• Vacation Rentals
    • California
    • Hawai’i
    • Washington
    • Dominican Republic
    • Stay for the Holidays
    • Free Night Promotion
  • Experiences
  • Vacation Rental Management
  • About Gather
    • Meet the Team
    • Our Property Managers
    • Blog
    • FAQ
    • Terms & Conditions
    • Privacy
    • Contact Us
  • Vacation Rentals
    • California
      • Del Mar
      • La Jolla
      • Rancho Santa Fe
      • San Diego Area
      • Napa Valley Area
    • Hawai’i
      • Big Island
      • Kauai
      • Maui
      • Oahu
      • Resorts
    • Washington
      • Bellingham
      • Birch Bay
    • Dominican Republic
      • Casa de Campo
    • Stay for the Holidays
    • Free Night Promotion
  • Experiences
  • Vacation Rental Management
  • About Gather
    • Meet the Team
    • Our Property Managers
    • Blog
    • FAQ
    • Terms & Conditions
    • Privacy
    • Contact Us
  • 877-692-1050

Diamond Head Luxury Vacation Rentals, Beachfront Homes & Villas

Start Your Vacation Rental Search > Hawai’i Vacation Rentals and Villas > Oahu Luxury Vacation Rentals & Villas > Diamond Head Luxury Vacation Rentals, Beachfront Homes & Villas

Popular Oahu neighborhoods

Aina Haina | Hawaii Kai | Kahala | Kailua | Kaka’ako | Kuilima Estates | Lanikai | Makaha | North Shore | Turtle Bay | Waikiki | Waimanalo
Clear dates

Duration

Starting Month

October

November

December

January

February

March

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

Where to?

Search For

When

Who

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

Filters

Price range

The average night price is $806

$
$

Rooms

Baths

Property Type

Amenities

Page 1 of 1

    Your own modern, luxurious oasis on Oahu complete with private pool and hot tub Pool and ocean views from the comfort of your private lanai From the Primary Bedroom, step outside on your own private balcony to take in the gorgeous views Primary bedroom with a king bed and ocean views The open-concept common spaces are aptly fit for entertaining There's another living area with a flat screen TV to keep everyone entertained The kitchen overlooks the living area

Holiday Availability

Diamond Head Grandeur

5 Beds
5.5 Baths
10 Sleeps

Starting at $1,800/night

Seaside Hideaway 5BR Estate*

5 Beds
4 Baths
10 Sleeps

Starting at $2,000/night

    Living Room with Vaulted Ceiling. Private Yard with Loungers Private Pool With Diamond Head Views Living Room opens up to the Oceanside Yard Dining Table Living Room area opens to Private Pool Dining Room/Kitchen
(18)

Hale Makai at Diamond Head

3 Beds
3.5 Baths
8 Sleeps

Starting at $1,250/night

    Oceanside lanai offers both lounge and table seating options. Entrance looking towards Living Room and Oceanside Lanai. Dining Room/Kitchen looking towards Oceanside lanai. Oceanside View of Diamond Head Surf House. Living Room opens up to the Oceanside Lanai and Yard. Lanai looking towards Living Room and Dining Room/Kitchen. Living Room area, looking makai (toward the ocean)
(1)

Diamond Head Surf House

3 Beds
3.5 Baths
8 Sleeps

Starting at $550/night

    Backyard with heated swimming pool Lounge poolside or cool off in the private pool Living Room Fully equipped gourmet kitchen. Dining Room Fully equipped gourmet kitchen. Backyard with heated swimming pool

Casa de Makalei

4 Beds
4.5 Baths
8 Sleeps

Starting at $517/night

    Welcome to our bright and open living area with panoramic ocean views, blending comfort with a serene coastal vibe for a perfect retreat. Chic dining nook with stylish decor and expansive Diamon Head views, offering an inspiring backdrop for meals and conversations. Relaxing balcony offering expansive tropical views for a serene and exclusive getaway. Chic dining nook with stylish furnishings for intimate meals and serene moments. Stunning aerial view encompassing lush landscapes and crystalline waters for a truly majestic Diamond Head setting. Plush sofas with open and airy living space, welcoming the island breeze. Inviting dining space with ocean views for memorable meals and relaxation.

Colony Surf Getaway

2 Beds
2 Baths
6 Sleeps

Starting at $277/night

    Large Private Backyard with Lush Tropical Garden and Seating areas Balcony Upstairs with seating area and Diamond Head views Living Room Upstairs Open concept living, kitchen, and dining area Upstairs leads to Balcony Open-concept floor plan Kitchen overlooks dining area
(2)

Hale Nui

4 Beds
3 Baths
9 Sleeps

Starting at $333/night

    Pool overlooking the ocean Spa and pool Covered lanai with ocean views Main house entrance Kitchen by Sie Matic Germany Living Room with Ocean Views Dining for Eight Guests

Seaside Hideaway*

3 Beds
2 Baths
6 Sleeps

Starting at $1,250/night

    Spanish Colonial Revival style The front porch is the perfect spot to sit and enjoy your morning coffee while planning what adventures you will go on nearby! Dining room and kitchen. This chef's dream kitchen includes top-of-the-line appliances and extra amenities like a KitchenAid mixer Main level reading nook is inviting and cozy A 10-minute walk from Waikiki, discover your own private paradise nestled at the base of Diamond Head in Honolulu’s renowned Gold Coast Use this cute reading nook to relax with a good book Peaceful office space for those who wish to get a little work done while on vacation
(1)

Hale Mahie

4 Beds
3.5 Baths
8 Sleeps

Starting at $333/night

Kaimana Retreat*

3 Beds
2.5 Baths
6 Sleeps

Starting at $850/night

    Recently renovated swimming pool. Exquisite Diamond Head views with floor-to-ceiling windows, for an indoor/outdoor living experience. Open-concept kitchen, ideal for entertaining. Dine with a party of six, with Diamond Head in the background. Beautiful oceanfront views. Full gourmet kitchen with stainless steel appliances, including refrigerator, dishwasher, microwave, stove, oven, wine cooler, and trash compactor. Primary bedroom with Diamond Head views. Window AC unit is not pictured.

Executive Gold Coast Oceanfront Suite

2 Beds
2 Baths
4 Sleeps

Starting at $250/night

    Discover a hidden paradise, immerse yourself in a secluded tropical haven nestled within the vibrant heart of Waikiki. Your private oasis awaits Experience the charm of our lanai, equipped with a BBQ for delightful grills and a setup for al fresco dining, inviting you to savor meals under the open sky. Step into nature's embrace, surrounded by lush greenery and towering trees, with the melodic symphony of birdsongs serenading your senses. Sink into serenity in our home, where every corner is crafted for your ultimate relaxation, making each moment an oasis of calm. Step onto the outdoor lanai, where gentle breezes and serene views create the perfect backdrop for moments of reflection and relaxation. Serene living area filled with natural lighting. Guest suite access to the balcony with furniture, a perfect spot to sip your morning coffee.

Diamond Head Bali Retreat**

3 Beds
2 Baths
6 Sleeps

Starting at $250/night

    Let the crystal clear pool sooth your soul Poolside fire pit where to gather with friends at night Enjoy outdoor dining for 8 on the deck with pool views Downstairs pool room and bar Entrance to Hale Le'ahi Step inside this beautiful, expansive plantation home Spacious living area with a lanai overlooking the pool
(2)

Hale Le'ahi*

5 Beds
4 Baths
10 Sleeps

Starting at $823/night

  • 1
  • 1