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97 Houses

    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. 40 minutes

    Price per night from

    $126

      9

      Louisville Short Term Condo Rentals

      Kentucky / Saint Matthews

      Saint Matthews condo

      1 3 30 nights min

      • 1 bedroom
      • sleeps 3
      • 30 nights min
      • Child Friendly
      • Air conditioning
      • Pet Friendly

      Price per night from

      $69

      Price per night from

      $69

        24

        LOUISVILLE - DERBY DONE RIGHT! Centrally located -near everything

        Kentucky / Saint Matthews

        Saint Matthews house

        4 11 2 nights min

        • 4 bedrooms
        • sleeps 11
        • 2 nights min
        • Child Friendly
        • Car not necessary
        • Air conditioning

        Price per night from

        $1,317

        Price per night from

        $1,317

        Great rentals within 20 miles that match your search

        Distance approx 9.6 km from Saint Matthews

          19

          Kentucky Home In Derby City

          Kentucky / Louisville

          Louisville house

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Child Friendly

          Price per night from

          $171

          Responds fast!
          avg. 15 minutes

          Price per night from

          $171

          Distance approx 4.81 km from Saint Matthews Show on Map

            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

            $2,850

            Price per night from

            $2,850

            Distance approx 2.55 km from Saint Matthews Show on Map

              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

              $2,850

              Price per night from

              $2,850

              Distance approx 5.04 km from Saint Matthews Show on Map

                10

                KENTUCKY OAKS DERBY WEEK OR WEEKEND RENTAL

                Indiana / Jeffersonville

                Jeffersonville townhouse

                2 6 3 nights min

                • 2 bedrooms
                • sleeps 6
                • 3 nights min
                • Air conditioning

                Price per night from

                $798

                Price per night from

                $798

                Distance approx 6.4 km from Saint Matthews Show on Map

                  33

                  NEW! Historic Anchorage Cabin w/ Patio & Pool!

                  Kentucky / Anchorage

                  Anchorage cottage

                  4 14 min stay varies

                  • 4 bedrooms
                  • sleeps 14
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $525

                  Responds fast!
                  avg. 33 minutes

                  Price per night from

                  $525

                  Distance approx 2.26 km from Saint Matthews Show on Map

                    10

                    Charming Kentucky Derby rental

                    Kentucky / Louisville

                    Louisville house

                    3 7 2 nights min

                    • 3 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Child Friendly
                    • Air conditioning
                    • Private garden

                    Price per night from

                    $1,568

                    Price per night from

                    $1,568

                    Distance approx 2.62 km from Saint Matthews Show on Map

                    (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

                      $400

                      Responds fast!
                      avg. 7 minutes

                      Price per night from

                      $400

                      Distance approx 12.64 km from Saint Matthews

                        11

                        Wooded Retreat PLUS Derby

                        Kentucky / Louisville

                        Louisville house

                        5 14 4 nights min

                        • 5 bedrooms
                        • sleeps 14
                        • 4 nights min
                        • Child Friendly
                        • Air conditioning
                        • Pet Friendly

                        Price per night from

                        $1,714

                        Price per night from

                        $1,714

                        Distance approx 8.98 km from Saint Matthews Show on Map

                          24

                          NEW! Louisville Area Home Mins to Churchill Downs!

                          Indiana / New Albany

                          New Albany house

                          3 6 min stay varies

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

                          Price per night from

                          $115

                          Responds fast!
                          avg. 33 minutes

                          Price per night from

                          $115

                          Distance approx 10.88 km from Saint Matthews

                            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 6.44 km from Saint Matthews Show on Map

                              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

                              $1,999

                              Price per night from

                              $1,999

                              Distance approx 3.4 km from Saint Matthews Show on Map

                                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

                                $914

                                Price per night from

                                $914

                                Distance approx 10.23 km from Saint Matthews Show on Map

                                  19

                                  A Grand Louisville - Prospect Home on a Pond & Horse Farm

                                  Kentucky / Goshen

                                  Goshen guest house

                                  2 8 min stay varies

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

                                  Price per night from

                                  $177

                                  Responds fast!
                                  avg. 1 hour 46 minutes

                                  Price per night from

                                  $177

                                  Distance approx 3.93 km from Saint Matthews Show on Map

                                    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

                                    $257

                                    Price per night from

                                    $257

                                    Distance approx 4.77 km from Saint Matthews Show on Map

                                      40

                                      Sunny Side of Louisville

                                      Indiana / Jeffersonville

                                      Jeffersonville house

                                      2 4 3 nights min

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

                                      Price per night from

                                      $1,143

                                      Price per night from

                                      $1,143

                                      Distance approx 6.8 km from Saint Matthews Show on Map

                                      (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 13.56 km from Saint Matthews

                                          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

                                          Price per night from

                                          $157

                                          Distance approx 9.93 km from Saint Matthews Show on Map

                                            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

                                            $2,856

                                            Price per night from

                                            $2,856

                                            Distance approx 3.86 km from Saint Matthews Show on Map

                                              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

                                              $429

                                              Price per night from

                                              $429

                                              Distance approx 3.93 km from Saint Matthews Show on Map

                                              (1) Excellent 

                                                7

                                                Carriage House-Second Floor

                                                Kentucky / Louisville

                                                Louisville apartment

                                                3 6 min stay varies

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

                                                Price per night from

                                                $95

                                                Price per night from

                                                $95

                                                Distance approx 5.43 km from Saint Matthews Show on Map

                                                (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

                                                  $402

                                                  Price per night from

                                                  $402

                                                  Distance approx 5.71 km from Saint Matthews Show on Map

                                                  (3) Very Good 

                                                    16

                                                    Derby City Digs

                                                    Kentucky / Louisville

                                                    Louisville house

                                                    2 6 2 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Child Friendly

                                                    Price per night from

                                                    $102

                                                    Responds fast!
                                                    avg. 1 hour 24 minutes

                                                    Price per night from

                                                    $102

                                                    Distance approx 6.4 km from Saint Matthews Show on Map

                                                      32

                                                      My Old Kentucky Home

                                                      Kentucky / Anchorage

                                                      Anchorage house

                                                      5 12 3 nights min

                                                      • 5 bedrooms
                                                      • sleeps 12
                                                      • 3 nights min
                                                      • Child Friendly

                                                      Price per night from

                                                      $571

                                                      Price per night from

                                                      $571

                                                      Distance approx 8.94 km from Saint Matthews

                                                        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

                                                        $3,427

                                                        Price per night from

                                                        $3,427

                                                        Distance approx 3.93 km from Saint Matthews Show on Map

                                                        (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 3.96 km from Saint Matthews Show on Map

                                                            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 10.01 km from Saint Matthews

                                                              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

                                                              $571

                                                              Price per night from

                                                              $571

                                                              Distance approx 3.3 km from Saint Matthews Show on Map

                                                              (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

                                                                $566

                                                                Price per night from

                                                                $566

                                                                Distance approx 5.47 km from Saint Matthews Show on Map

                                                                  32

                                                                  Kentucky Derby House Rental

                                                                  Kentucky / Louisville

                                                                  Louisville house

                                                                  4 8 3 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $2,061

                                                                  Price per night from

                                                                  $2,061

                                                                  Distance approx 10.82 km from Saint Matthews

                                                                    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 13.56 km from Saint Matthews

                                                                      24

                                                                      1BR ‘Governor’s Mansion Overlook’ Near Louisville!

                                                                      Indiana / Charlestown

                                                                      Charlestown apartment

                                                                      1 4 min stay varies

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

                                                                      Price per night from

                                                                      $109

                                                                      Responds fast!
                                                                      avg. 40 minutes

                                                                      Price per night from

                                                                      $109

                                                                      Distance approx 4.3 km from Saint Matthews Show on Map

                                                                        25

                                                                        Huge Historic Home with Modern Syle, Walk to All

                                                                        Kentucky / Louisville

                                                                        Louisville house

                                                                        5 12 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 12
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $338

                                                                        Responds fast!
                                                                        avg. 2 hours 50 minutes

                                                                        Price per night from

                                                                        $338

                                                                        Distance approx 8.91 km from Saint Matthews Show on Map

                                                                          26

                                                                          NEW! Waterfront Prospect Home-20 Mi. to Louisville

                                                                          Kentucky / Prospect

                                                                          Prospect house

                                                                          3 8 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $418

                                                                          Responds fast!
                                                                          avg. 40 minutes

                                                                          Price per night from

                                                                          $418

                                                                          Distance approx 5.65 km from Saint Matthews Show on Map

                                                                            14

                                                                            IMMACULATE ONLY 2.6mi frm Churchill Dwns,4bed 3bat

                                                                            Kentucky / Louisville

                                                                            Louisville house

                                                                            4 11 2 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 11
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $682

                                                                            Price per night from

                                                                            $682

                                                                            Distance approx 7.69 km from Saint Matthews

                                                                            (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

                                                                              $458

                                                                              Responds fast!
                                                                              avg. 1 hour 12 minutes

                                                                              Price per night from

                                                                              $458