Vacation rentals with a pool in Jessamine County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Jessamine County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Salvisa

4.97 out of 5 average rating, 131 reviews

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!

Guest favorite

Home in Lexington

4.89 out of 5 average rating, 163 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

Guest favorite

Cabin in Paris

4.94 out of 5 average rating, 68 reviews

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

Guest favorite

Home in Midway

4.99 out of 5 average rating, 80 reviews

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

Guest favorite

Home in Lexington

4.87 out of 5 average rating, 99 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!

Guest favorite

Guesthouse in Lexington

4.93 out of 5 average rating, 189 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.

Guest favorite

Home in Lexington

4.99 out of 5 average rating, 91 reviews

Fam/Friendly Holiday Fun! Hottub! Pool! 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, hottub, 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!

Guest favorite

Home in Lexington

4.99 out of 5 average rating, 76 reviews

Close to Everything! Beautiful two-story home

Beautiful home in a great location. Easy access to major highways. Less than 10 minutes to Bluegrass Airport, Keeneland, Restaurants, Downtown & Shopping. This awesome two-story home has a fenced yard with pool, (additional charge for heated pool), fire pit and outdoor area for entertaining or relaxing. 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.

Guest favorite

Home in Georgetown

4.98 out of 5 average rating, 93 reviews

Modern Farmhouse/20 acres/9 miles from Horse Park

Beautiful new home (built in 2018) on 20 acres just outside Lexington. 19 miles from the Blue Grass Airport & Keeneland Racetrack. 9 miles from the Horse Park. In-ground pool (open beginning of May-end of Sept, not heated). Marble wrap around porch provides stunning views of the bluegrass. *Please note that we are firm on our '4 night minimum' policy, no exceptions. **Please read about our WIRELESS INTERNET SIGNAL before booking**

Superhost

Home in Lawrenceburg

4.82 out of 5 average rating, 162 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

This spacious and cozy three-bedroom home is less than one mile from Lawrenceburg's city center - nestled in a quiet, residential neighborhood with a swimming pool and dual-level deck. Downtown restaurants, grocery stores, Wild Turkey Bourbon Distillery, Four Roses Bourbon Distillery, and the city park are all within close proximity. The property was completely renovated in Spring 2019 and contains all new furniture and flooring.

Superhost

Cabin in Harrodsburg

5 out of 5 average rating, 3 reviews

Shawnee Creek Bourbon Trail Chalet

Forget your worries and escape to the ultimate getaway nestled in the heart of the Bourbon Trail. Perfect for large groups, this spacious retreat boasts a luxurious hot tub, breathtaking views of a serene horse farm, and a tranquil creek to unwind by. Enjoy the expansive porch for grilling or simply taking in the peaceful surroundings. This idyllic retreat promises a relaxing and rejuvenating experience for all.

Guest favorite

Farm stay in Harrodsburg

4.95 out of 5 average rating, 136 reviews

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.