Holiday rentals with a pool in Lexington

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lexington

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Salvisa

4.97 out of 5 average rating, 131 reviews

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

Guest favourite

Home in Bagdad

5 out of 5 average rating, 24 reviews

Stone Spring Farm Bourbon Trail

Welcome! Bring the whole family to Horse & Bourbon Country with plenty of room for fun. Enjoy a day at any of the local Distilleries with Bulleit, Wild Turkey, Buffalo Trace and many more within a 25 minute drive and then come back to a relaxing sunset on a spacious back deck with a view of the pool, hot tub and fully stocked 1 acre pond. You can enjoy a night of Billiards, Shuffleboard or a movie inside the Theatre room. Situated between Churchill and Keeneland there is something for everyone!

Guest favourite

Home in Midway

4.99 out of 5 average rating, 80 reviews

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

Superhost

Home in Lexington

4.86 out of 5 average rating, 102 reviews

4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!

Welcome to The Komi. This 4 bed, 3 bath home is an oasis in the middle of Lexington. This cozy getaway has SO much to offer; in ground pool, hot tub, stone fire pit, basketball court, and thats just the outside! Inside boasts an open floor plan living area with a HUGE dining table. Three bedrooms upstairs along with two baths. Downstairs is the perfect place for the kids with bunk bed trundles that sleeps up to 8. Oh, and did I mention the home movie theater! The Komi has it all!

Guest favourite

Guest house in Lexington

4.92 out of 5 average rating, 221 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Guest favourite

Home in Lexington

4.98 out of 5 average rating, 96 reviews

Home for the Holidays! Hottub! Pool! GameRm!

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! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

Guest favourite

Farm stay in Georgetown

4.97 out of 5 average rating, 124 reviews

Beautiful farm stay apartment, rural Georgetown KY

Creekside Hideaway is your home away from home. Nestled in rural horse country, come for a relaxing stay with the whole family. Book this 1,100 sq ft full basement, 1-bedroom, 1-bath Georgetown vacation rental! (This is not a full home.) Tour the elite thoroughbred farms, take a trip on the Bourbon Trail, visit the KY Horse Park, have a day at the races during historic Keeneland (April & October), or drive a bit further for Churchill downs or the Ark Encounter.

Guest favourite

Home in Lexington

4.99 out of 5 average rating, 77 reviews

Close to Everything! Beautiful two-story home

Beautiful home in a great location. Less than 10 minutes to Bluegrass Airport, Keeneland, Restaurants, Downtown & Shopping. Three bedrooms and three full baths. Open concept with large, fully equiped kitchen with two dining areas and wet bar. Fireplaces in living area and master bedroom. This awesome two-story home has a fenced yard with heated pool, fire pit and outdoor area for entertaining and relaxing. Contact owner for extra charge for pool heater.

Guest favourite

Campervan/Motorhome in Georgetown

5 out of 5 average rating, 16 reviews

2019 Aria Motorcoach

You won’t forget your time in this memorable place. Glamping in style in a nice Motorcoach! Enjoy numerous amenities on site. Enjoy our pool with dual tube water slides, relax outside on your picnic table or around the fire ring, take your dog to the dog park, show the kids the playground and bounce house area, fish in the lake, and much more! Placed in a gorgeous RV Park located in Northern Georgetown, KY. Plenty to do and much to enjoy!

Guest favourite

Home in Georgetown

5 out of 5 average rating, 11 reviews

Horse Country at The Palm House-Update Ranch home

The Palm house is a spacious updated 4-bedroom 2-bath home in Georgetown, Ky. Located minutes from all of what Georgetown has to offer. Situated near the interstate for easy access to Lexington, Frankfort, Richmond and surrounding counties. Located 10 minutes to the Kentucky Horse Park, Old Friends Farm and Toyota. 20 minutes to Keeneland, Bluegrass Airport, and Buffalo Trace. In the hot summer months (May-Sept) enjoy the in ground pool.

Guest favourite

Home in Lexington

5 out of 5 average rating, 70 reviews

House w/private pool & hot tub, dogs ok

Enjoy exclusive access to incredible amenities including a heated in-ground pool, hot tub, BBQ grills, fire pit, playset, hammock, and yard games surrounded by a fenced backyard. Located on Lexington's west side, just 3 miles from Keeneland Race Course & Bluegrass Airport, and a short 4.9-miles to downtown. The pool is CLOSED until about April 2025. Dogs welcome with prior written agreement from host and an additional pet fee per pet.

Superhost

Home in Lawrenceburg

4.82 out of 5 average rating, 162 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

This spacious and cozy three-bedroom home is less than one mile from Lawrenceburg's city center - nestled in a quiet, residential neighborhood with a swimming pool and dual-level deck. Downtown restaurants, grocery stores, Wild Turkey Bourbon Distillery, Four Roses Bourbon Distillery, and the city park are all within close proximity. The property was completely renovated in Spring 2019 and contains all new furniture and flooring.