Luxury Vacation Rentals in Kentucky

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 55 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kentucky

Williamstown Retreat

11 bedrooms•9 baths

•

~$180 less than other sites

Penthouse Grand Executive Suite. 6 Bed, 3 Bath with Rooftop Private Deck

6 bedrooms•3 baths

•

~$145 less than other sites

Historic District Hideaway. 4bed

4 bedrooms•2 baths

•

~$35 less than other sites

Bourbon Retreat: Luxe Downtown Condo w/ Spa Baths & Central Access

4 bedrooms•2 baths

•

~$40 less than other sites

Cadiz Lake Barkley

5 bedrooms•3.5 baths

•

~$95 less than other sites

Cadiz Barkley

4 bedrooms•2 baths

•

~$55 less than other sites

Hollyhock Suite 501: 4 bed/2 bath with soaking tub

4 bedrooms•2 baths

•

~$35 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$150 less than other sites

Welcome to Kentucky

Explore our handpicked luxury vacation rentals in Kentucky. With homes in Louisville, Rogers, and Frankfort, choose the setting that fits your plans, from city energy to quiet countryside.

Every stay looks just like the photos, with pristine housekeeping, ultra fast WiFi, dedicated work setups, and 24/7 concierge support. Expect chef-ready kitchens, spa-like touches, and inspiring views, plus private gyms or pools in select homes.

Destinations in Kentucky

Louisville

Rogers

Frankfort

Available soon in Kentucky

Hollyhock Suite 303: 2 Bed/1 Bath

2 bedrooms•1 bath

•

New

~$30 less than other sites

Hollyhock Suite 302: 4 Bed/2 Bath

4 bedrooms•2 baths

•

New

~$35 less than other sites

Hollyhock Suite 301: 4 Bed/2 Bath

4 bedrooms•2 baths

•

New

~$35 less than other sites

Hollyhock Suite 313

5 bedrooms•2 baths

•

New

~$45 less than other sites

Hollyhock Room 312

1 bedroom•1 bath

•

New

~$10 less than other sites

Hollyhock Room 310

2 bedrooms•1 bath

•

New

~$25 less than other sites

Hollyhock Studio Room 309

1 bedroom•1 bath

•

New

~$10 less than other sites

Hollyhock Room 307

3 bedrooms•2 baths

•

New

~$30 less than other sites

Featured vacation rentals in Kentucky

Penthouse Grand Executive Suite. 6 Bed, 3 Bath with Rooftop Private Deck

6 bedrooms•3 baths

•

~$145 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$150 less than other sites

Highlights in Kentucky

Discover Kentucky's rich heritage through its legendary bourbon distilleries, historic horse racing tracks, and breathtaking natural wonders like Mammoth Cave.

Mammoth Cave National Park

Churchill Downs

Cumberland Falls State Resort Park

Red River Gorge Geological Area

Maker's Mark Distillery

Keeneland

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kentucky

Williamstown Retreat

11 bedrooms•9 baths

•

~$180 less than other sites

Penthouse Grand Executive Suite. 6 Bed, 3 Bath with Rooftop Private Deck

6 bedrooms•3 baths

•

~$145 less than other sites

Historic District Hideaway. 4bed

4 bedrooms•2 baths

•

~$35 less than other sites

Bourbon Retreat: Luxe Downtown Condo w/ Spa Baths & Central Access

4 bedrooms•2 baths

•

~$40 less than other sites

Cadiz Lake Barkley

5 bedrooms•3.5 baths

•

~$95 less than other sites

Cadiz Barkley

4 bedrooms•2 baths

•

~$55 less than other sites

Hollyhock Suite 501: 4 bed/2 bath with soaking tub

4 bedrooms•2 baths

•

~$35 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$150 less than other sites

View all homes

Most popular amenities for vacation rentals in Kentucky

More popular destinations in Kentucky

Other popular amenities & vacation types in Kentucky

Family vacation rentals in Kentucky

Large group vacation rentals in Kentucky

Pet-friendly vacation rentals in Kentucky

Hot tub vacation rentals in Kentucky

Discover more of Kentucky

Kentucky blends heritage and dramatic landscapes in a way that feels both refined and alive. In Louisville, riverside culture sets a sophisticated pace, while Frankfort brings stately architecture and intimate capital charm. Rogers opens the door to the Red River Gorge, with sandstone arches, forested valleys, and brilliant night skies.

From rolling horse country to winding scenic byways, the state rewards unhurried journeys and bold seasonal color. Tour storied distilleries, meet local makers, and tap into a creative music scene that hums year-round. This is why Wander's luxury vacation rentals in Kentucky are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Kentucky

Why should I book a Wander in Kentucky over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Kentucky delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Kentucky?

Some of our most popular vacation rentals in Kentucky include Wander Williamstown Retreat, Penthouse Grand Executive Suite. 6 Bed, 3 Bath with Rooftop Private Deck!, and Historic District Hideaway. 4bed. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Kentucky?

Wander offers 55 vacation rentals in Kentucky, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Kentucky?

You can check-in to Wander vacation rentals in Kentucky after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Kentucky have WiFi access?

Yes. Every Wander home in Kentucky has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.