Luxury Vacation Rentals for Large Groups 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 22 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Kentucky

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

6 bedrooms•3 baths

•

~$80 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$145 less than other sites

Cadiz Lake Barkley

5 bedrooms•3.5 baths

•

~$80 less than other sites

Cadiz Barkley

4 bedrooms•2 baths

•

~$50 less than other sites

Williamstown Retreat

11 bedrooms•9 baths

•

~$160 less than other sites

Luxury City Escape. Peaceful Retreat by Hollyhock

4 bedrooms•3 baths

•

~$60 less than other sites

Downtown Mansion-1.5 Miles to Buffalo Trace

5 bedrooms•2.5 baths

•

~$140 less than other sites

The Aristides Suite: 8 beds/4 bath

8 bedrooms•4 baths

•

New

~$95 less than other sites

Welcome to your large group retreat in Kentucky

Bring everyone together in style with luxury large-group vacation rentals in Kentucky. Set in Louisville and Frankfort, our collection features expansive, design-forward homes made for reunions, retreats, and milestone celebrations. Every home looks exactly like the photos and pairs hotel polish with the privacy of a whole home.

Spread out across generous living areas, multiple bedroom suites, and indoor-outdoor gathering spaces. Expect ultra fast WiFi, pristine cleaning, and 24/7 concierge support, along with hotel-grade amenities like gyms and pools. Pro-grade kitchens and long dining tables keep meals easy, while smart entertainment makes downtime effortless for the entire crew.

Available soon in Kentucky

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

6 bedrooms•3 baths

•

~$80 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$145 less than other sites

Cadiz Lake Barkley

5 bedrooms•3.5 baths

•

~$80 less than other sites

Cadiz Barkley

4 bedrooms•2 baths

•

~$50 less than other sites

Luxury City Escape. Peaceful Retreat by Hollyhock

4 bedrooms•3 baths

•

~$60 less than other sites

Downtown Mansion-1.5 Miles to Buffalo Trace

5 bedrooms•2.5 baths

•

~$140 less than other sites

The Aristides Suite: 8 beds/4 bath

8 bedrooms•4 baths

•

New

~$95 less than other sites

Hollyhock Suite 313

5 bedrooms•2 baths

•

New

~$40 less than other sites

Featured large group vacation rentals in Kentucky

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

6 bedrooms•3 baths

•

~$80 less than other sites

Highlights in Kentucky

Gather your group to experience Kentucky's legendary bourbon distilleries, historic horse venues, and massive underground wonders perfect for shared adventures.

Mammoth Cave National Park

Churchill Downs

Ark Encounter

Kentucky Horse Park

Louisville Mega Cavern

Maker's Mark Distillery

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

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

6 bedrooms•3 baths

•

~$80 less than other sites

The Churchill Suite 8 Beds/4 baths

8 bedrooms•4 baths

•

~$145 less than other sites

Cadiz Lake Barkley

5 bedrooms•3.5 baths

•

~$80 less than other sites

Cadiz Barkley

4 bedrooms•2 baths

•

~$50 less than other sites

Williamstown Retreat

11 bedrooms•9 baths

•

~$160 less than other sites

Luxury City Escape. Peaceful Retreat by Hollyhock

4 bedrooms•3 baths

•

~$60 less than other sites

Downtown Mansion-1.5 Miles to Buffalo Trace

5 bedrooms•2.5 baths

•

~$140 less than other sites

The Aristides Suite: 8 beds/4 bath

8 bedrooms•4 baths

•

New

~$95 less than other sites

View all homes

Most popular amenities for large group vacation rentals in Kentucky

Exercise equipment (1)

Pool table (3)

More popular large group destinations in Kentucky

Large group vacation rentals in Louisville

Large group vacation rentals in Frankfort

Other popular amenities & vacation types in Kentucky

Family vacation rentals in Kentucky

Pet-friendly vacation rentals in Kentucky

Hot tub vacation rentals in Kentucky

Discover more large groups activities in Kentucky

Kentucky welcomes groups with big horizons and distinctive character. Bluegrass hills, storied horse country, and a vibrant calendar of racing and events create an atmosphere you can feel. Louisville’s riverfront energy and Frankfort’s capital charm place culture, history, and green space within an easy drive.

Bourbon country invites unhurried tastings, while scenic byways lead to sandstone arches at Red River Gorge, sprawling lakes, and quiet valleys perfect for day trips. With live music, seasonal festivals, and endless room to roam, coordinating plans for every interest stays simple. This is why Wander’s luxury large-group vacation rentals in Kentucky are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Kentucky

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

Wander offers a level of consistency and quality you won’t find with most large group 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 large group vacation rentals in Kentucky?

Some of our most popular large group vacation rentals in Kentucky include Penthouse Grand Executive Suite. 6 Bed, 3 Bath with Rooftop Private Deck!, The Churchill Suite 8 Beds/4 baths, and Wander Cadiz Lake Barkley. 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 large group vacation rentals does Wander have available in Kentucky?

Wander offers 22 large group 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 large group vacation rentals in Kentucky?

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

Do Wander’s large group 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.