Holiday rentals with a pool in Jessamine County

4.97 out of 5 average rating, 140 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!

4.9 out of 5 average rating, 188 reviews

Pool | Hot Tub | Covered Porch | Patio | Game Room

Only minutes from Kroger field and 15 min to Keeneland. The warm and inviting floor plan offers plenty of room for entertainment. Home is equipped with new luxury Tempurpedic mattresses 4 king beds, 2 queens and 2 air mattresses. This house has a vaulted screen porch overlooking the park-like back yard which opens freely to Merrick Park . Patio is set up to BBQ and enjoy your favorite sports with an outdoor TV. Plenty of restaurants and entertainment nearby. The swimming pool is open from Apri

4.96 out of 5 average rating, 134 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.

Holiday home in Nicholasville

5 out of 5 average rating, 24 reviews

Stone & Cedar Lodge - pool, hot tub, fire pit, EV

Relax with the whole family at this peaceful country ranch in the heart of the Bluegrass. Sleeps 16 - 5 Bedrooms, 8 Beds, 3 Baths Located just outside of Lexington and only 12 miles from Keeneland. New 7 seat hot tub The solar heated pool is open from April until September. The tree house, swings and trampoline are big hit. Play a game of pool, basketball or corn hole. Enjoy quiet walks around the pond or roast marshmallows around a cozy campfire. Wheelchair access Level 2 EV charger.

Superhost

Cottage in Winchester

4.87 out of 5 average rating, 103 reviews

Life is Better On The River

Make lasting memories at this unique and family-friendly cottage on the Kentucky River. Enjoy nature at its best, along with all the comforts of home. Guests return year after year. * WiFi is sometimes unreliable. It connects via satellite, as this is the only option available in our neighborhood. WIFI Riverstar, Pw 12345678 This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations, but occasional cobwebs happen.

4.86 out of 5 average rating, 122 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!

Superhost

Guesthouse in Lexington

4.89 out of 5 average rating, 282 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.

4.97 out of 5 average rating, 126 reviews

Bluegrass Fall FunZone! 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!

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, 76 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.

4.95 out of 5 average rating, 145 reviews

Farm stay in Harrodsburg

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.