Vacation Rentals By Owner In Lexington, KY

$459.65

Luxury Chevy Chase Cottage - close to UK

Lexington, Kentucky, United States

This charming stone cottage in the heart of the Chevy Chase neighborhood has been completely renovated to feature modern amenities while preserving the original character of the home. Perfect for those wanting to be a quick drive or a 2-mile walk to UK's campus or downtown. Kitchen is fully stocked with essentials, including a Moccamaster coffee maker (and local coffee) and non-toxic cookware. The home is sparkling clean - kick off your shoes and cozy in for a peaceful, quiet, and convenient stay.brbrIn the cozy primary bedroom, dive into the king bed with Pillow Guy sheets and pillows (including extra) to read or watch your latest streaming pick on a 42 TV. The spacious second bedroom features a queen bed, also with Pillow Guy sheets and pillows (plus extra), and the third bedroom has a charming pair of twin beds.brbrMake yourself at home in the completely remodeled kitchen, which features all new major appliances as well as a Moccamaster coffee maker, a Keurig coffee maker, and non-toxic cookware. The kitchen comes fully stocked with all your cooking essentials (coffee, creamer, oil, salt, pepper, butter, milk, sugar, vinegar) and many small appliances (blender, mixer, water kettle) as well as complimentary local coffee.brbrThe bathroom features a newly reglazed bathtub, new toilet, and original floor tile. We provide shampoo, conditioner, shower gel, a hair dryer, and extra Turkish cotton towels.brbrThis home is sparkling clean, and it is a single-story home with no stairs.brbrOne last note: We have spent many nights staying in 5-star hotels around the world. We strive to make this house a luxury accommodation that can rival a 5-star hotel stay.

3

Bed

1

Bath

5

Sleeps

$235.0

/ Nightly

Private Vacation Home

Spacious 5-bedroom house with fitness room in charming Lexington

Lexington, Kentucky, United States

Lexington is waiting for you at this 5-bedroom house. This gorgeous property features 2 king beds, 2 queen beds, and 1 twin bed, perfect for a group getaway. With amenities like AC, a fitness room, and a jetted bathtub, guests will feel right at home. We think our place will help you experience everything Lexington has to offer.

Bed

Bath

Sleeps

$716.1

/ Nightly

Private Vacation Home

Relaxing getaway in the heart of Lexington

Lexington, Kentucky, United States

Welcome to your spacious and inviting home away from home! This 5-bedroom, 3-bathroom retreat combines classic design with modern comforts, creating the perfect blend of elegance and homely warmth. Step into this charming residence, and you'll be greeted by comfort and convenience.

Bed

Bath

Sleeps

$414.37

/ Nightly

Country House

Beautiful 4-bedroom farmhouse in Lexington. Huge living room/kitchen.

Lexington, Kentucky, United States

The Ogden House. Experience Lexington like a local in this 4-bedroom farmhouse. The bedrooms feature 1 king bed, 2 queen beds, and 1 bunk bed, perfect for families or groups of friends. With 2 bathrooms equipped with showers, you'll have all the space you need to relax and unwind. Our place will help you feel at home while you're traveling in Lexington.

4

Bed

2

Bath

8

Sleeps

$116.0

/ Nightly

Cottage

Cozy Country Setting on 10 acres w/fishing pond, tennis and pickleball

Lexington, Kentucky, United States

Nestled in a serene area of Lexington, this charming cottage offers a perfect blend of comfort and style. Featuring 2 inviting bedrooms with full-size beds and 2 bathrooms complete with a shower and bathtub, the property is fully equipped for your convenience. Enjoy modern amenities such as a fully stocked and equipped kitchen, washer/dryer, central heating and AC, and high-speed WiFi. The beautifully designed interior, highlighted by tasteful period decor and a cozy ventless fireplace, creates a welcoming atmosphere for relaxation. Outdoors, the property spans 10 acres of lush, rolling fields and includes a section of East Hickman Creek for outdoor exploration. Guests will appreciate the on-site tennis court with pickleball, as well as a stocked one-acre fishing pond. Pet-friendly and ideally located just minutes from downtown, shopping, the airport, and major highways, this cottage is the ideal retreat for your next getaway. With over 10 years of hosting experience and glowing reviews (Google: Cozy Country Setting), we look forward to making your stay memorable.brbrbr

Bed

Bath

Sleeps

$318.47

/ Nightly

Private Vacation Home

Cute bungalow located in the Fairwood neighborhood of Lexington. #15081244-1

Lexington, Kentucky, United States

Stone bungalow located in the desirable 40502 area of Lexington, KY. Close to downtown Lex, distilleries, Keeneland, UK. Dog Friendly and child friendly. Fenced in backyard, deck. Walkable neighborhood.

Bed

Bath

Sleeps

$401.86

/ Nightly

Private Vacation Home

Unbeatable location for the best experiences in Central Kentucky

Lexington, Kentucky, United States

Unbeatable location for the best experiences in Central Kentucky!brbrYou 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.brbrThere are so many great restaurants nearby! Be sure to check out our Guidebook when you book a stay at Bluegrass Retreat.brbrWe’d love to make your stay as comfortable as possible. Please let us answer any questions you may have and address any concerns during your stay. We are available through the Airbnb app messenger.brbrThe neighborhood is quiet, family friendly, and very walkable.brbrPrior to check-in, guests will receive their own unique passcode to enter through the front door. A two car garage is available for parking, in addition to the driveway which can accommodate two vehicles.brbrLocation, Location, Location is where you will find this adorable NEW construction! Bluegrass Retreat is a vacation rental nestled in the heart of the outskirts of Downtown Lexington. Whether in town for a sporting event, horse racing, a show at Rupp Arena, work trip, Bourbon Trail, wedding, or just an incredible weekend getaway, this home offers a 5-Star experience every guest will enjoy.brbrBluegrass Retreat is warm and cozy and has comfortable, modern furniture. There is a natural gas fireplace that heats up the living room quickly with the flip of a switch. Above the fireplace is a Smart TV with access to our YouTube TV and Netflix subscriptions. The living room is decorative and inviting. brbrThere is a second living room with a cozy sofa and computer desk located just off the entry. It isthe perfect place to work remotely or read a book. The kitchen is full size with a dual fuel range and all features and utensils for cooking. Guests can enjoy the bar and dining table while staying with us. brbrOur 3 bedrooms are carpeted and have very comfortable beds with luxurious linens and pillows. The master bathroom has two vanities, a fully tiled shower, water closet, and soaker tub. brbrThe back patio has a hot tub that fits 5-6 adults, and a propane 2-burner Weber grill. The backyard has 6 Adirondack chairs and a large fire pit. We supply firewood, fire pit tools, roasting sticks, and S’mores ingredients.brbrThis is a single-story home with no steps into the house from the front porch or the garage. There are two steps from the dining room to the back patio.brbrRegistration #: 15078663-1brbrWe recommend guest use personal vehicles to navigate around Lexington. brbrGuests will self check-in with a unique passcode using the Lockly Secure Plus Smart Lock.

Bed

Bath

Sleeps

$291.03

/ Nightly

Private Vacation Home

Near KYSP & Fasig-Tipton The Kingston!! Equestrian & Bourbon Central

Lexington, Kentucky, United States

***Disclaimer*** After being in the Top 5% of VRBO rentals in Lexington, in summer of 2025, the city passed an ordinance allowing roosters within city limits. There are roosters in the neighborhood that can be periodically heard in the morning. While we can strive to provide an incredible experience, we can not promise there won't be noise and some things are out of our control. Most guests have said it is not a bother, while recently a few have raised concerns. If you have questions, please ask prior to booking! We believe in operating with honesty and integrity towards all our beloved guests :).brbrAmazing ranch style property! PERFECT location in an equestrian & bourbon hot spot! Completely updated and renovated vacation home. The decor pays homage to our love of all things equestrian and our familial Lexington roots. Smattering of authentic mid-century & Hollywood Regency vintage, with the best in modern amenities and comforts, this home is a perfect blend of old with new!brbr**Fur babies are welcome!br**Completely private fenced-in backyard with 10+ outdoor eating table :0br**Updated kitchen with 8 Person Dining Tablebr**Coffee/wine/drink bar with 20+ bottle chiller fridgebr**MCM piano, guitar, 65 inch streaming TV, Vinyl record player with Bluetooth connectivity.br**1500 sq ft of interior spacebr**3 bedrooms, 2 bathroomsbr2 Queens, 3 Twinsbr**Attached 2 car garage for guest accessbr**Level 2 ChargePoint EV charger. Free for guest use!br**Mudroom with washer, dryer and wash basin.br**More to explore...but you gotta book first! Adventure is out there!brGuest accessbrSelf/keyless entry to home!brbrGuests have complete access to entire home including the garage!brbrOwner's closet is locked at all times and guests will not have access to that area.brbrOther things to notebrFasiq-Tipton, Kentucky State Horse Park, Wild Health Field, Rupp Arena, University of Kentucky, Transylvania University, Lexington Country Club, Griffin Gate Country Club, NoLi, Greyline Station, West 6th Brewery and other popular venues all minutes from your home stay! Excellent location to start your Bourbon Trail tours near many of the best Bluegrass Distilleries. Close to everything, but also secluded to relax :). Close to I-75 off of exit 113.brbrInside of Lexington:brVERY CLOSE TO THE BEST DISTILLERIES! (Inquire for specifics)brKentucky Horse Park: ~ 9 minutesbr(Alltech Arena, Hunter Jumper Complex, Rolex Stadium, Claiborne Ring, Covered Arena, Parkwide)brTransylvania University - 9 minutesbrRupp Arena - 10 minutesbrRed Mile - 13 minutesbrLexington Opera House - 10 minutesbrThoroughbred Center - 5 minutesbrFasig-Tipton - 8 minutesbrLexington Country Club - 3 minutesbrGriffin Gate Country Club - 8 MinutesbrWild Health Field - 5 minutesbrToyota Stadium (Lexington's new FC SC soccer Team) - ~19 minutesbrWest 6th Street Brewing - 7 minutesbrNoLi/Grey Line Station - 7 minutesbrDowntown - 10 minutesbrUniversity of Kentucky - 16 minsbrKroger Field / UK Football Stadium - 15 minutesbrLexington Regional Airport - 16 minutesbrKeeneland - 17 minutesbrPlanet Fitness - 5 minutesbrYMCA - 10 minutesbrbrClose to the prestigious horse farms of Paris Pike!brClaiborne, Spendthrift, Rosemont, Hagyard, Gainesway and many more!brbrOutside of Lexington:brBourbon Drive-In Theater (A MUST DURING THE SPRING, SUMMER AND FALL!) - 23 minsbrArk Encounter Museum - 40 minutesbrNatural Bridge - 50 minutesbrRed River Gorge - 60 minutes

Bed

Bath

Sleeps

$292.5

/ Nightly

Private Vacation Home

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

Lexington, Kentucky, United States

Charming open concept ranch home in Hamburg w/easy access to I-75, shopping & dining, UK, Bourbon Trail & Keeneland. Accommodates up to a maximum of 10 guests. Master bdrm has king bed w/full bath & large walk-in closet. There are 2 add'l bdrms w/queen beds, one full pull out bed in the secondary living area that can be closed off w/doors at night for privacy & one pull out full bed in the great room. Washer/ Dryer, outdoor dining w/BBQ, dedicated work space w/printer & wifi & outdoor parking for up to 4 cars (Garage not available to guests). LFUCG STR Licence# 15073351

Bed

Bath

Sleeps

$753.44

/ Nightly

Private Vacation Home

Lexington Fun Zone! Pool! HotTub! Arcade! Games!

Lexington, Kentucky, United States

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, We have all the entertainment you need! Featuring a pool, hottub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table!brbrLooking to just relax Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!brThe spacebrThe fun goes on when you walk through our doors! With 3 full size bedrooms including a large Master bedroom suite! You can be assured our home is the perfect gathering spot for friends and family! I take pride in my places and want to make sure I can be as accommodating as possible! With me, I hope that you’ll receive a full, luxurious experience.brGuest accessbrGuests will have access to the whole house and surrounding grounds with a fenced in backyard!brOther things to notebrIf you have any questions before booking please don’t hesitate to reach out!brbrI understand your money is valuable and want you to feel as comfortable as possible when booking with me! I am a people pleaser and very hands on with my places for the upkeep so I hope you’ll take that into consideration knowing that I strive for the perfect experience EVERY week. I’m a small town, single entity so it is MY responsibility that to meet YOUR expectations! I view hosting as my future so I take what I do very seriously!

Bed

Bath

Sleeps

$322.3

/ Nightly

Private Vacation Home

Modern escape just outside Lexington

Lexington, Kentucky, United States

Escape to this home just outside Lexington, perfect for families or groups seeking comfort and convenience. The home features a fully equipped kitchen, ideal for preparing meals together, and a cozy living area to unwind after a day of exploring. Enjoy the outdoors in the fully fenced-in yard, offering privacy and space for pets& children to play. With plenty of room to relax & modern amenities throughout, this charming home provides the perfect Lexington getaway.

3

Bed

2

Bath

8

Sleeps

$69.98

/ Nightly

Apartment

The Walton House #1, A beautifully furnished cottage in the heart of Lexington

Lexington, Kentucky, United States

Welcome to The Walton House! A beautifully restored vintage cottage nestled in the heart of Lexington, transformed into a fiveplex. Each unit has its own entrance, and Unit 1, accessed through the inviting brown wood door at the front, offers a charming space.brThis apartment features a spacious kitchen with a dining nook, a living room, and a full bath on the first floor. The upstairs invites with a unique open concept, showcasing one queen bed, one full bed, a futon, an additional living and dedicated work area and a half bathroom. Our commitment is to provide a clean and cozy environment with all the essentials.brConveniently located within walking distance to breweries, restaurants, speakeasies, boutiques, coffee shops, and downtown, The Walton House offers onsite parking for one vehicke and plenty of off-street parking. brProximity to Rupp Arena (1.5 mi), the University of Kentucky (1.3 mi), and Limestone Hall (1.3 mi) makes it an ideal choice for your stay!br

Bed

Bath

Sleeps

$130.52

/ Nightly

Hotel

Nature Escape! Unit Near Attractions in GuestHouse Lexington, Parking!

Lexington, Kentucky, United States

Centrally-located near top attractions in Lexington bluegrass country.brbrThis listing is for a room within a hotel.brbr✦ Your room is 224 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open from 9:00AM to 11:00PM, available in the property.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The indoor pool is temporarily unavailable until further notice.brbr✦ Breakfast is served Mon-Fri 6 am-9 am and Sat-Sun 6:30 am-10 am.

Bed

Bath

Sleeps

$130.52

/ Nightly

Hotel

Relaxing Unit Near Attractions in GuestHouse Lexington, Parking!

Lexington, Kentucky, United States

Centrally-located near top attractions in Lexington bluegrass country.brbrThis listing is for a room within a hotel.brbr✦ Your room is 224 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open from 9:00AM to 11:00PM, available in the property.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The indoor pool is temporarily unavailable until further notice.brbr✦ Breakfast is served Mon-Fri 6 am-9 am and Sat-Sun 6:30 am-10 am.

1

Bed

1

Bath

4

Sleeps

$346.82

/ Nightly

Private Vacation Home

Charming 4-bedroom house with WiFi and AC in brilliant Lexington

Lexington, Kentucky, United States

Stay comfortably in Lexington at this 4-bedroom house. With 3 queen beds, 1 bunk bed, and 1 crib, this tremendous property is perfect for families or groups. Enjoy the gorgeous living room with a cozy sofa bed for extra space. Kickback, relax, and enjoy everything Lexington and our house has to offer.

Bed

Bath

Sleeps

$180.99

/ Nightly

Private Vacation Home

The Cozy Downtown Townhouse

Lexington, Kentucky, United States

Our townhouse is walking distance to the city center, Rupp Arena, and plenty of restaurant and dining options. You’ll love our cozy townhouse a few blocks from downtown Lexington. It is perfect for couples, solo adventurers, business travelers, and families (with kids).brbrOur cozy 2 bedroom and 2.5 bathroom townhome is a short walk to downtown Lexington, Rupp Arena, and a 10 minute drive to Keeneland. The townhome has two bedrooms each with an ensuite bathroom. A queen airbed is available to comfortably sleep 6. The Roku TV has basic Cable, Hulu, and Netflix.

Bed

Bath

Sleeps

$321.54

/ Nightly

Cottage

Springwood Cottage in the Heart of the Bluegrass

Lexington, Kentucky, United States

Set adjacent to a Thoroughbred horse farm, this 2 bedroom, 2 full bath, with central common living area cottage was completely renovated in 2018. It comes complete with modern touches and high end finishes. The property is located on a small lane and is quiet and peaceful. Visit Midway, Ky, a charming small town with resturants and shops. The cottage is 8 miles from Ky. Horse Park, 12 miles from Keeneland and Lexington Airport and 11 miles from downtown Lexington.

Bed

Bath

Sleeps

$376.66

/ Nightly

Private Vacation Home

Springwood Shed House the best view on the farm.

Lexington, Kentucky, United States

Our Springwood Shed House has the best view on the farm. Each room has floor to ceiling sliding glass doors so you can enjoy the view from your bed, living room, kitchen, porch and patio. There are ceiling fans, TVs, and independent thermostats for each room. We also have another listing, Springwood Cottage on the same farm lane for additional people you are traveling with.

Bed

Bath

Sleeps

$221.21

/ Nightly

Private Vacation Home

This house is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

Lexington, Kentucky, United States

Charming 2BR, 1BA restored cottage in the heart of Lexington! Filled with antiques and cozy character, this home features full-size beds, a newly remodeled kitchen and bath, and private parking. Just a short walk to Kroger Field, restaurants, and more. Centrally located for easy access to all Lexington has to offer. Perfect for a weekend getaway, game day stay, or exploring the city with vintage charm and comfort! Note: Cottage sits next to an active train track.brbrProfessionally managed by PURE Property Management, our team is readily available for any guest needs. We have created an automated stay experience, but can be available via the booking platform or phone at anytime. brbrLocated in the Southland Neighborhood, we are located just off of Rosemont Garden. It is important to note that we do face the train tracks and a train does run frequently throughout the day. brbrGuests will be provided a unique 4 digit code to access the home. Guests will have full access to the home besides the 2nd floor storage area. brbrWhile guests are able to walk to local attractions, we recommend accessing much of the City and Central KY through a personal vehicle.

Bed

Bath

Sleeps

$499.13

/ Nightly

Private Vacation Home

Modern Downtown with Parking - Keeneland - Horse Park

Lexington, Kentucky, United States

* STR Reg #15071157-4 - Maximum occupants 8 - No parties or gatherings. Guests aren’t allowed more than 8 people *brbrA well appointed kitchen w/ stainless steel appliances, comfortable beds, remodeled bathrooms, open living and dining space to gather with family and friends. Enjoy morning coffee or evening cocktails on the front porch swing or back deck. Fast WIFI with 65 smart TV. Wonderful bakeries, restaurants & breweries nearby. Short Uber ride Downtown, Kentucky Horse Park & Keeneland

3

Bed

2

Bath

8

Sleeps

Vacation Rentals By Owner In Lexington, KY

$459.65

$235.0

$716.1

$414.37

$116.0

$318.47

$401.86

$291.03

$292.5

$753.44

$322.3

$69.98

$130.52

$130.52

$346.82

$180.99

$321.54

$376.66

$221.21

$499.13

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