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

Train in Lawrenceburg

4.98 out of 5 average rating, 250 reviews

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

ﺩ.ﺇ559 per night
Guest favorite

Cottage in Lexington

4.94 out of 5 average rating, 644 reviews

Little House Dwntwn - Close to Rupp & Restaurants

1 BR, 1 bath, restored house on quiet street in downtown. Patio (with umbrella), & front porch - each with table & chairs, Off-street parking, TV in Living Room and in Bedroom, Broadband Internet, Cntl A/C, Complete kitchen w/microwave, refrigerator - freezer, toaster oven, regular oven and stove, flatware, dishes and cooking utensils, dishwasher, and washer-dryer. 15 min. to Keeneland or Horse Park. 1.5 miles to UK. 1/2 mile to Rupp (10 minute walk.) Walk to many restaurants and attractions.

Mar 22 – 29

ﺩ.ﺇ312 per night
Guest favorite

Guesthouse in Nicholasville

4.98 out of 5 average rating, 294 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Aug 30 – Sep 6

ﺩ.ﺇ357 per night

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

4.96 out of 5 average rating, 319 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

Dec 17 – 24

ﺩ.ﺇ672 per night
Guest favorite

Home in Lexington

4.98 out of 5 average rating, 281 reviews

Distillery District Diamond-pet friendly

Jun 29 – Jul 6

ﺩ.ﺇ451 per night
Guest favorite

Home in Stamping Ground

4.97 out of 5 average rating, 596 reviews

Buffalo Springs Distilling Company

Dec 1 – 8

ﺩ.ﺇ580 per night
Guest favorite

Home in Harrodsburg

4.92 out of 5 average rating, 197 reviews

Kentucky Horse Farm Barndo On The Bourbon Trail

Jan 22 – 29

ﺩ.ﺇ381 per night
Guest favorite

Home in Lexington

4.91 out of 5 average rating, 553 reviews

Lower Level of Home near UK, Eateries, 1000 sq ft

Jul 29 – Aug 5

ﺩ.ﺇ300 per night
Guest favorite

Home in Lexington

4.92 out of 5 average rating, 158 reviews

My Old Kentucky Home

Jun 11 – 18

ﺩ.ﺇ354 per night
Guest favorite

Home in Lexington

4.94 out of 5 average rating, 317 reviews

Big Rock Cottage

Aug 13 – 20

ﺩ.ﺇ459 per night
Guest favorite

Home in Berea

4.94 out of 5 average rating, 184 reviews

Little House

May 22 – 29

ﺩ.ﺇ375 per night
Guest favorite

Home in Lexington

4.94 out of 5 average rating, 653 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

Dec 28 – Jan 4

ﺩ.ﺇ492 per night
Guest favorite

Home in Lexington

4.82 out of 5 average rating, 228 reviews

Downtown Blue - A new remodeled house in Lexington

Dec 23 – 30

ﺩ.ﺇ341 per night
Guest favorite

Home in Paris

4.95 out of 5 average rating, 151 reviews

The Spring Valley Inn - charming rural home

Dec 6 – 13

ﺩ.ﺇ538 per night
Superhost

Home in Lexington

4.93 out of 5 average rating, 482 reviews

Purple Door, Tiny House

Nov 13 – 20

ﺩ.ﺇ418 per night

Other great vacation rentals in Lexington

Guest favorite

Guesthouse in Winchester

4.95 out of 5 average rating, 155 reviews

Carriage House on the Park

Apr 2 – 9

ﺩ.ﺇ254 per night
Superhost

Cabin in Lexington

4.81 out of 5 average rating, 437 reviews

Unique Stay - 1907 Log Cabin Near Kentucky River

Jan 31 – Feb 7

ﺩ.ﺇ309 per night
Guest favorite

Apartment in Lexington

4.99 out of 5 average rating, 172 reviews

City Chic Loft - Downtown

Aug 17 – 24

ﺩ.ﺇ446 per night
Guest favorite

Guesthouse in Nicholasville

4.95 out of 5 average rating, 168 reviews

The Grain House

Aug 12 – 19

ﺩ.ﺇ370 per night
Superhost

Condo in Lexington

4.88 out of 5 average rating, 224 reviews

*New Downtown Apartment*

Sep 10 – 17

ﺩ.ﺇ310 per night
Guest favorite

Guesthouse in Winchester

4.98 out of 5 average rating, 171 reviews

Escape and unwind in the country

Apr 30 – May 7

ﺩ.ﺇ281 per night
Guest favorite

Condo in Lexington

4.9 out of 5 average rating, 114 reviews

Across From UK Hospital-Weekly/Monthly Discounts!

Sep 10 – 17

ﺩ.ﺇ309 per night
Guest favorite

Guest suite in Lexington

5.0 out of 5 average rating, 102 reviews

The Gainesway Suite-Near UK/Hospitals/Keeneland

May 22 – 29

ﺩ.ﺇ391 per night
Guest favorite

Farm stay in Nicholasville

4.93 out of 5 average rating, 240 reviews

Moonlit Meadows: A Tranquil Getaway for Travelers

Nov 30 – Dec 7

ﺩ.ﺇ380 per night
Guest favorite

Cottage in Wilmore

4.97 out of 5 average rating, 158 reviews

River House - Cottage with KY River View & Access

Aug 6 – 13

ﺩ.ﺇ490 per night
Guest favorite

Guesthouse in Lexington

4.97 out of 5 average rating, 547 reviews

My Old Kentucky Home-Downtown LEX's Premier Stay!

Aug 19 – 26

ﺩ.ﺇ620 per night
Guest favorite

Treehouse in Georgetown

4.94 out of 5 average rating, 166 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Oct 7 – 14

ﺩ.ﺇ615 per night

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 1,120 vacation rentals in Liberty Area, and over 830 vacation rentals in Georgetown.

  • 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 condo rentals in Lexington?

    Experience the best of Lexington with our condo rentals, starting at about $20 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 360 house rentals with self check-in in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Lexington have a bbq area?

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

  • Do house rentals in Lexington have a gym?

    Absolutely! We offer over 60 house rentals with a gym in Lexington. Enjoy a tailored experience with all the comforts you desire.

  • Do bungalow rentals in Lexington have wifi?

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

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with a gym, over 300 homes with wifi, over 100 homes with self check-in, over 10 homes with a bbq area, 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