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Holiday rentals in Diamond Head

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Top-rated holiday rentals in Diamond Head

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Top guest favourite
A private lanai is shown, featuring a sleek outdoor dining table with two lanterns. The view captures the ocean with sailboats in the distance, alongside lush greenery and palm trees, creating a serene backdrop against the clear blue sky.
Apartment in Waikiki

Ocean View w/ 2 private balconies; Steps to Beach

BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!

4.92 out of 5 average rating, 177 reviews
Top guest favourite
A balcony view features a small round table set for breakfast, with fresh fruit and pastries arranged on plates. The ocean can be seen in the distance, along with tall buildings of the Honolulu skyline. Natural light brightens the space.
Flat in Waikiki

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen

Whether you are planning a perfect romantic getaway or a much deserved quality family time vacay for FOUR, this high floor apartment w/ocean views checks all the boxes. The 1 bedroom with the KING BED is ideal for the parents, while the kids share the QUEEN SLEEPER SOFA in the living room. The kitchen is fully stocked w/everything you will need to prepare meals, drinks and snacks. It's a 4 minute walk to the beach. There is 1 FREE PARKING spot and there's NO RESORT FEES. Close to shops & food.

4.95 out of 5 average rating, 122 reviews
Guest favourite
The spacious sleeping area features a king-size bed with ambient lighting, complemented by a plush area rug. Large glass doors lead to a balcony, offering unobstructed views of the ocean and sky, allowing natural light to fill the room.
Flat in Waikiki

Penthouse Upscale Oceanview King Studio Near Beach

This luxurious studio features an extraordinary ambiance that has been recently renovated with the most exquisite finishes, making it the ultimate getaway for couples & special occasions. Located on the penthouse floor, you will be able to enjoy unobstructed views of the surrounding area, as well as ocean views that will leave you in awe. In addition, this suite is located just a 5-min walk away from the beach, providing you with easy access to the crystal-clear waters of Waikiki Beach.

4.94 out of 5 average rating, 87 reviews
Guest favourite
A spacious living area features a king size bed with fresh linens, complemented by two boucle fabric chairs and a round coffee table. Natural light filters through a nearby window, highlighting the modern wood accent wall and a decorative wall clock.
Flat in Waikiki

39FL-Chic Modern in Waikiki-Upgraded King Studio

With high-end finishes and a newly renovated interior, this studio in Waikiki is picture-perfect. Located on the 39th floor, it boasts partial ocean views and views of the Waikiki skyline. The building is surrounded by amazing dining and shopping options. The world-famous Waikiki beach is only a few minutes' walk away. Whether you're traveling as a couple or a small family, this unique experience is perfect for you. You'll feel right at home with all the essential amenities provided.

4.95 out of 5 average rating, 138 reviews
Guest favourite
A vibrant beach scene is captured, featuring gentle ocean waves and lush palm trees swaying in the breeze. A stage is set up on the sandy beach, with visitors enjoying the surroundings. The colorful foliage adds to the lively atmosphere.
Apartment in Waikiki

ENCHANTED BAMBOO FOREST

As the sun dances through the cool breeze and lush green trees, the bamboo motif surrounds you with Aloha! Just a minute walk to the beach! Look to your right of the beach, and you will experience the lively exciting activities, exotic foods, merry song, hula shows and shopping! Look to your left of the beach and you will find the Honolulu Zoo, Aquarium, tennis courts, parks and how about an adventurous Diamond Head hike!

4.93 out of 5 average rating, 191 reviews
Guest favourite
A spacious bed with neutral bedding is featured in the foreground, accompanied by decorative pillows. Large glass doors open to a balcony with ocean views, and a seating area is visible outside. Three round mirrors adorn the wall above the bed.
Flat in Waikiki

Ocean View Studio in Waikiki

Ocean view studio with awesome balcony just minutes walk to the famous Waikiki Beach. Renovated bathroom with Toto Washlet system. Queen size hybrid bed with coffee maker, refrigerator and microwave. Brand new split AC. Interior of unit is small but there's a private balcony with awesome ocean views. It's hard to get a nice ocean view in Waikiki for this price! Location is in central Waikiki, only a minutes walk to the beach.

4.87 out of 5 average rating, 420 reviews
Top guest favourite
A panoramic view of Waikiki beach showcases golden sands and gentle waves lapping at the shore. High-rise buildings line the coast, with Diamond Head peak visible in the background against a clear blue sky.
Guest suite in Honolulu

DIAMOND ON DIAMOND HEAD

Located on the slope of Diamond Head, our apartment is at a walking distance of Waikiki beach, restaurants, nightlife, public transport. You’ll love my place because of the coziness, the location. I put a special attention on having the mattress spray monthly for bugs and also the apartment for insects. It is very important for me to offer a super clean, cozy, comfy and secure apartment. TA-182-790-8096-01

4.85 out of 5 average rating, 340 reviews
Top guest favourite
The modern living space features a sleek kitchen with stainless steel appliances and a dining area with a wooden table. A cozy seating area is present, highlighting a white coffee table. The bedroom area is separated by sliding doors, showcasing a king bed and wall-mounted TV.
Flat in Waikiki

Cozy 1 Bed in Waikiki w/ Parking

This cozy and newly renovated 1 bedroom apartment is centrally located in Waikiki at the Waikiki Banyan Hotel. Nightly rates include parking for one (1) regular sized vehicle. Wake up and watch the streets come alive on your private lanai. Unit has partial ocean views and is just a 5 minute walk from the famous beaches of Waikiki and steps from world class shopping, dining, and entertainment.

5.0 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Waikiki

Wake Up to Ocean Views! 2queen Apt w/ Free Parking

Experience absolute luxury in this newly renovated, impeccably designed 1BR residence. Every element has been meticulously crafted to offer guests an unparalleled experience. Positioned on the 15th floor, the panoramic ocean views overlooking Waikiki will leave you spellbound. Plus, enjoy the added convenience of complimentary parking in an unassigned stall, ensuring a hassle-free stay.

4.97 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Waikiki

Best Location | Renovated Studio | 2 Lanais

Welcome to the Hale Lanai. Location beats!! Stay in the heart of Waikiki, just a 5-minute walk to the world-famous beach and minutes from some of the island’s best food trucks and local eateries. Whether it’s sunrise surf sessions or late-night poke runs, this studio gives you the best of Oahu right outside your door. Perfect for Solo Trips, Couples, or a Small Family of 3!

5.0 out of 5 average rating, 43 reviews
Guest favourite
A bright studio features a spacious bed with a decorative ‘Aloha’ pillow. Large windows frame the view of the city and sky, and a small dining table with a chair is positioned near the window. The warm wood flooring complements the light decor.
Apartment in Honolulu

Oceanfront Diamond Head Beach Hotel

Diamond Head Beach Hotel featuring studio #1102 is what you expect in a Hawaii accommodation. Comfortable w awesome views! A hidden-gem get away! Enjoy the splendor of nature at Kapiolani Park featuring exotic trees and birds. Iconic Diamond Head Crater moments away.... A wonderful stroll along the shoreline path is breathtaking... No parking

4.91 out of 5 average rating, 82 reviews
Guest favourite
Apartment in Waikiki

Breathtaking Ocean view, free 1 parking

Enjoy easy access to everything from this perfect located home base. High floor w. Beautiful ocean view. Kitchen is fully equipped to prep meals. Walking distance to the famous Waikiki beach, restaurants, shops, Kapiolani park, zoo , diamond head crater etc. 1 king bed, pullout couch, central AC, big TV, WiFi, 1 free parking.

4.9 out of 5 average rating, 153 reviews

Popular amenities for Diamond Head holiday rentals

Frequently Asked Questions

  • Where is Diamond Head located?

    Diamond Head rises along the south shore of O‘ahu, near the eastern edge of Waikiki. Its volcanic crater and surrounding parks are easily recognized as part of Honolulu’s coastline.

  • When is the best time to visit Diamond Head?

    Visitors often suggest late spring through early fall for lighter rainfall and warm temperatures around 73–85°F (23–30°C). Morning hikes are frequently recommended to experience cooler breezes and gentler sunlight.

  • What are some things to do near Diamond Head?

    You can explore scenic coastal parks, visit Waikiki Beach, or enjoy local markets and eateries around the area. The neighborhood also has walking trails, viewpoints, and spaces for outdoor recreation.

  • How is the weather near Diamond Head?

    Diamond Head is surrounded by a warm, tropical climate, with daytime highs ranging from 78–85°F (26–30°C) for most of the year and cooler winter lows around 65–68°F (18–20°C). Rain is more frequent in winter, while summer months feature sunnier and drier conditions. Lightweight, sun-protective clothing is often suggested year-round.