Vacation rentals with a pool in Jessamine County

A spacious living area features a comfortable sectional sofa arranged around a wooden coffee table. A stone fireplace serves as a focal point, complemented by subtle decorative elements. Modern light fixtures illuminate the room, creating a welcoming environment.

4.9 out of 5 average rating, 194 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

Vacation home in Nicholasville

A spacious stone and cedar lodge is set against a clear blue sky, surrounded by well-maintained green lawns and trees. The front porch features a welcoming railing and an American flag, showcasing a traditional architectural style.

5 out of 5 average rating, 28 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.

Home in Nicholasville

The Hundred-Year Haven

108-year-old Lexington treasure that blends timeless character with modern comfort. Relax in the new hot tub, pool, or enjoy the backyard with a trampoline and fire pit. Inside, or create content in the upstairs bar area. The formal dining room great for birthdays or Thanksgiving. Just minutes to Keeneland, downtown Lexington, and local favorites like Euro Bar, this home offers a one-of-a-kind stay. Please note: no large parties, no smoking indoors, and quiet hours after 10 p.m.

Superhost

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

4.88 out of 5 average rating, 305 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.

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.

4.97 out of 5 average rating, 130 reviews

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!

A large, heated swimming pool is visible at the center, surrounded by comfortable lounge chairs. Umbrellas provide shade for relaxation. A spacious outdoor area features a deck and is bordered by a lush green lawn, enhancing the inviting atmosphere for entertaining.

4.99 out of 5 average rating, 93 reviews

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.

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

4.78 out of 5 average rating, 54 reviews

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.

4.9 out of 5 average rating, 10 reviews

A spacious villa is showcased from the front, featuring large arched windows and a welcoming entryway. Lush greenery surrounds the property, accentuating the stone exterior. A well-maintained lawn leads up to the steps, emphasizing the tranquil setting among the trees.

Home in Nicholasville

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.

4.92 out of 5 average rating, 299 reviews

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.

A spacious living area is centered around a decorative stone fireplace, complemented by a large flat-screen television mounted above. Comfortable leather seating and a wooden coffee table are arranged on a patterned area rug, with natural light entering through a nearby window.

4.88 out of 5 average rating, 42 reviews

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!!