Holiday 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.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Cottage in Salvisa

4.97 out of 5 average rating, 135 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 favourite

Home in Lexington

4.9 out of 5 average rating, 178 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

Top guest favourite

Holiday home in Nicholasville

5 out of 5 average rating, 15 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.

Top guest favourite

Home in Richmond

5 out of 5 average rating, 5 reviews

Heart of Richmond

Welcome to your home away from home in the heart of Richmond, KY. This beautiful retreat offers everything you need for a memorable and relaxing stay. Perfectly positioned to put you at the center of all things Richmond, this oasis combines convenience with comfort and style. The highlights of the property are the salt water pool and the covered back patio. Take a dip, read a book, lounge comfortably or fire up the grill, the choice is yours! Come see us and make some memories!

Guest favourite

Home in Lexington

4.87 out of 5 average rating, 108 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 favourite

Guest house in Lexington

4.91 out of 5 average rating, 252 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.

Top guest favourite

Home in Lexington

4.96 out of 5 average rating, 112 reviews

LexFunZone! Pool! Hottub! GameRm! Cozy Backyard!

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!

Top guest favourite

Home in Lexington

4.99 out of 5 average rating, 79 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.

Top guest favourite

Home in Georgetown

4.98 out of 5 average rating, 101 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

4.81 out of 5 average rating, 164 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.

Top guest favourite

Home in Lexington

5 out of 5 average rating, 71 reviews

House w/private pool & hot tub, dogs ok

Enjoy exclusive access to incredible amenities including a heated in-ground pool, hot tub, BBQ grills, fire pit, playset, hammock, and yard games surrounded by a fenced backyard. Located on Lexington's west side, just 3 miles from Keeneland Race Course & Bluegrass Airport, and a short 4.9-miles to downtown. The pool is OPEN for the 2025 season. Dogs welcome with prior written agreement from host and an additional pet fee.

Top guest favourite

Home in Lexington

5 out of 5 average rating, 96 reviews

Game room! 5 beds an 4 bedrooms

POOL!! Super convenient LOCATION!! Totally renovated home with 5 beds (4 bedrooms) 2 full bath Game room! POOL opens may 26th closes sept 5 Fully stocked kitchen 1 king bed , 1queen, 3 twin beds 2 miles to Kroger field(commonwealth stadium) 4 miles Rupp arena 8 miles to keenland Less than 2 miles to Fayette mall Kroger , Trader Joe’s , many Restaurants Main Event, 1 mile away! Lex premises id 15078999