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Saint Matthews Vacation Rentals

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50 rentals in Saint Matthews.
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Large Private Space in a Charming Historical Home, vacation rental in Saint Matthews
Large Private Space in a Charming Historical Home, vacation rental in Saint Matthews
Large Private Space in a Charming Historical Home, vacation rental in Saint Matthews

Large Private Space in a Charming Historical Home

Rental Home in East Louisville
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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There's a reason it's called The Sweet Spot. This is Louisville's ideal locale!, vacation rental in Saint Matthews
There's a reason it's called The Sweet Spot. This is Louisville's ideal locale!, vacation rental in Saint Matthews
There's a reason it's called The Sweet Spot. This is Louisville's ideal locale!, vacation rental in Saint Matthews

There's a reason it's called The Sweet Spot. This is Louisville's ideal locale!

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Suburban | Quiet | Perfect Layout | Families, vacation rental in Saint Matthews
Suburban | Quiet | Perfect Layout | Families, vacation rental in Saint Matthews
Suburban | Quiet | Perfect Layout | Families, vacation rental in Saint Matthews

Suburban | Quiet | Perfect Layout | Families

Rental Home in Hikes Point, East Louisville
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable 3br, 2bth--with front and back porches--in the heart of St. Matthews, vacation rental in Saint Matthews
Comfortable 3br, 2bth--with front and back porches--in the heart of St. Matthews, vacation rental in Saint Matthews
Comfortable 3br, 2bth--with front and back porches--in the heart of St. Matthews, vacation rental in Saint Matthews

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

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LOUISVILLE - DERBY DONE RIGHT!  Centrally located -near everything, vacation rental in Saint Matthews
LOUISVILLE - DERBY DONE RIGHT!  Centrally located -near everything, vacation rental in Saint Matthews
LOUISVILLE - DERBY DONE RIGHT!  Centrally located -near everything, vacation rental in Saint Matthews

LOUISVILLE - DERBY DONE RIGHT! Centrally located -near everything

Rental Home in East Louisville
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming Derby Getaway, sleeps 6-8, vacation rental in Saint Matthews
Charming Derby Getaway, sleeps 6-8, vacation rental in Saint Matthews
Charming Derby Getaway, sleeps 6-8, vacation rental in Saint Matthews

Charming Derby Getaway, sleeps 6-8

Rental Home in East Louisville
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exquisite home in St. Matthews for KY Derby!  Room for 6! 1-KING,2-Queen, 2 Bath, vacation rental in Saint Matthews
Exquisite home in St. Matthews for KY Derby!  Room for 6! 1-KING,2-Queen, 2 Bath, vacation rental in Saint Matthews
Exquisite home in St. Matthews for KY Derby!  Room for 6! 1-KING,2-Queen, 2 Bath, vacation rental in Saint Matthews

Exquisite home in St. Matthews for KY Derby! Room for 6! 1-KING,2-Queen, 2 Bath

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Derby rental in the Heart of St. Matthews, vacation rental in Saint Matthews
Spacious Derby rental in the Heart of St. Matthews, vacation rental in Saint Matthews
Spacious Derby rental in the Heart of St. Matthews, vacation rental in Saint Matthews

Spacious Derby rental in the Heart of St. Matthews

Rental Home in East Louisville
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Large Duplex | Great For Groups | Suburban Life, vacation rental in Saint Matthews
Large Duplex | Great For Groups | Suburban Life, vacation rental in Saint Matthews
Large Duplex | Great For Groups | Suburban Life, vacation rental in Saint Matthews

Large Duplex | Great For Groups | Suburban Life

Rental Home in East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Saint Matthews
2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Saint Matthews
2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Saint Matthews

2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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★ 3 Story Mansion ★  Private Parking, Excellent location!, vacation rental in Saint Matthews
★ 3 Story Mansion ★  Private Parking, Excellent location!, vacation rental in Saint Matthews
★ 3 Story Mansion ★  Private Parking, Excellent location!, vacation rental in Saint Matthews

★ 3 Story Mansion ★ Private Parking, Excellent location!

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Close To Downtown In Historic Crecent Hill, vacation rental in Saint Matthews
Close To Downtown In Historic Crecent Hill, vacation rental in Saint Matthews
Close To Downtown In Historic Crecent Hill, vacation rental in Saint Matthews

Close To Downtown In Historic Crecent Hill

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill, vacation rental in Saint Matthews
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill, vacation rental in Saint Matthews
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill, vacation rental in Saint Matthews

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Saint Matthews
Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Saint Matthews
Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Saint Matthews

Beautifully renovated home on Warwick Park in St. Matthews.

Rental Home in Lyndon, East Louisville
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Saint Matthews
Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Saint Matthews
Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Saint Matthews

Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting

Rental Home in Lyndon, East Louisville
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bourbon Bachelors and Bardstown Road - Epic Sky Deck - Sleeps 14+, vacation rental in Saint Matthews
Bourbon Bachelors and Bardstown Road - Epic Sky Deck - Sleeps 14+, vacation rental in Saint Matthews
Bourbon Bachelors and Bardstown Road - Epic Sky Deck - Sleeps 14+, vacation rental in Saint Matthews

Bourbon Bachelors and Bardstown Road - Epic Sky Deck - Sleeps 14+

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Cherokee Park Home, Highlands, Downtown, vacation rental in Saint Matthews
Cherokee Park Home, Highlands, Downtown, vacation rental in Saint Matthews
Cherokee Park Home, Highlands, Downtown, vacation rental in Saint Matthews

Cherokee Park Home, Highlands, Downtown

Rental Home
7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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❤ The Hillcrest House w/ Private Cottage--Near Frankfort Ave, Downtown, Expo!, vacation rental in Saint Matthews
❤ The Hillcrest House w/ Private Cottage--Near Frankfort Ave, Downtown, Expo!, vacation rental in Saint Matthews
❤ The Hillcrest House w/ Private Cottage--Near Frankfort Ave, Downtown, Expo!, vacation rental in Saint Matthews

❤ The Hillcrest House w/ Private Cottage--Near Frankfort Ave, Downtown, Expo!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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‘DERBY’ house available 10 minutes from track., vacation rental in Saint Matthews
‘DERBY’ house available 10 minutes from track., vacation rental in Saint Matthews
‘DERBY’ house available 10 minutes from track., vacation rental in Saint Matthews

‘DERBY’ house available 10 minutes from track.

Rental Home in Hikes Point, East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Crescent Hill Carriage House, vacation rental in Saint Matthews
Crescent Hill Carriage House, vacation rental in Saint Matthews
Crescent Hill Carriage House, vacation rental in Saint Matthews

Crescent Hill Carriage House

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Louisville Home w/ Sunroom - 3 Miles to Downtown!, vacation rental in Saint Matthews
Louisville Home w/ Sunroom - 3 Miles to Downtown!, vacation rental in Saint Matthews
Louisville Home w/ Sunroom - 3 Miles to Downtown!, vacation rental in Saint Matthews

Louisville Home w/ Sunroom - 3 Miles to Downtown!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Saint Matthews
Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Saint Matthews
Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Saint Matthews

Spacious home w/Hot tub! Monthly discounted rate.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Louisville GEM, newly furnished, super clean, in a safe trendy area, vacation rental in Saint Matthews
Louisville GEM, newly furnished, super clean, in a safe trendy area, vacation rental in Saint Matthews
Louisville GEM, newly furnished, super clean, in a safe trendy area, vacation rental in Saint Matthews

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Highlands Spectacular ★ Sky Deck // Perfect for Kentucky Derby 2020, vacation rental in Saint Matthews
Luxury Highlands Spectacular ★ Sky Deck // Perfect for Kentucky Derby 2020, vacation rental in Saint Matthews
Luxury Highlands Spectacular ★ Sky Deck // Perfect for Kentucky Derby 2020, vacation rental in Saint Matthews

Luxury Highlands Spectacular ★ Sky Deck // Perfect for Kentucky Derby 2020

Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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CORPORATE RENTAL in Louisville, vacation rental in Saint Matthews
CORPORATE RENTAL in Louisville, vacation rental in Saint Matthews
CORPORATE RENTAL in Louisville, vacation rental in Saint Matthews

CORPORATE RENTAL in Louisville

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax here when coming to the Derby or Breeders Cup, vacation rental in Saint Matthews
Relax here when coming to the Derby or Breeders Cup, vacation rental in Saint Matthews
Relax here when coming to the Derby or Breeders Cup, vacation rental in Saint Matthews

Relax here when coming to the Derby or Breeders Cup

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet & safe 2 bed 1 bath in Crescent Hill, vacation rental in Saint Matthews
Quiet & safe 2 bed 1 bath in Crescent Hill, vacation rental in Saint Matthews
Quiet & safe 2 bed 1 bath in Crescent Hill, vacation rental in Saint Matthews

Quiet & safe 2 bed 1 bath in Crescent Hill

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Kentucky Derby Classic Home, vacation rental in Saint Matthews
Kentucky Derby Classic Home, vacation rental in Saint Matthews
Kentucky Derby Classic Home, vacation rental in Saint Matthews

Kentucky Derby Classic Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious 6BR /2.5 Bath in Highlands!, vacation rental in Saint Matthews
Spacious 6BR /2.5 Bath in Highlands!, vacation rental in Saint Matthews
Spacious 6BR /2.5 Bath in Highlands!, vacation rental in Saint Matthews

Spacious 6BR /2.5 Bath in Highlands!

Rental Home
6 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
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Bright, Parkside condo with pool, vacation rental in Saint Matthews
Bright, Parkside condo with pool, vacation rental in Saint Matthews
Bright, Parkside condo with pool, vacation rental in Saint Matthews

Bright, Parkside condo with pool

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Kentucky Derby Rental - Close in, East End, vacation rental in Saint Matthews
Kentucky Derby Rental - Close in, East End, vacation rental in Saint Matthews
Kentucky Derby Rental - Close in, East End, vacation rental in Saint Matthews

Kentucky Derby Rental - Close in, East End

Rental Home in East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Home rental, vacation rental in Saint Matthews

Home rental

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Charming Kentucky Derby rental, vacation rental in Saint Matthews
Charming Kentucky Derby rental, vacation rental in Saint Matthews
Charming Kentucky Derby rental, vacation rental in Saint Matthews

Charming Kentucky Derby rental

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!, vacation rental in Saint Matthews
Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!, vacation rental in Saint Matthews
Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!, vacation rental in Saint Matthews

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

Rental Home in East Louisville
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
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Beautiful home near Cherokee and  Seneca parks, vacation rental in Saint Matthews
Beautiful home near Cherokee and  Seneca parks, vacation rental in Saint Matthews
Beautiful home near Cherokee and  Seneca parks, vacation rental in Saint Matthews

Beautiful home near Cherokee and Seneca parks

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Upscale Living with Concierge Services, vacation rental in Saint Matthews
Upscale Living with Concierge Services, vacation rental in Saint Matthews
Upscale Living with Concierge Services, vacation rental in Saint Matthews

Upscale Living with Concierge Services

Rental Home in East Louisville
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
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Centrally Located Home for Derby/Breeders Cup, vacation rental in Saint Matthews
Centrally Located Home for Derby/Breeders Cup, vacation rental in Saint Matthews
Centrally Located Home for Derby/Breeders Cup, vacation rental in Saint Matthews

Centrally Located Home for Derby/Breeders Cup

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautifully restored southern cottage in the heart of the city., vacation rental in Saint Matthews
Beautifully restored southern cottage in the heart of the city., vacation rental in Saint Matthews
Beautifully restored southern cottage in the heart of the city., vacation rental in Saint Matthews

Beautifully restored southern cottage in the heart of the city.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Kentucky Derby Home Base, vacation rental in Saint Matthews
Kentucky Derby Home Base, vacation rental in Saint Matthews
Kentucky Derby Home Base, vacation rental in Saint Matthews

Kentucky Derby Home Base

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Rental Duplex Brownsboro Nest (10 beds), vacation rental in Saint Matthews
Rental Duplex Brownsboro Nest (10 beds), vacation rental in Saint Matthews
Rental Duplex Brownsboro Nest (10 beds), vacation rental in Saint Matthews

Rental Duplex Brownsboro Nest (10 beds)

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Cozy & Posh Carriage House ( PARKSIDE HIGHLANDS), vacation rental in Saint Matthews
Cozy & Posh Carriage House ( PARKSIDE HIGHLANDS), vacation rental in Saint Matthews
Cozy & Posh Carriage House ( PARKSIDE HIGHLANDS), vacation rental in Saint Matthews

Cozy & Posh Carriage House ( PARKSIDE HIGHLANDS)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1 Bedroom 1 Bath Condo, vacation rental in Saint Matthews
1 Bedroom 1 Bath Condo, vacation rental in Saint Matthews
1 Bedroom 1 Bath Condo, vacation rental in Saint Matthews

1 Bedroom 1 Bath Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Kentucky Derby Home Rental, vacation rental in Saint Matthews
Kentucky Derby Home Rental, vacation rental in Saint Matthews
Kentucky Derby Home Rental, vacation rental in Saint Matthews

Kentucky Derby Home Rental

Rental Home in East Louisville
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Saint Matthews
Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Saint Matthews
Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Saint Matthews

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

Rental Home in East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Magnificent Home - Minutes to Churchill Downs With Concierge, vacation rental in Saint Matthews
Magnificent Home - Minutes to Churchill Downs With Concierge, vacation rental in Saint Matthews
Magnificent Home - Minutes to Churchill Downs With Concierge, vacation rental in Saint Matthews

Magnificent Home - Minutes to Churchill Downs With Concierge

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Triple Crown - Pet Friendly - Highlands/Cherokee Triangle, vacation rental in Saint Matthews
The Triple Crown - Pet Friendly - Highlands/Cherokee Triangle, vacation rental in Saint Matthews
The Triple Crown - Pet Friendly - Highlands/Cherokee Triangle, vacation rental in Saint Matthews

The Triple Crown - Pet Friendly - Highlands/Cherokee Triangle

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mockingbird Valley Spacious Entertaining, vacation rental in Saint Matthews
Mockingbird Valley Spacious Entertaining, vacation rental in Saint Matthews
Mockingbird Valley Spacious Entertaining, vacation rental in Saint Matthews

Mockingbird Valley Spacious Entertaining

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Saint Matthews
Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Saint Matthews
Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Saint Matthews

Convenient + Charming + Perfect for Derby Weekend!

Rental Home in East Louisville
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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3 Bedroom Home in the Highlands, close to everything, vacation rental in Saint Matthews
3 Bedroom Home in the Highlands, close to everything, vacation rental in Saint Matthews
3 Bedroom Home in the Highlands, close to everything, vacation rental in Saint Matthews

3 Bedroom Home in the Highlands, close to everything

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Duplex Brownsboro Nest, vacation rental in Saint Matthews
Duplex Brownsboro Nest, vacation rental in Saint Matthews
Duplex Brownsboro Nest, vacation rental in Saint Matthews

Duplex Brownsboro Nest

Rental Home
6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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