Holiday rentals with a pool in Jessamine County

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

Picture this: sunlight glints off the pool, the hot tub steams as evening settles over Lexington's Lanesdown Park, and fourteen of your favorite people crowd the dining table for one more story before bed. This is your Bluegrass basecamp — five bedrooms, three and a half baths, a basement game room, and a backyard built for slow mornings and long nights. The trip you'll talk about for years starts right here. WHO THIS HOME IS BEST FOR Multi-generational families in town for a Keeneland race da

Family · Location · Parking

Luxe Home w/htd. Pool+Hot Tub+Fire Pit+Brbn Trl

Pool open March 20! Welcome to your ultimate family + friends retreat, perfect for group getaways and family trips. Pet friendly with room for up to 10 guests (8 adults max), a heated, salt-water pool, hot tub, & multiple entertainment areas, there’s something here for all ages to enjoy & plenty of room to spread out! Located minutes away from Keeneland, the Bourbon Trail, UK, golfing, restaurants and shopping, you’ll have easy access to the best of KY while nestled away in a peaceful retreat.

Location · Family · Sleep quality

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. Located just outside of Lexington and only 12 miles from Keeneland. Sleeps 16 - 5 Bedrooms, 8 Beds, 3 Baths Solar heated pool is open April - September. All year: Hot tub and Sauna (Fall 2026) Play fort, 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.

Family · Location · Check-in

Central Lex Pool Oasis: HotTub! GameRm! Keeneland!

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, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

Location · Family · Hot tub

The Grand on Broadway - Pool, Hot Tub, Historic

Historic 4BR/2BA Nicholasville estate fully restored with $350K+ in upgrades, blending 19th-century elegance and modern comfort. Enjoy ornate trim, hardwood floors, soaring ceilings, 2 kitchens, grand dining, and multiple indoor and outdoor living areas. Enjoy the sounds of the birds on 1 acre with pool, hot tub, wraparound decks, porches and play field. Pet-friendly and perfect for families or groups, just minutes from Lexington, Keeneland, bourbon distilleries, and horse country.

Family · Location · Cleanliness

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.

Location · Family · Outdoor spaces

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.

Family · Value · Nearby

The Herrington

The home is located in the quiet Herrington Lake area with a short walk to view the Lake. This beautiful home features 3300 square feet with a cozy cabin feel and all the modern amenities including two kitchens. The cabin layout provides two comfortable common areas on both floors with TVs and complimentary Wifi. The perfect place to getaway from busy demands to reconnect or find exciting adventures on the Lake.

Family · Location · Pool

Country Villa

Visit this country villa to get away from the city or take a vacation with the family. This home has a great outdoor entertainment area with a pool, hot tub, and outdoor kitchen/bar. The home is surrounded by rolling pastures. This home has 5 bedrooms, 9 beds, 4.5 bathrooms, a large dining room, a living room up stairs and downstairs, and a garage turned into a game area for the kids.

Value · Family · Outdoor spaces

The Roosting Place

Enjoy the comforts of home while visiting charming Wilmore! We are located on a quiet street within walking distance to Asbury University and Asbury Seminary. Our guest suite is located in the daylight basement of our family home and can accommodate up to 4 guests. We are a 20-minute drive from Blue Grass Airport and Keeneland. Only 15 minutes from Shaker Village of Pleasant Hill.

Location · Value · Air conditioning

My Old Kentucky Home

The whole group will enjoy easy access to everything from this centrally located place. ONLY 10 Minutes from LEX airport, 10 Minuets from Keeneland, 10 Minuets from Kroger Field and 12 Minutes from RUPP ARENA & Downtown LEXINGTON KY!!

Location · Value · Backyard

Kentucky River Villa

Beautiful home atop the Kentucky Palisades with unparalleled views of the Bluegrass!

Location · Value · Hiking