Hawaiian Villa Rentals |

Wailele Villa


Bedroom(s): 4, Bathroom(s): 3.5, Max Occupancy: 9

TA- 004-170-5472-01

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.


Oahu Taxes on short term vacation rentals (calculated against rent only): 14.962%

Departure Cleaning Fee: $800.00

Refundable Security Deposit: $3,000.00

Reservation fee: 2.5% on entire amount.


1. A/C in all rooms.

1. Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible DISCOUNTS.

2. 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.

3. This Hawaii vacation rental home has been registered as a Transient Accommodation with the State of Hawaii.

4. 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.

Hawaiian Villa Rentals specializing in Luxury Vacation Rentals in Kailua / Lanikai, Kahala / Diamond Head on Oahu.


AC all rooms
Ocean View
Walk to Beach
Washer & Dryer
Hot Tub/Spa
Wireless Internet
Cable TV
4.71 out of 5 stars based on 14 user reviews

Perfect get away

5 out of 5 stars 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.
5 out of 5 stars 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.
4 out of 5 stars 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?!?!

Amazing Home

Review by Rick B.
5 out of 5 stars 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.
5 out of 5 stars 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.

Perfect Honolulu location and million dollar view!

Review by Sue T.
5 out of 5 stars 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!

Sony Open Vacation

Review by Tom F.
5 out of 5 stars 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.

El Paso, Texas Review

5 out of 5 stars 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.
5 out of 5 stars 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 Teresa L.
5 out of 5 stars 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

4 out of 5 stars 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.

unmatched views

4 out of 5 stars 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.


5 out of 5 stars 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!

Diamondhead Gem

Review by Robert K.
4 out of 5 stars Great property with stunning ocean views throughout home. Top floor has a huge master bedroom, bathroom and a private patio. Main floor has large living room, dining room and kitchen area. The kitchen has all the amenities you need and more. Be prepared to see some bugs from time to time as you are in a tropical environment. Pool area features a waterfall and amazing views. The pool is small but was enough for my family.

Seasonal Rates

Christmas and New Years still available.... 10 night min stay!

Date Range Daily Weekly Monthly
12/14/2018 - 01/14/2019 $2,350.00 $16,450.00 $49,350.00
01/15/2019 - 04/30/2019 $1,225.00 $8,575.00 $25,725.00
05/01/2019 - 05/31/2019 $995.00 $6,965.00 $20,895.00
06/06/2019 - 09/30/2019 $1,225.00 $8,575.00 $25,725.00
10/01/2019 - 10/31/2019 $995.00 $6,965.00 $20,895.00
11/01/2019 - 12/12/2019 $1,225.00 $8,575.00 $25,725.00
12/13/2019 - 01/12/2020 $2,350.00 $16,450.00 $49,350.00
* Seasonal rates are only estimates and do not reflect taxes or additional fees.