Vacation 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

Stone&Cedar Lodge pool, hot tub, sauna, fire, 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.

Charming & Comfortable Furnished Stay

This inviting furnished home offers everything needed for a comfortable and convenient stay. The living room features cozy seating and a TV, while the fully equipped kitchen includes stainless steel appliances, a dishwasher, microwave, and everyday essentials. Enjoy meals at the dining table, relax in the comfortable bedroom, or get some work done at the dedicated desk. The bathroom includes a full tub and shower, and ample storage throughout makes it easy to settle in and feel at home.

Football SZN 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!

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.

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.

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.

Modern & Comfortable Retreat

This welcoming apartment offers a comfortable, fully furnished setting designed for everyday living. The home features a cozy living room with a TV, a dedicated dining area, and a well-equipped kitchen with stainless steel appliances, ample cabinetry, and essential countertop appliances. The bedrooms includes comfortable beds, nightstands, and closet storage, while the bathrooms feature a tub and shower combination, vanity, and illuminated mirror.

Charming Furnished Getaway

This inviting furnished home is designed for a comfortable and convenient stay. The living room features cozy seating and a TV for relaxing, while the fully equipped kitchen includes stainless steel appliances, a dishwasher, microwave, coffee maker, and everyday essentials. A dining area provides a convenient place to enjoy meals, and the bedroom include comfortable furnishings, bedside storage, and a dedicated workspace.

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.

Modern Retreat with Everyday Comfort

This inviting furnished unit offers everything needed for a comfortable and convenient stay. Enjoy a welcoming living room with a TV, a fully equipped kitchen with stainless steel appliances, a dining area, and a relaxing bedroom with a dedicated workspace. The unit also includes a full bathroom, in-unit washer and dryer, ample storage, and thoughtful furnishings throughout, making it ideal for extended stays.

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.