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Crestwood Holiday Rentals

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49 rentals in Crestwood.
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Beautiful Executive Home - Perfect for Entertaining & Derby, holiday rental in Crestwood

Beautiful Executive Home - Perfect for Entertaining & Derby

6 bedrooms
5 bathrooms
Sleeps 12
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NEW! Louisville Apt w/ Patio, Fire Pit & Game Room, holiday rental in Crestwood

NEW! Louisville Apt w/ Patio, Fire Pit & Game Room

1 bedroom
1 bathroom
Sleeps 4
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Charming cape cod on wonderfully wooded acre, holiday rental in Crestwood

Charming cape cod on wonderfully wooded acre

4 bedrooms
3 bathrooms
Sleeps 8
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Spacious riverfront retreat, 20 minute easy drive to downtown Louisville., holiday rental in Crestwood

Spacious riverfront retreat, 20 minute easy drive to downtown Louisville.

4 bedrooms
3 bathrooms
Sleeps 10
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Historically Registered 1847 log Cabin, holiday rental in Crestwood

Historically Registered 1847 log Cabin

3 bedrooms
3 bathrooms
Sleeps 10
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RIVERFRONT - Boat Slips - 10 Min to Dtown Lville, holiday rental in Crestwood

RIVERFRONT - Boat Slips - 10 Min to Dtown Lville

2 bedrooms
1 bathroom
Sleeps 6
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Quaint & Cozy 4 Bedroom Home in Country Setting, holiday rental in Crestwood

Quaint & Cozy 4 Bedroom Home in Country Setting

East Louisville
4 bedrooms
2 bathrooms
Sleeps 6
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Captain's Cabin Bed & Breakfast: Historic & Romantic, holiday rental in Crestwood

Captain's Cabin Bed & Breakfast: Historic & Romantic

East Louisville
1 bedroom
1 bathroom
Sleeps 2
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DERBY  TIME RENTAL!!!, holiday rental in Crestwood

DERBY TIME RENTAL!!!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental, holiday rental in Crestwood

3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental

East Louisville
3 bedrooms
3 bathrooms
Sleeps 8
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Suburban | Quiet | Perfect Layout | Families, holiday rental in Crestwood

Suburban | Quiet | Perfect Layout | Families

Hikes Point, East Louisville
4 bedrooms
2 bathrooms
Sleeps 8
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7BD * Luxury Waterfront Property * Near Louisville, holiday rental in Crestwood

7BD * Luxury Waterfront Property * Near Louisville

5 bedrooms
3 bathrooms
Sleeps 16
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Your homebase for Louisville area attractions. Quiet, comfortable and convenient, holiday rental in Crestwood

Your homebase for Louisville area attractions. Quiet, comfortable and convenient

East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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Convenient, Comfortable, Cute & Close to everything!, holiday rental in Crestwood

Convenient, Comfortable, Cute & Close to everything!

East Louisville
4 bedrooms
2 bathrooms
Sleeps 7
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Five bedroom House Rental with pool, holiday rental in Crestwood

Five bedroom House Rental with pool

5 bedrooms
4 bathrooms
Sleeps 10
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Large Private Space in a Charming Historical Home, holiday rental in Crestwood

Large Private Space in a Charming Historical Home

East Louisville
1 bedroom
1 bathroom
Sleeps 2
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New ('15) centrally located new 6400+ sq ft + 6 bedrooms w/ 5 full bathroom, holiday rental in Crestwood

New ('15) centrally located new 6400+ sq ft + 6 bedrooms w/ 5 full bathroom

East Louisville
5 bedrooms
6 bathrooms
Sleeps 14
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Quiet & safe 2 bed 1 bath in Crescent Hill, holiday rental in Crestwood

Quiet & safe 2 bed 1 bath in Crescent Hill

2 bedrooms
1 bathroom
Sleeps 5
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Relax here when coming to the Derby or Breeders Cup, holiday rental in Crestwood

Relax here when coming to the Derby or Breeders Cup

East Louisville
3 bedrooms
3 bathrooms
Sleeps 6
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Louisville GEM, newly furnished, super clean, in a safe trendy area, holiday rental in Crestwood

Louisville GEM, newly furnished, super clean, in a safe trendy area

2 bedrooms
1 bathroom
Sleeps 4
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Derby City Home Baby Home, holiday rental in Crestwood

Derby City Home Baby Home

East Louisville
5 bedrooms
4 bathrooms
Sleeps 15
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Historic Cottage with modern amenities, holiday rental in Crestwood

Historic Cottage with modern amenities

East Louisville
2 bedrooms
1 bathroom
Sleeps 2
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Kentucky suite with the comforts of home., holiday rental in Crestwood

Kentucky suite with the comforts of home.

2 bedrooms
1 bathroom
Sleeps 4
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Comfortable 3br, 2bth--with front and back porches--in the heart of St. Matthews, holiday rental in Crestwood

Comfortable 3br, 2bth--with front and back porches--in the heart of St. Matthews

East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Cottage 2 bdrm w/ wrap porch, 1 mile to xway, shops and entertainment, holiday rental in Crestwood

Cozy Cottage 2 bdrm w/ wrap porch, 1 mile to xway, shops and entertainment

East Louisville
2 bedrooms
1 bathroom
Sleeps 4
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Kentucky Derby Rental - Close in, East End, holiday rental in Crestwood

Kentucky Derby Rental - Close in, East End

East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
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Home rental, holiday rental in Crestwood

Home rental

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!, holiday rental in Crestwood

Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!

East Louisville
4 bedrooms
5 bathrooms
Sleeps 7
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Beautiful KY Derby Home/15 miles from track, holiday rental in Crestwood

Beautiful KY Derby Home/15 miles from track

4 bedrooms
5 bathrooms
Sleeps 8
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Brand New 2 Bedroom Townhouse, holiday rental in Crestwood

Brand New 2 Bedroom Townhouse

East Louisville
2 bedrooms
2 bathrooms
Sleeps 4
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Louisville Short Term Condo Rentals, holiday rental in Crestwood

Louisville Short Term Condo Rentals

1 bedroom
1 bathroom
Sleeps 3
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Beautiful home near Cherokee and  Seneca parks, holiday rental in Crestwood

Beautiful home near Cherokee and Seneca parks

East Louisville
3 bedrooms
2 bathrooms
Sleeps 7
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Wooded Retreat PLUS Derby, holiday rental in Crestwood

Wooded Retreat PLUS Derby

East Louisville
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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LOUISVILLE - DERBY DONE RIGHT!  Centrally located -near everything, holiday rental in Crestwood

LOUISVILLE - DERBY DONE RIGHT! Centrally located -near everything

East Louisville
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Kentucky Derby Oasis, holiday rental in Crestwood

Kentucky Derby Oasis

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Upscale Living with Concierge Services, holiday rental in Crestwood

Upscale Living with Concierge Services

East Louisville
5 bedrooms
5 bathrooms
Sleeps 14
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Waterfront Prospect Home-20 Mi. to Louisville, holiday rental in Crestwood

Waterfront Prospect Home-20 Mi. to Louisville

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming house on Golf Course, holiday rental in Crestwood

Charming house on Golf Course

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Large 2020 Derby Rental, holiday rental in Crestwood

Beautiful Large 2020 Derby Rental

5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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2 bedroom , cottage, easy and close location to shopping, restaurants and away, holiday rental in Crestwood

2 bedroom , cottage, easy and close location to shopping, restaurants and away

East Louisville
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, holiday rental in Crestwood

Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown

East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom ranch style home in historic Prospect, holiday rental in Crestwood

3 bedroom ranch style home in historic Prospect

3 bedrooms
2 bathrooms
Sleeps 6
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East End Louisville Home on Quiet Street!, holiday rental in Crestwood

East End Louisville Home on Quiet Street!

East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large Duplex | Great For Groups | Suburban Life, holiday rental in Crestwood

Large Duplex | Great For Groups | Suburban Life

East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW Construction Derby Rental - 25 Min from Churchill Downs, holiday rental in Crestwood

NEW Construction Derby Rental - 25 Min from Churchill Downs

East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Elle’s Old Kentucky Home, holiday rental in Crestwood

Elle’s Old Kentucky Home

3 bedrooms
3 bathrooms
Sleeps 8
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Newly Renovated. Spotless. Secure Neighborhood, holiday rental in Crestwood

Newly Renovated. Spotless. Secure Neighborhood

East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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Home Baby Home, holiday rental in Crestwood

Home Baby Home

East Louisville
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Modern Louisville Condo ~ 8 Mi from Downtown!, holiday rental in Crestwood

NEW! Modern Louisville Condo ~ 8 Mi from Downtown!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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One Bedroom Cottage on Historic Property, 7 minutes from downtown, holiday rental in Crestwood

One Bedroom Cottage on Historic Property, 7 minutes from downtown

1 bedroom
1 bathroom
Sleeps 1
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