Holiday Rentals in Key West

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Our top choices for Key West holiday rentals

Holiday Home in The Galena Territory

Scenic Getaway – Cozy Stay Near Golf & Trails
10.0 out of 10, Exceptional, (70)
"What a beautiful location! We had a great time and a fun place for a girls weekend!"
United States
Christy L.
The price is €214
includes taxes & fees
8 Jan - 9 Jan
Scenic Getaway – Cozy Stay Near Golf & Trails
10.0 out of 10, Exceptional, (48)
"My family and I had a great time in this property, it’s cozy, clean and well located."
United States
fernando
The price is €254
includes taxes & fees
7 Jan - 8 Jan
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
10.0 out of 10, Exceptional, (75)
"this vacation house was amazing. It was so comfortable. I love how close it was to everything. My family and I had a great time. Will definitely recommend."
United States
Julio M.
Winter Escape in Galena - Wood-Burning Fireplace, Pool Access, 2 King Beds, Ski
10.0 out of 10, Exceptional, (41)
"Beautiful and peaceful location for our girls weekend in Galena."
United States
Alyssa S.
The price is €230
includes taxes & fees
7 Jan - 8 Jan
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
9.8 out of 10, Exceptional, (9)
"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 €262
includes taxes & fees
6 Feb - 7 Feb
1103#201-Charming 2-bedroom apartment with AC, WiFi in brilliant Dubuque

Apartment in Historic Millwork District

Drake House- Fleur De Lis (Private hot tub)
10.0 out of 10, Exceptional, (170)
"Beautiful/fun little place to stay and located in a great area"
United States
Ashley S.
The price is €200
includes taxes & fees
13 Jan - 14 Jan
Drake House- Fleur De Lis (Private hot tub)

Apartment in Downtown Dubuque

Masterpiece on Main #1
2.0 star property
10.0 out of 10, Exceptional, (3)
"Very nice clean spacious"
United States
Darius M.
The price is €200
includes taxes & fees
7 Jan - 8 Jan
Masterpiece on Main #1
10.0 out of 10, Exceptional, (12)
"Great Stay! "
United States
erin y.
115#303 / Vintage Meets Modern: Contemporary Loft
10.0 out of 10, Exceptional, (53)
"Golf View is a lovely townhouse, bright, very clean, fun/well appointed decor & easy to access. "
United States
Diane
The price is €204
includes taxes & fees
12 Jan - 13 Jan
Boutique townhome w/ fire pit, KING bed, mezzanine loft & golf views!
9.8 out of 10, Exceptional, (27)
"Everything was so smooth and so great!!! Loved it and can’t wait to come back!"
United States
Nicholle H.
The price is €254
includes taxes & fees
7 Jan - 8 Jan
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
2.0 star property
10.0 out of 10, Exceptional, (7)
"It was a nice relaxing stay "
United States
Amber T.
The price is €142
includes taxes & fees
11 Jan - 12 Jan
1127 / Downtown Dubuque, first floor, free parking
10.0 out of 10, Exceptional, (24)
"Easy check-in, very clean, nicely updated, comfortable beds. "
United States
Rachel A J.
The price is €264
includes taxes & fees
7 Jan - 8 Jan
Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access
2.0 star property
9.0 out of 10, Wonderful, (12)
"Very nice property and very affordable. "
United States
Jennifer C.
The price is €96
includes taxes & fees
11 Jan - 12 Jan
1157#3 / Tiny studio, Great Location, Dubuque

Apartment in Historic Millwork District

Drake House: City View (Private Hot Tub)
10.0 out of 10, Exceptional, (157)
"Great stay. Very relaxing place."
United States
Carie W.
The price is €242
includes taxes & fees
13 Jan - 14 Jan
Drake House: City View (Private Hot Tub)

Apartment in Historic Millwork District

Drake House: The Loft (Private Hot Tub)
10.0 out of 10, Exceptional, (148)
"It was a great stay thank you"
United States
Scott G.
The price is €206
includes taxes & fees
13 Jan - 14 Jan
Drake House: The Loft (Private Hot Tub)

Cabin in Bellevue

Mississippi River Cabin
10.0 out of 10, Exceptional, (38)
"We loved the place great location very clean and we will be back . "
United States
Mary A.
The price is €194
includes taxes & fees
26 Jan - 27 Jan
Mississippi River Cabin

Holiday Home in Dubuque

Annie`s on Adair - NO Step Entry
10.0 out of 10, Exceptional, (2)
"The property was clean and comfortable with modern finishes. It was better than we expected. Possibly the best rental we have experienced."
United States
Chuck L.
The price is €200
includes taxes & fees
7 Jan - 8 Jan
Annie`s on Adair - NO Step Entry

Holiday Home in The Galena Territory

Private 3BR/2BA Territory Home Nestled in the Trees
10.0 out of 10, Exceptional, (137)
"Very comfortable condo with all the necessities! Would stay here again!"
United States
Del R.
The price is €234
includes taxes & fees
7 Jan - 8 Jan
Private 3BR/2BA Territory Home Nestled in the Trees

Apartment in Downtown Dubuque

1103#203 / Downtown Oasis: En-Suite Master
10.0 out of 10, Exceptional, (24)
"Clean and well-appointed. Good location. "
United States
Nicole W.
The price is €173
includes taxes & fees
1 Feb - 2 Feb
1103#203 / Downtown Oasis: En-Suite Master
10.0 out of 10, Exceptional, (39)
"The entire place was spotless and very nice. The location was perfect for downtown activities. I would highly recommend. The restaurant below is a must too! "
United States
Michele
The price is €155
includes taxes & fees
11 Jan - 12 Jan
115#202 / Charming Downtown Dubuque Apartment
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 €168 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?

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.: This holiday home rental outside of Key West is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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.