Holiday rentals with a pool in Lexington

4.97 out of 5 average rating, 139 reviews

Cottage in Salvisa

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!

4.96 out of 5 average rating, 129 reviews

Home in Richmond

Near to EKU; discounts to 10%

Located 5 minutes from I-75. Newly renovated basement apartment perfect for solo travelers, friends or couples and is pet friendly. Take it easy at this country setting and enjoy the pool. Convenient to EKU, stay after a day at Keeneland, exploring the Bourbon Trial, concerts or just a peaceful and relaxing getaway. Available small hot tub on request. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

Superhost

Cabin in Clay City

4.95 out of 5 average rating, 111 reviews

Hemlock Hideaway: Red River Gorge, Pool, game room

Hemlock Hideaway at Red River Gorge is a 3 bedroom, 2 bath cabin that can sleep up to 10. The cabin features a pool, hot tub, game room, and electric vehicle charger on a private 2.5 acre setting. The home has two king sized beds, three full sized beds, a twin trundle bed, twin sleeper chair and queen sleeper sofa. There is a fully stocked kitchen and free onsite laundry. All of this and so much more and only a 20 minute drive to the Red River Gorge, Natural Bridge State Park area.

4.87 out of 5 average rating, 121 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!

4.89 out of 5 average rating, 281 reviews

Guesthouse in Lexington

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.

4.97 out of 5 average rating, 124 reviews

Bluegrass Fall&FunZone Oasis! Pool!Hottub! 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, hot tub, 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!

4.97 out of 5 average rating, 149 reviews

Farm stay in Georgetown

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.

4.88 out of 5 average rating, 130 reviews

Tiny home in Clay City

Secluded 2 bedroom cabin w/pool and hot tub access

Enjoy the sounds of nature when you stay in this unique place. Secluded, cozy tiny cabin!! Located in the middle of 37 acres. Gate access! Close to Red River Gorge, Natural Bridge, Kentucky Dragway and kayaking. Private pool and hot tub access! Wi-Fi, Cornhole, grill, deck, fire pit, pond for fishing. Completely furnished…. Everything you could want! I raise Australian shepherd so there are four on the property. They are very friendly and love Airbnb guest.

4.99 out of 5 average rating, 86 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.

Superhost

4.73 out of 5 average rating, 187 reviews

Picadome Pool Getaway

Quiet home, with swimming pool, located in the heart of Lexington near UK, hospitals, schools, shopping, and downtown. This comfortable home is furnished with a mix of handcrafted furniture, antiques, and modern pieces. Modern kitchen appliances round out the picture. It has three bedrooms with queen beds, and a couch-bed (with a 14 inch memory foam mattress) in the den. The house can comfortably accommodate up to eight people.

5 out of 5 average rating, 75 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 OPEN for the 2025 season. Dogs welcome with prior written agreement from host and an additional pet fee.