Vacation Rentals with Pool in Kentucky

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Swimming pool

21 vacation rentals

(14) Very Good 

    13

    Furnished 1-Bedroom Apartment in South Lexington

    Kentucky / Lexington

    Lexington apartment

    1 2 2 nights min

    • 1 bedroom
    • sleeps 2
    • 2 nights min
    • Swimming pool
    • Child Friendly
    • Air conditioning
    “Park place apartments” That relocated us to a 2 bedroom it was very nice and nice area it didn't have a king bed in master bedroom it had double beds the mattresses were not good I sleep in a king bed at home it's a good mattress
    …see more

    Price per night from

    $90

    Responds fast!
    avg. 2 hours 58 minutes

    Price per night from

    $90

      45

      'Ledge Lodge' w/ Pool & Cumberland Valley Views!

      Kentucky / Burkesville

      Burkesville house

      4 10 min stay varies

      • 4 bedrooms
      • sleeps 10
      • min stay varies
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $252

      Responds fast!
      avg. 8 minutes

      Price per night from

      $252

        42

        little 'peace' of paradise - near Louisville

        Kentucky / Taylorsville

        Taylorsville cottage

        2 6 2 nights min

        • 2 bedrooms
        • sleeps 6
        • 2 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $148

        Price per night from

        $148

          15

          Southern Grace Bed and Breakfast

          Kentucky / Brandenburg

          Brandenburg b and b

          5 14 1 night min

          • 5 bedrooms
          • sleeps 14
          • 1 night min
          • Swimming pool
          • Child Friendly
          • Air conditioning

          Price per night from

          $1,042

          Price per night from

          $1,042

          (10) Very Good 

            8

            Furnished 2-Bedroom Apartment in East Lexington

            Kentucky / Lexington

            Lexington apartment

            2 4 2 nights min

            • 2 bedrooms
            • sleeps 4
            • 2 nights min
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $121

            Responds fast!
            avg. 2 hours 52 minutes

            Price per night from

            $121

              24

              Lake Cumberland Condo - Resort Pool & Golf Course

              Kentucky / Bronston

              Bronston apartment

              2 8 min stay varies

              • 2 bedrooms
              • sleeps 8
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $144

              Responds fast!
              avg. 8 minutes

              Price per night from

              $144

                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

                (2) Very Good 

                  7

                  Hidden Cabin at Lake Cumberland Resort

                  Kentucky / Burnside

                  Burnside house

                  3 7 2 nights min

                  • 3 bedrooms
                  • sleeps 7
                  • 2 nights min
                  • Beach / lakeside relaxation
                  • Nearest beach 1 mi
                  • Swimming pool

                  Price per night from

                  $160

                  Responds fast!
                  avg. 3 hours 15 minutes

                  Price per night from

                  $160

                    4

                    Southern Farmhouse

                    Kentucky / Rogers

                    Rogers log cabin

                    2 10 1 night min

                    • 2 bedrooms
                    • sleeps 10
                    • 1 night min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $458

                    Price per night from

                    $458

                    (4) Excellent 

                      34

                      Four Seasons Lake Cottage in Kentucky on the Bourbon Trail

                      Kentucky / Taylorsville

                      Taylorsville cottage

                      2 5 2 nights min

                      • 2 bedrooms
                      • sleeps 5
                      • 2 nights min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $178

                      Responds fast!
                      avg. 55 minutes

                      Price per night from

                      $178

                        17

                        Dramatique - A Black Beauty in Thriving Downtown Lexington

                        Kentucky / Lexington

                        Lexington condo

                        2 5 3 nights min

                        • 2 bedrooms
                        • sleeps 5
                        • 3 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $287

                        Responds fast!
                        avg. 1 hour 12 minutes

                        Price per night from

                        $287

                          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

                          $516

                          Responds fast!
                          avg. 8 minutes

                          Price per night from

                          $516

                          (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 13 minutes

                            Price per night from

                            $138

                              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

                              (2) Excellent 

                                17

                                Luxe in Lex. Your Bourbon Trail Adventure Starts Here

                                Kentucky / Lexington

                                Lexington apartment

                                2 5 2 nights min

                                • 2 bedrooms
                                • sleeps 5
                                • 2 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $287

                                Responds fast!
                                avg. 1 hour 12 minutes

                                Price per night from

                                $287

                                  16

                                  Downtown Lexington Cosmopolitan Condo Secure Covered Gated Parking Rooftop Pool

                                  Kentucky / Lexington

                                  Lexington condo

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $283

                                  Price per night from

                                  $283

                                    20

                                    Cozy furnished home away from home

                                    Kentucky / Lexington

                                    Lexington condo

                                    2 4 120 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 120 nights min
                                    • Swimming pool
                                    • Air conditioning

                                    Price per night from

                                    $54

                                    Price per night from

                                    $54

                                      12

                                      Ellie's Place- Beautiful Mountain Cabin Retreat

                                      Kentucky / Burnside

                                      Burnside house

                                      3 6 2 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $87

                                      Price per night from

                                      $87

                                        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

                                        $133

                                        Responds fast!
                                        avg. 3 hours 0 minutes

                                        Price per night from

                                        $133

                                          24

                                          NEW! Burkesville Apartment w/ Views & Pool Access!

                                          Kentucky / Burkesville

                                          Burkesville apartment

                                          2 6 min stay varies

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

                                          Price per night from

                                          $205

                                          Responds fast!
                                          avg. 8 minutes

                                          Price per night from

                                          $205

                                          (3) Excellent 

                                            47

                                            Enchanting Luxurious Vacation Oasis Great Location

                                            Kentucky / Louisville

                                            Louisville apartment

                                            1 6 min stay varies

                                            • 1 bedroom
                                            • sleeps 6
                                            • min stay varies
                                            • Swimming pool
                                            • Car not necessary
                                            • Air conditioning

                                            Price per night from

                                            $193

                                            Price per night from

                                            $193