Lexington vacation rentals

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Top-rated vacation rentals in Lexington

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Lexington
Adorable, Clean Lexington Cottage, Convenient to Everything
Browse the host's binder of hand-picked places to visit and dine; many menus are included. Cozy up with a good book from the host's large and diverse collection of books. Fully equipped kitchen that's great for cooking or entertaining. 4-legged visitors will appreciate the big, fenced-in yard. You'll love this bright, clean and airy Lexington cottage. Ten Reasons to stay here: 1. Bright and spacious despite it's small size. 2. So many personal touches that not only make this house feel homey, but also unique to Lexington. 3. I've tried to think of everything as far as making your stay as livable and care-free as possible. 4. Large kitchen with just about anything you’ll need for cooking meals or hosting dinner for a small group. 5. Great, large, fully fenced-in backyard (fire-pit coming soon!) 6. Comfy beds with nice linens and a shower with good water pressure 7. Good water pressure in kitchen and bathroom. 8. A binder with lots of hand-picked, local restaurant and activity suggestions. Menu's included! 9. TV with local channels and Netflix PLUS a blue ray player if you want to rent a Redbox movie to watch. 10. Probably the most convenient location in all of Lexington in that it's either close to where you need to be or it's easily accessible to where you need to be. You'll have the entire house, driveway, and yard all to yourself! **Driveway is located on the left side of house. Text me or message me any time of day or night if you need something or have questions. I'm happy to help and try to be quick to respond. Truly convenient to everything Lexington (and the surrounding area) has to offer! The University of Kentucky is less than 2 miles away and the area hospitals are all approximately one mile away. Rupp Arena/Downtown is a 5 min drive and Keeneland Race Track is less than 10 min away. Other Lexington attractions such as horse farm tours, the KY Horse park, and Bourbon Tours are all easily accessible from here. Safe, family-friendly street with large, fenced in backyard. Free parking in xtra long driveway (no garage or carport) ,close to bus stop. Biking distance to pretty much anywhere. Easy access to downtown...Plus there's always UBER! Great house and great neighbors. Feel free to bring your furry loved ones (potty trained and well-behaved only, please). I've had my dogs in the backyard many times and there is no escaping, so you can have a total peace of mind keeping your dog outside if you choose to do so. I'm fine with cats too as long as you can promise they won't scratch the furniture or pee on anything :) Southland drive is in walking distance. A few Southland notables include: Good- Foods Co-op grocery and cafe, Marrikas Bar (tons of beers on tap), Wenchell's (local food, sports bar), Southland Bowling Alley, Coffee Shop, Donut Days Bakery, Two Chicks & Company (gifts and accessories store), and a local farmers market on Sundays. University of Kentucky, The Arboretum, and downtown are all within a 3 mile radius (2.7 miles from downtown city center and approx. 1.3 miles from UK). Keeneland, KY Horse Park, Bourbon Tours, and Horse Farm tours are all within 15-30 min away regardless of time of day or traffic.
Dec 18 – 25
$117 per night
4.94 out of 5 average rating, 649 reviews
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.
Jun 7 – 14
$75 per night
4.93 out of 5 average rating, 100 reviews
Guest favorite
Train in Lawrenceburg
Bourbon Trail: Caboose on the Farm
Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!
Aug 30 – Sep 6
$129 per night
4.98 out of 5 average rating, 248 reviews

Popular amenities for Lexington vacation rentals

Stay near Lexington's top sights

Rupp Arena140 locals recommend
Keeneland164 locals recommend
Hamburg Pavilion46 locals recommend
Fayette Mall38 locals recommend
Kroger Field34 locals recommend
University of Kentucky66 locals recommend

House rentals in Lexington

Guest favorite
Home in Lexington
Chic Hartland Townhome
Aug 25 – Sep 1
$82 per night
4.9 out of 5 average rating, 459 reviews
Guest favorite
Home in Lexington
Silver Streak Equestrian Horse Haven
May 12 – 17
$75 per night
4.84 out of 5 average rating, 434 reviews
Guest favorite
Home in Versailles
Quaint little farm house close to Keeneland/horses
Nov 24 – Dec 1
$115 per night
4.94 out of 5 average rating, 115 reviews
Guest favorite
Home in Stamping Ground
Buffalo Springs Distilling Company
Dec 29 – Jan 5
$138 per night
4.97 out of 5 average rating, 594 reviews
Guest favorite
Home in Lexington
Cozy Country Setting
Oct 26 – Nov 2
$94 per night
4.95 out of 5 average rating, 101 reviews
Guest favorite
Home in Lexington
Centrally Located Bungalow | Outdoor Fireplace
Jun 22 – 29
$131 per night
4.88 out of 5 average rating, 130 reviews
Guest favorite
Home in Lexington
Purple Door, Tiny House
Aug 27 – Sep 3
$95 per night
4.93 out of 5 average rating, 482 reviews
Guest favorite
Home in Lexington
Perfect for Traveling Professionals & Vacation!
Dec 28 – Jan 4
$129 per night
4.88 out of 5 average rating, 113 reviews
Guest favorite
Home in Lexington
3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown
Aug 11 – 18
$154 per night
4.98 out of 5 average rating, 144 reviews
Guest favorite
Home in Lexington
Big Rock Cottage
Jun 26 – Jul 3
$98 per night
4.94 out of 5 average rating, 316 reviews
Guest favorite
Home in Lexington
Southern Hospitality! Best location close to UK!
Mar 19 – 24
$121 per night
4.95 out of 5 average rating, 101 reviews
Guest favorite
Home in Lexington
NoLi Bungalow w/ King Bed - Horse Park, Keeneland
Aug 22 – 29
$121 per night
4.92 out of 5 average rating, 133 reviews

Other great vacation rentals in Lexington

Guest favorite
Guest suite in Lexington
Close to Keeneland Charming Guest Suite
Jun 23 – 30
$76 per night
4.98 out of 5 average rating, 120 reviews
Guest favorite
Farm stay in Nicholasville
Moonlit Meadows: A Tranquil Getaway for Travelers
May 13 – 20
$88 per night
4.93 out of 5 average rating, 239 reviews
Superhost
Cabin in Lexington
Unique Stay - 1907 Log Cabin Near Kentucky River
Aug 20 – 27
$68 per night
4.8 out of 5 average rating, 434 reviews
Guest favorite
Cabin in Lawrenceburg
River Side Cabin - Bourbon Trail - HotTub
Nov 6 – 13
$250 per night
5.0 out of 5 average rating, 162 reviews
Guest favorite
Apartment in Lexington
The Statesman / Walk to Rupp / Superb Deck
Mar 29 – Apr 5
$219 per night
4.88 out of 5 average rating, 126 reviews
Guest favorite
Apartment in Lexington
Lovely Downtown Apt 1 Block from Rupp!
Jan 28 – Feb 4
$86 per night
4.89 out of 5 average rating, 122 reviews
Guest favorite
Townhouse in Lexington
Boutique House • Downtown • Historic Neighborhood
Jul 3 – 10
$90 per night
4.95 out of 5 average rating, 244 reviews
Guest favorite
Cabin in Versailles
Handcrafted Rustic Cabin on the Bourbon Trail
Nov 7 – 14
$127 per night
4.97 out of 5 average rating, 115 reviews
Guest favorite
Apartment in Versailles
High style on the Bourbon Trail
Aug 31 – Sep 7
$106 per night
4.99 out of 5 average rating, 257 reviews
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
Nov 27 – Dec 4
$67 per night
4.98 out of 5 average rating, 170 reviews
Guest favorite
Guesthouse in Lexington
Urban Guesthouse- Steps from Downtown
Jul 15 – 22
$82 per night
4.9 out of 5 average rating, 291 reviews
Guest favorite
Treehouse in Georgetown
★Escape & Relax ~ Breathtaking Creekside Getaway★
Sep 13 – 20
$151 per night
4.94 out of 5 average rating, 166 reviews

Quick stats about vacation rentals in Lexington

Total rentals

1.6K properties

Rentals with dedicated workspaces

890 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

660 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

89K reviews

Your guide to Lexington

All About Lexington

Located 70 miles east of Louisville in central Kentucky, Lexington has long attracted horse lovers. There are more than 450 horse farms here, surrounded by miles of rolling hills and pastures covered in the lush bluegrass. But there’s more than horses on the brain here.

Kentucky’s second biggest city is also home to a thriving arts scene, including numerous galleries, theatres, music venues. Some of the performance spaces have a long history, such as the Lexington Opera House, which dates back to 1886. Lexington’s universities add to the city’s robust arts calendars at venues like the University of Kentucky Opera Theatre and the Singletary Center for the Arts at the University of Kentucky College of Fine Arts.

You’ll find numerous parks to explore around town and an eclectic range of dining and drinking options, including several wineries and bourbon distilleries. Lexington is also part of the Kentucky Bourbon Trail, which highlights notable distilleries around the state.


The best time to stay in a vacation rental in Lexington

Spring and fall offer pleasant temperatures, making these great times to look for vacation rentals in Lexington. From April through October, the warm weather permits plenty of events to occur, such as a bluegrass festival, one of Kentucky’s oldest music festivals featuring three music stages and a music camp for kids. The Fourth of July celebrations are lively in Lexington as well and include several days of events with musical performances, a parade, food, and a firework display.

As the temperatures drop in late fall and winter, pack a warm coat and boots; however, it’s still a perfect time to tour one of the many distilleries in the area.


Top things to do in Lexington

Raven Run Nature Sanctuary

Located just outside of Lexington, Raven Run is a 734-acre nature sanctuary on the border of the Kentucky River. Miles of hiking and biking trails of varying difficulty levels pass through woodlands, meadows, and streams and provide you with scenic views of the native flora and fauna.

The Arboretum

The State Botanical Garden of Kentucky, also known as the Arboretum, offers 100 acres of green space and tranquility in the middle of busy downtown Lexington. You can wander along two miles of paved pathways and past manicured landscapes that include a Fragrance Garden of roses. Check out the Home Demonstration Garden to gather inspirational ideas for how to best make use of personal green space.

Aviation Museum of Kentucky

Located at the Blue Grass Airport in Lexington, the Aviation Museum of Kentucky covers 20,000 square feet with different aircraft, aviation artifacts and equipment, simulators, and interactive displays. You can watch from the observation area as they work on the airport’s planes or experience a jet taking off from the outdoor viewing area.

Frequently Asked Questions

  • Where should I stay in Lexington?

    Make yourself at home in Lexington by choosing from our most frequently booked neighborhoods. We have over 830 vacation rentals in Ashland, over 830 vacation rentals in Georgetown, and over 1,120 vacation rentals in Liberty Area.

  • Are there vacation rentals with a dedicated workspace in Lexington?

    Yes! Work meets play with ease at over 890 vacation rentals in Lexington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Lexington?

    Four-legged friends are welcome in Lexington. Choose from more than 660 vacation rentals for guests traveling with pets.

  • Are there Lexington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Lexington, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in cabin rentals in Lexington?

    Experience the best of Lexington with our cabin rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Lexington have self check-in?

    Absolutely! We offer over 370 house rentals with self check-in in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Lexington have a bbq area?

    Absolutely! We offer over 10 cabin rentals with a bbq area in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Lexington have a gym?

    Absolutely! We offer over 10 condo rentals with a gym in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Lexington have wifi?

    Absolutely! We offer over 10 cabin rentals with wifi in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Lexington?

    Enhance your stay in our House Rentals with the most popular amenities: over 240 homes with a bbq area, over 60 homes with a gym, over 900 homes with wifi, over 370 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Fayette County
  5. Lexington