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Lexington Holiday Rentals

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137 rentals in Lexington.
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Luxury Updated Chevy Chase Home - Close to UK

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 Bdr/3 Bath House in Andover Convenient to All of Lexington

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Historic Mansion in Downtown Lexington.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cottage on working Thoroughbred Horse Farm on Kentucky's Horse Parkway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Brick Cottage w/carriage house downtown Lexington sleeps 8

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cottage on horse farm close to Keeneland, Airport, Horse Park, Bourbon Trail

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cheerful and Cozy in the Heart of Chevy Chase!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Guest House on Kentucky Working Thoroughbred Horse Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury 5BR/4BA Updated Home In The Heart Of Lexington

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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The Martin House - In the heart of historic downtown Lexington

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect for Summer! Close to downtown & surrounding area attractions!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Wine Cellar Condominium

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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A hidden gem in Lexington's Historic District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Lake/Farm Retreat

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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KY Horse Park, Equestrian Events, Derby, Keeneland! 4 miles off I-75/I-64

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Brand New Cottage, 1 mile from Keeneland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful country house with pool 10 minutes from Lexington

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lexington Apt. with parking & private entrance Preview listing

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable Family Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena and Alltech

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Modern & Elegant Carriage House at Historic Warsaw

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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The Kentucky Bourbon Suite

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Kentucky River Cottages ~ Featured on the Live Well Network's Sweet Retreats!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Private Apartment in Downtown Lexington

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unique Stay in a 1907 Log Cabin on The Kentucky River

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Downtown Private Room and Bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Historic Home in Downtown Lexington

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Kentucky Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Completely refurbished downstairs apartment in 1920's home

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Townhome Near Rupp Arena

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Springwood Cottage in the Heart of the Bluegrass

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW Luxury Remodel 4BR/2.5BA Only 10 min to Keeneland and downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3,500 sq ft with All New Furnishings + Green Space

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Remodel with Private Backyard! 1 minute walk to dining and retail!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bourbon Country's Clubhouse Year Round Pool Estate

Holiday Rental House
8 bedrooms
11 bathrooms
Sleeps 40
Match: Sleeps
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Adorable 2 bedroom, 3 bathroom townhouse downtown with reclaimed boutique decor

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Your Home Away From Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Newly remodeled home central to downtown!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Downtown Lexington Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Horse country home - no stairs - sleeping and dining for 10

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Kentucky River Cottages ~ 2nd Floor Suite ~ On The Bourbon Trail!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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A Renovated 3 Bedroom, 2.5 Bath Townhouse In Downtown Lexington.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Black Bear Lodge

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1.7 miles to KY Horse Park

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradiso - Divine Condo, Perfect Location Walkable to Everything Downtown

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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