Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Bungalows
Cabins
Chalets
Condos
Cottages
Estates
Farmhouses
Hotels
Homes
Studios
Townhomes
Villas
Boats
Castles
Lodges
Yachts

Location Type

Even More Filters

Features

Managed By

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

Oahu Vacation Rental Estates(53)

53 Results
Book it Now!
6 night minimum stay
  • 9 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 20
    (13)
    Book it Now!
    3 - 4 night minimum stay
    • 10 BR,
    • 4 BA,
    • 3 HF BA,
    • Sleeps 30
      (12)
      $325
      per night
      3 night minimum stay
      • 3 BR,
      • 3 BA,
      • Sleeps 8
        (18)
        Book it Now!
        5 - 14 night minimum stay
        • 5 BR,
        • 1 BA,
        • 1 HF BA,
        • Sleeps 14
          (21)
          Book it Now!
          6 night minimum stay
          • 3 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 10
            (3)
            Book it Now!
            5 - 7 night minimum stay
            • 4 BR,
            • 2 BA,
            • Sleeps 8
              2 Reviews
              5 - 7 night minimum stay
              • 5 BR,
              • 5 BA,
              • 1 HF BA,
              • Sleeps 18
                (6)
                7 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 16
                  (18)
                  2 night minimum stay
                  • 4 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 18
                    (18)
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 12
                      (31)
                      3 - 5 night minimum stay
                      • 5 BR,
                      • 5 BA,
                      • 2 HF BA,
                      • Sleeps 12
                        1 Review
                        • 10 BR,
                        • 5 BA,
                        • 1 HF BA,
                        • Sleeps 40
                          (23)
                          4 - 7 night minimum stay
                          • 4 BR,
                          • 4 BA,
                          • Sleeps 10
                            • 9 BR,
                            • 4 BA,
                            • Sleeps 10
                              (5)
                              $3,400 - $4,600
                              per night
                              5 - 14 night minimum stay
                              • 7 BR,
                              • 7 BA,
                              • Sleeps 14
                                3 night minimum stay
                                • 5 BR,
                                • 4 BA,
                                • Sleeps 12
                                  5 night minimum stay
                                  • 10 BR,
                                  • 8 BA,
                                  • 2 HF BA,
                                  • Sleeps 22
                                    (41)
                                    4 - 7 night minimum stay
                                    • 4 BR,
                                    • 4 BA,
                                    • Sleeps 10
                                      1 Review
                                      Book it Now!
                                      7 night minimum stay
                                      • 4 BR,
                                      • 4 BA,
                                      • 1 HF BA,
                                      • Sleeps 10
                                        (4)
                                        14 night minimum stay
                                        • 5 BR,
                                        • 5 BA,
                                        • Sleeps 10
                                          14 night minimum stay
                                          • 8 BR,
                                          • 8 BA,
                                          • Sleeps 16
                                            Book it Now!
                                            5 - 7 night minimum stay
                                            • 5 BR,
                                            • 4 BA,
                                            • Sleeps 12
                                              (16)
                                              30 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                                (12)
                                                7 night minimum stay
                                                • 5 BR,
                                                • 4 BA,
                                                • 1 HF BA,
                                                • Sleeps 13
                                                  (10)
                                                  7 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 4
                                                    (10)
                                                    13 night minimum stay
                                                    • 4 BR,
                                                    • 6 BA,
                                                    • Sleeps 10
                                                      • 8 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 14
                                                        • 5 BR,
                                                        • 6 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 10
                                                          1 Review
                                                          • 5 BR,
                                                          • 4 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 12
                                                             

                                                            Recent Oahu Reviews

                                                            Beautiful house in a great location!

                                                            5 of 5
                                                            First of all, I really would like to thank Ryne as he was so great at communication while I was planning my holiday - genuinely trying to help to make the holiday most comfortable and enjoyable. The house itself, it was so clean and spacious in a beautiful neighbourhood- Kahala is one of the most exclusive areas in Oahu and just 10minutes drive away from Waikiki and 5minute walking distance from Kahala Resort Hotel. We enjoyed less crowded surrounding but still could enjoy the busy, lively Waikiki without any problem. I rented both main house and the cottage for party of 13 including small children and a baby. Even we were a big party, we felt the house very spacious. We had two sitting areas and kitchen, outside garden which all could use a great gathering space together or separated. All rooms were big and very tidy/well maintained and had loads of wardrobe space which was great. Bathroom was very clean and tidy and kitchen had everything we needed. Pool was very big and maintained excellently - it has a light in the water so we could enjoy night swim as well. Nearby the house (15 minute walk or 3-5minutes drive), there is Kahala Mall which has great shop collections and takeaway available restaurants and Whole Food market. I really recommand the Whole Food for grocery shopping or even takeaway meals. They were all very delicious and fresh. And we went to have brunch at Kahala Resort Hotel looking out the beautiful beach which was really great. At Kahala hotel, even you are not their guest, you can still rent their beach lounger or even cabana. And I really recommend to go there to enjoy beautiful beach. I personally enjoyed more Kahala beach than Waikiki or Lanakai as it was quieter but still you could do all sort of activities from hotel activity centre - fishing, canoeing, surfing, standing up paddle boarding,etc. really good to have kids playing as well as the water is not deep and quite tranqil near the beachside. Kahala has also a public beach but I think it's really worthy to go to Kahala Hotel's private beach. As it was my first experience to use Home rental holiday, I was very nervous but I can confidently say that Ryne is a really good communicator and trustful. When we were there, Linda was the person who helped us out as a property manager and she was so friendly and helpful as well. Always very easy to reach for anything... We really had a great holiday this summer and definitely recommand this home for your holiday!
                                                            • Submitted: Aug 25, 2014
                                                            • Stayed: Jul 2014

                                                            All that we had hoped for in a family reunion vacation

                                                            5 of 5
                                                            This is our first experience in renting from VRBO and being from Canada, we were very nervous about the accuracy of the photos, contract, etc. But we were attending a family wedding and with 3 families, we fit very nicely into this property (and guest house) with 13 people. The pictures are completely accurate and the backyard is incredible with the ocean view and exposure. The owner's family was very good to deal with and extremely patient with my nervousness around payment, etc. So thanks to them for working with us. We met the house caretaker when we arrived, got great information about the house and the vacation began immediately. The house supplies was very good. The house location besides the beachfront is incredible in that "Costco" is about 3 blocks away. We immediately went there to load up food and the location was great in that it was easy to get to Waikiki and to the east part of the island. Another great thing we did was to rent paddle boards for the duration of our trip. We found a store that delivered the rental and we spent much of the time paddle boarding as the ocean was generally very calm so great activity to do. Hanauma Bay is about 1 km away so that was another day well spent. And for the last night, we had dinner at the original "Roy's Restaurant" which is literally across the street. So very much enjoyed one of our best vacations. Thanks to the owner and family for ensuring that everything is in place. And we hope that we can come back for another visit. Would definitely consider staying here again.
                                                            • Submitted: Jul 22, 2014
                                                            • Stayed: May 2014

                                                            60thAnniversary .

                                                            4 of 5
                                                            "The Plantation Estate" was the ideal place to gather our family of 14 to celebrate our 60th Anniversary. Enough rooms for privacy and relaxing. A clean and inviting pool for refreshing cool-downs. The BBQ patio was transformed into an elegant dining area for our anniversary dinner. The large, breezy lanai was the perfect gathering place for family camaraderie. The friendly locals on the north shore of Oahu added to the Hawaiian experience. The manager, Tania,s joyful personality was part of this as she welcomed us with helpful suggestions. The close- by sandy beaches were perfect for enjoying many ocean sports. The hiking and other activities were enhanced by the breathtaking scenery. From all family reports an unforgettable vacation. Mahalo and Hang Loose!!!
                                                            • Submitted: Jul 5, 2014
                                                            • Stayed: Jun 2014