Vacation rentals with a pool in Lexington

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!

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

Heart of Richmond

Welcome to your home away from home in the heart of Richmond, KY. This beautiful retreat offers everything you need for a memorable and relaxing stay. Perfectly positioned to put you at the center of all things Richmond, this oasis combines convenience with comfort and style. The highlights of the property are the salt water pool and the covered back patio. Take a dip, read a book, lounge comfortably or fire up the grill, the choice is yours! Come see us and make some memories!

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!

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 Private Acres! HotTub/Pool | Pickleball | Arcade

Luxury Bourbon Trail Retreat • Spacious 4-bedroom, 2.5-bath cabin on 4 private acres, sleeps 12. • Features Hot Tub, seasonal Pool, Game Room, and rare indoor Pickleball/Cornhole Courts. • Cozy Fire Pit and stunning scenic views. • Minutes from Lover’s Leap Winery, Bourbon Trail Distilleries, and Kentucky River. • Short drive to Keeneland Race Course for horse racing enthusiasts. • Over 3,400 sf of upscale comfort, perfect for bourbon trail getaways or relaxing retreats.

Unique YEAR-ROUND Pool + Hibachi Grill + Game Room

Westover Reserve backyard resort getaway brings people together in style. One of a kind natatorium, in-ground pool, pool house with hibachi grill, game room, basketball, hot tub, barrel sauna, fire pit, and poker room. Nearby Bourbon Trail distilleries: Woodford Reserve, Buffalo Trace, Bulleit, Castle & Key. Splash with the kids, sip bourbon under the stars, or gather for a weekend escape, Westover Reserve - resort-style experience designed for every kind of traveler.

Lexington Holiday FUN-ZONE! 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!

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.

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. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

The Bunkhouse at Big Red Stables

There is no better way to experience Kentucky than horseback riding the rolling hills of the Bluegrass. Big Red Stables is happy to offer the Bunkhouse to visitors who want to ride horses, travel to nearby bourbon distilleries, go to the races or events at the Kentucky Horse Park, or just get away from it all on a third generation family farm. Horseback riding by appointment only as arranged with your hosts.

Game room! 6 beds 2 baths

Super convenient LOCATION!! Totally renovated home with 6 beds 2 full bath Gameroom Fully stocked kitchen 1 king bed , 1queen, 2 twin beds an 2 twin beds located in game room 2 miles to Kroger field(commonwealth stadium) 4 miles Rupp arena 8 miles to keenland Less than 2 miles to Fayette mall Kroger , Trader Joe’s , many Restaurants Main Event, 1 mile away! Lex premises id 15078999