Key West Holiday Rentals

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Our top choices for Key West holiday rentals

9.6 out of 10, Exceptional, (115 reviews)
"Great place to stay. "
United States
Michael
The price is HK$633
HK$1,542 total
includes taxes & fees
12 Mar - 13 Mar
Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.

Cabin in Bellevue

Mississippi River Cabin
10.0 out of 10, Exceptional, (41 reviews)
"We loved the place great location very clean and we will be back . "
United States
Mary A.
The price is HK$929
HK$1,803 total
includes taxes & fees
14 Mar - 15 Mar
Mississippi River Cabin
9.8 out of 10, Exceptional, (9 reviews)
"Everything was as expected. Thanks for a great stay!"
United States
Kevin W.
The price is HK$1,071
HK$1,813 total
includes taxes & fees
29 Mar - 30 Mar
The Eagle's View - Tiny Home 4
10.0 out of 10, Exceptional, (11 reviews)
"Had a wonderful time."
United States
Christina S.
The price is HK$1,071
HK$1,813 total
includes taxes & fees
30 Mar - 31 Mar
The River's Edge - Tiny Home 3
9.8 out of 10, Exceptional, (27 reviews)
"Great place. Clean, nice layout, easy access to activities. Owners were responsive. Would stay there again"
United States
Rich R.
The price is HK$947
HK$2,295 total
includes taxes & fees
12 Mar - 13 Mar
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
10.0 out of 10, Exceptional, (50 reviews)
"My family and I had a great time in this property, it’s cozy, clean and well located."
United States
fernando
The price is HK$857
HK$2,332 total
includes taxes & fees
15 Mar - 16 Mar
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
10.0 out of 10, Exceptional, (6 reviews)
"The history of the building was very unique as well as very clean."
United States
Sarah
The price is HK$1,071
HK$1,997 total
includes taxes & fees
12 Mar - 13 Mar
Riverstone Villa #2 - Accessible Family Suite
10.0 out of 10, Exceptional, (42 reviews)
"Host was great at communicating! Our stay was peaceful and comfortable."
United States
Michelle H.
The price is HK$626
HK$1,874 total
includes taxes & fees
8 Apr - 9 Apr
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
9.4 out of 10, Exceptional, (19 reviews)
"Yes, I was very relaxing."
United States
Larry H.
The price is HK$704
HK$1,450 total
includes taxes & fees
5 Apr - 6 Apr
A MUST SEE! 2BR Lakefront Home w/ Boats & More!
10.0 out of 10, Exceptional, (14 reviews)
"We really enjoyed our 2 nights in the tiny cabin. We cooked, watched a movie (it rained one night), and used the hot tub. It was easy to find, clean, and safe. Thanks!"
United States
Erin H.
The price is HK$1,071
HK$1,813 total
includes taxes & fees
30 Mar - 31 Mar
The Riverbottom - Tiny Home 2
10.0 out of 10, Exceptional, (39 reviews)
"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 HK$587
HK$1,498 total
includes taxes & fees
15 Mar - 16 Mar
115#202 / Charming Downtown Dubuque Apartment
3.0 star property
The price is HK$719
HK$2,922 total
includes taxes & fees
12 Mar - 13 Mar
1 Mi to Downtown Dubuque! Spacious Home
10.0 out of 10, Exceptional, (5 reviews)
"The hosts were very helpful. The cabin was very clean amd comfortable."
United States
Ryan C.
The price is HK$1,848
HK$2,306 total
includes taxes & fees
23 Mar - 24 Mar
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
10.0 out of 10, Exceptional, (26 reviews)
"Easy check-in, very clean, nicely updated, comfortable beds. "
United States
Rachel A J.
The price is HK$894
HK$2,406 total
includes taxes & fees
17 Mar - 18 Mar
Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access
9.8 out of 10, Exceptional, (47 reviews)
"This is a great place for a quick getaway. The hosts are very responsive and accommodating. It was storming and they made sure to have everything we needed. "
United States
Kevin W.
The price is HK$782
HK$1,621 total
includes taxes & fees
23 Mar - 24 Mar
Amazing! 2 Bed Townhouse in the HEART of Dbq!
9.8 out of 10, Exceptional, (27 reviews)
"Check in was easy and the place was very cozy and cute! "
United States
McKenna W.
The price is HK$704
HK$963 total
includes taxes & fees
15 Mar - 16 Mar
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!
10.0 out of 10, Exceptional, (11 reviews)
"This property was hands-down on the nicest places we have stayed. The hot tub was super clean and very nice, we also used the outdoor fire pit, which was wonderful. The location is perfect to walk downtown easily, and the view of the river is very nice. This is a beautiful, very large property that is so tastefully decorated. The beds were also super comfortable!"
United States
Kimberly G.
The price is HK$1,250
HK$2,206 total
includes taxes & fees
22 Mar - 23 Mar
Riverview Villa - Hot Tub - Beach - River Views
9.8 out of 10, Exceptional, (23 reviews)
"Host is very welcoming, house had everything you could need. "
United States
Lance E.
The price is HK$782
HK$1,621 total
includes taxes & fees
25 Mar - 26 Mar
JACUZZI SUITE 2 Queen Beds Private and Romantic!
10.0 out of 10, Exceptional, (80 reviews)
"Had a wonderful time! Melissa was a wonderful host. Very welcoming and spoiled us! Thank you!"
United States
Lisa W.
The price is HK$845
HK$2,030 total
includes taxes & fees
15 Mar - 16 Mar
Wake Up to Golf Course Views - Galena Townhome - 2 King Beds - Pool Access
9.6 out of 10, Exceptional, (24 reviews)
"Thanks for great stay"
United States
Christy G.
The price is HK$493
HK$1,296 total
includes taxes & fees
29 Mar - 30 Mar
Check It Out! Great Location Large Priv w/Parking
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

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:

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

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?

Private 3BR/2BA Territory Home Nestled in the Trees - Stonecrest: This holiday home rental outside of Key West is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden 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.