OwnersDirect uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
OwnersDirect uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

Just half an hour away from the popular resort of Funchal on the south coast of Madeira, holiday rental accommodation in Calheta will put you in an altogether more peaceful village with an atmosphere that is distinctly laid-back and carefree, and even though a traditional cottage rental in Calheta is sure to give you a truly authentic experience of rural life on the island, you'll still be within easy reach of some cosmopolitan vibrancy to add a touch of urban excitement to your holiday. Accommodation in Calheta can be found to suit whatever your requirements may be, particularly if you're planning a quietly romantic break for two, although when you realise how many opportunities there are for sport, leisure, entertainment and recreation right along the south coast of Madeira, villa rentals in Calheta make the ideal base from where your whole family can find something to appeal to their sense of adventure. Surrounded by wild and rugged landscapes that beg to be explored and overlooking a vast blue ocean that is perfect for scuba-diving and snorkelling, anyone with a love of nature and the great outdoors will find plenty to see and do beyond the doorstep of their holiday rental in Calheta, and when you can rely on fabulous weather virtually all year round in Madeira, holiday accommodation in Calheta will give you the perfect excuse to escape to the sun whenever you feel the need for a complete change of scenery.

  • Showing 1-50 of 300+
  View Map Map
Additional service fee may apply.
    Exceptional! 5/5
    (17 reviews)
    avg/night
    Villa #430466
    • 1 BR
    • 1 BA
    • Sleeps 4
    17
    Viewed 35 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      Wonderful! 4.8/5
      (10 reviews)
      avg/night
      Villa #1773865
      • 3 BR
      • 4 BA
      • Separate Toilet
      • Sleeps 6
      10
      Viewed 9 times in the last 48 hours

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        Exceptional! 5/5
        (6 reviews)
        avg/night
        Villa #1851426
        • 2 BR
        • 2 BA
        • Separate Toilet
        • Sleeps 5
        6
        Viewed 19 times in the last 48 hours

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Exceptional! 5/5
          (21 reviews)
          avg/night
          Villa #1000231
          • 2 BR
          • 2 BA
          • Sleeps 4
          21
          Viewed 16 times in the last 48 hours

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            Excellent! 4.4/5
            (7 reviews)
            avg/night
            House #8041405
            • 4 BR
            • 3 BA
            • Sleeps 10
            7
            Viewed 24 times in the last 48 hours

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Exceptional! 5/5
              (17 reviews)
              avg/night
              Villa #1985482
              • 4 BR
              • 4 BA
              • Sleeps 8
              17
              Viewed 167 times in the last 48 hours

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                Exceptional! 5/5
                (55 reviews)
                avg/night
                Villa #426077
                • 4 BR
                • 3 BA
                • Separate Toilet
                • Sleeps 8
                55
                Viewed 74 times in the last 48 hours

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  Exceptional! 5/5
                  (26 reviews)
                  avg/night
                  Villa #2122627
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  26
                  Viewed 68 times in the last 48 hours

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Wonderful! 4.9/5
                    (64 reviews)
                    avg/night
                    Cottage #898940
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    64
                    Viewed 13 times in the last 48 hours

                    Instant confirmation

                    Your booking request will be confirmed immediately.

                      Excellent! 4.4/5
                      (19 reviews)
                      avg/night
                      Villa #1704052
                      • 3 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 9
                      19
                      Viewed 13 times in the last 48 hours

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        Wonderful! 4.8/5
                        (23 reviews)
                        avg/night
                        House #1100543
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        23
                        Viewed 32 times in the last 48 hours

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          Excellent! 4.4/5
                          (7 reviews)
                          avg/night
                          Cottage #1625351
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          7
                          Viewed 35 times in the last 48 hours

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Wonderful! 4.8/5
                            (14 reviews)
                            avg/night
                            Cottage #1403309a
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            14
                            Viewed 106 times in the last 48 hours

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              Wonderful! 4.9/5
                              (12 reviews)
                              avg/night
                              House #1669046
                              • 3 BR
                              • 3 BA
                              • Sleeps 7
                              12
                              Viewed 55 times in the last 48 hours

                              Confirmation within 24 hours

                              Your booking request will be confirmed or denied within 24 hours.

                                Exceptional! 5/5
                                (25 reviews)
                                avg/night
                                Villa #869794
                                • 2 BR
                                • 2 BA
                                • Sleeps 5
                                25
                                Viewed 42 times in the last 48 hours

                                Instant confirmation

                                Your booking request will be confirmed immediately.

                                  Excellent! 4.7/5
                                  (19 reviews)
                                  avg/night
                                  House #860784
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  19
                                  Viewed 47 times in the last 48 hours

                                  Confirmation within 24 hours

                                  Your booking request will be confirmed or denied within 24 hours.

                                    Wonderful! 4.9/5
                                    (16 reviews)
                                    avg/night
                                    House #3888514
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 5
                                    16
                                    Viewed 56 times in the last 48 hours

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      Wonderful! 4.9/5
                                      (34 reviews)
                                      avg/night
                                      Villa #1000229
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      34
                                      Viewed 16 times in the last 48 hours

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        Wonderful! 4.8/5
                                        (12 reviews)
                                        avg/night
                                        Villa #478602
                                        • 3 BR
                                        • 2 BA
                                        • Separate Toilet
                                        • Sleeps 6
                                        12
                                        Viewed 6 times in the last 48 hours

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          Wonderful! 4.9/5
                                          (24 reviews)
                                          avg/night
                                          Villa #811414
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          24
                                          Viewed 21 times in the last 48 hours

                                          Instant confirmation

                                          Your booking request will be confirmed immediately.

                                            Wonderful! 4.8/5
                                            (8 reviews)
                                            avg/night
                                            Villa #1004779
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 6
                                            8
                                            Viewed 19 times in the last 48 hours

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Wonderful! 4.9/5
                                              (29 reviews)
                                              avg/night
                                              Multiple rentals Cottage #6602602
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              29
                                              Viewed 22 times in the last 48 hours

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Wonderful! 4.9/5
                                                (13 reviews)
                                                avg/night
                                                Cottage #1403172a
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                13
                                                Viewed 22 times in the last 48 hours

                                                Instant confirmation

                                                Your booking request will be confirmed immediately.

                                                  Exceptional! 5/5
                                                  (12 reviews)
                                                  avg/night
                                                  House #1006863
                                                  • 2 BR
                                                  • 1 BA
                                                  • Separate Toilet
                                                  • Sleeps 4
                                                  12
                                                  Viewed 51 times in the last 48 hours

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    Wonderful! 4.8/5
                                                    (11 reviews)
                                                    avg/night
                                                    Multiple rentals House #6602602
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    11
                                                    Viewed 47 times in the last 48 hours

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      Excellent! 4.6/5
                                                      (21 reviews)
                                                      avg/night
                                                      House #868729
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      21
                                                      Viewed 19 times in the last 48 hours

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        Wonderful! 4.9/5
                                                        (24 reviews)
                                                        View details for price
                                                        Villa #406317
                                                        • 3 BR
                                                        • 2 BA
                                                        • Separate Toilet
                                                        • Sleeps 6
                                                        24

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Wonderful! 4.8/5
                                                          (47 reviews)
                                                          avg/night
                                                          Villa #1005941
                                                          • 2 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          47
                                                          Viewed 15 times in the last 48 hours

                                                          Instant confirmation

                                                          Your booking request will be confirmed immediately.

                                                            Excellent! 4.6/5
                                                            (9 reviews)
                                                            avg/night
                                                            House #6805017
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            9
                                                            Viewed 62 times in the last 48 hours

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              avg/night
                                                              Villa #1982674
                                                              • 4 BR
                                                              • 5 BA
                                                              • Sleeps 8
                                                              1
                                                              Viewed 29 times in the last 48 hours

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                Exceptional! 5/5
                                                                (32 reviews)
                                                                avg/night
                                                                Villa #1504248
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                32
                                                                Viewed 26 times in the last 48 hours

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  Wonderful! 4.8/5
                                                                  (25 reviews)
                                                                  avg/night
                                                                  Cottage #1056047
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 5
                                                                  25
                                                                  Viewed 34 times in the last 48 hours

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    Excellent! 4.7/5
                                                                    (6 reviews)
                                                                    avg/night
                                                                    Villa #1411008a
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 12
                                                                    6
                                                                    Viewed 79 times in the last 48 hours

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      Wonderful! 4.9/5
                                                                      (11 reviews)
                                                                      avg/night
                                                                      Villa #1776053
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • Sleeps 6
                                                                      11
                                                                      Viewed 20 times in the last 48 hours

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        Excellent! 4.6/5
                                                                        (21 reviews)
                                                                        avg/night
                                                                        Apartment #854857
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        21
                                                                        Viewed 24 times in the last 48 hours

                                                                        Instant confirmation

                                                                        Your booking request will be confirmed immediately.

                                                                          Wonderful! 4.8/5
                                                                          (43 reviews)
                                                                          avg/night
                                                                          Cottage #868500
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          43
                                                                          Viewed 16 times in the last 48 hours

                                                                          Instant confirmation

                                                                          Your booking request will be confirmed immediately.

                                                                            Exceptional! 5/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            House #6725124
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            5
                                                                            Viewed 15 times in the last 48 hours

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Exceptional! 5/5
                                                                              (14 reviews)
                                                                              avg/night
                                                                              Villa #1091785
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 6
                                                                              14
                                                                              Viewed 23 times in the last 48 hours

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Wonderful! 4.8/5
                                                                                (4 reviews)
                                                                                avg/night
                                                                                House #1773808
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                4
                                                                                Viewed 13 times in the last 48 hours

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  Exceptional! 5/5
                                                                                  (55 reviews)
                                                                                  avg/night
                                                                                  Villa #1005641
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 4
                                                                                  55
                                                                                  Viewed 57 times in the last 48 hours

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Exceptional! 5/5
                                                                                    (14 reviews)
                                                                                    avg/night
                                                                                    House #6496785
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 6
                                                                                    14
                                                                                    Viewed 35 times in the last 48 hours

                                                                                    Instant confirmation

                                                                                    Your booking request will be confirmed immediately.

                                                                                      Excellent! 4.4/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      Villa #1763494
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 5
                                                                                      10
                                                                                      Viewed 35 times in the last 48 hours

                                                                                      Instant confirmation

                                                                                      Your booking request will be confirmed immediately.

                                                                                        Excellent! 4.4/5
                                                                                        (17 reviews)
                                                                                        avg/night
                                                                                        Cottage #6583031
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        17
                                                                                        Viewed 51 times in the last 48 hours

                                                                                        Instant confirmation

                                                                                        Your booking request will be confirmed immediately.

                                                                                          Exceptional! 5/5
                                                                                          (14 reviews)
                                                                                          avg/night
                                                                                          Villa #6102522
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                          14
                                                                                          Viewed 31 times in the last 48 hours

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            Cottage #6303259
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            3
                                                                                            Viewed 7 times in the last 48 hours

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              Wonderful! 4.9/5
                                                                                              (7 reviews)
                                                                                              avg/night
                                                                                              Villa #872044
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              7
                                                                                              Viewed 15 times in the last 48 hours

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Excellent! 4.5/5
                                                                                                (4 reviews)
                                                                                                avg/night
                                                                                                Villa #1782637
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 4
                                                                                                4
                                                                                                Viewed 6 times in the last 48 hours

                                                                                                Instant confirmation

                                                                                                Your booking request will be confirmed immediately.

                                                                                                  Cottage #1403290a
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  6

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    Wonderful! 4.8/5
                                                                                                    (4 reviews)
                                                                                                    avg/night
                                                                                                    House #875336
                                                                                                    • 3 BR
                                                                                                    • 3 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 6
                                                                                                    4
                                                                                                    Viewed 11 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      Excellent! 4.7/5
                                                                                                      (20 reviews)
                                                                                                      avg/night
                                                                                                      Apartment #1040129
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      20
                                                                                                      Viewed 13 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Holiday Accommodation Calheta (300+)