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Middletown Vacation Rentals

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50 rentals in Middletown.
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Convenient, Comfortable, Cute & Close to everything!, vacation rental in Middletown
Convenient, Comfortable, Cute & Close to everything!, vacation rental in Middletown
Convenient, Comfortable, Cute & Close to everything!, vacation rental in Middletown

Convenient, Comfortable, Cute & Close to everything!

Rental Home in East Louisville
4 bedrooms
2 bathrooms
Sleeps 7
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Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford M, vacation rental in Middletown
Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford M, vacation rental in Middletown
Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford M, vacation rental in Middletown

Great Value! 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford M

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
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Cozy Cottage 2 bdrm w/ wrap porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown
Cozy Cottage 2 bdrm w/ wrap porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown
Cozy Cottage 2 bdrm w/ wrap porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown

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

Rental Home in East Louisville
2 bedrooms
1 bathroom
Sleeps 4
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Brand New 2 Bedroom Townhouse, vacation rental in Middletown
Brand New 2 Bedroom Townhouse, vacation rental in Middletown
Brand New 2 Bedroom Townhouse, vacation rental in Middletown

Brand New 2 Bedroom Townhouse

Rental Home in East Louisville
2 bedrooms
2 bathrooms
Sleeps 4
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2 bedroom , cottage, easy and close location to shopping, restaurants and away, vacation rental in Middletown
2 bedroom , cottage, easy and close location to shopping, restaurants and away, vacation rental in Middletown
2 bedroom , cottage, easy and close location to shopping, restaurants and away, vacation rental in Middletown

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

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 4
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EZ Living with 3 bdrm, 2000 sf, private yard, & location, vacation rental in Middletown
EZ Living with 3 bdrm, 2000 sf, private yard, & location, vacation rental in Middletown
EZ Living with 3 bdrm, 2000 sf, private yard, & location, vacation rental in Middletown

EZ Living with 3 bdrm, 2000 sf, private yard, & location

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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Delightful Derby Home on a Quiet Street!, vacation rental in Middletown
Delightful Derby Home on a Quiet Street!, vacation rental in Middletown
Delightful Derby Home on a Quiet Street!, vacation rental in Middletown

Delightful Derby Home on a Quiet Street!

Rental Home in East Louisville
4 bedrooms
2 bathrooms
Sleeps 13
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Great for Business Travelers! Free Breakfast Buffet + Shared Outdoor Pool., vacation rental in Middletown
Great for Business Travelers! Free Breakfast Buffet + Shared Outdoor Pool., vacation rental in Middletown
Great for Business Travelers! Free Breakfast Buffet + Shared Outdoor Pool., vacation rental in Middletown

Great for Business Travelers! Free Breakfast Buffet + Shared Outdoor Pool.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | G, vacation rental in Middletown
Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | G, vacation rental in Middletown
Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | G, vacation rental in Middletown

Comfortable Suite in Louisville! Free Breakfast Buffet + Shared Outdoor Pool | G

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Perfect for Business Travelers | King Suite with Flat-Screen TV, vacation rental in Middletown
Perfect for Business Travelers | King Suite with Flat-Screen TV, vacation rental in Middletown
Perfect for Business Travelers | King Suite with Flat-Screen TV, vacation rental in Middletown

Perfect for Business Travelers | King Suite with Flat-Screen TV

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Mo, vacation rental in Middletown
Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Mo, vacation rental in Middletown
Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Mo, vacation rental in Middletown

Comfortable Suite! Free Breakfast Buffet + Shared Outdoor Pool. Close to Ford Mo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Cottage 2 bdrm w/ covered  porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown
Cozy Cottage 2 bdrm w/ covered  porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown
Cozy Cottage 2 bdrm w/ covered  porch, 1 mile to xway, shops and entertainment, vacation rental in Middletown

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

Rental Home in East Louisville
2 bedrooms
1 bathroom
Sleeps 4
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2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Middletown
2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Middletown
2 Living Rooms, Backyard, Parking, Close 2 Shopping, Restaurants, Whole Foods, vacation rental in Middletown

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

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 8
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Historically Registered 1847 log Cabin, vacation rental in Middletown
Historically Registered 1847 log Cabin, vacation rental in Middletown
Historically Registered 1847 log Cabin, vacation rental in Middletown

Historically Registered 1847 log Cabin

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Captain's Cabin Bed & Breakfast: Historic & Romantic, vacation rental in Middletown
Captain's Cabin Bed & Breakfast: Historic & Romantic, vacation rental in Middletown
Captain's Cabin Bed & Breakfast: Historic & Romantic, vacation rental in Middletown

Captain's Cabin Bed & Breakfast: Historic & Romantic

Rental Home in East Louisville
1 bedroom
1 bathroom
Sleeps 2
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Quaint & Cozy 4 Bedroom Home in Country Setting, vacation rental in Middletown
Quaint & Cozy 4 Bedroom Home in Country Setting, vacation rental in Middletown
Quaint & Cozy 4 Bedroom Home in Country Setting, vacation rental in Middletown

Quaint & Cozy 4 Bedroom Home in Country Setting

Rental Home in East Louisville
4 bedrooms
2 bathrooms
Sleeps 6
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Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Middletown
Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Middletown
Beautifully renovated home on Warwick Park in St. Matthews., vacation rental in Middletown

Beautifully renovated home on Warwick Park in St. Matthews.

Rental Home in Lyndon, East Louisville
4 bedrooms
2 bathrooms
Sleeps 12
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3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental, vacation rental in Middletown
3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental, vacation rental in Middletown
3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental, vacation rental in Middletown

3BR / 2.5 BA LUXURIOUS Corporate/Derby Rental

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Middletown
Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Middletown
Charming Remodeled 1930's Cottage Retreat - City Convenience in Country Setting, vacation rental in Middletown

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

Rental Home in Lyndon, East Louisville
3 bedrooms
2 bathrooms
Sleeps 8
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Charming house in one of Louisville's most coveted neighborhoods, vacation rental in Middletown
Charming house in one of Louisville's most coveted neighborhoods, vacation rental in Middletown
Charming house in one of Louisville's most coveted neighborhoods, vacation rental in Middletown

Charming house in one of Louisville's most coveted neighborhoods

Rental Home in East Louisville
3 bedrooms
1 bathroom
Sleeps 6
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Suburban | Quiet | Perfect Layout | Families, vacation rental in Middletown
Suburban | Quiet | Perfect Layout | Families, vacation rental in Middletown
Suburban | Quiet | Perfect Layout | Families, vacation rental in Middletown

Suburban | Quiet | Perfect Layout | Families

Rental Home in Hikes Point, East Louisville
4 bedrooms
2 bathrooms
Sleeps 8
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Welcome Home to Quiet Comfort, vacation rental in Middletown
Welcome Home to Quiet Comfort, vacation rental in Middletown
Welcome Home to Quiet Comfort, vacation rental in Middletown

Welcome Home to Quiet Comfort

Rental Home in East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
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Your homebase for Louisville area attractions. Quiet, comfortable and convenient, vacation rental in Middletown
Your homebase for Louisville area attractions. Quiet, comfortable and convenient, vacation rental in Middletown
Your homebase for Louisville area attractions. Quiet, comfortable and convenient, vacation rental in Middletown

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

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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‘DERBY’ house available 10 minutes from track., vacation rental in Middletown
‘DERBY’ house available 10 minutes from track., vacation rental in Middletown
‘DERBY’ house available 10 minutes from track., vacation rental in Middletown

‘DERBY’ house available 10 minutes from track.

Rental Home in Hikes Point, East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
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Paradise  in  town  with heated  pool, garden, patios and acres of privacy., vacation rental in Middletown
Paradise  in  town  with heated  pool, garden, patios and acres of privacy., vacation rental in Middletown
Paradise  in  town  with heated  pool, garden, patios and acres of privacy., vacation rental in Middletown

Paradise in town with heated pool, garden, patios and acres of privacy.

Rental Home in East Louisville
7 bedrooms
4 bathrooms
Sleeps 10
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Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Middletown
Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Middletown
Spacious home w/Hot tub!  Monthly discounted rate., vacation rental in Middletown

Spacious home w/Hot tub! Monthly discounted rate.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Derby City Home Baby Home, vacation rental in Middletown
Derby City Home Baby Home, vacation rental in Middletown
Derby City Home Baby Home, vacation rental in Middletown

Derby City Home Baby Home

Rental Home in East Louisville
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Spacious New Home Perfect for KY Derby, vacation rental in Middletown
Spacious New Home Perfect for KY Derby, vacation rental in Middletown
Spacious New Home Perfect for KY Derby, vacation rental in Middletown

Spacious New Home Perfect for KY Derby

Rental Home in East Louisville
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Attention Derby Visitors- 5,000 sq ft, 5 Bedroom, 4 1/4 Bath - Sleeps 10, vacation rental in Middletown
Attention Derby Visitors- 5,000 sq ft, 5 Bedroom, 4 1/4 Bath - Sleeps 10, vacation rental in Middletown
Attention Derby Visitors- 5,000 sq ft, 5 Bedroom, 4 1/4 Bath - Sleeps 10, vacation rental in Middletown

Attention Derby Visitors- 5,000 sq ft, 5 Bedroom, 4 1/4 Bath - Sleeps 10

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Spacious, Family-Friendly Executive Home. Long term renters welcome!, vacation rental in Middletown
Spacious, Family-Friendly Executive Home. Long term renters welcome!, vacation rental in Middletown
Spacious, Family-Friendly Executive Home. Long term renters welcome!, vacation rental in Middletown

Spacious, Family-Friendly Executive Home. Long term renters welcome!

Rental Home in East Louisville
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Kentucky suite with the comforts of home., vacation rental in Middletown
Kentucky suite with the comforts of home., vacation rental in Middletown
Kentucky suite with the comforts of home., vacation rental in Middletown

Kentucky suite with the comforts of home.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Executive Home - Perfect for Entertaining & Derby, vacation rental in Middletown
Beautiful Executive Home - Perfect for Entertaining & Derby, vacation rental in Middletown
Beautiful Executive Home - Perfect for Entertaining & Derby, vacation rental in Middletown

Beautiful Executive Home - Perfect for Entertaining & Derby

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Suburban Loft - One Large Bedroom Apartment w/Sofa Sleeper, vacation rental in Middletown
Suburban Loft - One Large Bedroom Apartment w/Sofa Sleeper, vacation rental in Middletown
Suburban Loft - One Large Bedroom Apartment w/Sofa Sleeper, vacation rental in Middletown

Suburban Loft - One Large Bedroom Apartment w/Sofa Sleeper

Rental Home in Lyndon, East Louisville
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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KY Derby 5,000 sq. ft. home w/huge salt H2O pool, vacation rental in Middletown
KY Derby 5,000 sq. ft. home w/huge salt H2O pool, vacation rental in Middletown
KY Derby 5,000 sq. ft. home w/huge salt H2O pool, vacation rental in Middletown

KY Derby 5,000 sq. ft. home w/huge salt H2O pool

Rental Home in East Louisville
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming cape cod on wonderfully wooded acre, vacation rental in Middletown
Charming cape cod on wonderfully wooded acre, vacation rental in Middletown
Charming cape cod on wonderfully wooded acre, vacation rental in Middletown

Charming cape cod on wonderfully wooded acre

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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NEW Construction Derby Rental - 25 Min from Churchill Downs, vacation rental in Middletown
NEW Construction Derby Rental - 25 Min from Churchill Downs, vacation rental in Middletown
NEW Construction Derby Rental - 25 Min from Churchill Downs, vacation rental in Middletown

NEW Construction Derby Rental - 25 Min from Churchill Downs

Rental Home in East Louisville
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cheerful Historical 6-bedroom Vacation Home in Derby City, vacation rental in Middletown
Cheerful Historical 6-bedroom Vacation Home in Derby City, vacation rental in Middletown
Cheerful Historical 6-bedroom Vacation Home in Derby City, vacation rental in Middletown

Cheerful Historical 6-bedroom Vacation Home in Derby City

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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SPECTACULAR MODERN VILLA, vacation rental in Middletown
SPECTACULAR MODERN VILLA, vacation rental in Middletown
SPECTACULAR MODERN VILLA, vacation rental in Middletown

SPECTACULAR MODERN VILLA

Rental Home in East Louisville
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully restored southern cottage in the heart of the city., vacation rental in Middletown
Beautifully restored southern cottage in the heart of the city., vacation rental in Middletown
Beautifully restored southern cottage in the heart of the city., vacation rental in Middletown

Beautifully restored southern cottage in the heart of the city.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Palace for Derby Week, vacation rental in Middletown
Palace for Derby Week, vacation rental in Middletown
Palace for Derby Week, vacation rental in Middletown

Palace for Derby Week

Rental Home in East Louisville
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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5 Bedroom Home located in Crestwood KY, vacation rental in Middletown
5 Bedroom Home located in Crestwood KY, vacation rental in Middletown
5 Bedroom Home located in Crestwood KY, vacation rental in Middletown

5 Bedroom Home located in Crestwood KY

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Middletown
Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Middletown
Updated & Stylish! Perfect for DERBY close to dining, shopping & downtown, vacation rental in Middletown

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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Perfect Kentucky Derby Home / Minutes from Churchill Downs, vacation rental in Middletown
Perfect Kentucky Derby Home / Minutes from Churchill Downs, vacation rental in Middletown
Perfect Kentucky Derby Home / Minutes from Churchill Downs, vacation rental in Middletown

Perfect Kentucky Derby Home / Minutes from Churchill Downs

Rental Home in East Louisville
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden, vacation rental in Middletown
Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden, vacation rental in Middletown
Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden, vacation rental in Middletown

Derby Destination (20 Minutes to Churchill Downs): Lovely House and Garden

Rental Home in East Louisville
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Middletown
Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Middletown
Convenient + Charming + Perfect for Derby Weekend!, vacation rental in Middletown

Convenient + Charming + Perfect for Derby Weekend!

Rental Home in East Louisville
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated. Spotless. Secure Neighborhood, vacation rental in Middletown
Newly Renovated. Spotless. Secure Neighborhood, vacation rental in Middletown
Newly Renovated. Spotless. Secure Neighborhood, vacation rental in Middletown

Newly Renovated. Spotless. Secure Neighborhood

Rental Home in East Louisville
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home Baby Home, vacation rental in Middletown
Home Baby Home, vacation rental in Middletown
Home Baby Home, vacation rental in Middletown

Home Baby Home

Rental Home in East Louisville
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Home, Perfect Location, vacation rental in Middletown
Perfect Home, Perfect Location, vacation rental in Middletown
Perfect Home, Perfect Location, vacation rental in Middletown

Perfect Home, Perfect Location

Rental Home
5 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Derby stay in a quiet suburb of Louisville , vacation rental in Middletown
Cozy Derby stay in a quiet suburb of Louisville , vacation rental in Middletown
Cozy Derby stay in a quiet suburb of Louisville , vacation rental in Middletown

Cozy Derby stay in a quiet suburb of Louisville

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Be my guest, be my guest, put my magic to the test/MANY things 5-20 minutes away, vacation rental in Middletown
Be my guest, be my guest, put my magic to the test/MANY things 5-20 minutes away, vacation rental in Middletown
Be my guest, be my guest, put my magic to the test/MANY things 5-20 minutes away, vacation rental in Middletown

Be my guest, be my guest, put my magic to the test/MANY things 5-20 minutes away

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Frequently Asked Questions about Middletown