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Holiday rentals in Diamond Head

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Top-rated holiday rentals in Diamond Head

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An inviting balcony space is visible, featuring a round, cushioned chair beside a small, white table. The ocean stretches out in the background, framed by palm trees and gentle waves lapping against the shore, creating a serene coastal view.
Apartment in Waikiki
4.93 out of 5 average rating, 102 reviews

Dreamy Beachfront Home (Car & Parking Available)

* Aloha! Welcome to our happy place - our beachfront home! * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. The location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls and more. Every time I come to Hawaii, I am happy. I hope our place can bring you happiness too. :-)

Top guest favourite
A breathtaking ocean view is framed by large windows, showcasing vibrant colors of the sunset reflecting on the water. The horizon extends into the distance, where boats can be seen navigating the tranquil sea, alongside nearby high-rise buildings.
Apartment in Waikiki
5.0 out of 5 average rating, 92 reviews

*RARE* Nami 1BR SUITE | Luxurious Ocean View

Nami, meaning "waves" in Japanese, symbolizing resilience and the ever-changing nature of life, is an integral part of the vibrant Hawaiian and Japanese culture surrounding Waikiki Beach. Our Nami Suite with breathtaking ocean view is 1 block away from Waikiki Beach. The renovated interior and upscale accommodations include a full kitchen in a spacious 600 sq ft one bedroom, beach equipment, and FREE parking. Book your stay with us and create unforgettable memories by the ocean's edge in Oahu

Top guest favourite
Flat in Waikiki
4.97 out of 5 average rating, 64 reviews

Waikiki Beach & Diamond Head View | 18F Luxe 1B

This newly renovated 18th-floor 1-bedroom apartment is a perfect retreat for up to 4 guests, featuring breathtaking ocean views and iconic Diamond Head vistas in the heart of Waikiki. • 3-minute walk to the beach and ocean • Dining, coffee shops, nightlife, and convenience stores right downstairs • On-site gated parking: $45/day with electric car charging stations • Coin-operated laundry facilities on the 3rd floor • 34th-floor rooftop with pool, hot tub, sauna, bbq grill & stunning views

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
4.95 out of 5 average rating, 117 reviews

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.

Top guest favourite
A panoramic view from a high balcony captures the vibrant blue ocean and lush greenery below. Diamond Head's iconic profile stands prominently in the distance, framed by a clear sky dotted with fluffy clouds. Nearby residential buildings add to the scenic landscape.
Flat in Waikiki
4.99 out of 5 average rating, 135 reviews

Ocean View Sunset, Free Parking, Pool, 5m to Beach

Aloha and welcome to one of the most amazing complete remodels you will find in Waikiki - completed end of 2022. This one-of-a-kind 1 bedroom with free 1 parking stall, pool and gym boasts spectacular ocean & Diamond Head views and is only 0.2 miles (5 min walk) from Waikiki Beach and closer to endless restaurants, shopping & so much more. We would love to have you stay with us and create memories in this truly magical place that is centrally-located, well appointed, and with fabulous views!

Top guest favourite
Apartment in Waikiki
4.98 out of 5 average rating, 59 reviews

31F-08 Waikiki Ocean View Condo • Pool • Park FREE

Welcome to your MOANA Suite at the Waikiki Banyan, where every detail has been thoughtfully chosen for your comfort. Inspired by the serenity of the ocean, we hope your suite is a place where you can unwind, recharge, and enjoy a memorable island stay. Located on the 31st floor, this 1-bedroom suite offers: ✔ BREATHTAKING views of Waikiki and the Pacific ocean ✔ NEW Pool Recreation Deck ✔ STEPS to the beach and Waikiki's restaurants and shops ✔ FREE parking included ✔ NO HIDDEN resort fees

Guest favourite
A spacious bedroom is highlighted by a large bed with soft white bedding. Natural light enters through glass sliding doors, leading to a balcony with views of the mountains. Wooden accent walls complement the minimalist decor, and bedside tables feature small green plants.
Apartment in Waikiki
4.89 out of 5 average rating, 126 reviews

Newly Renovated | Low-Toxic Waikiki Airbnb

At Kind Legacy Properties, we understand the importance of reducing exposure to harmful chemicals, toxins, and heavy metals for optimal health. Our newly renovated 1 bed | 1 bath Low-toxic Airbnb features Organic bedding, Organic tea + coffee, along with air + water + shower filters, as well as low-toxic household and kitchen items! Enjoy the convenience of FREE parking and a short walk (0.3 miles) to the beach. Book your stay now and experience the ultimate wellness retreat!

Guest favourite
Apartment in Waikiki
4.92 out of 5 average rating, 36 reviews

25F Waikiki Banyan Ocean View Suite • FREE Parking

Aloha and welcome to Unit 2502 in Mauka Tower 2 at the Waikiki Banyan — your private island retreat with breathtaking ocean views from the 25th floor. From sunrise coffee on your private lanai to sunset cocktails overlooking the sparkling Pacific Ocean and Waikiki skyline, every moment here feels like paradise. This beautifully appointed 1-bedroom condo is designed for both comfort and convenience, creating the perfect setting for unforgettable island memories.

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
4.84 out of 5 average rating, 333 reviews

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

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
5.0 out of 5 average rating, 41 reviews

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.

Top guest favourite
Flat in Waikiki
4.97 out of 5 average rating, 31 reviews

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.

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
4.98 out of 5 average rating, 87 reviews

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 :)

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.