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96 Houses

    5

    Brand New 2 Bedroom Townhouse

    Kentucky / Middletown

    Middletown townhouse

    2 4 4 nights min

    • 2 bedrooms
    • sleeps 4
    • 4 nights min
    • Air conditioning
    • Private garden

    Price per night from

    $2,182

    Price per night from

    $2,182

      21

      DERBY HOUSE - 8200 SQ FT/ VIEWS OF GLISTENING LAKE AND ARNOLD PALMER GOLF COURSE

      Kentucky / Middletown

      Middletown house

      8 16 3 nights min

      • 8 bedrooms
      • sleeps 16
      • 3 nights min
      • Child Friendly

      Price per night from

      $3,435

      Price per night from

      $3,435

      Great rentals within 20 miles that match your search

      Distance approx 13.22 km from Middletown

        25

        Louisville Home w/Fire Pit-Min to Churchill Downs

        Kentucky / Louisville

        Louisville house

        3 6 min stay varies

        • 3 bedrooms
        • sleeps 6
        • min stay varies
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $155

        Responds fast!
        avg. 47 minutes

        Price per night from

        $155

        Distance approx 10.17 km from Middletown

        (9) Excellent 

          15

          2 bed/2.5 bath Historic District Luxury Townhouse

          Kentucky / Louisville

          Louisville apartment

          2 7 min stay varies

          • 2 bedrooms
          • sleeps 7
          • min stay varies
          • Child Friendly
          • Car not necessary
          • Air conditioning
          “Super location - highly recommend” Stayed with spouse and two teenaged children while visiting family. The condo was located in an area with a lot of restaurants within walking distance that worked for both groups. It was well stocked and really com
          …see more

          Price per night from

          $212

          Responds fast!
          avg. 2 hours 56 minutes

          Price per night from

          $212

          Distance approx 9.97 km from Middletown

          (1) Excellent 

            5

            Carriage House, First Floor

            Kentucky / Louisville

            Louisville house

            2 5 min stay varies

            • 2 bedrooms
            • sleeps 5
            • min stay varies
            • Child Friendly
            • Air conditioning

            Price per night from

            $95

            Price per night from

            $95

            Distance approx 6.03 km from Middletown

              20

              Exquisite executive retreat!

              Kentucky / Eastwood

              Eastwood villa

              5 10 7 nights min

              • 5 bedrooms
              • sleeps 10
              • 7 nights min
              • Child Friendly
              • Pet Friendly

              Price per night from

              $1,309

              Price per night from

              $1,309

              Distance approx 9.01 km from Middletown

              (4) Very Good 

                32

                Comfortable 3bed/2bath Home - Highlands, Louisville

                Kentucky / Louisville

                Louisville house

                3 6 3 nights min

                • 3 bedrooms
                • sleeps 6
                • 3 nights min
                • Child Friendly
                • Air conditioning

                Price per night from

                $138

                Responds fast!
                avg. 3 hours 15 minutes

                Price per night from

                $138

                Distance approx 10.11 km from Middletown

                (4) Excellent 

                Certificate of Excellence

                  33

                  Large Historic Home, Walk to Dinner, parks, cafes!

                  Kentucky / Louisville

                  Louisville house

                  6 16 min stay varies

                  • 6 bedrooms
                  • sleeps 16
                  • min stay varies
                  • Child Friendly
                  • Car not necessary
                  • Air conditioning

                  Certificate of Excellence

                  Price per night from

                  $361

                  Responds fast!
                  avg. 2 hours 56 minutes

                  Price per night from

                  $361

                  Distance approx 1.19 km from Middletown Show on Map

                    36

                    Private In-Law Suite, Business Travel

                    Kentucky / Anchorage

                    Anchorage house

                    1 2 2 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 2 nights min
                    • Swimming pool
                    • Air conditioning
                    • Private garden

                    Price per night from

                    $85

                    Price per night from

                    $85

                    Distance approx 5.61 km from Middletown

                    (1) Excellent 

                      18

                      Kentucky suite with the comforts of home.

                      Kentucky / Louisville

                      Louisville apartment

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Child Friendly
                      • Air conditioning
                      • Private garden

                      Price per night from

                      $126

                      Price per night from

                      $126

                      Distance approx 9.17 km from Middletown

                        24

                        NEW! Louisville Home - 7 Miles to Churchill Downs!

                        Kentucky / Louisville

                        Louisville house

                        3 8 min stay varies

                        • 3 bedrooms
                        • sleeps 8
                        • min stay varies
                        • Suitable for children age 5+
                        • Air conditioning

                        Price per night from

                        $172

                        Responds fast!
                        avg. 8 minutes

                        Price per night from

                        $172

                        Distance approx 6.06 km from Middletown

                          19

                          Kentucky Derby Rental - Close in, East End

                          Kentucky / Louisville

                          Louisville house

                          4 8 3 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 3 nights min
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $2,863

                          Price per night from

                          $2,863

                          Distance approx 11.31 km from Middletown

                          (1) Excellent 

                            13

                            GERMANTOWN GEM CLOSE TO EVERYTHING DERBY!

                            Kentucky / Louisville

                            Louisville house

                            3 6 3 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 3 nights min
                            • Child Friendly
                            • Air conditioning
                            • Private garden

                            Price per night from

                            $403

                            Price per night from

                            $403

                            Distance approx 10.76 km from Middletown

                            (2) Excellent 

                              40

                              Home away from home

                              Kentucky / Okolona

                              Okolona house

                              7 20 1 night min

                              • 7 bedrooms
                              • sleeps 20
                              • 1 night min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $138

                              Responds fast!
                              avg. 2 hours 15 minutes

                              Price per night from

                              $138

                              Distance approx 9.98 km from Middletown

                                11

                                Great location on Cherokee Road -Second Floor

                                Kentucky / Louisville

                                Louisville apartment

                                1 2 min stay varies

                                • 1 bedroom
                                • sleeps 2
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Car not necessary

                                Price per night from

                                $78

                                Price per night from

                                $78

                                Distance approx 6.53 km from Middletown

                                  25

                                  Cozy St. Matthews Home w/ Deck & Prime Walkability!

                                  Kentucky / Saint Matthews

                                  Saint Matthews house

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $126

                                  Responds fast!
                                  avg. 8 minutes

                                  Price per night from

                                  $126

                                  Distance approx 8.93 km from Middletown

                                    23

                                    Charming shotgun in walkable district | Louisville

                                    Kentucky / Louisville

                                    Louisville house

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Child Friendly

                                    Price per night from

                                    $287

                                    Responds fast!
                                    avg. 8 minutes

                                    Price per night from

                                    $287

                                    Distance approx 10.08 km from Middletown

                                    (9) Excellent 

                                    Certificate of Excellence

                                      27

                                      6 Bedroom Italianate Mansion in Historic Zone, Wall to All!

                                      Kentucky / Louisville

                                      Louisville house

                                      6 16 min stay varies

                                      • 6 bedrooms
                                      • sleeps 16
                                      • min stay varies
                                      • Ask about children
                                      • Car not necessary
                                      • Air conditioning
                                      “Great House!” We stayed for Ford Iron Man for 5 nights. 7 adults, 2 teens, 1 child. Stunning home- not your average rental house, but a huge, stately place that still has everything from plasma TVs to wifi. We arrived a little early to find the home
                                      …see more

                                      Certificate of Excellence

                                      Price per night from

                                      $825

                                      Responds fast!
                                      avg. 2 hours 56 minutes

                                      Price per night from

                                      $825

                                      Distance approx 15.39 km from Middletown

                                        67

                                        Deluxe Condo for Derby KY 2018

                                        Indiana / Floyds Knobs

                                        Floyds Knobs condo

                                        2 4 4 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 4 nights min
                                        • Child Friendly
                                        • Air conditioning
                                        • Private garden

                                        Price per night from

                                        $2,863

                                        Price per night from

                                        $2,863

                                        Distance approx 11.36 km from Middletown

                                          24

                                          NEW! Cozy Louisville Home w/Yard in Shelby Park!

                                          Kentucky / Louisville

                                          Louisville house

                                          2 6 min stay varies

                                          • 2 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $103

                                          Responds fast!
                                          avg. 9 minutes

                                          Price per night from

                                          $103

                                          Distance approx 8.68 km from Middletown

                                          (1) Excellent 

                                            13

                                            Close To Downtown In Historic Crecent Hill

                                            Kentucky / Louisville

                                            Louisville house

                                            4 9 min stay varies

                                            • 4 bedrooms
                                            • sleeps 9
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $401

                                            Responds fast!
                                            avg. 7 minutes

                                            Price per night from

                                            $401

                                            Distance approx 6.56 km from Middletown

                                              14

                                              Beautiful KY Derby Home/15 miles from track

                                              Kentucky / Prospect

                                              Prospect house

                                              4 8 3 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 3 nights min
                                              • Air conditioning
                                              • Private garden

                                              Price per night from

                                              $2,863

                                              Price per night from

                                              $2,863

                                              Distance approx 7.91 km from Middletown

                                                4

                                                Home rental

                                                Kentucky / Louisville

                                                Louisville house

                                                3 9 3 nights min

                                                • 3 bedrooms
                                                • sleeps 9
                                                • 3 nights min
                                                • Child Friendly
                                                • Air conditioning
                                                • Ask about pets

                                                Price per night from

                                                $567

                                                Price per night from

                                                $567

                                                Distance approx 12.29 km from Middletown

                                                  7

                                                  Old Louisville---Where It All Began

                                                  Kentucky / Louisville

                                                  Louisville apartment

                                                  1 2 1 night min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 1 night min
                                                  • Air conditioning

                                                  Price per night from

                                                  $58

                                                  Price per night from

                                                  $58

                                                  Distance approx 3.77 km from Middletown

                                                    17

                                                    Derby Apartment

                                                    Kentucky / Louisville

                                                    Louisville apartment

                                                    3 7 1 night min

                                                    • 3 bedrooms
                                                    • sleeps 7
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Private garden

                                                    Price per night from

                                                    $68

                                                    Price per night from

                                                    $68

                                                    Distance approx 9.97 km from Middletown

                                                      10

                                                      Tree House Apartment

                                                      Kentucky / Louisville

                                                      Louisville apartment

                                                      1 4 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $258

                                                      Price per night from

                                                      $258

                                                      Distance approx 9.42 km from Middletown

                                                        8

                                                        Historic Home in Amazing Location

                                                        Kentucky / Louisville

                                                        Louisville house

                                                        4 6 1 night min

                                                        • 4 bedrooms
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Child Friendly
                                                        • Car not necessary
                                                        • Air conditioning

                                                        Price per night from

                                                        $916

                                                        Price per night from

                                                        $916

                                                        Distance approx 16.85 km from Middletown

                                                          26

                                                          FULLY RENOVATED 2br/2ba; 10min to Louisville. LOVELY new furnishings. QUIET!

                                                          Indiana / New Albany

                                                          New Albany house

                                                          2 8 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          Price per night from

                                                          $171

                                                          Price per night from

                                                          $171

                                                          Distance approx 12.53 km from Middletown

                                                            28

                                                            FANTASTIC HOME!!!☆DERBY CITY HOUSE☆

                                                            Kentucky / Louisville

                                                            Louisville house

                                                            4 9 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 9
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Price per night from

                                                            $172

                                                            Price per night from

                                                            $172

                                                            Distance approx 10.7 km from Middletown

                                                              15

                                                              The Orange Door - Derby Perfect Sleeps 10

                                                              Kentucky / Louisville

                                                              Louisville house

                                                              4 10 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 10
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $343

                                                              Price per night from

                                                              $343

                                                              Distance approx 15.22 km from Middletown

                                                                15

                                                                Charlestown Holiday Apartment 25171

                                                                Indiana / Charlestown

                                                                Charlestown house

                                                                1 1 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 1
                                                                • 3 nights min
                                                                • Air conditioning

                                                                Price per night from

                                                                $157

                                                                Responds fast!
                                                                avg. 3 hours 58 minutes

                                                                Price per night from

                                                                $157

                                                                Distance approx 16.14 km from Middletown

                                                                  15

                                                                  Last Minute Large Group Kentucky Derby Rental

                                                                  Kentucky / Pleasure Ridge Park

                                                                  Pleasure Ridge Park house

                                                                  6 14 2 nights min

                                                                  • 6 bedrooms
                                                                  • sleeps 14
                                                                  • 2 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $2,505

                                                                  Price per night from

                                                                  $2,505

                                                                  Distance approx 9.92 km from Middletown

                                                                    12

                                                                    Luxury Loft in Historci Butchertown

                                                                    Kentucky / Louisville

                                                                    Louisville apartment

                                                                    2 8 2 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 8
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $430

                                                                    Price per night from

                                                                    $430

                                                                    Distance approx 10 km from Middletown

                                                                      16

                                                                      Turnkey Furnished 1 BR in Desirable Highlands with Pool and off-steet parking

                                                                      Kentucky / Louisville

                                                                      Louisville condo

                                                                      1 2 90 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 90 nights min
                                                                      • Swimming pool
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $132

                                                                      Responds fast!
                                                                      avg. 3 hours 0 minutes

                                                                      Price per night from

                                                                      $132

                                                                      Distance approx 12.42 km from Middletown

                                                                        4

                                                                        Kentucky Derby Rental (Main Front)

                                                                        Kentucky / Louisville

                                                                        Louisville b and b

                                                                        1 2 3 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 3 nights min

                                                                        Price per night from

                                                                        $2,004

                                                                        Price per night from

                                                                        $2,004

                                                                        Distance approx 15.56 km from Middletown

                                                                          5

                                                                          Spacious house that sleeps up to 6

                                                                          Kentucky / Shively

                                                                          Shively house

                                                                          2 6 4 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 4 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          • Private garden

                                                                          Price per night from

                                                                          $573

                                                                          Price per night from

                                                                          $573

                                                                          Distance approx 9.38 km from Middletown

                                                                          (3) Excellent 

                                                                            46

                                                                            Luxurious Frankfort Ave CoachHouse Stay/Event 6BD

                                                                            Kentucky / Louisville

                                                                            Louisville house

                                                                            3 16 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 16
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $567

                                                                            Price per night from

                                                                            $567

                                                                            Distance approx 11.29 km from Middletown

                                                                              18

                                                                              Downtown Loft

                                                                              Kentucky / Louisville

                                                                              Louisville condo

                                                                              2 3 1 night min

                                                                              • 2 bedrooms
                                                                              • sleeps 3
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $261

                                                                              Price per night from

                                                                              $261