Photo by Michael Schuier

Jessamine County vacation rentals

We found 572 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 13 homes and other vacation rentals in Jessamine County that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, including parking and a garden. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Find the perfect vacation rental for your Jessamine County getaway

Learn about the unique charm of Jessamine County with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Jessamine County

Are you hoping to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Jessamine County a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Talon Winery (7.3 mi / 11.7 km)
  • Keeneland Racing Course (11.7 mi / 18.8 km)
  • The Kentucky Castle (12.3 mi / 19.7 km)
  • Kearney Hills Golf Links (16.7 mi / 26.8 km)
  • Equus Run Vineyard & Winery (19.6 mi / 31.6 km)
  • Peninsula Golf Course (10.3 mi / 16.6 km)

Exploring the natural features in Jessamine County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Jessamine County. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Raven Run Nature Sanctuary (10 mi / 16.1 km)
  • Herrington Lake (12.3 mi / 19.8 km)
  • Masterson Station Park (15.2 mi / 24.4 km)
  • Kentucky Horse Park (18.9 mi / 30.5 km)
  • Lake Reba (20.2 mi / 32.6 km)
  • Arboretum (10 mi / 16.1 km)

Frequently asked questions

What is the best area to stay in Jessamine County when booking a vacation rental?

Wilmore is among the most popular areas for a Vrbo vacation home in Jessamine County. Consider our range of comfortable stays and then get ready to experience the best of this destination.

What is the most popular type of vacation rental accommodation in Jessamine County?

According to our data, houses are the most desirable vacation rental type in Jessamine County. But that goes without saying, everyone's idea of an epic trip isn't the same. Vrbo has vacation rentals in a variety of shapes and sizes, and we'll help you find the perfect fit for you.

How much does it cost to rent a vacation rental in Jessamine County?

The average price for a vacation home in Jessamine County is determined by a number of factors, such as property type, season and length of stay. Whether you're searching for a villa with space for extended family or a quaint cabin for just you and the kids, just enter your dates of travel to view stays with great value.

How much does it cost to rent a beach house in Jessamine County?

The average price for a vacation rental near the beach in Jessamine County depends on when you'll be there and the type and size of property you want. Find prices easily on Vrbo by entering your preferred travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.

What are popular rental amenities in Jessamine County?

When it comes to rental amenities that guests search for in Jessamine County, an oven, a stovetop and a fridge rank highest. With Vrbo vacation rentals, you'll find options to match your style and taste, whether you're taking a trip with family members, friends or even pets.

Are there large group vacation rentals in Jessamine County?

With four properties that can sleep 10 or more people in Jessamine County, you won't have to keep anyone off the invite list. From fun family vacations to special events like birthday parties and weddings, Vrbo will help you find a large group rental to match the occasion.

Can I find two-bedroom vacation rentals in Jessamine County?

Gather your family and experience complete comfort and privacy in one of the two two-bedroom vacation properties Jessamine County has to offer.

Are there vacation rentals with WiFi in Jessamine County?

Jessamine County has eight vacation rentals with WiFi, so you can stay connected while traveling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a cinch to get online.

How old do you have to be to rent a vacation rental in Jessamine County?

We recommend checking with the Jessamine County vacation property you're considering on Vrbo as the age limit varies. However, generally it's 16, 18 or 21.

How long can I rent a vacation rental in Jessamine County for?

It's down to the Jessamine County property. To look at a list of options offering extended stays, simply enter your dates and guest number into the Vrbo search page. Look forward to having the entire property to yourself, as well as amenities such as air conditioning, a kitchen and outdoor spaces where the kids can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.