Vacation rentals in Crestwood, KY

107 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best Vacation rentals and Airbnb offers in Crestwood, KY

Boulevard Stays Tranquil 1BR Getaway - Crestwood, KY

Boulevard Stays Tranquil 1BR Getaway

Apartment, Crestwood

Boulevard Stays Tranquil 1BR Getaway is a apartment in Crestwood, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About Boulevard Stays Tranquil 1BR Getaway

Boulevard Stays Tranquil 1BR Getaway is a apartment in Crestwood, 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 $758.

From$108/night
Show
Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details - Crestwood, KY

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details

Apartment, Crestwood

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details is a apartment in Crestwood, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable…

Read more

About Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details

Boulevard Stays Comfy 1BR Haven Pool, Free Parking & Cozy Details is a apartment in Crestwood, with pet-friendly space, pool access, 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 $847.

From$121/night
Show
Great Location! Comfortable Studio Suite | Pool Access - Crestwood, KY

Great Location! Comfortable Studio Suite | Pool Access

Apartment, Crestwood

Great Location! Comfortable Studio Suite · Pool Access is a apartment in Crestwood, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Great Location! Comfortable Studio Suite | Pool Access

Great Location! Comfortable Studio Suite · Pool Access is a apartment in Crestwood, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $882.

From$126/night
Show
Boulevard Stays Spacious 1BR Suite Pool, Parking Gym D - Crestwood, KY

Boulevard Stays Spacious 1BR Suite Pool, Parking Gym D

Apartment, Crestwood

Boulevard Stays Spacious 1BR Suite Pool, Parking Gym D is a apartment in Crestwood, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for…

Read more

About Boulevard Stays Spacious 1BR Suite Pool, Parking Gym D

Boulevard Stays Spacious 1BR Suite Pool, Parking Gym D is a apartment in Crestwood, with pet-friendly space, pool access, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $910.

From$130/night
Show

Browse Vacation Rentals with a Pool in Crestwood, KY

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

Exclusive Farmhouse w/ a Romantic Garden View! - Crestwood, KY

Exclusive Farmhouse w/ a Romantic Garden View!

Apartment, Crestwood

Exclusive Farmhouse w/ a Romantic Garden View! is a apartment in Crestwood, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Exclusive Farmhouse w/ a Romantic Garden View!

Exclusive Farmhouse w/ a Romantic Garden View! is a apartment in Crestwood, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,404.

From$201/night
Show
Cozy City Condo in Norton Commons - Crestwood, KY

Cozy City Condo in Norton Commons

Apartment, Crestwood

Cozy City Condo in Norton Commons is a apartment in Crestwood, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Cozy City Condo in Norton Commons

Cozy City Condo in Norton Commons is a apartment in Crestwood, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,380.

From$340/night
Show
Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company! - Crestwood, KY

Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company!

Condo, Crestwood

Great Value! 2 Bedroom Suite · Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company! is a condo in Crestwood, with pool access, kitchen access, and room for a group. This stay…

Read more

About Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company!

Great Value! 2 Bedroom Suite · Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company! is a condo in Crestwood, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,895.

From$414/night
Show
Hilltop on the Ridge Executive Get Away - Crestwood, KY

Hilltop on the Ridge Executive Get Away

Holiday Home, Crestwood

Hilltop on the Ridge Executive Get Away is a holiday home in Crestwood, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Hilltop on the Ridge Executive Get Away

Hilltop on the Ridge Executive Get Away is a holiday home in Crestwood, with pool access 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, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,322.

From$1,760/night
Show

Best Crestwood, KY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Luxe Lyndon Home < 11 Mi to Dtwn Louisville! - Crestwood, KY

Luxe Lyndon Home < 11 Mi to Dtwn Louisville!

Holiday Home, Crestwood

Luxe Lyndon Home < 11 Mi to Dtwn Louisville! is a holiday home in Crestwood, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Luxe Lyndon Home < 11 Mi to Dtwn Louisville!

Luxe Lyndon Home < 11 Mi to Dtwn Louisville! is a holiday home in Crestwood, 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,628.

From$165/night
Show
28 Mi to Downtown Louisville: Serene Farm Getaway - Crestwood, KY

28 Mi to Downtown Louisville: Serene Farm Getaway

Cabin, Crestwood

28 Mi to Downtown Louisville: Serene Farm Getaway is a cabin in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 28 Mi to Downtown Louisville: Serene Farm Getaway

28 Mi to Downtown Louisville: Serene Farm Getaway is a cabin in Crestwood, 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 $1,219.

From$174/night
Show
Lagrange Loft - Small Town USA - Bourbon Trail - Crestwood, KY

Lagrange Loft - Small Town USA - Bourbon Trail

Apartment, Crestwood

Lagrange Loft - Small Town USA - Bourbon Trail is a apartment in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Lagrange Loft - Small Town USA - Bourbon Trail

Lagrange Loft - Small Town USA - Bourbon Trail is a apartment in Crestwood, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,297.

From$185/night
Show
The Rickhouse Apartment - Crestwood, KY

The Rickhouse Apartment

Apartment, Crestwood

The Rickhouse Apartment is a apartment in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About The Rickhouse Apartment

The Rickhouse Apartment is a apartment in Crestwood, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$321/night
Show

Best Pet-Friendly Vacation Rentals in Crestwood, KY

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

Relaxing stay near Louisville's top attractions! - Crestwood, KY

Relaxing stay near Louisville's top attractions!

Holiday Home, Crestwood

Relaxing stay near Louisville's top attractions! is a holiday home in Crestwood, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

Read more

About Relaxing stay near Louisville's top attractions!

Relaxing stay near Louisville's top attractions! is a holiday home in Crestwood, with pet-friendly 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,059.

From$151/night
Show
Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking - Crestwood, KY

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking

Apartment, Crestwood

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking is a apartment in Crestwood, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable…

Read more

About Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking

Boulevard Stays Stylish 3BR Getaway Pool, Gym Access & Free Parking is a apartment in Crestwood, with pet-friendly space, pool access, 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 $1,299.

From$186/night
Show
2-bdrm house in Louisville. Near highway, stores, & 20 mins from Churchill Downs - Crestwood, KY

2-bdrm house in Louisville. Near highway, stores, & 20 mins from Churchill Downs

Holiday Home, Crestwood

2-bdrm house in Louisville. Near highway, stores, & 20 mins from Churchill Downs is a holiday home in Crestwood, with pet-friendly space, parking, and kitchen access. This stay gives…

Read more

About 2-bdrm house in Louisville. Near highway, stores, & 20 mins from Churchill Downs

2-bdrm house in Louisville. Near highway, stores, & 20 mins from Churchill Downs is a holiday home in Crestwood, 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 $2,516.

From$359/night
Show
Exclusive Buckner retreat w/ theater & game room! - Crestwood, KY

Exclusive Buckner retreat w/ theater & game room!

Holiday Home, Crestwood

Exclusive Buckner retreat w/ theater & game room! is a holiday home in Crestwood, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

Read more

About Exclusive Buckner retreat w/ theater & game room!

Exclusive Buckner retreat w/ theater & game room! is a holiday home in Crestwood, with pet-friendly 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,613.

From$373/night
Show

Best Crestwood, KY vacation rentals with a kitchen

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

Louisville Retreat w/ Deck ~ 11 Mi to Downtown! - Crestwood, KY

Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

Holiday Home, Crestwood

Louisville Retreat w/ Deck ~ 11 Mi to Downtown! is a holiday home in Crestwood, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

Louisville Retreat w/ Deck ~ 11 Mi to Downtown! is a holiday home in Crestwood, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,550.

From$221/night
Show
Luxe Lyndon Home < 11 Mi to Dtwn Louisville! - Crestwood, KY

Luxe Lyndon Home < 11 Mi to Dtwn Louisville!

Holiday Home, Crestwood

Luxe Lyndon Home < 11 Mi to Dtwn Louisville! is a holiday home in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Luxe Lyndon Home < 11 Mi to Dtwn Louisville!

Luxe Lyndon Home < 11 Mi to Dtwn Louisville! is a holiday home in Crestwood, 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 $1,565.

From$224/night
Show
Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers - Crestwood, KY

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers

Holiday Home, Crestwood

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers is a holiday home in Crestwood, with kitchen access. This stay gives travelers a comfortable base for…

Read more

About Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers

Valhalla View Home-Minutes to Golf Course-Perfect for Golfers, Horses, Trailers is a holiday home in Crestwood, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,856.

From$265/night
Show
Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! - Crestwood, KY

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Holiday Home, Crestwood

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! is a holiday home in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable…

Read more

About Stylish Home on water, minutes from downtown. Secluded and Convenient to it all!

Stylish Home on water, minutes from downtown. Secluded and Convenient to it all! is a holiday home in Crestwood, 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 $2,632.

From$376/night
Show

Our Favorite Family-Friendly Vacation Rentals in Crestwood, KY

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

31 Mi to Louisville: Cabin on 235 Acres! - Crestwood, KY

31 Mi to Louisville: Cabin on 235 Acres!

Cottage, Crestwood

31 Mi to Louisville: Cabin on 235 Acres! is a cottage in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About 31 Mi to Louisville: Cabin on 235 Acres!

31 Mi to Louisville: Cabin on 235 Acres! is a cottage in Crestwood, 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 $1,410.

From$174/night
Show
Horse Farm Retreat w/ Pond View Near Louisville - Crestwood, KY

Horse Farm Retreat w/ Pond View Near Louisville

Cottage, Crestwood

Horse Farm Retreat w/ Pond View Near Louisville is a cottage in Crestwood, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

Read more

About Horse Farm Retreat w/ Pond View Near Louisville

Horse Farm Retreat w/ Pond View Near Louisville is a cottage in Crestwood, 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 $1,410.

From$174/night
Show
28 Mi to Downtown Louisville: Serene Farm Getaway - Crestwood, KY

28 Mi to Downtown Louisville: Serene Farm Getaway

Cottage, Crestwood

28 Mi to Downtown Louisville: Serene Farm Getaway is a cottage in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 28 Mi to Downtown Louisville: Serene Farm Getaway

28 Mi to Downtown Louisville: Serene Farm Getaway is a cottage in Crestwood, 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 $1,464.

From$181/night
Show
La Grange Cabin on a Racehorse Farm w/ Pond Views! - Crestwood, KY

La Grange Cabin on a Racehorse Farm w/ Pond Views!

Cottage, Crestwood

La Grange Cabin on a Racehorse Farm w/ Pond Views! is a cottage in Crestwood, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About La Grange Cabin on a Racehorse Farm w/ Pond Views!

La Grange Cabin on a Racehorse Farm w/ Pond Views! is a cottage in Crestwood, 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 $1,503.

From$186/night
Show