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
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Diamond Head: Luxury Vacation Rentals (152)

  • 1 - 50 of 152
Additional fees apply. Taxes may be added.
    • 4 BR
    • 5 BA
    • 1 HF BA
    • Sleeps 10
    Villa #3815597
    1 Review
      • 4 BR
      • 3 BA
      • 1 HF BA
      • Sleeps 8
      House #838182vb
        • 5 BR
        • 6 BA
        • Sleeps 10
        Villa #4268942
        Viewed 6 times in the last 48 hours
          • 4 BR
          • 5 BA
          • Sleeps 10
          Villa #481740vb
          1 Review
            • 3 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 7
            Villa #3586318
            2 Reviews
              • 2 BR
              • 2 BA
              • Sleeps 4
              Condo #910600vb
                • 3 BR
                • 2 BA
                • Sleeps 6
                Villa #4027215
                  • 4 BR
                  • 4 BA
                  • 1 HF BA
                  • Sleeps 8
                  Villa #4249431
                    Wonderful! 4.9/5
                    (15 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 5
                    Condo #469139vb
                    15
                    Viewed 5 times in the last 48 hours
                      Excellent! 4.4/5
                      (16 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      Condo #7106953
                      16
                      Viewed 19 times in the last 48 hours
                        • 1 BR
                        • 1 BA
                        • Sleeps 5
                        Condo #316877vb
                        32
                          • 2 BR
                          • 2 BA
                          • Sleeps 6
                          Villa #7026850
                          37
                            • 4 BR
                            • 3 BA
                            • Sleeps 8
                            House #746371vb
                            9
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              Condo #762281vb
                              Viewed 8 times in the last 48 hours
                                Excellent! 4.3/5
                                (17 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                Condo #7113377
                                17
                                Viewed 13 times in the last 48 hours
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 6
                                  Condo #762320vb
                                    • 3 BR
                                    • 3 BA
                                    • 1 HF BA
                                    • Sleeps 9
                                    House #719611vb
                                    2 Reviews
                                      avg/night
                                      • 6 BR
                                      • 4 BA
                                      • Sleeps 12
                                      House #766229vb
                                      3
                                      Viewed 7 times in the last 48 hours
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Condo #762274vb
                                        Viewed 7 times in the last 48 hours
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 6
                                          Condo #762298vb
                                            • 5 BR
                                            • 4 BA
                                            • Sleeps 14
                                            House #496478vb
                                            2 Reviews
                                              • 5 BR
                                              • 3 BA
                                              • Sleeps 10
                                              House #766467vb
                                              1 Review
                                              Viewed 6 times in the last 48 hours
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 6
                                                Condo #762297vb
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Cottage #756790vb
                                                  3
                                                  Viewed 6 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    Condo #762302vb
                                                      Exceptional! 5.0/5
                                                      (5 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 6 BA
                                                      • Sleeps 16
                                                      House #497812vb
                                                      5
                                                      Viewed 21 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (7 reviews)
                                                        avg/night
                                                        • 6 BR
                                                        • 3 BA
                                                        • Sleeps 14
                                                        Villa #469879vb
                                                        7
                                                        Viewed 6 times in the last 48 hours
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Condo #762278vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            Condo #762284vb
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Condo #762280vb
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Condo #786455vb
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Condo #762283vb
                                                                  1 Review
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 9
                                                                    House #614566vb
                                                                    Viewed 22 times in the last 48 hours
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      Condo #762315vb
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Condo #762326vb
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          House #594792vb
                                                                          4
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • Sleeps 15
                                                                            House #614565vb
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Condo #762325vb
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Condo #762340vb
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 7 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 12
                                                                                  House #831591vb
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    Condo #762299vb
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Condo #762334vb
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        Condo #762308vb
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 12
                                                                                          House #890545vb
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 6
                                                                                            House #7088923
                                                                                            1 Review
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Condo #762279vb
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Condo #762290vb
                                                                                                1 Review
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  Condo #786454vb
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    Apartment #762288vb
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #762275vb
                                                                                                      • 1 - 50 of 152
                                                                                                       

                                                                                                      Recent Diamond Head Reviews

                                                                                                      1090 Ilikai Marina

                                                                                                      4 of 5
                                                                                                      The best feature of the property is the view. There is a beautiful view of the marina, the Ala Moana Beach park and the western end of Waikiki. It is a short walk to the beach. The property has undergone a renovation with tiled floors and nice kitchen. However, a known problem with the microwave turntable that wasn't functioning properly was not addressed during our stay. There is a double bed in the bedroom and the second bed is a pull out bed from the sofa in the living room. We were advised that the original air mattress in the pull out was not functioning and another blow-up mattress was provided. However, when we opened the boxed mattress, the necessary batteries weren't included and we didn't have the use of the air mattress the first evening. We contacted the property manager/owner and were given the option of purchasing the batteries and being reimbursed. The same issue applied to the malfunction hair dryer in the unit. Additionally the thermostat wasn't easy to use and I had to find the operation manual online in order to get the unit to our desired temperature and it continually turned off and we had to reset the thermostat frequently. We'd say that the place is a bit tight for 4 people (2 adults and a 16 and 17 year old) but overall wasn't bad. The unit is a reasonable value for the price. The parking in the building was convenient but for the 6 day stay, it ran us $120.
                                                                                                      • Submitted: Nov 13, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Calming, lovely, peaceful. Very impressed with the amenities.

                                                                                                      5 of 5
                                                                                                      Would stay over and over again. More room than shown in the pictures. The layout was perfect and the decor was very modern. Accommodations were on point. The owner, Thuhu, was quick to respond to our every question and concerns. The property was clean and inviting. Hot tub was enjoyed most evenings after a day of snorkeling and swimming in the lagoon. Staff were friendly and not intrusive. Wonderful place to stay. Would highly recommend this unit. Easy access to grocery stores and highway for traveling around the island.Thank you for a beautiful place to relax and get away from everyday worries at home. Thank you!
                                                                                                      • Submitted: Oct 17, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Wonderful location with attentive property owners.

                                                                                                      4 of 5
                                                                                                      We loved our stay and we loved our little home away from home. Our first impression was that the carpets in the hallways were a bit tired and old and the building seemed to be in a not so great neighborhood. After settling in for a few days (we were greeted by a tiny gecko in our room upon arrival) we quickly changed our tune. This was a wonderful property. The condo itself was very clean with clean sheets and towels. We only got one bath towel and one beach towel per person (there were 6 of us) for two weeks, so we had to do laundry, but the laundry facilities were very good. The people that lived in the building were all very friendly and we started to look forward to being greeted by the property manager (Brad) when we left the building in the mornings. We made use of the barbecues on the roof top and they were very clean and of good quality. The tables up there were clean and spacious also. The location was perfect, with a very short walk to the beach and all markets/stores. The pool, although small, was a wonderful bonus and the kids (who ranged in age from 17 - 19) played in it every single day and my husband and I enjoyed using the hot tub at night. We loved being up high in the condo unit and would sit outside on the spacious lanai every morning with our coffee and look at the ocean and watch the city wake up. We got very good at manipulating the fans and louvered windows, so cooling down at night became easy to do (with the help of the air conditioners in the rooms). Two of our teens slept on the pull out couch and they said it was very comfortable, and the other two teens slept in one of the bedrooms and were happy with the beds there also. We made use of the boogie boards provided (we actually spent hours on them playing in the waves) and we also took our lawn chairs to the beach. They were both wonderful additions. We had a few requests of the owners (a late checkout request and a few other questions) and they were very accommodating and quick to respond. I already miss our home away from home and would definitely stay there again. As I said, don't let the initial impression of the hallways and elevator fool you - this is a wonderful space for a holiday and I would definitely recommend it to family and friends!
                                                                                                      • Submitted: Sep 12, 2016
                                                                                                      • Stayed: Aug 2016