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, 408 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.

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, 196 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

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

4.94 out of 5 average rating, 170 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!

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.

4.99 out of 5 average rating, 128 reviews

Good times on Woodbine! Close to UK/Downtown.

Fully renovated home in the southland neighborhood which provides 4 bedrooms (2 kings, 2 queens) and 2 ½ baths. Additionally, the first floor offers a spacious living and dining room, den and a new kitchen which includes all the essentials to make your visit a pleasant one. Centrally located and minutes to downtown, UK Campus, Kroger Field, hospitals, and the Distillery District. Plus, it is just 10 minutes from historic Keeneland and the airport. Premises ID/Local Registration #15082967-1

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, 147 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!

4.98 out of 5 average rating, 511 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

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, 260 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!

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.

4.91 out of 5 average rating, 317 reviews

NoLi Bungalow w/ King Bed - Horse Park, Keeneland

Welcome to your Kentucky Home Amazing beds, modern kitchen, fast WIFI in a beautifully designed space located in the vibrant, artistic NoLi district. This up and coming neighborhood is located North of Limestone (NoLi) w/ delicious restaurants, bars, bakeries and coffee shops nearby. * Rupp Arena 3 miles * Keeneland Racetrack 9.5 miles * Kentucky Horse Park 11 miles * STR Reg #15071157-5 - Maximum occupants 4 - Guests are prohibited from allowing more than maximum occupancy *

5.0 out of 5 average rating, 120 reviews

Home in Lawrenceburg

Bourbon Speakeasy 6BR Estate · Hot Tub · Sleeps 14

Bourbon Trail Hideaway – Where Luxury Meets Fun Gather your favorite people and settle into this stunning 6-bedroom, 4.5-bath modern farmhouse, built for connection, comfort, and fun. With room for up to 14 guests, enjoy spacious living areas, relaxing spa amenities, and entertainment everyone will love. Whether you’re here for the Bourbon Trail or simply to unwind together, this home delivers an unforgettable stay. 🥃 Reserve your dates today and make it a trip to remember.

Superhost

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.

Popular amenities for Lexington house rentals

Kitchen

Wi-Fi

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!

Superhost

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!

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

4.99 out of 5 average rating, 106 reviews

Close to Everything! Beautiful two-story home

4.98 out of 5 average rating, 176 reviews

POOL/ game room! 8 beds 2 baths 3 bedrooms

4.82 out of 5 average rating, 181 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

4.94 out of 5 average rating, 81 reviews

Luxe Home w/htd. Pool+Hot Tub+Fire Pit+Brbn Trl

4.9 out of 5 average rating, 49 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

Weekly house rentals

A welcoming front porch features a solid door with an address number visible. A small, potted evergreen plant stands next to the door. A black chair with a red cushion is positioned nearby, alongside a geometric decorative table. The porch floor is finished in dark wood.

4.93 out of 5 average rating, 470 reviews

Big Rock Cottage

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, 153 reviews

Newly renovated upscale house with high ceilings

Superhost

Home in Chevy Chase

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

4.85 out of 5 average rating, 123 reviews

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, 204 reviews

El Retro- Mid Century Ranch near Horse Park & Rupp

4.88 out of 5 average rating, 114 reviews

Boho-Glam, Pet-Friendly w/ Fenced Yard & 2 Kings

4.98 out of 5 average rating, 128 reviews

Home in Nicholasville

Cuttawa House

4.95 out of 5 average rating, 100 reviews

Minutes to Keeneland/Airport/UK & more!

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, 123 reviews

Cozy 1-bedroom in Lexington

Private house rentals

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!

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, 163 reviews

Kentucky Comfort Near all the best REG#150830301

A charming brick home is framed by lush greenery, featuring a distinctive peaked roof. A well-maintained front yard includes neatly trimmed shrubs. Stairs lead to a welcoming entryway with a decorative wrought-iron door, while large windows allow natural light to fill the interior.

4.94 out of 5 average rating, 130 reviews

Lexington's Commonwealth Cottage STR:15070620-1

A cozy living room features a white sofa adorned with decorative pillows, paired with a round dark coffee table and two accent chairs. Soft light is provided by a ceiling fan and lamps. Elegant decor elements are displayed on the walls and furniture, complementing a warm atmosphere.

4.9 out of 5 average rating, 166 reviews

Spacious 5BR/5BA Near Keeneland | UK | Rupp<10 min

4.97 out of 5 average rating, 35 reviews

Hot Tub/Firepit/King Beds/Fenced Yard/Playground

4.99 out of 5 average rating, 82 reviews

Ralph Lauren Inspired, Walk to Rupp Arena, Parking

A spacious bedroom is highlighted by a plush bed adorned with soft bedding and decorative pillows. Accent chairs in rich colors provide seating, while a unique mirror reflects light. Warm tones and textured rugs contribute to the inviting atmosphere.

4.97 out of 5 average rating, 73 reviews

New! Stylish Historic Downtown Home | Walk to Rupp

A bright living room is showcased with large windows allowing natural light to fill the space. Two leather armchairs and a light-colored ottoman provide seating. A round table sits at the center, and a flat-screen television is mounted on the wall, above a modern fireplace.