Vacation rentals in Jessamine County, KY

Best vacation rentals and Airbnb offers in Jessamine County, KY

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington

Apartment, Jessamine County

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington is a apartment in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay gives…

Read more

About Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington

Charming 2-bedroom apartment with AC, WiFi in brilliant Lexington is a apartment in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $778.

From$111/night

Show›

Location location location-#15015318-1

Apartment, Jessamine County

Location location location-#15015318-1 is a apartment in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Location location location-#15015318-1

Location location location-#15015318-1 is a apartment in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $793.

From$113/night

Show›

Peaceful Bluegrass Getaway on 10-Acre Farm!

Holiday Home, Jessamine County

Peaceful Bluegrass Getaway on 10-Acre Farm! is a holiday home in Jessamine County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Peaceful Bluegrass Getaway on 10-Acre Farm!

Peaceful Bluegrass Getaway on 10-Acre Farm! is a holiday home in Jessamine County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,282.

From$122/night

Show›

2BR Central Loft w/ Garage, near NCR & Downtown

Holiday Home, Jessamine County

2BR Central Loft w/ Garage, near NCR & Downtown is a holiday home in Jessamine County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About 2BR Central Loft w/ Garage, near NCR & Downtown

2BR Central Loft w/ Garage, near NCR & Downtown is a holiday home in Jessamine County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $998.

From$143/night

Show›

Vacation rentals with a pool in Jessamine County, KY

Add a pool to the search when you want an easy place to cool off between outings.

Picadome Pool Getaway

Holiday Home, Jessamine County

Picadome Pool Getaway is a holiday home in Jessamine County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Picadome Pool Getaway

Picadome Pool Getaway is a holiday home in Jessamine County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,981.

From$283/night

Show›

Private Home located at Lake Herrington

Holiday Home, Jessamine County

Private Home located at Lake Herrington is a holiday home in Jessamine County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Private Home located at Lake Herrington

Private Home located at Lake Herrington is a holiday home in Jessamine County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,750.

From$393/night

Show›

Pool | Hot Tub | Covered Porch | Patio | Game Room

Holiday Home, Jessamine County

Pool · Hot Tub · Covered Porch · Patio · Game Room is a holiday home in Jessamine County, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable…

Read more

About Pool | Hot Tub | Covered Porch | Patio | Game Room

Pool · Hot Tub · Covered Porch · Patio · Game Room is a holiday home in Jessamine County, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,623.

From$518/night

Show›

Lexington Fun Zone! Pool! HotTub! Arcade! Games!

Holiday Home, Jessamine County

Lexington Fun Zone! Pool! HotTub! Arcade! Games! is a holiday home in Jessamine County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

Read more

About Lexington Fun Zone! Pool! HotTub! Arcade! Games!

Lexington Fun Zone! Pool! HotTub! Arcade! Games! is a holiday home in Jessamine County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,140.

From$591/night

Show›

Vacation rentals with parking in Jessamine County, KY

Find vacation rentals that make arriving by car easier.

Newly remodeled home central to downtown!

Holiday Home, Jessamine County

Newly remodeled home central to downtown! is a holiday home in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Newly remodeled home central to downtown!

Newly remodeled home central to downtown! is a holiday home in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,108.

From$158/night

Show›

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Condo, Jessamine County

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington is a condo in Jessamine County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

Read more

About Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington

Cozy 2-bedroom condo with WiFi, AC in marvelous Lexington is a condo in Jessamine County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,119.

From$160/night

Show›

Great Location | Patio | Grill | Tempurpedic Beds

Holiday Home, Jessamine County

Great Location · Patio · Grill · Tempurpedic Beds is a holiday home in Jessamine County, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base…

Read more

About Great Location | Patio | Grill | Tempurpedic Beds

Great Location · Patio · Grill · Tempurpedic Beds is a holiday home in Jessamine County, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,269.

From$181/night

Show›

THE ROSE: modern+cozy home close to Keeneland & UK

Holiday Home, Jessamine County

THE ROSE: modern+cozy home close to Keeneland & UK is a holiday home in Jessamine County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About THE ROSE: modern+cozy home close to Keeneland & UK

THE ROSE: modern+cozy home close to Keeneland & UK is a holiday home in Jessamine County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,312.

From$187/night

Show›

Pet-friendly vacation rentals in Jessamine County, KY

Bring your pet along with stays that welcome four-legged travelers.

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

Holiday Home, Jessamine County

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY. is a holiday home in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay gives…

Read more

About This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY. is a holiday home in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,105.

From$158/night

Show›

Peaceful Bluegrass Getaway on 10-Acre Farm!

Holiday Home, Jessamine County

Peaceful Bluegrass Getaway on 10-Acre Farm! is a holiday home in Jessamine County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Peaceful Bluegrass Getaway on 10-Acre Farm!

Peaceful Bluegrass Getaway on 10-Acre Farm! is a holiday home in Jessamine County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,135.

From$162/night

Show›

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Holiday Home, Jessamine County

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's is a holiday home in Jessamine County. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's is a holiday home in Jessamine County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,266.

From$181/night

Show›

Modern escape just outside Lexington

Holiday Home, Jessamine County

Modern escape just outside Lexington is a holiday home in Jessamine County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Modern escape just outside Lexington

Modern escape just outside Lexington is a holiday home in Jessamine County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,418.

From$203/night

Show›

Vacation rentals with a kitchen in Jessamine County, KY

Compare stays with kitchen access for longer trips and easier meals.

Stylish & Central - Walk to UK Campus/Hospital, Mins to DT/Rupp/Keeneland

Apartment, Jessamine County

Stylish & Central - Walk to UK Campus/Hospital, Mins to DT/Rupp/Keeneland is a apartment in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base…

Read more

About Stylish & Central - Walk to UK Campus/Hospital, Mins to DT/Rupp/Keeneland

Stylish & Central - Walk to UK Campus/Hospital, Mins to DT/Rupp/Keeneland is a apartment in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,157.

From$165/night

Show›

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington

Apartment, Jessamine County

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington is a apartment in Jessamine County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington is a apartment in Jessamine County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,679.

From$172/night

Show›

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington

Apartment, Jessamine County

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington is a apartment in Jessamine County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington

3 Mi to Dtwn: Updated Home w/ Hot Tub in Lexington is a apartment in Jessamine County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,321.

From$189/night

Show›

Hillside Farm & Creek - A Bourbon Trail Retreat

Country House, Jessamine County

Hillside Farm & Creek - A Bourbon Trail Retreat is a country house in Jessamine County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Hillside Farm & Creek - A Bourbon Trail Retreat

Hillside Farm & Creek - A Bourbon Trail Retreat is a country house in Jessamine County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,333.

From$190/night

Show›

Family-friendly vacation rentals in Jessamine County, KY

Plan a trip with stays that give families more room to spread out.

Lake Getaway at Lake Herrington with Golf Cart

Cottage, Jessamine County

Lake Getaway at Lake Herrington with Golf Cart is a cottage in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Lake Getaway at Lake Herrington with Golf Cart

Lake Getaway at Lake Herrington with Golf Cart is a cottage in Jessamine County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,460.

From$209/night

Show›

Cozy 3 bedroom home perfect for families or work.

Holiday Home, Jessamine County

Cozy 3 bedroom home perfect for families or work. is a holiday home in Jessamine County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Cozy 3 bedroom home perfect for families or work.

Cozy 3 bedroom home perfect for families or work. is a holiday home in Jessamine County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,493.

From$213/night

Show›

Our Lakeside Retreat w/ Deck on Lake Herrington!

Cottage, Jessamine County

Our Lakeside Retreat w/ Deck on Lake Herrington! is a cottage in Jessamine County, with outdoor space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

Read more

About Our Lakeside Retreat w/ Deck on Lake Herrington!

Our Lakeside Retreat w/ Deck on Lake Herrington! is a cottage in Jessamine County, with outdoor space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$226/night

Show›

Cozy 4-bedroom house in enjoyable Lexington with WiFi, AC. Centrally located.

Holiday Home, Jessamine County

Cozy 4-bedroom house in enjoyable Lexington with WiFi, AC. Centrally located. is a holiday home in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay…

Read more

About Cozy 4-bedroom house in enjoyable Lexington with WiFi, AC. Centrally located.

Cozy 4-bedroom house in enjoyable Lexington with WiFi, AC. Centrally located. is a holiday home in Jessamine County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,658.

From$237/night

Show›