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
Apartment in Waikiki

Stunning Diamond Head Views, Free Parking, Pool

Welcome to our Ke'lani Suite, a stylish condo that offers a traditional feel and look of old Hawaii, along with the most modern amenities. Offering sweeping vistas of Diamond Head, our condo comes with fast Wi-Fi, 65" Roku TV, central A/C, and a fully stocked kitchen. Relax in comfort while soaking in the stunning scenery and enjoy being just a short distance to famous Waikiki Beach, Honolulu Zoo, as well as numerous restaurants and boutique shops. Perfect for families, groups, or couples.

4.95 out of 5 average rating, 43 reviews
Guest favourite
A spacious studio layout is visible with a comfortable bed in the foreground. A small pedestal table with two stools is situated on the private balcony, which offers views of the ocean and surrounding skyscrapers. Large glass doors allow natural light to enter the room.
Flat in Waikiki

31FL-Upscale Ocean View Studio-2-min Walk to Beach

Experience an unforgettable stay on the 31st floor of the iconic Pacific Monarch Condos in central Waikiki. The location is prime and one of the best among many. Just a short block away, you’ll be able to soak up the Hawaiian sun and feel the crystal azure waters of Waikiki beach. Enjoy a short and convenient walk to the International Marketplace and Royal Hawaiian Center. You’ll be surrounded by shopping plazas, world renowned restaurants, and cultural activities!

4.98 out of 5 average rating, 53 reviews
Superhost
A modern bathroom is showcased with a deep soaking tub positioned next to large windows, providing panoramic views of the sunset over the ocean. Natural stone accents are featured throughout, while a decorative vase with flowers adds a touch of elegance.
Apartment in Waikiki

(Golden Week) Nr beach! Imperial Resort

Vacation Rental in Waikiki, Honolulu, Hawaii! This is a 2 bed/ 1.5 bath Penthouse suite on the Floor Rooftop of 205 Lewers Street. Spacious luxury with panoramic views of Ocean and Waikiki Resort area. With Ka Lai LXR resort, Sheraton Waikiki, Embassy Suites and Halekulani Hotel all in the same block..we wanted to match the Five Star appeal with Luxury accommodations. Parking is not included. Valet parking is available for $20/ day or $100/week.

4.93 out of 5 average rating, 40 reviews
Guest favourite
The living room features a spacious sectional sofa and a large 75-inch 4K smart TV mounted on the wall. A stylish kitchen island with seating is visible in the foreground, while expansive windows showcase stunning views of the Hawaiian Mountains.
Flat in Waikiki

17F-Beautiful & Upscale-Waikiki Beach 1BR/Parking~

This newly renovated, sophisticated one-bedroom condo exudes elegance and charm with its premium, upscale improvements. Located on the 17th floor, it offers an extraordinary view of the majestic Hawaiian Mountains. The condo has been meticulously renovated with modern interiors, making it an ideal choice for families and groups traveling together. Moreover, one free parking stall is included to save on parking fees during your stay.

4.96 out of 5 average rating, 83 reviews
Superhost
Flat in Waikiki

2b2b Spacious Apartment central waikiki parking

This apartment is located in the heart of Honolulu, just a block walk from the world-famous Waikiki Beach, offering stunning views of the sand and ocean. Popular attractions like the International Market and Ala Moana Center are within walking distance. The apartment is close to public transport and major roads, making it easy to explore Pearl Harbor and Diamond Head. The quiet and friendly neighborhood ensures a comfortable stay

4.89 out of 5 average rating, 53 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, 339 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, 36 reviews
Guest favourite
A panoramic view of the ocean is captured, showcasing vibrant blue waters and gentle waves. Lush palm trees frame the scene in the foreground, while a distant sailboat can be seen on the horizon, creating a serene coastal atmosphere.
Apartment in Waikiki

Ocean View Corner Unit Full Kitchen Seashore Condo

Amazing Ocean View studio w/ full kitchen in the heart of Waikiki - 1/2 block from the ocean! Enjoy the view of the ocean and Diamond Head from your corner unit's private lanai! Equipped w/ full Kitchen & Bathroom. NEW QUEEN Bed. Fantastic location for beach activities, dining, shopping and absolutely everything that Waikiki has to offer!

4.86 out of 5 average rating, 385 reviews
Top guest favourite
A bright and airy interior showcases a modern dining area with a round table, surrounded by woven chairs. Large windows frame a stunning ocean view, while a comfortable sofa area provides a relaxing space, enhanced by natural light and contemporary lighting fixtures.
Apartment in Waikiki

Chic&Cozy 1BR - Stunning Oceanview Suite @Waikiki

Welcome to your cozy 1-bedroom luxury suite, just a 2-minute walk to the world-famous Waikiki Beach! Our place offers a stunning oceanfront view. Enjoy the breathtaking scenery from your room, and with Waikiki Beach just steps away, endless beach excitement awaits. This is our home in Hawaii, and we hope you love it as much as we do :)

4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Manoa

Hale Malino Home with Fireworks & Diamond Head Vie

Charming Manoa Valley home with Diamond Head views and Friday night fireworks from the lanai. Three bedrooms, 2.5 baths, spacious living areas, and outdoor BBQ space. Minutes to UH Manoa, Manoa Marketplace, Manoa Falls, Waikiki, and Ala Moana.

5.0 out of 5 average rating, 7 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.