Holiday Rentals in Key West

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Holiday Rentals in Key West

View from Quality Hill overlooking historic district, quick walk to downtown
10.0 out of 10, Exceptional, (142)
"Gorgeous view, pretty home. It was fully of charm and had everything you need. The owners were easy to reach out to with any questions and were super friendly and helpful!"
View from Quality Hill overlooking historic district, quick walk to downtown
The Cottage on Lake Galena
9.8 out of 10, Exceptional, (227)
"Pictures did not show how spacious and open this lovely cabin is. I can't wait for a return trip! If i could say one thing that would have made it better, it would be a king size bed in downstairs bedroom.Everything else was PERFECT!"
The Cottage on Lake Galena
Close 2 Town ~ Dog Friendly ~ Private ~ Wildlife all around ~ EV Car Charger
9.8 out of 10, Exceptional, (123)
"We thought we would be closer to Main Street. We couldn’t walk. Overall very good experience."
Close 2 Town ~ Dog Friendly ~ Private ~ Wildlife all around ~ EV Car Charger
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"The Original" Galena Coach House * Fireplace * Private Parking * WIFI*
9.8 out of 10, Exceptional, (186)
"Clean and comfortable stay in Galena. Great place to visit."
"The Original" Galena Coach House * Fireplace * Private Parking * WIFI*
Steps 2 Main St & Turner Hall 3 BR Historical Beauty-We are a GUEST FAVORITE!
10.0 out of 10, Exceptional, (116)
"Great time !!!!"
Steps 2 Main St & Turner Hall 3 BR Historical Beauty-We are a GUEST FAVORITE!
2 BR, 2 BA Galena Townhouse Near Downtown Shopping, Golf, Skiing, Hiking Trails!
10.0 out of 10, Exceptional, (317)
"things went well for our stay. Only hiccup was burnt out lights in the bathroom that the owner promptly resolved. "
2 BR, 2 BA Galena Townhouse Near Downtown Shopping, Golf, Skiing, Hiking Trails!
Rustic Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
9.4 out of 10, Exceptional, (13)
"Our stay was cut short due to the weather. The location was good for going to Galena and around Dubuque. Were allowed to drop off our personal items early which was nice. Sad the hot tub had leak we were looking forward to using. The bed main floor was comfortable. My daughter stated upstairs was not and she didnt get a lot of sleep."
The price is €213
includes taxes & fees
24 Jun - 25 Jun
Rustic Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Linen&Stone Inn Unit 1, Charming, Historic, 1.5 Blocks to Main St.
9.8 out of 10, Exceptional, (22)
"We had a great stay at Linen and Stone Inn. Easy checking in , very comfortable room and walking distance to the shops and restaurants in Downtown Galena. The common areas were very comfortable. The manager was very attentive. We enjoyed our stay"
The price is €196
includes taxes & fees
9 Jul - 10 Jul
Linen&Stone Inn Unit 1, Charming, Historic, 1.5 Blocks to Main St.
Outstanding Location, Beautifully Updated, Warm, Inviting and Dog Friendly!
10.0 out of 10, Exceptional, (71)
"Beautiful and very comfortable home! Will always try to book it for our yearly trip!"
Outstanding Location, Beautifully Updated, Warm, Inviting and Dog Friendly!
Welcome to your Galena Get Away!!!
10.0 out of 10, Exceptional, (231)
"We needed a place to stay for a wedding and were very happy to find this gem! I felt a bit needy before our stay, but the hosts were very communicative and accomodating. The weather did not cooperate with our outdoor plans for the remainder of the weekend but we were set with board games, movies, and some quick hiking trails nearby."
Welcome to your Galena Get Away!!!
At the Edge of the Woods ~ Dog Friendly & Family Friendly
10.0 out of 10, Exceptional, (56)
"It couldn't have done my health any better. You have to go there and see how peaceful and beautiful it is. Just wish check in was maybe 2 hour's earlier. Otherwise perfect."
At the Edge of the Woods ~ Dog Friendly & Family Friendly
Mississippi River waterfront cabin just steps from the beach and boat launch
9.8 out of 10, Exceptional, (176)
"It is a property that is ideal for boating, fishing and beach loving people. It’s a great location for all of the above mentioned"
Mississippi River waterfront cabin just steps from the beach and boat launch
Beautiful Golf Villa!
10.0 out of 10, Exceptional, (128)
"Good location and had all the supplies and amenities we needed to make it a nice weekend stay."
Beautiful Golf Villa!
Popular 2-story End Unit Townhome with Awesome Views. One bedroom per level.
9.2 out of 10, Wonderful, (135)
"We had an enjoyable stay"
Popular 2-story End Unit Townhome with Awesome Views. One bedroom per level.
2 Bedroom, 2 bath townhouse in The Galena Territory.
9.8 out of 10, Exceptional, (123)
"The location was perfect and amenities were great to have. Would stay again!"
2 Bedroom, 2 bath townhouse in The Galena Territory.
Spacious! Private Hot Tub and Fire Pit, Great Games! Close to Shopping and Food!
10.0 out of 10, Exceptional, (25)
"Good communication, nice property, close to downtown Galena. Wonderful stay"
Spacious! Private Hot Tub and Fire Pit, Great Games! Close to Shopping and Food!
Getaway Galena Home walking distance to downtown
9.4 out of 10, Exceptional, (8)
"We had a very peaceful & enjoyable weekend. You can walk down to town to get a GREAT lower body workout as downhill there & uphill back!! Back yard is nice to sit, relax, have a drink and talk!!"
Getaway Galena Home walking distance to downtown
Driftless Get Away
10.0 out of 10, Exceptional, (62)
"Historic property next to another historic property in an historic town. So much easily accessible by walking or by car. Practically on the Galena River Trail."
Driftless Get Away
Galena Luxury Penthouse Downtown Parking New
10.0 out of 10, Exceptional, (10)
"We loved the condo for our Family's Bachelorette Weekend! Bedroom perfect for 7 girls and 3 full bathrooms. Big dining room table for us to play games at night. Good price for what we got. Had everything we needed. Perfect Location - one block from Main Street where tons of restaurants and shopping. We loved our stay. Highly recommended and we will come back and stay again!!!"
Galena Luxury Penthouse Downtown Parking New
Mississippi River House with unobstructed views!
10.0 out of 10, Exceptional, (32)
"Quick response to our question when we got there. Quiet and peaceful, I never heard the barges go by. Easy to find. Short drive to town for groceries and to Maquoketa Cave State Park. Daughters thought their beds upstairs were a little hard (personal preference), but the one downstairs was very comfortable. Well stocked kitchen. Best set of skillets I have seen in a rental."
Mississippi River House with unobstructed views!
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See all available properties in Key West
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.

Other types of properties in Key West you may be interested in

Wyndham Garden Galena Hotel & Day Spa
4.0 star property
9.4 out of 10, Exceptional, (278)
"Very close to gas, dining, and shopping options. Staff was friendly and kept the place spotless. "
The price is €105
includes taxes & fees
25 Jun - 26 Jun
Wyndham Garden Galena Hotel & Day Spa
Stoney Creek Inn Galena
2.0 star property
9.2 out of 10, Wonderful, (1018)
"Located right off the main highway, this is very easy to find. I also found the staff to generally be very helpful and possitive. "
The price is €103
includes taxes & fees
25 Jun - 26 Jun
Stoney Creek Inn Galena
Days Inn by Wyndham Dubuque
2.0 star property
7.0 out of 10, Good, (1007)
"Rooms clean the doors on rooms are flimsy "
The price is €53
includes taxes & fees
24 Jun - 25 Jun
Days Inn by Wyndham Dubuque
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.

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 €196 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 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 Five Flags Center.

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.

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