is NZ$406
includes taxes & fees
18 Oct - 19 Oct
1103#203 / Downtown Oasis: En-Suite Master

10. Bluff Street Escape • Modern 1BR Near Downtown

Bluff Street Escape • Modern 1BR Near Downtown
Dubuque
8.4 out of 10, Very good, (17 reviews)
"Nice place to stay for a weekend getaway"
United States
Austin K.
The price is NZ$359
includes taxes & fees
26 Oct - 27 Oct
Bluff Street Escape • Modern 1BR Near Downtown

11. 1103#201-Charming 2-bedroom apartment with AC, WiFi in brilliant Dubuque

1103#201-Charming 2-bedroom apartment with AC, WiFi in brilliant Dubuque
Downtown Dubuque
10.0 out of 10, Exceptional, (13 reviews)
"The property is conveniently located with food and entertainment close by, and the host provides all essentials, as well as thoughtful notes/labels to make it easier to feel at home."
United States
Amanda G.
The price is NZ$363
includes taxes & fees
18 Oct - 19 Oct
1103#201-Charming 2-bedroom apartment with AC, WiFi in brilliant Dubuque

12. The Emmett. Great downtown Dubuque location

The Emmett. Great downtown Dubuque location
Dubuque
9.8 out of 10, Exceptional, (91 reviews)
"Great place, would definitely stay again"
United States
Chess W.
The price is NZ$528
includes taxes & fees
19 Oct - 20 Oct
The Emmett. Great downtown Dubuque location

13. Cheerful home by Millwork District/Farmers Market

Cheerful home by Millwork District/Farmers Market
Historic Millwork District
9.6 out of 10, Exceptional, (36 reviews)
"We love staying near the Millwork District and Ken’s properties are always comfortable and beautifully decorated."
United States
Cele P.
The price is NZ$424
includes taxes & fees
25 Oct - 26 Oct
Cheerful home by Millwork District/Farmers Market

14. Stylish Historic Loft in Downtown Dubuque .Walk to Dining & Riverwalk

Stylish Historic Loft in Downtown Dubuque .Walk to Dining & Riverwalk
Downtown Dubuque
10.0 out of 10, Exceptional, (18 reviews)
"Great location and very clean! We enjoyed being able to walk to the restaurants near by. Thanks!"
United States
Michelle B.
The price is NZ$378
includes taxes & fees
18 Oct - 19 Oct
Stylish Historic Loft in Downtown Dubuque .Walk to Dining & Riverwalk

15. Drake House: The Loft (Private Hot Tub)

Drake House: The Loft (Private Hot Tub)
Historic Millwork District
10.0 out of 10, Exceptional, (162 reviews)
"Place was clean and tidy, as advirtised, and a fantastic central location for the million district and saturday farmers market."
United States
Andrew F.
The price is NZ$433
includes taxes & fees
25 Oct - 26 Oct
Drake House: The Loft (Private Hot Tub)

16. 115#202 / Charming Downtown Dubuque Apartment

115#202 / Charming Downtown Dubuque Apartment
Downtown Dubuque
10.0 out of 10, Exceptional, (50 reviews)
"Once again Ken’s place did not disappoint. We love staying at his places when we are in the area. "
United States
Grant H.
The price is NZ$411
includes taxes & fees
18 Oct - 19 Oct
115#202 / Charming Downtown Dubuque Apartment

17. Impressive Private 2BR Suite w/Parking Univ Area

Impressive Private 2BR Suite w/Parking Univ Area
Dubuque
10.0 out of 10, Exceptional, (18 reviews)
"Had private (off the street) parking, walking distance to nice amenities. Very clean and thoughtful hosts of property. Nicest stay I've ever had traveling."
United States
Brett
The price is NZ$367
includes taxes & fees
16 Nov - 17 Nov
Impressive Private 2BR Suite w/Parking Univ Area

18. JACUZZI SUITE 2 Queen Beds Private and Romantic!

JACUZZI SUITE 2 Queen Beds Private and Romantic!
Dubuque
9.8 out of 10, Exceptional, (33 reviews)
"Nice place to stay"
United States
Valorie L.
The price is NZ$367
includes taxes & fees
16 Nov - 17 Nov
JACUZZI SUITE 2 Queen Beds Private and Romantic!

19. Amazing! 2 Bed Townhouse in the HEART of Dbq!

Amazing! 2 Bed Townhouse in the HEART of Dbq!
Dubuque
9.8 out of 10, Exceptional, (52 reviews)
"The hosts were amazing! Always available to answer any questions. And honestly, it’s one of the cleanest places I have ever been in!"
United States
Kristin N.
The price is NZ$367
includes taxes & fees
16 Nov - 17 Nov
Amazing! 2 Bed Townhouse in the HEART of Dbq!

20. Modern 2 bedroom loft in downtown Dubuque

Modern 2 bedroom loft in downtown Dubuque
Dubuque
9.8 out of 10, Exceptional, (8 reviews)
"Very unique set up and comfortable, perfect for us as my son was in town for a week regarding Hockey."
United States
Bob S.
The price is NZ$449
includes taxes & fees
17 Nov - 18 Nov
Modern 2 bedroom loft in downtown 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.
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Top Key West Hotel Reviews

Find out more about Key West

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

New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena: This holiday home rental outside of Key West is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a selection of games.

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 Mines of Spain State Recreation Area and University of Dubuque.

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.