Diamond Head Vacation Rentals
Diamond Head vacation rentals place you just steps from one of Hawaii's most iconic natural wonders. Whether you're seeking a luxury oceanview condo or a hillside home with privacy and charm, these rentals offer easy access to Waikiki Beach, surfing, hiking, and world-class dining.
Located along Oahu's scenic Gold Coast, vacation rentals near Diamond Head Crater offer a peaceful retreat minutes from the action of Waikiki. Choose from beachfront villas, modern high-rise condos, or tropical hideaways with panoramic views of the Pacific and the famous volcanic cone.
Popular with couples, digital nomads, and families alike, these rentals provide the ideal blend of adventure and serenity. Spend your days hiking the Diamond Head trail, snorkeling at nearby beaches, or strolling to Kapiolani Park and Honolulu Zoo. Many properties also include private lanais, gourmet kitchens, air conditioning, and reserved parking.
Key Features of Diamond Head Rentals
- Walkable to Waikiki Beach and Diamond Head trail
- Oceanview lanais and sunset-facing balconies
- Upscale condos and private homes in the Gold Coast area
- Close to Honolulu Zoo, Kapiolani Park, and farmers markets
- Peaceful setting minutes from shopping, dining, and nightlife
- Ideal for couples, families, and longer stays
Not finding availability here? Browse more nearby options in Ala Moana, Honolulu, or Waikiki for additional oceanfront escapes.
Diamond Head & Oceanview Retreat – Two Condos in Waikiki Banyan
This listing is a combination of 2 separate units close to one another.Disclaimer: The calendar is not perfect and we encourage clients to make an inquiry first to check the availability before booking.Please inquire before booking. Dates are not confirmed until...
Kaimana Beach Penthouse by Gather: Luxury Ocean & Diamond Head Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kaimana Beach Penthouse by Gather,...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Find peace and tranquility in your very own...
Diamond Head View Condo, Steps to Beach + Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Relaxing tropical retreat near Diamond Head. Unwind and rejuvenate your senses.
Experience a calming Oasis at the Kahala Beach Apartments. This peaceful retreat is a fully furnished 2 bedroom, 2 bath dwelling located on the 1st floor and has 1 parking stall included. Cool off comfortably with fully integrated air conditioning throughout the space...
Oceanfront Styling Diamond Head Condo on Pacific- Free parking
LOCATION, LOCATION, LOCATION!! Our condo is located in one of the premier buildings on Oahu's Gold Coast, on the ocean, with unobstructed Diamond Head views, withtrade winds and the sounds of the Pacific. Not your typical rental. Very comfortable luxury bedding with...
Waikiki Dream! 3 Amazing Units, Outdoor Pool, Close to Diamond Head
Come for the beaches, stay for the adventure! With comfortable amenities and convenience to local attractions, you’ll have everything you need for a relaxing getaway or exciting family vacation. Take a dip in the rooftop pool with views of Waikiki. Enjoy a meal at the...
Diamond Head and Ocean Views! 2BR/2BA + Parking Condo in Waikiki
Nestled in bustling Waikiki, this bright and airy condo is a welcoming retreat for guests. Pocket windows open up to the expansive Diamond Head, Fort Derussy Park, and Ocean View. With 2 bedrooms featuring a king bed and a full bed, along with 2 bathrooms equipped with...
2 Great Units, Just Steps to the Beach, Pool, Dining, Spa, Diamond Head
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
2 Awesome Units, Just Steps to the Beach, Pool, Dining, Spa, Diamond Head
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Beautiful Condo in the heart Diamond Head Honolulu, HI
This beautiful condo is across from Kapiolani Park and near Waikiki shell is a quiet neighborhood below Diamond Head and steps outside of Waikiki.Beautifully decorated, top floor unit has wonderful views of Diamond Head & Waikiki.Full kitchen, Washer Dryer Free Wi-Fi &...
Diamond Head Ocean View 1 King
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
26F Partial Diamond Head & Ocean view Waikiki 1BR w/ 1 Free Parking!!
Your vacation getaway, just a quick stroll to the beach! This 1 Bedroom /1 Bath /1 Free PARKING included! Sleeps up to 4 guests. All 3 Brand NEW Beds (July 2022) - 2 x Full Bed in the Bedroom and 1 x Queen size sofaBed in the Living Room.Great location! Just two blocks...
Picturesque views of the ocean and Diamond Head
Mesmerizing panoramic views of Diamond Head, the blue Pacific Ocean, the moon and stars! This spacious corner condo is as close as you can get to the sand without being on the beach. Step back in time for this rare opportunity to stay for a while in the home of a...
Chic Studio w/ Lanai, Rooftop Pool & Quick Access to Waikiki Beach, Diamond Head
Find a peaceful vacation retreat in the heart of Waikiki. Located just 2 blocks from famous-for-a-reason Waikiki Beach, you are in the middle of both city life and a short ride from local attractions, like Diamond Head, Honolulu Zoo, Waikiki Aquarium and many more.This...
3-bedroom Diamond Head Floor-Through Apartment On Ocean - Minimum 3 months
The ultimate diamond head apartment. 2000 square feet on ocean. Newly renovated. Surf in front @ Tonggs. Walk/Run around Diamond Head. Right off Kapiolani Park. The ultimate super chill; elegant; breezy and easy place to hang/enjoy/live.
Colony Surf Getaway: Elegant Condo, Designer Touches &Amazing Diamond Head Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Colony Surf Getaway by Gather, a...
Royal Kuhio 1707 - Spacious Studio w/ Diamond Head and City Views in Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1707, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiKitchen: Fully equipped with oven, microwave, modern appliances, cookware, and...