Holiday Rentals in Key West

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Holiday Rentals in Key West

Newly renovated 2-bedroom house with Hottub in lovely Galena countryside

10.0 out of 10, Exceptional, (8)
"This place is just the best!!!! Amazing to think it was a schoolhouse at one point. The beds were so comfortable! Close to things but still very quiet and private. And we loved having an equal number of bathrooms to bedrooms ratio. That is very difficult to find at properties. "
The price is €464
includes taxes & fees
15 Oct - 16 Oct
Newly renovated 2-bedroom house with Hottub in lovely Galena countryside

1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

9.6 out of 10, Exceptional, (28)
"Wonderful place in an area that makes seeing the Dubuque surrounding area easy. "
The price is €271
includes taxes & fees
3 Nov - 4 Nov
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.

9.4 out of 10, Exceptional, (160)
"Spacious and comfortable place that worked well for our group of 8. Would definitely stay again. "
The price is €373
includes taxes & fees
6 Oct - 7 Oct
Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.

An Artistic retreat in the heart of downtown Galena

10.0 out of 10, Exceptional, (19)
"Very nice ,and clean place close to all attractions. Had a great time. "
The price is €189
includes taxes & fees
9 Oct - 10 Oct
An Artistic retreat in the heart of downtown Galena

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (125)
"Really enjoyed our stay. Everything was so nice, clean and convenient to everything. "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

Scenic Getaway – Cozy Stay Near Golf & Trails

10.0 out of 10, Exceptional, (64)
"Unit was clean and had everything that we needed!"
The price is €246
includes taxes & fees
5 Oct - 6 Oct
Scenic Getaway – Cozy Stay Near Golf & Trails

Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

9.0 out of 10, Wonderful, (4)
"Great location, good sleeping options "
The price is €202
includes taxes & fees
6 Oct - 7 Oct
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

Convenient & Spacious Downtown - Private Parking Included

10.0 out of 10, Exceptional, (195)
"We had a great time!"
Convenient & Spacious Downtown - Private Parking Included

One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

9.8 out of 10, Exceptional, (14)
"Wonderful. The whole stay was great."
The price is €276
includes taxes & fees
5 Oct - 6 Oct
One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table

10.0 out of 10, Exceptional, (358)
"This was perfect for our family! Was impressed with the kitchen, it was well stocked with all necessary cooking supplies.My children want us to book it again"
Escape! Hot Tub, Fire Pit, 3 Decks, WiFi, Pool Table

2 Bedroom, 2 bath townhouse in The Galena Territory.

9.4 out of 10, Exceptional, (163)
"Everything we needed was available. Perfect size for three of us. "
2 Bedroom, 2 bath townhouse in The Galena Territory.

Amazing! 2 Bed Townhouse in the HEART of Dbq!

10.0 out of 10, Exceptional, (34)
"Great property. Close to what we needed to do!!"
The price is €181
includes taxes & fees
6 Oct - 7 Oct
Amazing! 2 Bed Townhouse in the HEART of Dbq!

115#202 / Charming Downtown Dubuque Apartment

10.0 out of 10, Exceptional, (34)
"Very clean and comfortable! "
The price is €155
includes taxes & fees
5 Oct - 6 Oct
115#202 / Charming Downtown Dubuque Apartment

Drake House: The Loft (Private Hot Tub)

10.0 out of 10, Exceptional, (140)
"It was a great stay thank you"
The price is €202
includes taxes & fees
12 Oct - 13 Oct
Drake House: The Loft (Private Hot Tub)

Step Into a Soulful Hideaway In This Restored 1860s Country Church!

10.0 out of 10, Exceptional, (1)
"Super charming and comfortable space. The host was very easy to communicate with. Very welcoming little neighborhood. What fun to ring the church bell at the end of our visit!"
The price is €180
includes taxes & fees
5 Oct - 6 Oct
Step Into a Soulful Hideaway In This Restored 1860s Country Church!

The Nautical House-Downtown Galena

9.8 out of 10, Exceptional, (100)
"The house had everything we needed. It was uniquely decorated with a nautical theme. We enjoyed sitting on the front porch people watching and seeing the park across the channel. Great place overall. "
The Nautical House-Downtown Galena

1129#4 / Prime Downtown Dubuque, Cozy Brick Charm

9.8 out of 10, Exceptional, (17)
"great place, especially for the market in the morning! lovely little place with plenty of amenities!"
The price is €151
includes taxes & fees
19 Oct - 20 Oct
1129#4 / Prime Downtown Dubuque, Cozy Brick Charm

The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL

10.0 out of 10, Exceptional, (87)
"This place is amazing! We enjoyed our stay and will definitely recommend this loft to others!!"
The price is €610
includes taxes & fees
6 Oct - 7 Oct
The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL

The Nook: Downtown Galena Cottage w/ hot tub & fire pit!

10.0 out of 10, Exceptional, (127)
"This property was great for a weekend Galena visit with friends! Close enough to downtown to walk, but far enough away to stay quiet at night. The hosts were communicative and helpful! Would stay here again."
The price is €366
includes taxes & fees
3 Nov - 4 Nov
The Nook: Downtown Galena Cottage w/ hot tub & fire pit!

Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities

9.2 out of 10, Wonderful, (15)
"I stayed overnight with a friend is this cabin. Everything was super cute right down to the sign at the drive entrance showing you how far you were from certain places… including the Beer Barn! Highly recommend. "
The price is €379
includes taxes & fees
5 Oct - 6 Oct
Wooden Head Cabin Early1800's Log Cabin with a View and Modern Amenities
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

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 €151 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?

Newly renovated 2-bedroom house with Hottub in lovely Galena countryside : This holiday home rental outside of Key West is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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.