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Saint Matthews Holiday Rentals

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49 rentals in Saint Matthews.
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Suburban | Quiet | Perfect Layout | Families, holiday rental in Saint Matthews

Suburban | Quiet | Perfect Layout | Families

Hikes Point, East Louisville
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Lemon Drop in St Matthews! 3 bed / 2 ba - walk to fun!, holiday rental in Saint Matthews

The Lemon Drop in St Matthews! 3 bed / 2 ba - walk to fun!

3 bedrooms
2 bathrooms
Sleeps 6
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Louisville Short Term Condo Rentals, holiday rental in Saint Matthews

Louisville Short Term Condo Rentals

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

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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LOUISVILLE - DERBY DONE RIGHT!  Centrally located -near everything, holiday rental in Saint Matthews

LOUISVILLE - DERBY DONE RIGHT! Centrally located -near everything

East Louisville
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Large Duplex | Great For Groups | Suburban Life, holiday rental in Saint Matthews

Large Duplex | Great For Groups | Suburban Life

East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
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Large Private Space in a Charming Historical Home, holiday rental in Saint Matthews

Large Private Space in a Charming Historical Home

East Louisville
1 bedroom
1 bathroom
Sleeps 2
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Elegant Home Steps to Restaurant Row!, holiday rental in Saint Matthews

Elegant Home Steps to Restaurant Row!

2 bedrooms
1 bathroom
Sleeps 6
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Perfect Spot, 3 bd/2.5 bath, Quick access to I64/Watterson/11 miles to downtown, holiday rental in Saint Matthews

Perfect Spot, 3 bd/2.5 bath, Quick access to I64/Watterson/11 miles to downtown

East Louisville
3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Property In Historic Highland w/ Hot Tub & Expansive Pool!, holiday rental in Saint Matthews

Beautiful Property In Historic Highland w/ Hot Tub & Expansive Pool!

5 bedrooms
4 bathrooms
Sleeps 13
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RIVERFRONT - Boat Slips - 10 Min to Dtown Lville, holiday rental in Saint Matthews

RIVERFRONT - Boat Slips - 10 Min to Dtown Lville

2 bedrooms
1 bathroom
Sleeps 6
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Bed and Bourbon I The Ultimate Bourbon Experience, holiday rental in Saint Matthews

Bed and Bourbon I The Ultimate Bourbon Experience

Clifton
3 bedrooms
2 bathrooms
Sleeps 8
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NEWLY RENOVATED Loft in Vibrant Louisville Neighborhood, holiday rental in Saint Matthews

NEWLY RENOVATED Loft in Vibrant Louisville Neighborhood

2 bedrooms
1 bathroom
Sleeps 4
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The Thoroughbred Retreat - Walk to it all in the Highlands!, holiday rental in Saint Matthews

The Thoroughbred Retreat - Walk to it all in the Highlands!

1 bedroom
1 bathroom
Sleeps 2
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High Above Highlands, holiday rental in Saint Matthews

High Above Highlands

5 bedrooms
4 bathrooms
Sleeps 16
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Bourbon Bachelors and Bardstown Road - Epic Sky Deck - Sleeps 14+, holiday rental in Saint Matthews

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

6 bedrooms
4 bathrooms
Sleeps 16
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Kentucky Derby - Ideal Bardstown Rd area Close Restaurnts/Bars, holiday rental in Saint Matthews

Kentucky Derby - Ideal Bardstown Rd area Close Restaurnts/Bars

4 bedrooms
3 bathrooms
Sleeps 8
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Central and Charming, holiday rental in Saint Matthews

Central and Charming

Clifton
3 bedrooms
2 bathrooms
Sleeps 6
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Quiet & safe 2 bed 1 bath in Crescent Hill, holiday rental in Saint Matthews

Quiet & safe 2 bed 1 bath in Crescent Hill

2 bedrooms
1 bathroom
Sleeps 5
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Hilltop Craftsman - Walk to dining / 2 car Garage - Superb Renovation!, holiday rental in Saint Matthews

Hilltop Craftsman - Walk to dining / 2 car Garage - Superb Renovation!

Clifton
4 bedrooms
3 bathrooms
Sleeps 9
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Relax here when coming to the Derby or Breeders Cup, holiday rental in Saint Matthews

Relax here when coming to the Derby or Breeders Cup

East Louisville
3 bedrooms
3 bathrooms
Sleeps 6
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Kentucky Derby Classic Home, holiday rental in Saint Matthews

Kentucky Derby Classic Home

4 bedrooms
4 bathrooms
Sleeps 10
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Hip 3BR/2BA Highlands Loft on BEST Part of Bardstown Road. Comfy & Convenient!, holiday rental in Saint Matthews

Hip 3BR/2BA Highlands Loft on BEST Part of Bardstown Road. Comfy & Convenient!

3 bedrooms
2 bathrooms
Sleeps 8
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The Louis on Longest - Prime Louisville Location!, holiday rental in Saint Matthews

The Louis on Longest - Prime Louisville Location!

7 bedrooms
4 bathrooms
Sleeps 18
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3BR/1.5BA Home w/ Relaxing HOT TUB in Popular Area, holiday rental in Saint Matthews

3BR/1.5BA Home w/ Relaxing HOT TUB in Popular Area

3 bedrooms
2 bathrooms
Sleeps 6
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2 BR Frankfort AVE *Best Location! Clean Pet Free, holiday rental in Saint Matthews

2 BR Frankfort AVE *Best Location! Clean Pet Free

Clifton
2 bedrooms
1 bathroom
Sleeps 4
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Lovely Gem in the Vibrant Highlands close to it all!, holiday rental in Saint Matthews

Lovely Gem in the Vibrant Highlands close to it all!

3 bedrooms
3 bathrooms
Sleeps 6
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New ('15) centrally located new 6400+ sq ft + 6 bedrooms w/ 5 full bathroom, holiday rental in Saint Matthews

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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Louisville GEM, newly furnished, super clean, in a safe trendy area, holiday rental in Saint Matthews

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

2 bedrooms
1 bathroom
Sleeps 4
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Sunny House | Safe Neighborhood | Families Welcome, holiday rental in Saint Matthews

Sunny House | Safe Neighborhood | Families Welcome

4 bedrooms
2 bathrooms
Sleeps 8
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Hideaway - Walk to it all in the Highlands!, holiday rental in Saint Matthews

Hideaway - Walk to it all in the Highlands!

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

Kentucky Derby Rental - Close in, East End

East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Home rental, holiday rental in Saint Matthews

Home rental

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Historic Home in Amazing Location, holiday rental in Saint Matthews

Historic Home in Amazing Location

4 bedrooms
3 bathrooms
Sleeps 6
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Charming Kentucky Derby rental, holiday rental in Saint Matthews

Charming Kentucky Derby rental

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming shotgun in walkable district | Louisville, holiday rental in Saint Matthews

Charming shotgun in walkable district | Louisville

Clifton
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Home In Prestigious Neighborhood For Derby and other Select Dates!!!, holiday rental in Saint Matthews

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

East Louisville
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Butchertown Suites Boutique Getaway, holiday rental in Saint Matthews

Butchertown Suites Boutique Getaway

Butchertown
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful home near Cherokee and  Seneca parks, holiday rental in Saint Matthews

Beautiful home near Cherokee and Seneca parks

East Louisville
3 bedrooms
2 bathrooms
Sleeps 7
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Louisville Home w/ Sunroom - 3 Miles to Downtown!, holiday rental in Saint Matthews

Louisville Home w/ Sunroom - 3 Miles to Downtown!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upscale Living with Concierge Services, holiday rental in Saint Matthews

Upscale Living with Concierge Services

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

Centrally Located Home for Derby/Breeders Cup

3 bedrooms
3 bathrooms
Sleeps 10
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OPEN FOR BUSINESS! Tyler House - located in the HEART of the Highlands!, holiday rental in Saint Matthews

OPEN FOR BUSINESS! Tyler House - located in the HEART of the Highlands!

4 bedrooms
2 bathrooms
Sleeps 8
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Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, holiday rental in Saint Matthews

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

East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse & Cottages with River Views,  7 minutes from downtown, holiday rental in Saint Matthews

Farmhouse & Cottages with River Views, 7 minutes from downtown

East Louisville
4 bedrooms
3 bathrooms
Sleeps 10
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Historic Cottage with modern amenities, holiday rental in Saint Matthews

Historic Cottage with modern amenities

East Louisville
2 bedrooms
1 bathroom
Sleeps 2
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Highlands Derby Rental, holiday rental in Saint Matthews

Highlands Derby Rental

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Executive Carriage House Rental in Highlands, holiday rental in Saint Matthews

Executive Carriage House Rental in Highlands

1 bedroom
1 bathroom
Sleeps 2
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Pet friendly home in the Highlands, holiday rental in Saint Matthews

Pet friendly home in the Highlands

4 bedrooms
2 bathrooms
Sleeps 10
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One Bedroom Cottage on Historic Property, 7 minutes from downtown, holiday rental in Saint Matthews

One Bedroom Cottage on Historic Property, 7 minutes from downtown

1 bedroom
1 bathroom
Sleeps 1
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