Condo vacation rentals in Kentucky

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Top-rated condo rentals in Kentucky

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Guest favorite

Condo in Louisville

4.96 out of 5 average rating, 209 reviews

The Garret in Butchertown's Bed N Brothel

Soak up the sunlight in this 1000sf penthouse of this retired historic 19th-century Butchertown brothel. Blanketed in natural light, this 3rd story Garret has the feel of a sun-bleached tree-top tent, and is ideal for a couple's retreat or a friends' outing. A few of the city’s top restaurants and bars are less than a block walk away. Endless other drinking, shopping, and attractions are nearby in Nulu, Frankfort Ave, and the Waterfront. & don’t miss our other listing, the Hilltop Hideaway!

Jan 21 – 28

R2,363 ZAR per night

Guest favorite

Condo in Elizabethtown

4.97 out of 5 average rating, 147 reviews

Lavish Downtown ROOFTOP Condo - Sleeps 6

Your whole group will enjoy easy access to everything from this beautiful centrally located condo in downtown Elizabethtown. Be right in the middle of all the action with new restaurants, bars and shopping. Condo is 1 bedroom, 1 bath but can sleep up to 6. Bedroom has queen size bed, living room has pull out bed in couch and there is also a full size murphy bed. Fully equipped kitchen and a pool table! The rooftop offers a great view of the city that you can enjoy while relaxing in the hammock.

Dec 20 – 27

R3,425 ZAR per night

Guest favorite

Condo in Louisville

4.98 out of 5 average rating, 166 reviews

★ Victorian Louisville ★ 1000 sqft Glassworks Loft

Fresh, modern and sleek 950 SqFt loft style unit. Constructed inside the historic glassworks building, this condo is one of the most unique in the city. You will be amazed by the style, but also the amenities nearby. With a 2 minute walk to Museum row, and a 7 minute walk whiskey row, the convention center, the YUM! center and the center for the arts - everything is nearby. With Wifi, Netflix, and Hulu provided you have everything you need. The perfect spot for relaxing or going out on the town.

Oct 18 – 25

R2,838 ZAR per night

Guest favorite

Condo in Paducah

4.96 out of 5 average rating, 524 reviews

Downtown Loft - Cozy studio in The Foxbriar

Home of the former Foxbriar Inn, this condo is located inside a beautiful historic building. This space is great for your weekend away or a longer term stay. Exposed brick and high ceilings make it a charming and cozy experience. Enjoy the perks of walking to lots of great restaurants, specialty shopping and boutiques. We are just seconds from a beautiful stroll along the River. Bakery and coffee shop underneath. Enjoy brunch on the weekends or a sweet treat anytime in the week.

Oct 2 – 9

R2,565 ZAR per night

Guest favorite

Condo in Paducah

4.97 out of 5 average rating, 113 reviews

Stylish Condo on Broadway

Experience the beauty of downtown Paducah at our stunning historic condo. Curated by local interior designer, this space boasts stylish design elements combined with modern amenities to create a truly unique stay. You'll love the large windows, soaring ceilings, and original hardwood floors. You'll also have 24 hour access to a state-of-the-art gym. With its prime location overlooking Broadway, you'll be just steps away from top dining, shopping, and entertainment options.

Nov 22 – 29

R2,935 ZAR per night

Guest favorite

Condo in Louisville

4.98 out of 5 average rating, 117 reviews

Charming Penthouse/Rooftop Patio/Downtown

Unwind and enjoy sweeping river views on the rooftop patio while staying in this private 5th floor Penthouse apartment. Intentionally designed and decorated. Features include: a full upscale kitchen, open concept living and dining area, cozy King bed, large plush bathroom, and laundry in the suite. Whether visiting for work or pleasure, this spacious urban suite is located on The Bourbon Trail and within walking distance to Louisville's most popular venues!

Aug 22 – 29

R5,601 ZAR per night

Guest favorite

Condo in Shelbyville

4.93 out of 5 average rating, 123 reviews

Horses, Bourbon, and More .... Shelbyville Condo

Beautiful condo duplex features 2 bedrooms / 2 full bathrooms, light open floor plan, private entrance with parking at the door.. Close to shopping, expressway, local wineries, bourbon distilleries, horse farms and much more!! Fully Furnished including linens, towels, dishes and more! Work or travel, we welcome you to your home away from home! Located Close to shopping, farms, local interests and I64.. 25 minutes to Louisville, 45 minutes to Lexington.

Sep 18 – 25

R2,050 ZAR per night

Guest favorite

Condo in Frankfort

4.97 out of 5 average rating, 120 reviews

Bourbon Trail R&R

Our condo is conveniently located in walking distance of the capital. Peaceful neighborhood with wide streets. PLEASE NOTE: The condo is located up two flights of stairs. Kitchen is completely equipped with everything you’ll need to enjoy your stay, including a K-cup coffee machine. (Just bring your K-cups) Frankfort is a vibrant town located in the heart of the Bourbon Trail. 1 small dog may be permitted with pre-approval - $75/stay

Jul 15 – 22

R2,584 ZAR per night

Guest favorite

Condo in Paducah

5.0 out of 5 average rating, 106 reviews

Luxury 2 BR 2 Bath Downtown Double Condo

This luxury 2 bed 2 bath 1900 square foot double condo is centrally located in downtown Paducah across the street from Maiden Alley, the Carson Center, and the Market House Theater. Built in 1870, “The Parlour” is a historic property that has been renovated with modern touches while preserving yesterday’s charm. Guests can walk to many local attractions and Paducah’s best bars, shops, and restaurants.

Jan 8 – 15

R3,623 ZAR per night

Guest favorite

Condo in Louisville

4.96 out of 5 average rating, 223 reviews

The Highlands Modern Condo

Our brand new renovated 1BR condo is located in a famous Highlands' neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Centre, Center for the Art, Downtown Distilleries, Paristown, Nulu and Germantown area, 12 minutes from Airport. Walking distance to many great restaurants, bars, shops, and parks.

Dec 30 – Jan 6

R1,935 ZAR per night

Guest favorite

Condo in Elizabethtown

4.99 out of 5 average rating, 189 reviews

*New* Kentucky Industrial Bourbon Downtown Loft!

Updated Listing!* The updated industrial downtown loft welcomes you in with a stunning entry staircase, topped with a unique hand railing with a large open living area & wood flooring throughout. All walking distance to downtown activities. Enjoy the coffee shop just below you along with the many boutiques, yoga, restaurants, bourbon trail & more!

Jun 27 – Jul 4

R3,054 ZAR per night

Guest favorite

Condo in Louisville

4.99 out of 5 average rating, 277 reviews

Louisville's Best Neighborhood Gallery Square NuLu

One bedroom contemporary condo with plenty of amenities including TV in bedroom and living room, fully furnished kitchen, washer/dryer, ironing board, walk-in closet and secured parking for one vehicle. Located in the trendy NuLu area of downtown Louisville with bars, shops and numerous restaurants that are just minutes away from the front door.

May 29 – Jun 3

R2,781 ZAR per night