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Holiday Rentals in Key West

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Our top choices for Key West holiday rentals

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

1129#1- Market view studio/steps Millwork district
Downtown Dubuque
9.6 out of 10, Exceptional, (49 reviews)
"Clean rooms, comfortable bed, excellent location, communicative host."
United States
Berta Y.
1129#1- Market view studio/steps Millwork district

2. 1127 / Downtown Dubuque, first floor, free parking

1127 / Downtown Dubuque, first floor, free parking
Downtown Dubuque
10.0 out of 10, Exceptional, (15 reviews)
"It was a nice relaxing stay "
United States
Amber T.
The price is €133
includes taxes & fees
30 Aug - 31 Aug
1127 / Downtown Dubuque, first floor, free parking

3. Private king suite DBQ

Private king suite DBQ
Dubuque
9.6 out of 10, Exceptional, (10 reviews)
"Property was as described. We enjoyed our stay very much. Very clean and comfortable. "
United States
Timothy A.
The price is €162
includes taxes & fees
27 Aug - 28 Aug
Private king suite DBQ

4. Large & Private w/King Bed Great Location

Large & Private w/King Bed Great Location
Dubuque
9.6 out of 10, Exceptional, (10 reviews)
"A lovely, clean place in a great location."
United States
Karol B.
Large & Private w/King Bed Great Location

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

1157#5-Urban Oasis: Steps from Millwork district
Downtown Dubuque
10.0 out of 10, Exceptional, (42 reviews)
"Ken is amazing as is the property. "
United States
Michelle
The price is €133
includes taxes & fees
20 Sept - 21 Sept
1157#5-Urban Oasis: Steps from Millwork district

6. 1103#203 / Downtown Oasis: En-Suite Master

1103#203 / Downtown Oasis: En-Suite Master
Downtown Dubuque
10.0 out of 10, Exceptional, (30 reviews)
"AC was great being downtown we walked to everything friendly area"
United States
rick
The price is €185
includes taxes & fees
30 Aug - 31 Aug
1103#203 / Downtown Oasis: En-Suite Master

7. JACUZZI SUITE 2 Queen Beds Private and Romantic!

JACUZZI SUITE 2 Queen Beds Private and Romantic!
Dubuque
9.8 out of 10, Exceptional, (29 reviews)
"Nice clean stay, close to amenities, comy beds, hosts that respond promptly."
United States
Cassie H.
The price is €182
includes taxes & fees
27 Aug - 28 Aug
JACUZZI SUITE 2 Queen Beds Private and Romantic!

8. 1129#3 / Ken’s place-cute / Free Parking

1129#3 / Ken’s place-cute / Free Parking
Downtown Dubuque
9.4 out of 10, Exceptional, (14 reviews)
"Very well maintained and set up. "
United States
David B.
The price is €127
includes taxes & fees
30 Aug - 31 Aug
1129#3 / Ken’s place-cute / Free Parking

9. 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, (33 reviews)
"1 person staying 1 night... was perfect for me. Bed very comfy! Host very responsive! Would stay again. "
United States
Linda S.
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!

10. 1129#4 / Prime Downtown Dubuque, Cozy Brick Charm

1129#4 / Prime Downtown Dubuque, Cozy Brick Charm
Downtown Dubuque
9.8 out of 10, Exceptional, (33 reviews)
"Great location! The rental had everything we needed. Very responsive host. Would definitely stay again!"
United States
Mariann
1129#4 / Prime Downtown Dubuque, Cozy Brick Charm

11. Cheerful home by Millwork District/Farmers Market

Cheerful home by Millwork District/Farmers Market
Historic Millwork District
9.6 out of 10, Exceptional, (35 reviews)
"Very clean with everything we needed. Good millwork district location with multiple walkable breweries, restaurants, and coffee shops. Would say again."
United States
Mic H.
The price is €200
includes taxes & fees
30 Aug - 31 Aug
Cheerful home by Millwork District/Farmers Market

12. 115#202 / Charming Downtown Dubuque Apartment

115#202 / Charming Downtown Dubuque Apartment
Downtown Dubuque
10.0 out of 10, Exceptional, (48 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.
115#202 / Charming Downtown Dubuque Apartment

13. 1157#3 / Tiny studio, Great Location, Dubuque

1157#3 / Tiny studio, Great Location, Dubuque
Downtown Dubuque
9.2 out of 10, Wonderful, (14 reviews)
"Very nice property and very affordable. "
United States
Jennifer C.
The price is €116
includes taxes & fees
13 Sept - 14 Sept
1157#3 / Tiny studio, Great Location, Dubuque

14. 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, (50 reviews)
"I can’t say enough-host,amenities,location… everything was perfect!"
United States
Maria C.
The price is €181
includes taxes & fees
31 Aug - 1 Sept
Amazing! 2 Bed Townhouse in the HEART of Dbq!

15. 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
Impressive Private 2BR Suite w/Parking Univ Area

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

Drake House: The Loft (Private Hot Tub)
Historic Millwork District
10.0 out of 10, Exceptional, (159 reviews)
"Great rental property. Location and hot tub were ideal for a quick weekend away. "
United States
Timothy N.
The price is €214
includes taxes & fees
1 Sept - 2 Sept
Drake House: The Loft (Private Hot Tub)

17. 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 €183
includes taxes & fees
30 Aug - 31 Aug
1103#201-Charming 2-bedroom apartment with AC, WiFi in brilliant Dubuque

18. A MUST SEE! 2BR Lakefront Home w/ Boats & More!

A MUST SEE! 2BR Lakefront Home w/ Boats & More!
East Dubuque
9.2 out of 10, Wonderful, (25 reviews)
"My husband and I had a nice stay!"
United States
Diane L.
The price is €190
includes taxes & fees
27 Aug - 28 Aug
A MUST SEE! 2BR Lakefront Home w/ Boats & More!

19. Drake House- Fleur De Lis (Private hot tub)

Drake House- Fleur De Lis (Private hot tub)
Historic Millwork District
10.0 out of 10, Exceptional, (180 reviews)
"Great place to call home for a day or two. Lots of great restaurants nearby and Charlotte’s at the bottom of the stairs is a morning bonus!"
United States
Jason H.
The price is €209
includes taxes & fees
1 Sept - 2 Sept
Drake House- Fleur De Lis (Private hot tub)

20. Elegant 2 BR With Stunning Kitchen Prime Location!

Elegant 2 BR With Stunning Kitchen Prime Location!
Dubuque
9.6 out of 10, Exceptional, (18 reviews)
"Great location "
United States
John C.
The price is €182
includes taxes & fees
27 Aug - 28 Aug
Elegant 2 BR With Stunning Kitchen Prime Location!
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

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, apart-hotels, 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 favorite 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 depends 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 €201 per night. Entering your travel dates in the search wizard you might find 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

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?

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory: This holiday home rental outside of Key West is located next to a golf course, 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 an arcade/games room.

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 Port of Dubuque Marina.

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.