Vacation rentals with a pool in Jessamine County

4.94 out of 5 average rating, 81 reviews

Home in Lexington

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.

Vacation home in Nicholasville

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.

5.0 out of 5 average rating, 39 reviews

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.

4.97 out of 5 average rating, 153 reviews

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

Home in Lexington

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!

Home in Nicholasville

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.

4.31 out of 5 average rating, 13 reviews

A private heated salt-water pool is surrounded by a spacious concrete deck, featuring two black lounge chairs for relaxation. Lush green trees provide a natural backdrop, enhancing the tranquil outdoor space. The pool's clear blue water invites enjoyment and leisure.

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.

4.83 out of 5 average rating, 369 reviews

4.99 out of 5 average rating, 106 reviews

Home in Lexington

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.

4.75 out of 5 average rating, 57 reviews

The exterior of the home features a welcoming porch with wooden rocking chairs, surrounded by grassy areas and bare trees. The facade showcases a mix of stone and vinyl siding, and large windows provide natural light. The clear sky enhances the inviting appearance.

Home in Lancaster

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.

4.92 out of 5 average rating, 326 reviews

Guest favorite

A cozy living area features a light gray couch and a wooden loveseat with soft cushions. A coffee table sits between them, positioned in front of an electric fireplace. A small TV is placed on a stand nearby, and large windows allow natural light into the space.

Guest suite in Wilmore

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.

Charming Home with Modern Features

Enjoy a comfortable stay in this beautifully furnished home, thoughtfully designed with everything you need for everyday living. The home features a fully equipped kitchen, inviting living area, dedicated dining area, comfortable bedrooms, and well-appointed bathrooms. With modern conveniences and tasteful furnishings throughout, this home is ready for a relaxing and enjoyable stay.