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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Wailele Villa on the slopes of Diamond Head! Pool and Hot Tub!

Bedrooms 4
Half Baths1
Space 5,363 sq. ft.
Property type house
Minimum Stay 7 nights


About the property

Wailele Villa is a 4 Bedrooms 3.5 Bathrooms and Sleeps 8



Seated along a winding, private drive perched on the slopes of 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.


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

2. Online bookings are subject to manager or owner approval.

3.This vacation 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.

5.Electric pool heat now available at $125/day if pre-ordered or $150/day upon arrival.

6. HOUSE ON THE MARKET FOR SALE AND ONLY BOOKS 60 DAYS PRIOR TO ARRIVAL. You may be asked to accommodate real estate showings with 24 hours notice.

More Details

Property Manager
Robin with Hawaiian Villa Rentals
Speaks: english
Manager indicates their response time is:
Within an hour
Calendar last updated:
March 24, 2018

Guestbook comments from the manager

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.
Feb 2014
  • 1 of 2


Diamond Head - Kapahulu - St. Louis House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 5363 sq. ft.
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 8
  • Min. age of primary renter: 30
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Near The Ocean
  • Ocean View
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 10 people
  • 3 Bathrooms
  • 1 Half Bath
  • Bathroom 2 - toilet , shower
    Bathroom 3 - toilet , shower
    Half Bathroom 4 - toilet
    Master Bathroom 1 - toilet , shower , jetted tub , Walk-in Shower, separate jetted tub and ocean views!
  • 4 Bedrooms, Sleeps 8
  • Bedroom 2 - 1 king , CA King
    Bedroom 4 - 1 king , CA King
    Master Bedroom - 1 king , Ca King bed
    Bedroom 3 - 1 double , Bedroom with double bed has it's own split A/C unit.
  • Books ...
  • DVD Player ...
  • Music Library ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • Video Library ...
  • Balcony ...
  • Bicycles ...
  • Deck / Patio ...
  • Outdoor Grill ...
  • 3 bicycles
Pool / Spa:
  • Hot Tub
  • Private Pool ...
  • duty free shops
  • marina
  • museums
  • playground
  • restaurants
  • zoo
Leisure Activities:
  • beachcombing
  • bird watching
  • luaus
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • golf
  • hiking
  • sailing
  • snorkeling
  • surfing
  • swimming
  • tennis
  • wind-surfing


4.4/5 -
(5 traveler reviews)

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Wailele Villa on the slopes of Diamond Head! Pool and Hot Tub!
average rating of 4.4 based on 7 reviews
Atlanta, Ga

Poor condition for the price

  • 2 of 5

Overall, the house was the perfect size and set up. It was also extremely welll equipped and we were very appreciative of all the supplies, appliances, and sporting equipment available for our use. However, the house, and everything in it, appears to be well overdue for a thorough deep cleaning, preventative maintenance, repairs and updating.

All the appliances, pots and pans, cookware, the insides of much of the cabinetry throughout the house, the kitchen pantry, the decorative bedding, bed pillows, decorative pillows, etc were not very clean and these items smelled bad and were dusty.

The ice machine never worked.

The white shelving in the master closet had something yucky on the underneath of one of the shelves that I was not able to clean off (mold, perhaps).

The ants situation in the kitchen was a real issue - no matter how meticulously we kept the kitchen clean, they swarmed constantly.

The steps outside the kitchen leading to the hot tub were covered in an accumulation of wet leaves, dirt, and a little mold. When the landscaper came to service the yard I was hoping he would clean that area but he never went over there. The plant material in that area is in need of heavy pruning.

The leaks in the skylight where water came down into the kitchen/waterfall area appeared to be happening from a lack of regular inspection and preventative maintenance to the roof skylights.

Inside, if the waterfall was not kept running, a very unpleasant odor permeated the first floor kitchen and foyer area.

The wood floors as well as the beautiful stone on the kitchen counters desperately need to be deep cleaned and properly sealed. It's a shame these natural materials are being neglected so. The stains on the stone are permanent until a professional deep cleans and seals those countertops. Same with the wood floors.

The list goes on.

The property managers were quick to respond to the large complaints but, overall, way too much money for the condition of this property.

  • Submitted: Nov 28, 2016
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
Owner's Response: Dearest Steven, We are sorry you feel this way as we take cleanliness and maintenance very seriously. Everything is thoroughly cleaned prior to each guest. We specifically purchased new linens prior to your arrival as per your request to make certain they were satisfactory for you. As is the case in older homes, items can and will break, however we happily take steps to rectify the issue immediately, so long as we are notified. We informed you that the ice maker was not working as we were waiting on replacement parts (which can unfortunately be slow arriving to the islands), and offered to bring you bags of ice during your stay, which you declined. In tropical climates, ants and other critters can make appearances. If this shall occur in the future, it is best to inform the property managers as soon as possible so the situation can be rectified, not only if you see ants, but in regards to any of the items you found to your dislike. We truly strive to ensure our guests have a wonderful stay.
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5 0

A Magical Experience of Excellence in Paradise!

  • 5 of 5

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!

  • Submitted: Apr 14, 2016
  • Stayed: January 2016
  • Source: HomeAway
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5 0

Amazing property!

  • 5 of 5

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!!

Tom Faye

San Clemente, CA

  • Submitted: Feb 3, 2016
  • Stayed: January 2016
  • Source: HomeAway
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1 0

Amazing holiday rental!

  • 5 of 5

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!

  • Submitted: Jan 13, 2016
  • Stayed: December 2015
  • Source: HomeAway
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  • 5 of 5

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!

  • Submitted: Mar 4, 2015
  • Stayed: February 2015
  • Source: HomeAway
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Nearest Airport
11.2 Miles
Honolulu International


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $800
Damage Deposit $3,000

**The State of Hawaii has authorized an increase in the transient accommodations tax (TAT) from 9.25% to 10.25% effective January 1st 2018. This combined with our current general excise tax (GET) of 4.712%, brings our new vacation rental tax percentage to 14.962% for all rentals starting January 1st 2018 or later.** Rate will be adjusted to 13.962% for rental before Dec 31st 2017.

Tax (calculated against rent only): 13.962%
Departure Cleaning Fee: $800.00
Refundable Security Deposit: $3000.00
Reservation fee: 2.5% on entire amount.
Property accepts only one booking per 30 day period.
**Please email or phone for last minute rates and off season rates!**

*No option to heat pool.

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund