House holiday rentals in Lexington

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

4.96 out of 5 average rating, 404 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

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A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

4.93 out of 5 average rating, 932 reviews

Updated 1910 charm! Walk to Rupp/near Keeneland!

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

LocationFamilyLayout

A warm living area is highlighted by natural light from a front window. A cozy seating arrangement is set against a decorative fireplace. A wooden dining table stands nearby, with greenery and décor enhancing the space. A wooden ladder and plants add character to the room.

4.99 out of 5 average rating, 191 reviews

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

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4.93 out of 5 average rating, 165 reviews

Charming Home in Southland – Cozy & Spacious!

Welcome to this charming 4-bed, 2-bath home in Lexington's Southland Drive area. Perfect for families, groups, or business travelers, it's within walking distance to local restaurants and cafes. Minutes away, explore downtown Lexington’s rich history, visit the iconic Keeneland Racecourse, or tour the University of Kentucky. Outdoor enthusiasts will love nearby parks and trails, while Bourbon fans can discover local distilleries. This home is your ideal gateway to Lexington’s finest attractions!

ValueFamilyLaundry

4.99 out of 5 average rating, 133 reviews

The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.

Home in Frankfort

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

LocationFamilyGetting around

A spiral slide in vibrant burgundy extends from a wooden ceiling to the floor, creating a playful focal point in the space. Natural light filters through windows, illuminating the smooth wood flooring and surrounding area, which includes modern appliances and a stylish chair.

4.96 out of 5 average rating, 146 reviews

Maryland Luxury Downtown Manor

Our Maryland Manor was designed to be a true Home away from Home.. with an indoor Slide for extra Fun!! Grab coffee, sit in the sleeping porch and slide back down for a refill! A creative, historic oasis perfect for exploring downtown Lexington! Located Downtown, Minutes walk to Rupp, Dining, Galleries, Night Life and Next Door to the Apiary. Paired with Off Street Parking and a large backyard, this stylish place to stay is perfect for group trips. We can’t wait to welcome you to our Home!

LocationFamilyCheckout

The exterior of a two-story brick home is captured on a clear day, showcasing a sloped roof and large windows. An attached two-car garage is present at the front, surrounded by well-maintained landscaping and trees displaying autumn foliage.

4.98 out of 5 average rating, 124 reviews

MiCasa Es SuCasa - Tranquil Bluegrass Home

Clean and convenient 3 bedroom 2.5 bath home close to everything that you want in Lexington: 9 minutes to Horsepark; 15 minutes to downtown; 14 minutes to Airport and Keeneland Racetrack; 17 minutes to UK. Come and enjoy all that central Kentucky has to offer in this beautiful well appointed home. Located in an upscale neighborhood on a quiet cul-de-sac. Pets are encouraged. Attached two car garage. Easily and comfortably sleeps up to 8 people. Includes a full kitchen with all essentials.

FamilyValueLaundry

4.98 out of 5 average rating, 506 reviews

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

LocationFamilyHeating

A spacious living area features a comfortable grey sofa and armchairs arranged around a white coffee table. Light-colored curtains frame large windows, while a dining area with a dark wood table is visible in the background, alongside a modern kitchen with stainless steel appliances.

4.89 out of 5 average rating, 255 reviews

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

ValueFamilyGetting around

A bright living area features a light-colored sofa and two beige armchairs arranged around a glass coffee table. Natural light enters through two large windows, complemented by white curtains. A green front door adds a pop of color to the welcoming space.

4.98 out of 5 average rating, 184 reviews

The Rosewood Cottage of Lexington I Elegant & Cozy

Rosewood Cottage is one of Lexington's most unique and charming properties. Located steps away from Ashland Park and under 5 minutes to Downtown, this picturesque 1920's cottage offers history, charm and elegance in one extraordinary home. Relax with a bubble bath & champagne while reading a book from the host's curated collection, roast s'mores by the backyard firepit, or dive into some southern cooking in the newly renovated kitchen. This home away from home is not one to miss.

FamilyLocationSleep quality

The living room showcases a combination of blue and brown sofas with colorful throw pillows, centered around a natural gas fireplace. A Smart TV is mounted above the mantel. Open space leads to a kitchen with a breakfast bar and dining area in the background.

4.91 out of 5 average rating, 145 reviews

Bluegrass Retreat with Hot Tub! Near Horse Park!

Unbeatable location for the best experiences in Central Kentucky! You will be close to the Kentucky Horse Park, historic Keeneland, downtown Midway, the Ark Encounter, Rupp Arena and downtown Lexington, UK sporting events, golf courses, and several highly desirable distilleries including our personal favorite - Buffalo Trace Distillery. There are so many great restaurants nearby! Be sure to check out our Guidebook when you book a stay at Bluegrass Retreat.

FamilyLocationDecor

A living room is filled with natural light, featuring a mix of comfortable seating options, including a leather couch and a fabric sofa. A coffee table holds magazines, and a TV is positioned against a wall. Nearby bookshelves display books and decorative items.

4.92 out of 5 average rating, 585 reviews

Castlewood Park Cottage

Welcome to your home‑away‑from‑home in this charming cottage tucked into a peaceful neighborhood just north of downtown Lexington. Thoughtfully designed for comfort and relaxation, this inviting space offers the perfect blend of quiet retreat and all the essentials you need for a restful stay with easy access to the city’s best dining, culture, and attractions.

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Popular amenities for house rentals in Lexington

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

4.97 out of 5 average rating, 153 reviews

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

LocationValueParks

4.99 out of 5 average rating, 108 reviews

A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.

Home in Midway

The Bees Wing

LocationFamilyCleanliness

A large, in-ground pool reflects the surroundings, framed by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a spacious deck attached to the house. The inviting outdoor space is ideal for relaxation and enjoyment.

4.83 out of 5 average rating, 145 reviews

4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!

FamilyValueGrill

4.91 out of 5 average rating, 212 reviews

Pool | Hot Tub | Covered Porch | Patio | Game Room

LocationFamilyIndoor spaces

4.99 out of 5 average rating, 105 reviews

Close to Everything! Beautiful two-story home

FamilyValueCheck-in

A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.

4.98 out of 5 average rating, 174 reviews

POOL/ game room! 8 beds 2 baths 3 bedrooms

LocationValueLayout

4.82 out of 5 average rating, 180 reviews

A hot tub is illuminated with blue LED lights, creating a serene atmosphere in a cozy corner. The tub features multiple seating positions and control buttons for easy adjustments. A wooden bench is placed nearby, offering a place to relax before or after use.

Home in Lawrenceburg

Restful Bourbon Trail Lodge with Pool and Hot Tub

FamilyLocationOutdoor spaces

4.9 out of 5 average rating, 48 reviews

A refreshing inground pool is set against a backdrop of rolling hills and greenery. Lounge chairs under umbrellas provide seating options. Decorative pink flowers in planters frame the pool area, while large inflatable floats add a playful touch to the water.

Home in Versailles

Sugar Hill Farm-Gorgeous Farmhouse w FirePit

FamilyLocationOutdoor spaces

Weekly house rentals

4.96 out of 5 average rating, 203 reviews

A serene outdoor area is highlighted by a covered patio featuring comfortable seating and a hot tub. Ambient lighting creates a cozy atmosphere, while lush green grass and carefully placed shrubs enhance the inviting outdoor space.

Home in Georgetown

The Luxe/Hot Tub/12min to Horse Park/30 Min to Ark

ValueLocationEV charging

A cozy living area showcases a leather couch and a plush chair, inviting relaxation. A wooden coffee table sits in the center, while natural light filters through the windows with blinds. A minimalist artwork hangs on the green accent wall, enhancing the overall aesthetic.

4.88 out of 5 average rating, 203 reviews

El Retro- Mid Century Ranch near Horse Park & Rupp

ValueLocationLong stay

A cozy living area displays a comfortable sofa, complemented by a light gray wall. A coffee table sits centrally, with a television mounted on a light wood stand. Natural light filters through two large windows, dressed with blue curtains.

4.89 out of 5 average rating, 122 reviews

Cozy 1-bedroom in Lexington

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A charming exterior of a single-story home is displayed, featuring dark blue siding and a welcoming front porch. Neatly trimmed shrubs frame the entrance, and an American flag hangs by the door. Sunlight bathes the scene, highlighting the surrounding greenery.

4.98 out of 5 average rating, 186 reviews

Cheerful and Cozy in the Heart of Chevy Chase!

ValueFamilyCheckout

A spacious two-story house features a charming front porch framed by wooden columns. The facade combines gray siding with a warm shingle roof and black shutters. Lush greenery is planted along the pathway leading to the welcoming front door.

4.97 out of 5 average rating, 161 reviews

Kentucky Comfort Near all the best REG#150830301

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The exterior of a charming ranch home is displayed, featuring a brick facade and a two-car garage. A well-maintained driveway leads to the entrance, framed by landscaping including shrubs and small flower beds. Sunlight brightens the scene with a clear blue sky above.

4.93 out of 5 average rating, 149 reviews

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

LocationValueBack garden

4.85 out of 5 average rating, 123 reviews

Home in Chevy Chase

*Chevy Chase TH (1) mile to UK | EV Charging*

LocationFamilyDecor

A spacious living area is highlighted by two dark sofas positioned around a wooden coffee table. A light fixture hangs from the ceiling, while a textured rug covers the floor. An open kitchen and dining area are visible through the doorway, showcasing a blend of modern and rustic design.

4.94 out of 5 average rating, 366 reviews

4br/3ba/5bed Home, Walk to Chevy Chase/UK/downtown

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Private house rentals

The kitchen features smooth beige cabinetry and granite countertops, complemented by a stylish tile backsplash. Modern stainless steel appliances, including a refrigerator, oven, and microwave, are present. Ample storage is provided with numerous cabinets, creating a functional cooking space.

4.95 out of 5 average rating, 235 reviews

Southern Hospitality! Best location close to UK!

LocationValueAmenities

A modern living room features a large flat-screen TV mounted on the wall above an electric fireplace. Two comfortable black sofas with yellow accents surround a circular wooden coffee table, positioned on a patterned area rug. The open kitchen is visible in the background.

4.82 out of 5 average rating, 109 reviews

Beautiful house 3BR/2BTH

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The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.

4.98 out of 5 average rating, 152 reviews

Newly renovated upscale house with high ceilings

FamilyValueBack garden

A historic brick duplex features a welcoming front porch with white railings and steps leading to the entrance. Lush greenery borders the walkway, and large windows reflect natural light, enhancing the home's classic architectural details.

4.97 out of 5 average rating, 263 reviews

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

FamilyLocationAccess

5.0 out of 5 average rating, 150 reviews

The home is nestled amidst a backdrop of gently rolling hills, framed by trees showcasing autumn foliage. A welcoming front porch is visible, accompanied by a small staircase leading to the entrance. Large windows allow natural light to filter into the living space.

Home in Versailles

Birdsong Valley on Bourbon Trail

FamilyValueAmenities

The kitchen showcases wooden cabinetry extending to the ceiling, paired with a dark granite countertop. Stainless steel appliances, including a microwave and oven, are featured. The backsplash is adorned with a mosaic pattern, and ample lighting illuminates the space from recessed ceiling fixtures.

4.99 out of 5 average rating, 117 reviews

HORSES, WILDCATS & BOURBON

FamilyLocationAccuracy

4.95 out of 5 average rating, 247 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

ValueLocationDecor

The exterior of the home is characterized by a stone façade and a welcoming covered porch. Lush green lawn and trees frame the house, creating a pleasant environment. Windows are symmetrically arranged, allowing for natural light, while flower planters add a touch of color at the entrance.