This property rents for a minimum 30 day period. Please inquire about rates.
Seated along a winding, private drive perched on the slopes of Hawaii’s Diamond Head, Wailele Villa boasts a breathtaking 180 degree view of Oahu’s south shore. This modern, architect designed home is the epitome of tropical luxury, featuring an indoor water feature, a dramatic pool deck, and private lanai off the kitchen with a spa for quiet relaxation. A modern Hawaiian paradise, Wailele Villa is the perfect combination of proximity and privacy— a short 10 minute walk from the beach, and only a few miles from the excitement of Waikiki. Overlook the coastline and feel the salty tropical breeze as you watch for whales in the distance, or catch some sun on the upper master suite terrace. This breathtaking hillside villa will have you vacationing like a celebrity, and you won’t ever want to leave the spotlight!
Master bedroom – Encompassing the entire upper level of the home, the master bedroom provides spectacular ocean views and wonderful sea breezes. Complete with a CA King-size bed and an en-suite bathroom with His & Hers sinks and large soaking tub. Also features private entrance with security panel, safe, laundry room, large closet, wall-mounted TV with DirecTV, central air-conditioning, sliding glass doors lead to a large deck with magnificent views!
Bedroom 2 – Located on the ground floor of the home, this large bedroom has a CA King-size bed, en suite bathroom with a spacious shower, large walk-in closet, TV with DirecTV, central air-conditioning, security alarm panel, safe, and a lanai with garden and partial ocean views.
Bedroom 3 – Located on the ground floor, this bedroom features a CA king-size bed, floor-to-ceiling windows, TV with DirecTV. Central air and shared bath.
Bedroom 4: Located on the ground floor, this bedroom features a double-size bed, TV, safe, window seat for relaxing and reading, wall-mounted air conditioning unit, and shared bath.
|AC all rooms|
|Walk to Beach|
|Washer & Dryer|
This property rents only monthly with 30 day contracts. Please inquire directly about your specific dates.
* rates do not reflect taxes or additional fees.
Oahu Taxes on short term vacation rentals (calculated against rent, departure clean, early check ins, late check outs and any excess occupancy fees): 14.962%
Departure Cleaning Fee: $800.00 + GET/TAT = $919.70
Refundable Security Deposit: $3,000.00
Reservation fee: 2.55% on entire amount.
1. A/C in all rooms.
2. Rates and fees are subject to change.
3. City and County of Honolulu regulations require a minimum 30 day rental agreement, therefore your vacation rental agreement will be for a minimum of 30 days. Please discuss this requirement with your reservations agent.
4. This Hawaii vacation rental home has been registered as a Transient Accommodation with the State of Hawaii.
5. Please note there is no child safety fence option for around the pool area. All children must be supervised by adult. Optional electric pool heat now available at $125/per day if pre-ordered. $150/day if ordered upon arrival. Wailele pool approximately 6 foot at best in small deep end.
6. WAILELE VILLA IS ON THE MARKET FOR SALE AND YOU MAY BE ASKED TO ACCOMMODATE REAL ESTATE SHOWINGS WITH 24 HOURS NOTICE.
7. This property books only 60 days prior to arrival and only on 30 day contracts.
Hawaiian Villa Rentals specializing in Luxury Vacation Rentals in Kailua / Lanikai, Kahala / Diamond Head on Oahu.
Review by Darrell D.
A lovely home with everything you could possibly need! I would highly recommend this property. The home is a 30 minute walk to the heart of Waikiki beach and still very private. The kids affectionately referred to the property as “the bird’s nest” with phenomenal views and complete privacy! And Alora was very helpful with questions about the home and the island. The property and people exceeded our every expectation!
Vacation Ruined Renting This Property!
We paid the extra fee for the pool to be heated for our 4 year old, but upon arrival discovered the pool was cold — it took days to have it fixed and finally heat the pool. We also came to find many broken items in the home, which for a luxury property in this price-range was shocking — including a leaky window, a refrigerator door that didn’t seal properly and broken tiles throughout the house (one of which became lodged in the bottom of my daughter’s foot and had to be removed.) While insects are a common problem that everyone on the Island combats, we were continually killing large cockroaches in the kitchen. Finally and of major consequence, the owner did not have a suitable locking mechanism on the back door of the home. When we left one day, locked all doors and set the alarm, we came back only to find out that someone had broken in through that back door and had stolen our son’s backpack (which was the easiest thing to grab when the alarm was triggered as the perpetrator ran in and then quickly out of the house.) Loaded with a laptop, GoPro etc, my son was devastated to have these items stolen. As was noted by the police who upon arrival tested the lock on the back door, they were easily able to gain access to the house in less than 10 seconds by jiggling the insufficient locking mechanism on the door. The next day a hook-latch style lock was installed. A detective with Honolulu PD visited us prior to our departure and noted that while the newly installed hook lock was helpful, it was still wholly deficient as were the windows which could be easily opened with the same insufficient locking mechanisms in the back area of the home. When you pay as much as we did for an exclusive property you expect, at the VERY LEAST, sufficient and reasonable home security and repairs to be made to basic elements and items in the home etc. This vacation home was a major disappointment – RENTERS BEWARE would be an understatement!
Can’t wait to get back!
Review by Donna F.
Great location, accomodations, amenities…all of it was A+
Review by Cindy T.
Soooo much better in person! The house was spacious and clean. Zero issues during our stay; easy check in, great ammenities, overall fantastic home. One of our best holidays ever… being able to see the beautiful Oahu during the day and going back to a gorgeous home, away from busy Waikiki. Waking up to the incredible beach view and sipping coffee was by far the highlight of my trip. Thanks for giving us such a fantastic stay, can’t wait to take the family back again
Living the dream
Review by Jay K.
Wow! What can I say! Fabulous house with the most amazing water views from nearly every window. This house has it all. The pool has a rock waterfall and has amazing views. There is a spa that is great for afternoon drinks. The beds are so so comfy. The master ensuite upstairs is spectacular with a private balcony, ensuite and private access. We loved the fully equipped kitchen for cooking with a bbq. It was light and bright and is furnished very high end. The art work is stunning as well. Would definitely come back to this paradise home. Located central to beaches and only 15 minute walk into Waikiki. Can’t wait to be back. Living the dream!!!
Perfect get away
Had another great relaxing time at this villa. Love the location. Beaches within walking distance across the street. Beautiful view from the pool looking out on to the ocean. Go to an ABC store and get water shoes. Small beach by the house but rocky. Water shoes come in handy everywhere. Aloha.
Family Fun in Wailele Villa
Review by Stephanie V.
We had a great time staying in Wailele Villa. There were 8 adults and 1 baby. The house was beautiful and even better in person then in the photos. We have all had multiple friends/family ask where we stayed and comment on how amazing it looked. The top balcony was perfect to watch the sunset every night. I would definitely recommend it for a large group. It is not very baby friendly but was fine since there was only 1 baby for us to look after. The customer service was great as well. We had to reach out to customer service a couple of times for things but they answered very quickly. The location was perfect! It was close to everything we wanted to do. I would recommend this property to a friend or relative.
Amazing views but property management ???
Review by Michelle K.
The place was gorgeous in a fantastic location. Management was good while we were there but trying to get our security deposit back is not good. They told us they had mailed it but two weeks later we still didn’t received our money back and when I asked them to resend, NO response & another week has gone by! Not sure what’s going on there?!?!
Review by Rick B.
From the staff at Trinity, to the well appointed and beautiful home with amazing views, this was truly a memorable vacation. You can walk to the beach in minutes, stores, restaurants and shopping are all close and the pool was amazing. The friends and family that came with us were amazed and truly appreciative of how perfect the home and views are at the villa.
Amazing Home & Trinity is Top Shelf
Review by Alicia M.
The pictures of this house do it little justice. This house is HUGE, has more there then is shown in pictures. They supply you with shampoo, conditioner, soap, all your basics. I found this to be great. There is a washer and dryer in master & on lower level. Lots of towels for in and outside and beach. Toys, floats and such. Ask to be shown how to use torches outside, where lights are and how all works in this house.The staff is more then amazing. All of them from Regan to Elizabeth to Eva & alorah are Top notch. I used the grocery service they offered online “Island Grocery” Michael not only got my order wrong and brought me wrong groceries, he forgot a whole page. Then he over charged me by $450.00 ( prob thought I would not notice) and no invoice. Eva got me refunded and said they will no longer use him. Be ware of Island grocery, not only not competent but, will rip you off. If you have any such issues, call Eva any of them will take care of the situation for you. The staff is AMAZING. The house is AMAZING. I will only use trinity for now on, for the way they serviced me before, during and after the vacation. My vacation would of been dreamy just being in this gorgeous house but these girls made the experience go to a whole new level of top shelf. You will love this house, this company and the whole staff. I got my deposit returned fast. Again, this is a dreamy gorgeous, HUGE Amazing house and I cannot say enough about the house, the company the staff or my stay. Thank you, trinity, Eva, Elizabeth, Regan whom I miss and of coasre Alorah! Amazing jus does not say enough.
A Magical Experience of Excellence in Paradise!
Review by Scott S.
Over the years, I have rented many excellent villas on more than one Hawaiian island and I can easily say that the only thing which could be equal to the awe-inspiring views from this incredible property is the impeccable service so thoughtfully provided by Trinity Villa Rentals. From the initial contact with Robin at Trinity to the staff at check-in and walk-through, Trinity Villa Rentals exceeded our every expectation…and beyond! The property, the views and the service with Trinity Villa Rentals is astounding! We will certainly be returning to both the Hawaiian Islands and Trinity Villa Rentals for many years to come. I highly recommend both this property and Trinity Villa Rentals for anyone who wishes to have a magical experience of excellence in paradise! Mahalo nui to everyone at Trinity Villa Rentals and a warm aloha to all!
Perfect Honolulu location and million dollar view!
Review by Sue T.
The property was perfect if you have to be near Honolulu with its traffic and crowds. We were 3 couples staying for 8 nights and it was a great fit. The fourth bedroom would less equal so 4 couples would have been a squeeze. Each of us could do what activity we wanted during the day without needing a car – stay near the pool or go to the beach, snorkel or just walk all around. The views were incredible from almost every room. We had such fun watching activities on the ocean – sailing, surfers, long boarders, freighters and whales. The house was beautifully furnished, tastefully decorated and had wonderful artwork. We spent a lot of time on the patio/pool. The location was so great as we would drive further east around Diamond Head to get around more easily to grocery store and getting onto H1. We walked and biked (though the bikes were in sad shape)down to Waikiki or parked at Kapiolani Park and walked. There were beaches in each direction. We cooked dinner twice, had a private chef in for 60th birthday dinner and then ate at these great restaurants: Town, 12th Avenue Grill, Duke’s Waikiki. Had malasadas from Leonards (yum!) and went to the farmer’s market at Kapiolani Community College on Saturday. We toured Pearl Harbor, Doris Duke’s house, Honolulu Museum of Art and drove east to Kailua and west to Ko Molina. There were tons of places to hike too. We enjoyed Elizabeth and all her help during our stay – checking us in and answering questions during our stay. I would definitely love to stay at Wailele Villa again. Thank you!
Review by Tom F.
My family, a total of 9, showed up at the Wailele Villa on January 10th for an eight night stay and from the second we walked in the front door we knew we were on vacation. Every room we walked into had an unbelievable view of the water and the house could not have been more prepared for our stay. Having the pool and Jacuzzi made the stay even more enjoyable. As soon as the adults got up in the morning we had a cup of coffee and jumped in the pool, the kids just went straight for the pool. The kitchen and bathrooms had everything you needed to cook and clean and the utility closet had extra boogie boards and chairs. It may be difficult to get the family back together like that again, but if we do and we go to Hawaii, we will definitely stay at Wailele Villa!!
Sony Open Vacation
Review by Thomas F.
From the time we checked in until our last day we had a blast. We enjoyed morning coffee watching the sun come up from the pool patio, we swam, ate, drank and watched the sun go down from the same pool patio. Although we spent a lot of time at the Sony Open, any and all extra time was spent at the house. Everything we needed or wanted was at the house.
Amazing holiday rental!
Review by Joyce C.
My family of 10 stayed at this house for 10 days in December and it was a stunning property. The kitchen was fully equipped, the property was gorgeous, and the location was so convenient to Waikiki. Plenty of towels, full size bath and shower amenities and laundry machines upstairs AND downstairs which was great for a family of our size. Would highly recommend this property and we look forward to staying here again!
El Paso, Texas Review
A wonderful House rental experience, a beautiful home with lots of room and very handy to the beach as well as shopping and dining out.
Great location and fabulous house
Review by Claudia M.
Our party of 6 had a great stay in this wonderful house. It is huge and so open. We loved it. The hot tub was big enough for all 6 of us and you had an amazing view off the pool and master bedroom. It was just interesting to not have the hot tub next to the pool.
Review by Lovelin T.
Our family time at this beautiful home holds memories of a lifetime! We did not want to leave. Management staff took care of a couple of little things in a professional way and immediate. The home exceeded our expectations! We’ll be back. I literally cried when leaving – this home is beyond the stars and the moon!
Review by Teresa L.
Our family together in this beautiful home was amazing. I cried when we had to leave. A stay we will treasure. I still look at the online pictures. We’ll be back! Wailele is Wowie
Diamond Head hideaway
We had a lovely stay. It was wonderful to wake up to the gorgeous view from the master bedroom and then enjoy the view from all the other rooms as well. The property was spotlessly clean and the mangers were very responsive to the couple of equipment failures we experienced. It was hard to find shaded areas outside and the pool is quite small but otherwise everything was very comfortable. The house is a short walk to a small beach where the ocean was calm enough to swim at. It was easy to taxi into Waikiki.
great house and location. views are fantastic. visit would be improved by an additional bike and detailed written instructions on how to use the a/v equipment. traffic noise is ever present but hardly detracts from view and weather.
We have traveled to Diamond Head many many times over the last ten years, and Wailele Villa was by far and away the best house we have ever rented. From the moment you walk in, you know you are in a special place. We love venturing out but found ourselves happy to enjoy Hawaii at home at WV. The views from every spot in the house, the pool, the furnishings, the bedrooms- everything was top notch. We will definitely be returning again and again!