Key West Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Key West holiday rentals

3.0 star property
The price is AU$533
includes taxes & fees
8 Mar - 9 Mar
1 Mi to Downtown Dubuque! Spacious Home

Cabin in The Galena Territory

HoneyComb Hideaway Galena Territories
9.8 out of 10, Exceptional, (8 reviews)
"Great, comfy and cozy stay, space was great for a long weekend with family and area is beautiful. Definitely recommend! "
United States
Montse B.
The price is AU$856
includes taxes & fees
20 Mar - 21 Mar
HoneyComb Hideaway Galena Territories
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 AU$425
includes taxes & fees
7 Apr - 8 Apr
Drifter Cabin|Riverview+ Sauna+ Hot Tub+ Pickleball

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 AU$333
includes taxes & fees
12 Mar - 13 Mar
Mississippi River Cabin
9.2 out of 10, Wonderful, (17 reviews)
"The cabin itself was beautiful and had a lot of charm ,we really enjoyed the surroundings and the overall setup. However, we did have issues with bugs and flies inside the property in both bedrooms which made the stay less comfortable than expected. With a bit more attention to pest control and cleanliness, this place could be an excellent stay."
United States
BRANKA M.
The price is AU$424
includes taxes & fees
9 Mar - 10 Mar
Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities

Holiday Home in The Galena Territory

Quiet getaway with wooded views
10.0 out of 10, Exceptional, (71 reviews)
"Very clean and beautiful views. "
United States
chandra m.
Quiet getaway with wooded views
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 AU$365
includes taxes & fees
8 Mar - 9 Mar
Riverstone Villa #2 - Accessible Family Suite
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 AU$436
includes taxes & fees
8 Mar - 9 Mar
Pet-Friendly Wooded Villa w/ Fireplace, Pool & Club Access — Oak Haven Galena
9.8 out of 10, Exceptional, (54 reviews)
"We loved having coffee in the screened in porch! Very clean and comfortable!"
United States
Rose G.
Lakeview, End unit Condo! Golf! Family! Private pool; 3 BR/3 Bath! Sleeps 8
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 AU$366
includes taxes & fees
8 Mar - 9 Mar
Riverview Villa - Hot Tub - Beach - River Views
3.0 star property
The price is AU$577
includes taxes & fees
9 Mar - 10 Mar
'the Fiveten Federal' - Downtown Galena Gem!
10.0 out of 10, Exceptional, (22 reviews)
"The house was absolutely adorable! Super clean, well organized, beautifully decorated. We had a wonderful time there."
United States
Denise
The price is AU$636
includes taxes & fees
5 Apr - 6 Apr
Hot Tub 2-bedroom 2 full bath all comforts of home in Galena countryside
10.0 out of 10, Exceptional, (60 reviews)
"Very clean and nice place for a quick weekend get away for my wife, pet and me. "
United States
Anonymous traveller
The price is AU$424
includes taxes & fees
12 Mar - 13 Mar
New - Country Chic, Corner Unit, Dog Friendly - Only 12 Min to Downtown Galena
9.8 out of 10, Exceptional, (9 reviews)
"Everything was as expected. Thanks for a great stay!"
United States
Kevin W.
The price is AU$340
includes taxes & fees
30 Mar - 31 Mar
The Eagle's View - Tiny Home 4
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable & clean. We enjoyed our stay. "
United States
Iris O.
The price is AU$438
includes taxes & fees
8 Mar - 9 Mar
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
10.0 out of 10, Exceptional, (78 reviews)
"Perfect for small groups and families looking for a weekend getaway."
United States
Ross W.
The price is AU$798
includes taxes & fees
7 Apr - 8 Apr
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
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 AU$353
includes taxes & fees
9 Mar - 10 Mar
Charming, Farmhouse Chic, Cozy|Fireplace|12 Min to Town|Beautiful View
9.6 out of 10, Exceptional, (66 reviews)
"Few items not working but the property manager was excellent to communicate with. Very spacious - appreciated each bedroom had a bathroom. Warm and inviting. Hope to be back soon!"
United States
christine p.
The price is AU$946
includes taxes & fees
9 Mar - 10 Mar
Picturesque Galena Escape | Spacious 5BR | All Ensuites | 2 Fireplaces! Hot Tub!
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
Fresh! 2BR Golf Villa w/ King Beds, Dog-Friendly, Amenity Access, Near Trails
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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 favourite 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 depend 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 AU$303 per night. Entering your travel dates in the search wizard might find you 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.