Vacation rentals with a hot tub in Jessamine County

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

Hot tub, lake view, tremendous deck/outdoor space

Welcome to the most private lake home for rent on Herrington. Direct lake access and centrally located to 4 marinas with-in 1.5 miles. This peaceful home is on a 1.7 acre double lot with over 300’ of frontage and backyard with dozens of mature trees. The private cove is perfect for swimming, kayaking, and hanging out on the water throughout the day. The 2,500’ SF 4 bedroom home was remodeled in 2024 with large groups in mind. If you’re looking for a one of a kind private setting, this is it!

Spacious retreat w/Pool, Hot Tub, Games & Fire Pit

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 private, heated, salt-water pool, year-round hot tub, & multiple entertainment areas, there’s something here for every age to enjoy and 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 space

Cozy, quiet, comfortable apartment. In the woods.

Take a break and unwind in this quiet basement apartment in a cabin in the woods. Gated community with no through traffic. Nestled on over five acres of woods. Lots of easy groomed trails with fire pits. 3 miles from historic Shakers Village. 12 miles from Fort Harrod. 8 miles from Harrington lake. 20 miles from Perrysville Historic Battlefield. Conveniently located on the Bourbon trail. only 23 miles from Lexington Bluegrass airport. 22 miles from Keenland horse track and Red mile gaming.

New Construction/ Close to Herrington Lake

The White Chalet is a brand NEW construction home centrally located in a peaceful neighborhood in Lancaster, KY. Whether you are going to Keeneland, a sporting event, Herrington Lake, or just looking for a fun getaway, you will only be a short commute to all that Central KY has to offer! Featuring 4BR, 3BA, high end kitchen, hot tub, game room, and sauna, we have all the amenities needed for a short or long stay. We are 21mi to Downtown Lexington & 20mi to Wilderness Trail Distillery.

Luxury lake house with must see view

This 3791sqft home on Herrington Lake is a new rental with brand new furnishings throughout as of May 2023. You'll see the lake as soon as you pull into the drive, the view is simply breathtaking. With a large driveway and additional large parking pad complete with electrical outlets for electric cars there is plenty of parking so bring your boat/jet skis. Don't have a boat? There are 4 nearby marinas that offer boat rentals, dining, and activities. The closest is only 3 minutes away!

Bluegrass Fall FunZone! 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!

13mi to Keeneland/C&K Property/ Historic Farm

This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key. Featuring 4 bedrooms, 4.5 bathrooms, original Gothic style architecture, picturesque views of Kentucky’s rolling hills, curated antiques, original art & so much more! The Shanklin House is an extension of Castle & Key, where guests will enjoy considered finishes, bespoke Castle & Key welcome basket and a space designed to exceed all guest expectations.

Guest Fav/ 2 Kings / Fenced Yard/ Prime Lexington

Guest Favorite Stay in Lexington’s desirable Hartland area! Relax in 2 comfy king bedrooms, enjoy a fenced yard perfect for pets, and unwind on the patio with fire pit & string lights. Fully renovated with a stocked kitchen, smart TVs, and in-home laundry. Walk to parks, jog-friendly sidewalks, and local dining. Minutes to downtown, UK, and distilleries. Perfect for families, friends, or pups—your Lexington getaway starts here!