Vacation Rentals By Owner In Lexington, KY

Escape to this fantastic apartment in picturesque Lexington. Guests will enjoy a cozy bedroom with a queen bed, perfect for a restful night. The bathroom includes a hair dryer for added convenience. Stay comfortable year-round with heating and AC, and take advantage of thoughtful touches like an iron to keep your clothes fresh. Whether you’re here to relax or explore, this soothing space offers a marvelous retreat after a busy day. We think our place will help you experience everything Lexington has to offer.

Waterstone at Hamburg 1BR/1BA – Lexington Comfort

Lexington, Kentucky, United States

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Sleeps

$84.0

Welcome to the Glendover! This neighborhood provides easy access to Lexington and is quiet and walkable. Perfect for those seeking comfort and convenience. Enjoy the peaceful backyard, ideal for relaxing. Just minutes from Lexington Hospitals and the arboretum. This is one half of a duplex. Please reach out if you are visiting with others and would like to explore renting the other side!brbrThe spacebrEnjoy the peaceful backyard, ideal for relaxing, entertaining, or letting kids play freely. The inviting front porch is another favorite feature, offering a quiet retreat in a friendly neighborhood just minutes from UK Hospital, nearby parks and local dining options. This home has previously been rented to traveling nurses and is now ready for its next tenant to enjoy comfort, charm, and a fantastic location.

Charming and Conveniently Located 2-Bedroom House with AC in Lexington

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(2)

$169.66

Forget your worries in this spacious and serene space. Feel welcomed and prepare to relax in roomy comfort. Just minutes away from Rupp Arena, University of Kentucky, fine dining and shopping. A short drive to Keenland horse park.brbrGuest accessbrYou have access to the entire house, including living area, kitchen, bedrooms, bathrooms and laundry.

TNT’s Kentucky Estate

Lexington, Kentucky, United States

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Select Dates for Price

Charming 2-bedroom apartment in Hamburg Area

Lexington, Kentucky, United States

Your home away from home in Lexington with 2 bedrooms. This lovely apartment features two queen beds, perfect for a restful night’s sleep. Guests enjoy a comfortable living space with heating and AC to keep the temperature just right. The bathroom includes a hair dryer for added convenience. Whether you’re relaxing indoors or exploring nearby, this fabulous spot offers a tremendous base for your stay. Experience what Lexington has to offer with a stay at our apartment.

Bed

Bath

Sleeps

Exceptional(20)

$231.81

May be the closest STR to Keeneland and Bluegrass Airport! Located Harrodsburg Rd/Man O War. Close to restaurants, grocery stores, shopping centers, and downtown. Backing up to green space, this 3-bedroom, 2-full bath home features an open floor plan, 9' ceilings, formal dining room w/ lots of natural light, spacious vaulted great room, luxury vinyl plank flooring, stainless and granite kitchen open to the family room, generous sized bedrooms. Patio area with table for 4, grill and umbrella.brbrNewly Remolded, quite neighborhood - Keeneland & Bluegrass Airport are only 6 minutes away!! Restaurants, fast food, gas station, grocery store, Pharmacy, dry cleaners, and banks only 2 minutes away. 15 minutes from downtown.brbrParking in driveway or on street.brNo smoking or vaping indoors.brNo parties loud music or events.brNo open flame candles.brAll cooking oil discarded in trash.brNO PETSbrPlease only use toilet paper.brNo flush items: Paper-towels, feminine items, flushable wipes etc.

Keeneland- LEX Airport Darling

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(1)

$245.07

With plenty of restaurants, bars, and shopping just a short walk away. The spacious and comfortable space offers everything you need for a comfortable stay, from a fully equipped kitchen to cozy beds and a welcoming atmosphere.brbrDuring your stay, be sure to visit the renowned horse farms and distilleries, explore the vibrant downtown area, and indulge in delicious Southern cuisine. With its convenient location, this place is the perfect base for experiencing all that Lexington has to offer.brbrSo whether you're in town for a leisurely trip or a work assignment, this place has you covered with its prime location and amenities. Book now and allow us to make your stay in Lexington a truly unforgettable one!

Legacy Trail Getaway

Lexington, Kentucky, United States

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Bath

Sleeps

$248.98

This spacious and well-lit home is the perfect place to relax after a long day of exploring all that Lexington has to offer. With 4 comfortable queen beds, you'll have plenty of room to spread out and get a good night's rest. Whether you're here for business or pleasure, this centrally located home is the ideal spot for your stay. Don't miss your chance to experience the charming and welcoming atmosphere of Lexington from the comfort of this lovely home. Book now and make your trip unforgettable.

Home at Heart of the Southside

Lexington, Kentucky, United States

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Sleeps

$148.68

Keep it simple at this peaceful and centrally-located Bourbon themed bungalow. This home is tucked away on a large lot close to Manchester Street Distillery District, Rupp Arena and downtown Lexington, with an easy drive to Keeneland and surrounding counties. This home has been recently remodeled and has everything you need for a getaway. The outdoor space features a large furnished deck, hot tub (with additional fee of $25/night), a fire pit, and a charcoal grill.brbrThis is a 2 bedroom home with queen beds in each room, a living room, kitchen and bathroom with a washer/dryer. brbrThere is a chair in the living room that folds to a twin sized bed that could be used for extra sleeping for a child.brbrThe guests will have access to the entire home.brbrClose to Downtown Lexington, 1.8 miles to Rupp Arena and Central Bank Center - less than 1/4 mile to Manchester Street and the Distillery District.brbrA long driveway that would hold several cars.brbr**If the Hot Tub is not requested it will not be cleaned or heated for your stay** The hot tub is an optional feature that requires an additional fee of $25/night. Please request the hot tub at the time of booking and we will send you a Special Offer to include that cost. br**If the Hot Tub is not requested it will not be cleaned or heated for your stay**brbr*No more than maximum occupancy is allowed on the property.brbrPremises ID: #15069288-1brPlease do not smoke in the home. If smoking occurs we will have to charge a $250 smoking fee.

Town Branch Bungalow

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(2)

$214.53

A comfy and secure property in thriving downtown Lexington just a half-block from Rupp Arena and Centrsl Bank Center. Walk to everything downtown has to offer plus easy access to the airport and Keeneland.

Condo

The Retreat- a perfect-sized condo for your Bourbon Trail adventure

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(6)

$522.32

Enjoy your stay in the recently renovated historic Matthew Walker House! Originally built in 1789, it was disassembled and moved down the street in 1977, then reassembled and added onto. This fantastic downtown location is 5-minute walk to Rupp Arena, Lexington Opera House, the Jefferson Street corridor, and loads of great restaurants. It's a short trip to The Distillery District and the rest of downtown.

Historic charm in the heart of downtown Lexington

Lexington, Kentucky, United States

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$365.55

Your cozy getaway awaits in Lexington at this peaceful townhome with a yard and firepit. With three bedrooms featuring a king, queen, and twin beds, Living room, dining room and full kitchen guests find plenty of space to relax. The bathroom offers a soothing jetted bathtub, perfect for unwinding after a day of exploring. Enjoy the comfort of heating and air conditioning throughout the home. Whether you’re curling up with a book or preparing a meal, this brilliant space feels like a true home away from home. You’re sure to make fantastic memories with a stay at our place.

SouthernBelle/Walk to Rupp Arena

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(2)

$138.12

This recently renovated turn-of-the-century carriage house is located just a few minutes from both the I-75 exit and the Hamburg area of Lexington: quick, easy interstate access but in a country setting! Downtown Lexington is just 12-15 minutes drive. The apartment is very cozy, featuring a deck and large yard on filled with trees and flowers. There is a comfortable futon as a 2nd bed. Come as a quick stop off the interstate or as a weekend getaway from the city, we look forward to hosting you!brbr Registration 15059527 Six

‘Edith’ Carriage House Getaway - Hamburg/I-75!

Lexington, Kentucky, United States

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Bath

Sleeps

Wonderful(3)

$140.45

This apartment, located in a historic multi-unit house, is located within walking distance of both downtown Lexington and the University of Kentucky. Transylvania University is also nearby. Rupp Arena is 3/4ths of a mile away. brbrThe apartment is very spacious, with high ceilings and fireplaces in two rooms, and was recently remodeled and restored. The house dates to 1908 and features a bedroom, living room, dining room and kitchen.brbrI have stayed in short term rentals myself, and my aim is to make your stay easy, pleasant and comfortable.brbrbrRegistration 15059527 Three

'Fred' - Walk to UK/Downtown!

Lexington, Kentucky, United States

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Bath

Sleeps

$146.24

Only STEPS away from I-75 exit 113 (Paris/Lexington), this DUPLEX unit features a fully fenced back yard, 2 full bedrooms with queen sized beds, a living room with wall mounted Roku TV and comfy couch, as well as a kitchen and dining room equipped with basic types of cookware and a variety of foods. 24 hour check-in convenience using a keypad lock.brbrbrbrbrbrbrRegistration: 15059527 Five

'Emmett' Just off I-75! 2 full bedrooms!

Lexington, Kentucky, United States

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$542.05

Kentucky Charm Retreat | 4BR Modern Gem with Spiral Staircase, Pet-Friendly, Near Hospitals & DowntownbrbrWelcome to The Kentucky Charm Retreat — a rare four-bedroom, three-bath sanctuary tucked away on a quiet no-outlet street in one of Lexington’s most desirable neighborhoods. This elegant two-story home blends Southern charm with modern comfort, offering a peaceful stay for families, professionals, and guests seeking a home away from home.brbrPerfectly located near downtown Lexington, UK, CHI St. Joseph, and Baptist Health hospitals, this retreat is ideal for medical assignments, corporate housing, or insurance relocations.brbrProperty Highlightsbr• 4 Bedrooms | 3 Bathrooms | Sleeps 8+br• Pet-Friendly (with approval)br• High-Speed Wi-Fi + Smart TVsbr• Private fenced backyard & patiobr• Quiet cul-de-sac with mature treesbr• Walk to Lansdowne Shoppes, Merrick Park, and restaurantsbr• 5-minute drive to hospitals and 10 minutes to downtownbrbrLiving SpacesbrA spacious, sunlit living room invites connection and relaxation, featuring a plush sectional, 65 Smart TV, and an electric fireplace. The open layout flows into the dining area and fully equipped kitchen, complete with stainless appliances, a coffee station, breakfast bar, and dining for up to eight. French doors lead to the private patio, perfect for morning coffee or outdoor dinners.brBedrooms & BathsbrbrUpstairs:brPrimary Suite: King bed, ensuite bath with walk-in shower, Smart TVbrQueen Room: Soft bedding and closet spacebrDouble Twin Room: Perfect for kids or guestsbrSecond full bath with tub/showerbrbrDownstairs:brPrivate suite with queen bed, desk, Smart TV, and nearby full bath — ideal for in-laws, teens, or long-term guests.brbrOutdoor & AmenitiesbrEnjoy Lexington’s seasons in a fenced backyard with patio dining, grill, and string lighting. Quiet, safe streets make it perfect for walking pets or evening strolls.brbrAdditional features:br• 1GB Fiber Wi-Fibr• Work-from-home spacesbr• In-unit washer/dryerbr• Smart home entry & thermostatbrbrPrime Lexington LocationbrbrHospitals:brUK, CHI St. Joseph, and Baptist Health – 5 minutesbrbrUniversities & Venues:brTransylvania University, Rupp Arena, The Summit at Fritz Farm – 10 minutesbrbrAttractions:brKeeneland Race Course – 20 min | Kentucky Horse Park – 25 min | Woodford Reserve & Buffalo Trace – 30 minbrbrWalk to OBC Kitchen, Malone’s, Drake’s, Fresh Market, and Merrick Park for local dining, groceries, and green space.brbrPet PolicybrSmall, well-behaved dogs welcome (limit two, fee applies). Fenced yard for safe play.brbrClean & SecurebrProfessionally cleaned and sanitized after each stay with contactless check-in, smoke/CO detectors, and smart locks for peace of mind.brbrPerfect Forbr• Families between homes or renovationsbr• Insurance relocations (flood/fire recovery)br• Traveling nurses & medical staffbr• Corporate stays or long-term visitsbr• Pet-friendly family travelbrbrDesigned for comfort, privacy, and ease — this retreat brings warmth, function, and Lexington charm together effortlessly.brbrYour Lexington Home Away From HomebrbrFrom the graceful spiral staircase to the inviting light-filled rooms, every detail of The Kentucky brCharm Retreat has been crafted for rest and renewal. Whether you’re here for a week or a few months, this home offers the space, serenity, and convenience that make every stay unforgettable.brbrReserve your stay at 3388 Moundview Court and experience Lexington living at its best.

Five Star Kentucky Charm - 4BR Gem w/ Spiral Staircase & Modern Comfort

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(4)

$222.85

Welcome to “El Retro.” Unwind in this comfortable Mid-Century Modern Home with a dedicated office space. When it’s time to relax, sit back on a comfy leather couch, watch your favorite shows or movies on a Smart TV, or cook delicious meals in our fully stocked kitchen.brbrExplore Lexington with ease. “El Retro” is a short 10 minute drive to the Kentucky Horse Park, Keeneland, and downtown Lexington, and less than 20 minutes to the University of Kentucky, Rupp Arena, and Kroger Field!!brbrPremises ID/Local Registration #15085095-1brbrThe spacebrThis home features 2 bedrooms, 1 bath, and a private office space perfect for anyone working away from home. Both of the bedrooms include black-out curtains, fans, and noise machines to ensure our guests are well rested.brbrA ramp in the front of the house makes the home accessible to wheel chair users or people with disabilities.brbrWake up in the morning with a Nespresso Machine and milk frother. We provide a variety of Nespresso pods to choose from.brbrGuest accessbrGuests have access to the entire house and backyard, excluding the shed.brOther things to notebr*Note* brNO PETS ON ANY FURNITURE PLEASE!

El Retro - Mid Century Ranch near Horse Park and downtown Lexington!

Lexington, Kentucky, United States

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Bath

Sleeps

Exceptional(29)

$1206.55

The ultimate KY experience! Nestled on a peaceful 10 acres right outside of Lexington, this home has everything you could want to enjoy a peaceful week away with family or a memorable weekend exploring the bourbon trail or Keeneland with friends.brbrThis 6 bedroom 4.5 bath home features heated concrete floors, high-beamed ceilings, and unique architecture for a luxurious and cozy feel. Enjoy the incredible outdoor areas featuring a salt water pool with swim up bar and hot tub, 3 covered patios, a black stone griddle, and much more – all while being 20 minutes from the heart of Lexington.brbr- 25 minutes to Keenelandbr- 10 minutes to Talon Winerybr- 25 minutes from LEX airportbr- 30 minutes to Kentucky Horse ParkbrbrIf you’re searching for a one of a kind home in Lexington with a great view & location, then look no further. Save your dates now and secure a trip you’ll always remember! Registration Number 15005031-1

ONE OF A KIND Sanctuary with POOL. Keeneland, Bourbon Trail

Lexington, Kentucky, United States

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Bath

Sleeps

$2265.66

Welcome to Yarnallton Manor — Your Lexington Escape!brbrExperience the charm, beauty, and elegance of Yarnallton Manor, a breathtaking 9-bedroom, 10-bathroom estate nestled in the heart of Lexington, Kentucky. Whether you’re planning a wedding, corporate retreat, family reunion, or a relaxing getaway, this enchanting property offers the perfect combination of Southern sophistication and modern luxury.brbrFrom intimate gatherings to grand celebrations, Yarnallton Manor provides a one-of-a-kind setting that feels both inviting and unforgettable.brbrThe Estate:brbrThis remarkable property boasts nine beautifully designed bedrooms, each offering unique charm and comfort. With spacious suites for both the bride and groom, the manor is ideal for wedding parties who wish to prepare for their big day in style. The Bride’s Suite features elegant décor, full-length mirrors, a vanity area, and plenty of natural light—perfect for makeup and photos. The Groom’s Suite offers a relaxing lounge setting where the wedding party can unwind before the ceremony.brbrThe 11 bathrooms ensure every guest enjoys privacy and convenience throughout their stay.brbrPremium Amenities:brbrIndoor Theater Room – Enjoy movie nights with family and friends in your private cinema featuring plush seating and top-quality sound.brbrFitness Center (Coming Soon) – Stay active and refreshed with our upcoming on-site gym, designed for guests who want to maintain their wellness routine while away from home.brbrHeated Outdoor Pool – Take a dip or relax poolside year-round. Perfect for pre-wedding photos, afternoon lounging, or casual evening gatherings.brbrModern Kitchen & Dining Spaces – Fully equipped kitchen with high-end appliances, expansive counter space, and dining areas that comfortably host large groups.brbrSpacious Living Areas – Elegant common rooms designed for conversation, comfort, and connection.brbrOptional Event Services:brbrYarnallton Manor goes beyond accommodations — it’s a complete event destination. Guests can take advantage of our exclusive in-house services to make any celebration seamless and unforgettable:brbrFloral Design & Décor – Custom floral arrangements and event styling tailored to your vision.brbrCatering Services – Delicious menu options from trusted local partners who specialize in weddings, corporate events, and private dinners.brbrLinens & Tableware – Premium linens, place settings, and event furnishings to elevate your gathering.brbrProfessional Photography & Videography – Capture every moment beautifully with access to talented local creatives.brbrWhether you’re planning a romantic wedding, a bachelorette weekend, a corporate leadership retreat, or a family reunion, Yarnallton Manor offers a versatile backdrop and an experienced support team to help bring your event to life.brbrPerfect for Every Occasion:brbrWeddings – A magical venue for ceremonies, receptions, and bridal preparation. With bride and groom suites on-site, everything you need is under one roof.brbrBachelor & Bachelorette Gatherings – Celebrate in style with plenty of space for entertainment, relaxation, and photo-worthy moments.brbrCorporate Retreats – Enjoy a productive yet peaceful setting for workshops, planning sessions, or executive stays.brbrFamily Reunions – Nine bedrooms mean everyone can stay together and enjoy shared spaces for bonding.brbrFilm & Photography Shoots – The estate’s grand architecture and scenic surroundings create a cinematic setting for photos and video productions.brbrLocation:brbrLocated just minutes from downtown Lexington, the manor offers easy access to the area’s top attractions — including Keeneland Racecourse, local distilleries on the Bourbon Trail, horse farms, and boutique shopping. Yet, the property maintains a private, peaceful atmosphere surrounded by Kentucky’s signature rolling bluegrass hills.brbrComfort & Convenience:brbrEvery corner of Yarnallton Manor has been designed with guests in mind:brbrHeating & Air Conditioning for year-round comfortbrbrIron & Hair Dryer in every suitebrbrHigh-Speed WiFi throughout the propertybrbrAmple Parking for guests and event attendeesbrbrLaundry Facilities for extended staysbrbrYour Lexington Experience Awaits:brbrAt Yarnallton Manor, you’re not just booking a stay — you’re curating an experience. Whether it’s exchanging vows beneath the Kentucky sky, gathering your team for an inspiring corporate event, or simply spending quality time with loved ones, this extraordinary property offers everything you need to create lifelong memories.brbrOur team takes pride in providing exceptional hospitality and personalized service, ensuring your time with us is as comfortable and magical as the setting itself.

Luxurious 9-Bedroom Mansion with Bridal Suites in Lexington, Kentucky.

Lexington, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(22)

$167.14