Holiday Homes in Kentucky

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Kentucky

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Holiday home in Nicholasville

5.0 out of 5 average rating, 39 reviews

Stone & Cedar Lodge - pool, hot tub, fire pit, EV

Relax with the whole family at this peaceful country ranch in the heart of the Bluegrass. Located just outside of Lexington and only 12 miles from Keeneland. Sleeps 16 - 5 Bedrooms, 8 Beds, 3 Baths Solar heated pool is open April - September. All year: Hot tub and Sauna (Fall 2026) Play fort, swings and trampoline are big hit. Play a game of pool, basketball or corn hole. Enjoy quiet walks around the pond or roast marshmallows around a cozy campfire. Wheelchair access Level 2 EV charger.

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Guest favourite

Holiday home in Cadiz

4.9 out of 5 average rating, 136 reviews

Spacious Lakehouse w/ Hot Tub, Firepit & Game Room

This house is a very spacious, and a well kept luxury home. Enjoy your day on the lake and come back to a house surrounded by nature. This house was specifically designed to offer the most to our guest. FEATURES: - Full service kitchen - 4 Bedrooms with a pullout couch - Deck with table, lounge area, and grill - 3 Smart TVs - Fast Wifi - Hot Tub w/ powerful jets - Outdoor firepit - 2 Relaxing daybeds - Huge game room with foosball, skee-ball, connect-4, and big sectional for movies.

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Guest favourite

The entrance features a sleek black door with the number 121 prominently displayed. A decorative brass handle and a vintage-style lantern are visible, adding to the welcoming appearance. The brick wall surrounding the door complements the overall design.

Holiday home in Glasgow

5.0 out of 5 average rating, 14 reviews

The Wilbur - Stay in Historic Glasgow!

Great place to unwind with lots of space! Only about 20 minutes to Mammoth Cave, 15 minutes to Barren River Lake, 30 minutes to the Corvette Museum. Just off Glasgow's downtown square where you can walk to local restaurants and shops, hear local music, see a show at the Historic Plaza just out your back door, attend a church service, visit the Cultural Center or the Farmer's Market, or just enjoy the church bells. Whatever you're in town for, we hope you'll choose to stay with us!

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Guest favourite

Holiday home in Lewisburg

4.93 out of 5 average rating, 27 reviews

Lake Shore home on water with private boat dock

Boasting best views of Lake Malone. A Shore Thing has lots to offer for families, couples, individuals or Hunters wanting a relaxing vacation. Right on water, private boat dock. Room to park your boat trailer on lot across street. Comes equipped with new kitchen appliances that the chef of the group will love. Lounge around the spacious porch while enjoying lake views w/ unique rock formations. 3 comfy bedrooms with a renovated bathroom shower. Lake has 788 acres to explore

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Top Guest favourite

The rear view of the house features a spacious patio area, complete with a fire pit surrounded by wicker chairs. Large windows provide ample natural light to the main living area above, enhancing the connection to the outdoors.

Holiday home in Gilbertsville

5.0 out of 5 average rating, 68 reviews

Little Bear Lodge

Kick back and relax in this calm, stylish space. Luxury farm retreat on 25 acres -partially wooded - stunning farm house - newly remodeled - just minutes away from Ky Lake/LBL/recreation. Sleeps 12 people comfortably- 3 large screen TV's. Enjoy the peace and quite of country living-breathe the fresh air and enjoy your coffee on the front porch-large parking area for autos/boats/trailers. Lots of deer/turkey/amazing songbirds. 10 minutes from great restaurants and grocery.

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Superhost

A serene view of a quiet creek is presented, with lush greenery lining the banks. A boat is docked at a wooden pier, providing access to the water. Sunlight filters through the trees, casting dappled light on the water's surface.

Holiday home in Prospect

4.82 out of 5 average rating, 74 reviews

Harrods Hideaway waterfront stay above the tavern

If you love the nightlife and water we have the place for you! It has a beautiful back deck overlooking the creek. Boat docks are available at no extra charge. We are right upstairs from Harrods Creek Tavern, which is a great place to hang out with the locals. Music is heard until late at night and you can play a game of pool, darts, scratchoffs, and we now have skilled games. You can enjoy a large selection of spirits and we even have food available from 11am-2am.

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Guest favourite

Holiday home in Somerset

4.94 out of 5 average rating, 47 reviews

Lake Cumberland Retreat #1 near Somerset and Ramps

Enjoy your time sitting on the large screened in porch or around a campfire when not on the lake. Don't be surprised to see deer or turkeys with your morning coffee and hear the boats on the lake. Have a Mobile Home with 2 bedrooms (1 king, 1 full, and queen couch bed). Property has a full size kitchen, laundry, WIFI, AC and boat parking. Dog Friendly (2 dog limit) Please let owner know if you are planning on bringing a boat.

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Superhost

A spacious kitchen features wooden cabinets and a granite countertop island. Four wooden dining chairs surround a rectangular table. A door leads outside, and natural light enters through two windows dressed with light curtains.

Holiday home in Owensboro

4.88 out of 5 average rating, 160 reviews

The little big cozy house

The little big cozy house offers you a place where you can relax and feel at home. a spacious kitchen with all the necessary elements such as The 3 bedrooms ,that invite you to rest with very suitable beds For you to spend a magnificent and comfortable night. The patio is a space where you can enjoy a grill surrounded by family or friends. This house is an excellent location that gives you quick access to any part of owensboro.

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The historical house features a brick façade with large windows framed by dark shutters. Lush greenery surrounds the property, providing shade and depth. A spacious gravel driveway leads to the entrance, inviting guests to explore the charm of this landmark property.

Holiday home in Louisville

4.78 out of 5 average rating, 36 reviews

Historical Mansion 7BD Vacation Home in Derby City

Stay in a historic landmark listed on the National Register of Historic Places and recognized by the Kentucky Heritage Council. This fully updated home sits on 7 private acres with a pond, outdoor space, and a private entrance. Perfect for family getaways or group stays. Enjoy peace and privacy while being just minutes from dining, shopping, and local attractions. A rare blend of history, comfort, and convenience.

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Guest favourite

A serene winter landscape showcases a blanket of snow covering the ground. Leafless trees stand next to a gently frozen lake, contributing to the tranquil ambiance. A home is partially visible in the background, surrounded by a peaceful forest setting.

Holiday home in Tompkinsville

4.89 out of 5 average rating, 45 reviews

Unique lakeside vacation home in Tompkinsville

This unique lakeside vacation home is located near Old Mulkey Meetinghouse State Historic Shrine and features 4 bedrooms, 2.5 baths. The open floor plan is decorated with Monroe County history and artwork and features 8 beds which can sleep up to 13 persons. Enjoy a walk along the lake's bank, kayak your afternoons away and enjoy the peaceful tranquility of small-town life.

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Top Guest favourite

Holiday home in Williamstown

5.0 out of 5 average rating, 64 reviews

Twin Peaks memories are made here!

Great fun for everyone to enjoy lake activities! From sunrise coffee to sunset wine! Best views on lake! Swimming, floating in lake sunbathing,grilling,relaxing vacation! Step out of the Aframe step into the lake! Lots of parking! We are 3 and 1/2 miles from the ARK! Great fishing off the docks! From dusk to dawn magic happens here! Come make your own memories!

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Guest favourite

A vibrant mural depicting mountains and a sun creates a striking backdrop. A cozy seating area is featured in front, with a teal couch contrasted against a wooden floor. A stylish lamp adds a touch of warmth to the space.

Holiday home in Prestonsburg

4.96 out of 5 average rating, 189 reviews

The Burg

Enjoy local venues, The MAC, Planetarium, Jenny Wiley Lake, 1620 Distilling Company, hiking, biking, wildlife, local artisans and crafts. Home to Loretta Lynn's, Butcher Holler. Civil War History. Close to downtown shopping, walking distance to dining, coffee shops, and bakery. There are 2 rather short flights of stairs to access this unit.

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