Key West Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Holiday Rentals in Key West

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

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 AU$653
includes taxes & fees
30 Sept - 1 Oct
Newly renovated 2-bedroom house with Hottub in lovely Galena countryside
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory
TV, fireplace

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (125)
"Best place to stay for our 15th anniversary "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Outdoor pool

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 AU$479
includes taxes & fees
29 Sept - 30 Sept
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings
Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.
Outdoor dining

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

9.4 out of 10, Exceptional, (159)
"Loved the view and the home was very clean. Owners are great in communication would rent it again. "
The price is AU$655
includes taxes & fees
30 Sept - 1 Oct
Beautiful townhome in Galena Territories Sleeps 9, 4 BR, close to Owners Club.
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Microwave, stovetop

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 AU$356
includes taxes & fees
1 Oct - 2 Oct
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC
Scenic Getaway – Cozy Stay Near Golf & Trails
Smart TV, fireplace

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 AU$441
includes taxes & fees
29 Sept - 30 Sept
Scenic Getaway – Cozy Stay Near Golf & Trails
An Artistic retreat in the heart of downtown Galena
Interior

An Artistic retreat in the heart of downtown Galena

10.0 out of 10, Exceptional, (19)
"Very Cozy and quite stay. My wife and I enjoyed the peacefulness. "
The price is AU$337
includes taxes & fees
29 Sept - 30 Sept
An Artistic retreat in the heart of downtown Galena
One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Fridge, microwave, oven, stovetop

One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

10.0 out of 10, Exceptional, (12)
"Wonderful. The whole stay was great."
The price is AU$487
includes taxes & fees
29 Sept - 30 Sept
One Bedroom Apartment Overlooking Main Street with One Designated Parking Spot
Convenient & Spacious Downtown - Private Parking Included
Dining

Convenient & Spacious Downtown - Private Parking Included

10.0 out of 10, Exceptional, (194)
"We had a great time!"
Convenient & Spacious Downtown - Private Parking Included
Step Into a Soulful Hideaway In This Restored 1860s Country Church!
Interior

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 AU$365
includes taxes & fees
29 Sept - 30 Sept
Step Into a Soulful Hideaway In This Restored 1860s Country Church!
115#202 / Charming Downtown Dubuque Apartment
Interior

115#202 / Charming Downtown Dubuque Apartment

10.0 out of 10, Exceptional, (34)
"Very clean and comfortable! "
The price is AU$274
includes taxes & fees
5 Oct - 6 Oct
115#202 / Charming Downtown Dubuque Apartment
The Loft Suite Sleeps 10! Located overlooking Main Street in downtown Galena, IL
4 bedrooms, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (86)
"This place is amazing! We enjoyed our stay and will definitely recommend this loft to others!!"
The price is AU$1,077
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!
Fridge, microwave, oven, stovetop

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 AU$625
includes taxes & fees
29 Sept - 30 Sept
The Nook: Downtown Galena Cottage w/ hot tub & fire pit!
10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,
Microwave, oven, stovetop, dishwasher

10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

10.0 out of 10, Exceptional, (53)
"Very clean & tastfully decorated including antique touches (40s) with modern conveniences. "
10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Outdoor dining

Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.

2.0 star property
10.0 out of 10, Exceptional, (63)
"Beautiful home. Tons of space. Owners very helpful and excellent communication. Beds were very comfortable. View was awesome. Loved the grazing sheep."
The price is AU$877
includes taxes & fees
29 Sept - 30 Sept
Lighted Hot Tub w/ 4 BD/2.5 Baths and VERY close to town.
Briarstone Inn | Historic 7-Room Inn w/ Private Baths | Walk to Downtown Galena
Exterior

Briarstone Inn | Historic 7-Room Inn w/ Private Baths | Walk to Downtown Galena

10.0 out of 10, Exceptional, (4)
"Easy to access the room, wifi worked fine, glad to have parking. We appreciated the mini fridge in the room. "
Briarstone Inn | Historic 7-Room Inn w/ Private Baths | Walk to Downtown Galena
Winter Sports/Fireplace/Owner Club Access/Steps to Pool!
Indoor pool, outdoor pool

Winter Sports/Fireplace/Owner Club Access/Steps to Pool!

10.0 out of 10, Exceptional, (116)
"Summer getaway we both had a fantastic time! "
Winter Sports/Fireplace/Owner Club Access/Steps to Pool!
Moon River Cabins
Exterior

Moon River Cabins

3.0 star property
9.4 out of 10, Exceptional, (63)
"Loved the cabin, the local food, the scenery, and Matt and Pauline, the hosts were awesome. We'll be back!"
Moon River Cabins
Close to Galena, close to perfect. Premier get away. Three beautiful suites.
Exterior

Close to Galena, close to perfect. Premier get away. Three beautiful suites.

10.0 out of 10, Exceptional, (128)
"We had a great time. It was a close drive to Galena and still secluded to feel like we had a private getaway. We had deer come to drink by the creek, and a nice area for a bond fire. The home was beautiful and the owners were really nice. We would definitely book again."
Close to Galena, close to perfect. Premier get away. Three beautiful suites.
Galena Chalet & Garden: Nature Lovers Haven - Spectacular Lakeview
Terrace/patio

Galena Chalet & Garden: Nature Lovers Haven - Spectacular Lakeview

9.8 out of 10, Exceptional, (117)
"From the bicycles, to the fishing poles, to the nice warm bedding and blankets, this get-away was everything my family of seven needed. I am very grateful and thankful to the very thoughtful owners. "
Galena Chalet & Garden: Nature Lovers Haven - Spectacular Lakeview
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

Country Inn & Suites by Radisson, Dubuque, IA

Country Inn & Suites by Radisson, Dubuque, IA

10/10 Excellent
" Great place to stay. "
Kim 3-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Dubuque, IA

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, 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$274 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?

1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings: This holiday home rental outside of Key West is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 private garden and a selection of books.

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.