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St. Matthews Rentals

From $305 per night (USD)
VRBO
The Chuckwick House - Sleeps 10 in Beds
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming stone property in the heart of St. Matthews, Louisville, Kentucky. This cozy retreat is perfect for travelers s ...
From $305 per night (USD)
VRBO
From $221 per night (USD)
VRBO
The Sweet Spot! - Live Like a Local
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Live like a local in Louisville’s most sought-after neighborhood for young professionals and families. Rich in history a ...
From $221 per night (USD)
VRBO
From $1633 per night (USD)
VRBO
Charming Derby Getaway, sleeps 6-8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestle yourself into this cozy St. Matthews home, perfectly situated less than a mile from popular locally owned restaur ...
From $1633 per night (USD)
VRBO
From $1588 per night (USD)
Expedia
Modern Executive Home with Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
About Home Summary Come soak your tired feet after a long day at the track. This home can sleep 8 and is close to everyt ...
From $1588 per night (USD)
Expedia
From $836 per night (USD)
VRBO
Great for large groups-The best location-Only steps from 6 bars & 40 restaurants
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
You'll be right in the middle of the action. There are 6 nightclubs right outside the front door and 40 restaurants wi ...
From $836 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy this centrally located 2 bedroom, 2 bathroom home in the heart of St. Matthews. This single family home has 2 bedr ...
From $144 per night (USD)
Expedia
Click For Pricing
VRBO
Derby Horse Farm Destination
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Overlooking a thoroughbred farm in one of the most prestigious Louisville neighborhoods, this Kentucky home does not dis ...
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VRBO
From $155 per night (USD)
Expedia
Heart of ST Mathews
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This three bedroom house located in the heart of ST Mathews is located close to everything! Walking distance to St. Math ...
From $155 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Three King Master Bedrooms all on Separate Floors; 7 Total Bedrooms
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This home built in 1938 has lots of charm but modern conveniences from a 2022 rehab and is centrally located, in the St. ...
From $618 per night (USD)
VRBO
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Expedia
Swanky, Retro, Artist's Home, St Matthews, KY.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
4060 is a one of a kind, Artists home in Louisville KY. Each room has been lovingly curated and designed, with no detail ...
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Expedia
From $2326 per night (USD)
VRBO
Make Derby Memories in this Charming 4-bedroom house located in St. Matthews!
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Create Unforgettable Derby Moments! This charming 4- bedroom house in St. Matthews is perfect for your Louisville getaw ...
From $2326 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Louisville Retreat w/ Deck ~ 11 Mi to Downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Whether you head to Kentucky to place your bets at the Kentucky Derby, catch a game at the Louisville Slugger Field, or ...
From $254 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Excellent 3BR/2BA PRIME Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEWLY RENOVATED 3 Bed 2 Bath lower level of duplex is perfect for small groups, couples, or business travelers. Upon arr ...
From $315 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Fall Haven - King Beds, Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
* 3 Bedrooms, 5 Beds, 2 Living Rooms. * 2 1/2 Baths * 2,500 sq ft (235sqm) * Private patio * 2 60” Smart TV w/B ...
From $456 per night (USD)
Expedia
From $1497 per night (USD)
VRBO
Make this your home base for the Kentucky Derby!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our recently remodeled ranch in the city is close to everything. We have 3 bedrooms and 3 baths perfect for 6 guests, ea ...
From $1497 per night (USD)
VRBO
From $403 per night (USD)
Expedia
⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Looking for a place to stay in Louisville with your family? This 4 Bedroom House is perfect! With a central location and ...
From $403 per night (USD)
Expedia
From $106 per night (USD)
VRBO
Adorable Ranch in East Lou!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to my adorable ranch in the heart of east Louisville! This is the perfect place for your Louisville stay. Spend ...
From $106 per night (USD)
VRBO
$Cozy Derby Home\n2 Bedroom Shotgun style home, with Large Adorable Loft$
From $172 per night (USD)
Expedia
Cozy Derby Home\n2 Bedroom Shotgun style home, with Large Adorable Loft
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this adorable house in picturesque Louisville. This charming property offers a serene retreat for guests seeki ...
From $172 per night (USD)
Expedia
From $528 per night (USD)
VRBO
5BR Very Spacious Home! Perfect for Family!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Experience the best of Louisville in our spacious and inviting 5-bedroom, 2.5-bathroom home located in the heart of the ...
From $528 per night (USD)
VRBO
From $370 per night (USD)
Expedia
Renovated 5BR Retreat•2 Living Rooms•Sleeps/Dining for 10, Close to major HWY's
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This newly renovated 5BR, 3BA home combines comfort, space, and convenience for groups of up to 10 guests. 4 Bedrooms wi ...
From $370 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Lovely 5BR Family-Friendly Home for a Relaxing Stay!
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
Bright, colorful, and spacious—this professionally decorated Louisville home is designed for comfort and fun! With room ...
From $226 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Open 4BR/2BA • Sleeps 8 • Huge Kitchen, Covered Deck & Easy Highway Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
PROPERTY OVERVIEW: Open 4BR/2BA home that sleeps 8 with a huge kitchen, covered deck, and easy highway access. Perfect ...
From $209 per night (USD)
Expedia
From $8139 per night (USD)
VRBO
Newly Renovated 5br/5bath- HUGE Outdoor Living - Perfect for DERBY
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This stunning 5 (five) bedroom / 4.5 bathroom, fully remodeled home is the perfect place to experience the Kentucky derb ...
From $8139 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Historic Woodlawn Park Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautiful centrally located Louisville neighborhood, Woodlawn Park is friendly, peaceful, and a quick trip to all major ...
From $303 per night (USD)
VRBO
From $716 per night (USD)
VRBO
This is How We Derby in Historic St. Matthew's
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Whether you are in town for the Derby or touring the numerous distilleries, we have it all! This historic house has all ...
From $716 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious Home 12 miles to Churchill Downs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful 3 bedroom home that is 12 miles to Churchill Downs. Close to restaurants, shopping and highways. Home has a d ...
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Expedia
From $305 per night (USD)
VRBO
Hidden Gem: Stylish Comfort, Prime Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to our newly remodeled 4-bedroom, 2.5-bathroom family home. Ideal for families, it features a king mast ...
From $305 per night (USD)
VRBO
Click For Pricing
Expedia
Kentucky Derby or PGA Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Best Location -9 miles from Churchill Downs Located in Louisville's most sought after neighborhood Located in the Heart ...
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Expedia
From $390 per night (USD)
VRBO
Centrally located retreat in Louisville! New hottub! Driveway and garage parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Spacious home in Louisville close to shopping and dining. You can be to any of Louisvilles attractions with a short dri ...
From $390 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Charming Louisville Retreat w/ Patio & Fireplace!
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Experience the best of Louisville, KY, in this spacious 5-bedroom, 2-bath vacation rental. Located just minutes away fro ...
From $428 per night (USD)
VRBO
From $1226 per night (USD)
VRBO
Castle St Matthews
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
The Castle is a 5,000 SF 8 Bedroom 5 bath house with 13 beds. Located in St Matthews you are walking distance to some of ...
From $1226 per night (USD)
VRBO
$A warm and inviting home located in one of Louisville’s sought-after areas. \n$
From $4411 per night (USD)
VRBO
A warm and inviting home located in one of Louisville’s sought-after areas. \n
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
A warm and inviting home located in one of Louisville’s most sought-after areas. Features plenty of opportunity for ind ...
From $4411 per night (USD)
VRBO

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St. Matthews Rentals

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Results: 32 Rentals

The Chuckwick House - Sleeps 10 in Beds

The Sweet Spot! - Live Like a Local

Charming Derby Getaway, sleeps 6-8

Modern Executive Home with Hot Tub

Great for large groups-The best location-Only steps from 6 bars & 40 restaurants

Cozy home in St. Matthews, 2 bedrooms, 2 bathrooms

Derby Horse Farm Destination

Heart of ST Mathews

Three King Master Bedrooms all on Separate Floors; 7 Total Bedrooms

Swanky, Retro, Artist's Home, St Matthews, KY.

Make Derby Memories in this Charming 4-bedroom house located in St. Matthews!

Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

Excellent 3BR/2BA PRIME Location!

Fall Haven - King Beds, Hot Tub

Make this your home base for the Kentucky Derby!

⭐Fully fenced yard⭐4 car driveway⭐firepit⭐central location⭐basement⭐

Adorable Ranch in East Lou!

Cozy Derby Home\n2 Bedroom Shotgun style home, with Large Adorable Loft

5BR Very Spacious Home! Perfect for Family!

Renovated 5BR Retreat•2 Living Rooms•Sleeps/Dining for 10, Close to major HWY's

Lovely 5BR Family-Friendly Home for a Relaxing Stay!

Open 4BR/2BA • Sleeps 8 • Huge Kitchen, Covered Deck & Easy Highway Access

Newly Renovated 5br/5bath- HUGE Outdoor Living - Perfect for DERBY

Historic Woodlawn Park Home

This is How We Derby in Historic St. Matthew's

Spacious Home 12 miles to Churchill Downs

Hidden Gem: Stylish Comfort, Prime Location

Kentucky Derby or PGA Rental

Centrally located retreat in Louisville! New hottub! Driveway and garage parking

Charming Louisville Retreat w/ Patio & Fireplace!

Castle St Matthews

A warm and inviting home located in one of Louisville’s sought-after areas. \n