Vacation rentals in Lexington

4.97 out of 5 average rating, 139 reviews

An inflatable hot tub is lit in calming blue tones, surrounded by a bamboo privacy fence. Soft lighting from outdoor string bulbs enhances the evening ambiance, casting a gentle glow across the scene.

Home in Georgetown

Hot Tub Hide-A-Way | Horse Park 11min/Ark 30min

Entire Luxury Home Hide-A-Way In Down Town Georgetown, KY. Featuring An Inflatable Hot Tub, Purple Mattress (Queen), Additional Pull Out Couch Bed, 65in 4K TV. *Please No Shoes* Security System/Cameras (Door Bell & Back Yard) 5 min Walk To Local Restaurants/Bars - Local Feed, Galvins etc 12 Min KY Horse Park 30 Min Ark Encounter 🚨 Ask about our 3 bedroom home “The Retro” directly behind this listing for traveling friends / family who would like to book close but stay in separate homes. 🚨

4.97 out of 5 average rating, 107 reviews

Hot Tub | Great Location | Patio | Grill | Ping Po

Welcome to Sixgen Rentals' fully remodeled 5-bedroom, 2.5-bathroom custom home, thoughtfully curated with elegant decor and designed for groups. This spacious retreat offers a perfect blend of comfort and style. The first-floor master bedroom features an ensuite bathroom, providing a private sanctuary for relaxation. A convenient half bathroom is located off the kitchen for easy access. Stay entertained with smart TVs in the living room, master bedroom, and upstairs common area. Step outside t

4.94 out of 5 average rating, 179 reviews

Cottage in Harrodsburg

Paradise Cottage Enjoy lake Views and Lake Access!

Relax and enjoy! Great Herrington Lake views with lake access at Paradise Cottage! Peaceful private setting on one of the most beautiful parts of the lake. Located Mins from Multiple marinas, Bourbon trail, golf courses, Centre College/Asbury University events. 3 bedrooms, 5 beds, 2 full bathrooms, washer/dryer, newly remodeled. Sleeps 9. Includes: wi-fi, Hulu, 2 TVs, multiple decks, covered side patio, fire pit, gas grill, corn hole, kayaks and lily pad included with stay! Four parking spaces!

4.9 out of 5 average rating, 111 reviews

Home in Kentucky

The Stagg House on the Ky River

Nestled on the Kentucky River in Frankfort, KY, our peaceful retreat is surrounded by historic chestnut trees and wildlife like deer & cardinals. Just 5 miles from Buffalo Trace, 6.7 miles from Castle & Key, and 10 miles from Woodford Reserve and Whiskey Thief, it’s ideal for bourbon enthusiasts. Enjoy the river beach, backyard BBQs in summer, or cozy nights by the fireplace in winter—wood provided. Fully stocked kitchen, pet and family-friendly, with a secluded vibe yet close to the main road.

4.95 out of 5 average rating, 134 reviews

Bungalow in Danville

WildernessTrace BarrelProof *Hottub/firepit*

Whether you’re here for Centre College, the Bourbon Trail, or romantic getaway, you’ll find this 2 bedroom bungalow exceeds expectations. This home is conveniently located 2 1/2 blocks from Main St. so you can enjoy a nice walk to dinner to one of Danvilles restaurants. The home features a bourbon theme throughout with knick knacks from “The Mandalorian.” From barrel barrel head tables, staves, bourbon bottle lamps, and other bourbon distillery keepsakes, this house is first class throughout.

A spacious wooden deck is featured, surrounded by natural greenery and trees. Flower pots are displayed along the railing. A metal chair and a small table are positioned nearby, with a view of the lawn and hills in the background.

4.96 out of 5 average rating, 123 reviews

Pinnacle Lodge now w/ Brand New Hot Tub!

Quietly tucked in at the base of the Berea Pinnacles, the lodge offers up a scenic panoramic view of Davis Holler to the west. Looking for PEACE and QUIET? Look no further! Want to GET THE BLOOD PUMPING? 8400 acres of forest behind you, 9 miles of hiking trails, 1.2 miles from the lodge to the new John B. Stephenson, run, walk, bike trail. Additional 2.1 miles will get you into Berea, (Arts & Crafts Capital of Ky.) or 1.1 miles the other way to Indian Fort Mountain. Plenty "to do" or "not".

4.89 out of 5 average rating, 102 reviews

The entrance features a bright red door framed by two large flower pots filled with vibrant flowers. A clean pathway leads from the door to the sidewalk, and the facade is complemented by gray siding and wooden support beams.

Apartment in Lexington

Hidden Gem|One Bedroom Apt Downtown Lexington

Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

4.99 out of 5 average rating, 201 reviews

A serene waterfront view captures lush greenery along the bank, with a mix of trees providing shade. The calm water reflects a blue sky dotted with fluffy clouds, creating a tranquil atmosphere in the peaceful surrounding area.

Guesthouse in Lancaster

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

5 out of 5 average rating, 118 reviews

Apartment in Lexington

Swanky Boho - Downtown

Discover a trendy and stylish bohemian-inspired oasis. Immerse yourself in the vibrant and artistic ambiance, perfect for a memorable stay. Relax amidst eclectic decor, embrace the laid-back bohemian lifestyle, and indulge in the inviting atmosphere. With modern amenities and a prime downtown location near hip cafes, coffee shops, and nightlife, this is the ultimate choice for those seeking the boho-chic vibe. Unforgettable memories await in this captivating retreat.

A bright living area showcases hardwood floors and tall ceilings, complemented by natural light from multiple windows. Comfortable seating arrangements include a sofa and armchair, while an artistic wall decor piece adds color. A stylish light fixture hangs from the ceiling, enhancing the room's inviting ambiance.

4.95 out of 5 average rating, 619 reviews

Traveler's Cottage

Beautiful Craftsman style Bungalow in the heart of Berea. This two bedroom, two bath cottage has off street parking and is a short walk to Artisan Village/Old Town, galleries, shoppes, and cafes. Step into a beautiful, comfortable, clean environment featuring original art, hardwood floors, tall ceilings, queen sized beds. Basic TV channels, Roku, and High Speed Internet. Walk to Nightjar dinner, Native Bagel for breakfast or an early lunch. Great neighborhood!

4.93 out of 5 average rating, 129 reviews

A spacious bathroom features a large soaking tub centered in the room, complemented by two double sinks with adjacent mirrors. Light wood cabinetry and decorative floral wall art enhance the design. Neutral-toned flooring completes the relaxing atmosphere.

Home in McKee

Big Ridge Retreat, LLC

Big Ridge Retreat Come stay for a peaceful getaway in the mountains of Kentucky. This property is Located in Jackson County and nestled in the Daniel Boone National Forest. Located in the Sandsprings Community (approximately 10 miles from McKee and 10 miles from SandGap) -located 15 miles from S-Tree Recreational Area -located 17 miles from Flatlick Falls -located 22 miles from Irvine -lots of nearby hiking trails & ATV/four wheeling areas.

4.98 out of 5 average rating, 143 reviews

A small fishing pond is surrounded by bare trees, with a wooden dock featuring two chairs for seating. Colorful kayaks are secured to the shore, adding to the natural setting. Soft ripples are visible on the water's surface under a clear blue sky.

Cabin in Mount Eden

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Lexington vacation rentals

Self check-in

Monthly stays

Pet friendly

Laptop-friendly workspace

Gym

Stay near Lexington's top sights

Kentucky Horse Park175 locals recommend

Rupp Arena69 locals recommend

Keeneland170 locals recommend

Keeneland Race Track station3 locals recommend

West Sixth Brewing31 locals recommend

Carson's Food & Drink72 locals recommend

Dog friendly vacation rentals in Lexington

4.92 out of 5 average rating, 146 reviews

A paved drive winds through a grassy area, leading towards a fenced pasture. The landscape features trees and multiple outbuildings, with fences enclosing a spacious green field. Overcast skies provide a soft, diffused light across the serene setting.

Farm stay in Winchester

LenMar Farm Country Stay near Lexington KY

A spacious backyard is depicted with a well-maintained lawn featuring patches of sunlight filtering through surrounding trees. A patio area with seating can be seen, providing an inviting space for outdoor activities. The rear of the house is visible, showcasing its brick exterior.

4.88 out of 5 average rating, 163 reviews

Perfect for Traveling Professionals & Vacation!

4.94 out of 5 average rating, 171 reviews

Farm stay in Berea

Barn Cottage on Horse Farm. Breakfast included.

4.93 out of 5 average rating, 157 reviews

A spacious backyard is surrounded by a privacy fence, featuring green grass and several turquoise Adirondack chairs arranged around a small fire pit. A small wooden storage shed is visible in the back, while the cozy cottage is framed by mature trees.

Cottage in Lexington

Retro Mid-Century English Cottage

4.98 out of 5 average rating, 647 reviews

A charming, two-story building features a green roof and a distinctive cupola topped with a weather vane. Lush green grass surrounds the structure, with a white wooden fence along the pathway leading to the entrance. Trees and shrubs provide a sense of natural tranquility.

Farm stay in Springfield

The Getaway in Bourbon Country with Breakfast

4.96 out of 5 average rating, 253 reviews

A wooden dock extends into a serene pond, framed by lush greenery. The calm water reflects the surrounding trees under a softly cloudy sky. Two benches are positioned at the end of the dock, providing a peaceful spot to enjoy nature.

Cabin in Mount Sterling

The Honey Hut, Think of “ On Golden Pond"

4.82 out of 5 average rating, 564 reviews

A charming cabin exterior is surrounded by vibrant flowers blooming in a lush garden. Stone steps lead up through greenery to the front door, accentuated by window boxes with colorful plants. The cabin's rustic log section features a contrast with the lighter siding of the main structure.

Cabin in Lexington

Unique Stay - 1907 Log Cabin Near Kentucky River

An outdoor patio area is furnished with multiple chairs and a table, surrounded by greenery. The furniture is accented with blue cushions. A white picket fence and trees provide a natural backdrop, enhancing the peaceful ambiance of the space.

4.89 out of 5 average rating, 156 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

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House rentals in Lexington

A modern kitchen is visible, featuring light gray cabinetry and a central island with seating. Stainless steel appliances and a sleek hood above the stove are included. A dining area with a round table and elegant chandelier is situated in the background, illuminated by natural light.

4.98 out of 5 average rating, 143 reviews

Winterberry Drive Entire house

4.99 out of 5 average rating, 170 reviews

The charming brick exterior of the older home is framed by vibrant flower beds, featuring colorful blooms and lush greenery. A neatly manicured pathway leads to the welcoming front door, flanked by decorative shutters and a covered entryway.

Home in Richmond

Richmond Retreat by Raydarr Properties, LLC

A charming brick home with a gabled roof is framed by lush green trees and landscaped garden beds. A stone pathway leads to the front porch, where two white chairs invite relaxation. The welcoming facade features multiple windows allowing natural light.

4.96 out of 5 average rating, 224 reviews

3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown

4.99 out of 5 average rating, 104 reviews

A cozy living area features dark leather sofas paired with a wooden coffee table. A soft area rug lies beneath, while natural light enters through a nearby window. In the background, a dining space with bar stools and a well-equipped kitchen is visible.

Home in Richmond

Stylish Richmond Home. Near EKU and Downtown

A wall-mounted television is positioned in a well-lit living area, providing a view of an adjacent dining space. The entrance door is visible, leading into a cozy atmosphere with neutral-colored walls and modern decor, enhancing the overall sense of openness.

4.9 out of 5 average rating, 136 reviews

Few and Proud

4.89 out of 5 average rating, 184 reviews

The exterior of a charming brick house is showcased, featuring a well-maintained lawn with shrubs and flowering plants. A concrete driveway leads to the front entrance, complemented by a tasteful umbrella over the entryway, framed by trees and greenery.

Home in Richmond

Downtown Charm - Walk to EKU & Parks Near I-75

A bright living room showcases a green sofa flanked by two decorative pillows, with a round coffee table at its center. A ceiling fan hangs above, while curtains frame the windows, allowing natural light to illuminate the space. A television is mounted on the opposite wall.

4.89 out of 5 average rating, 132 reviews

Cheerful 2 bedroom home with parking on premises

The kitchen features a spacious layout with modern appliances, including a refrigerator and stove. White cabinetry contrasts with natural wood paneling. A large window allows natural light to fill the room, enhancing the granite countertops and laminate flooring.

4.92 out of 5 average rating, 123 reviews

Mid-Century Modern

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Dog friendly house rentals Lexington

An outdoor dining area features a round table surrounded by two chairs, with a large striped umbrella providing shade. The space is paved with stones and is bordered by greenery. A barbecue grill is visible in the background, enhancing the outdoor experience.

4.91 out of 5 average rating, 117 reviews

Lovely 3 Bdrm Home w/Free Parking Close to I-75

4.91 out of 5 average rating, 231 reviews

Churchill Cottage- Cheerful, Historic 1 Bedroom

The fenced-in backyard features a lush green lawn surrounded by trees and a wooden fence. A fire pit area is visible, with a stack of firewood in the corner and some flower beds adding color to the space.

4.97 out of 5 average rating, 375 reviews

Distillery District Diamond-pet friendly

4.93 out of 5 average rating, 163 reviews

A fenced grassy area is visible, where a group of sheep grazes peacefully among trees. The wooden fence provides a clear boundary around the pasture, enhancing the tranquil rural setting.

Home in Stanford

Stella's Country R & R

4.77 out of 5 average rating, 141 reviews

Home in Georgetown

Bluegrass get-away

A spacious brick home with a welcoming front porch features white railings and steps leading up to a mint green door. Lush greenery and well-maintained landscaping create a charming entrance, complemented by a bright blue sky above.

4.97 out of 5 average rating, 238 reviews

Bell Ct-133 N Ashland Ave-Horse Park-Bourbon Trail

4.82 out of 5 average rating, 139 reviews

A spacious porch is visible, lined with wooden rocking chairs and a few side tables. Colorful cushions add comfort to the seating. The porch overlooks a tranquil lake, with trees visible in the background and soft natural light illuminating the area.

Home in Lawrenceburg

Bourbon Trail Lakefront * Hot Tub * Sleeps 8

A welcoming front porch features two comfortable rocking chairs positioned under a hanging fern. Lush greenery and a landscaped area are visible, with a view of the lively street and nearby houses, providing an inviting outdoor space for relaxation.