Key West Holiday Rentals

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Our top choices for Key West holiday rentals

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 NZ$386
includes taxes & fees
1 Mar - 2 Mar
Mississippi River Cabin
10.0 out of 10, Exceptional, (42 reviews)
"Beautiful and peaceful location for our girls weekend in Galena."
United States
Alyssa S.
The price is NZ$362
includes taxes & fees
2 Mar - 3 Mar
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
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 NZ$509
includes taxes & fees
4 Mar - 5 Mar
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
9.6 out of 10, Exceptional, (114 reviews)
"Great place to stay. "
United States
Michael
The price is NZ$329
includes taxes & fees
10 Mar - 11 Mar
Ranch styled home, in a quiet neighborhood, totally remodeled in 2020.
9.8 out of 10, Exceptional, (9 reviews)
"Everything was as expected. Thanks for a great stay!"
United States
Kevin W.
The price is NZ$386
includes taxes & fees
30 Mar - 31 Mar
The Eagle's View - Tiny Home 4
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 NZ$424
includes taxes & fees
1 Mar - 2 Mar
Riverstone Villa #2 - Accessible Family Suite
10.0 out of 10, Exceptional, (11 reviews)
"Had a wonderful time."
United States
Christina S.
The price is NZ$386
includes taxes & fees
30 Mar - 31 Mar
The River's Edge - Tiny Home 3
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 NZ$424
includes taxes & fees
3 Mar - 4 Mar
Riverview Villa - Hot Tub - Beach - River Views
10.0 out of 10, Exceptional, (25 reviews)
"Easy check-in, very clean, nicely updated, comfortable beds. "
United States
Rachel A J.
The price is NZ$487
includes taxes & fees
1 Mar - 2 Mar
Escape to Creekwood Pines - 2 King Beds, Near Golf, Dog-Friendly, Amenity Access
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 NZ$205
includes taxes & fees
30 Mar - 31 Mar
Private entrance/space. Peaceful getaway. Close to events. King bed. Amenities!
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 NZ$484
includes taxes & fees
1 Mar - 2 Mar
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
9.0 out of 10, Wonderful, (12 reviews)
"Very nice property and very affordable. "
United States
Jennifer C.
1157#3 / Tiny studio, Great Location, Dubuque

Holiday Home in The Galena Territory

Cozy 2BR Townhouse - Sleeps 6 - Fireplace
10.0 out of 10, Exceptional, (71 reviews)
"Very clean and beautiful views. "
United States
chandra m.
The price is NZ$471
includes taxes & fees
2 Mar - 3 Mar
Cozy 2BR Townhouse - Sleeps 6 - Fireplace
9.4 out of 10, Exceptional, (19 reviews)
"Yes, I was very relaxing."
United States
Larry H.
The price is NZ$309
includes taxes & fees
8 Mar - 9 Mar
A MUST SEE! 2BR Lakefront Home w/ Boats & More!
10.0 out of 10, Exceptional, (5 reviews)
"Extremely relaxing, very cozy even though it rained was able to get in the hot tub, beautiful scenery great communication with host will definitely be looking to book again"
United States
Katrina M.
The price is NZ$497
includes taxes & fees
3 Mar - 4 Mar
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball
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 NZ$386
includes taxes & fees
30 Mar - 31 Mar
The Riverbottom - Tiny Home 2
10.0 out of 10, Exceptional, (140 reviews)
"Had a great time, perfect location, great setup for a family. "
United States
William R.
The price is NZ$447
includes taxes & fees
1 Mar - 2 Mar
Private 3BR/2BA Territory Home Nestled in the Trees - Stonecrest
10.0 out of 10, Exceptional, (79 reviews)
"It was an awesome place!! We had a wonderful girls trip and the space was perfect for us!! Very relaxing! Will definitely return sometime! "
United States
Lisa S.
The price is NZ$399
includes taxes & fees
2 Mar - 3 Mar
Galena Golf View - Wood-Burning Fireplace, Pool Access, 2 Kings, Close to Ski
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 NZ$317
includes taxes & fees
29 Mar - 30 Mar
115#202 / Charming Downtown Dubuque Apartment
3.0 star property
The price is NZ$674
includes taxes & fees
2 Mar - 3 Mar
'the Fiveten Federal' - Downtown Galena Gem!
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, 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 NZ$447 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.