Key West Holiday Rentals

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Holiday Rentals in Key West

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

9.6 out of 10, Exceptional, (25)
"Decent "
The price is NZ$487
includes taxes & fees
24 July - 25 July
1850 Cabin Home, Waterfall, Family Getaway, Corporate Party, Weddings

Cozy little getaway in the heart of the city. A short drive from Galena.

9.6 out of 10, Exceptional, (169)
"Sure beats a motel!"
Cozy little getaway in the heart of the city. A short drive from Galena.

Private 3BR/2BA Territory Home Nestled in the Trees

10.0 out of 10, Exceptional, (115)
"Great place for a visit to Galena!!! Clubhouse was great for kids!! "
The price is NZ$510
includes taxes & fees
10 Aug - 11 Aug
Private 3BR/2BA Territory Home Nestled in the Trees

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

10.0 out of 10, Exceptional, (42)
"Such a great find! Perfect location. Fun and unique property. Had everything we needed."
10 Min Walk to Main St., Updated 1840s Historic Home, Stocked Kitchen, W/D,

Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside

10.0 out of 10, Exceptional, (2)
"We were fortunate to be the very first guests at this adorable property!! The owners did a fantastic job renovating the old schoolhouse, blending historic charm with cozy, modern comforts. The décor creates such a welcoming atmosphere, and the home is stocked with everything you could possibly need to make your stay enjoyable.Thoughtful touches like a welcome letter, festive 4th of July bling, baskets of goodies, and cold waters waiting in the fridge were above and beyond—small extras that made...
The price is NZ$773
includes taxes & fees
24 July - 25 July
Charming BRAND NEW 2-bedroom house with Hottub in lovely Galena countryside

Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

9.8 out of 10, Exceptional, (116)
"Loved my stay here. Very clean, perfect for a weekend getaway. "
Cozy 1 Bedroom, 2 Bath Townhome in the Galena Territory

JUST BUILT! Timber Ranch The Rocky Mountain Spirit Meets Galena, IL 4BR/4+BA

10.0 out of 10, Exceptional, (2)
"I’ve stayed at a lot of rental places in my life but nothing came close to the Timber Ranch. Great communication with the owners, perfect location, and had a ton of space for the bachelor party. Highly recommend staying here! "
JUST BUILT! Timber Ranch The Rocky Mountain Spirit Meets Galena, IL 4BR/4+BA

Welcome to your Galena Get Away!!!

10.0 out of 10, Exceptional, (267)
"Plenty of room. Used the grill for meals. Small but useful kitchen. Easy access to the owners club. Will stay here again. "
Welcome to your Galena Get Away!!!

At the Edge of the Woods ~ Dog Friendly & Family Friendly

10.0 out of 10, Exceptional, (75)
"We had a great time and lots fun things to do around Galena Territory. House had a great set up and the enclosed porch overlooking the woods was a great place to grill and relax."
At the Edge of the Woods ~ Dog Friendly & Family Friendly

Scenic Getaway – Cozy Stay Near Golf & Trails

10.0 out of 10, Exceptional, (58)
"Great stay in a peaceful location. The home was in a nice, quiet area but still conveniently close to town. It was clean, comfortable, and had everything we needed for a relaxing stay. Would definitely recommend and stay here again!"
The price is NZ$477
includes taxes & fees
6 Aug - 7 Aug
Scenic Getaway – Cozy Stay Near Golf & Trails

An Artistic retreat in the heart of downtown Galena

10.0 out of 10, Exceptional, (13)
"Very Cozy and quite stay. My wife and I enjoyed the peacefulness. "
The price is NZ$362
includes taxes & fees
28 July - 29 July
An Artistic retreat in the heart of downtown Galena

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

The price is NZ$362
includes taxes & fees
27 July - 28 July
Charming 1-bedroom apartment in fabulous Downtown Galena with WiFi, AC

Cozy Hideaway with 3 Season Lake View

9.4 out of 10, Exceptional, (13)
"A beautiful cottage in a beautiful community! Everything was perfect for our Honeymoon weekend. Will definitely be there again!"
Cozy Hideaway with 3 Season Lake View

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

10.0 out of 10, Exceptional, (122)
"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.

Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi

9.2 out of 10, Wonderful, (62)
"The condo was very clean. All the beds were very uncomfortable, owner should invest in better mattresses. Condo was advertised as golf course view and our unit had no visible golf course views. Also ads showed parking right in front of the unit and our parking was up on a hill with two sets of stairs to haul all our things. "
Two Bedroom + LOFT, Cozy Golf View Villa, Fast WiFi

2 Bedroom, 2 bath home in The Galena Territory. Close to Eagle Ridge Resort

9.4 out of 10, Exceptional, (178)
"We enjoyed our visit"
2 Bedroom, 2 bath home in The Galena Territory. Close to Eagle Ridge Resort

Galena Luxury Rental Suite 200 Downtown w/parking

9.6 out of 10, Exceptional, (18)
"Very clean, great location. Would stay here again the next time we’re in the area."
Galena Luxury Rental Suite 200 Downtown w/parking

Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

10.0 out of 10, Exceptional, (3)
"Cute place and a great location. The hosts were very kind and let us check in early. It comes with a parking space too which was very convenient. I would definitely stay again!"
The price is NZ$720
includes taxes & fees
24 July - 25 July
Two Bedroom Apartment Overlooking Main Street with One Designated Parking Spot

Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town

9.8 out of 10, Exceptional, (16)
"Very clean and comfortable."
The price is NZ$532
includes taxes & fees
20 Aug - 21 Aug
Worry Free! / Fireplace / Clean + Quiet / Close to Indoor Pool, Trails, Town

Driftless Get Away

9.8 out of 10, Exceptional, (80)
"Very comfortable. Great location. "
Driftless Get Away
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

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 Mines of Spain State Recreation Area. In the wider area, you’ll find Crystal Lake Cave 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.