Holiday houses in Diamond Head

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Top-rated holiday rentals in Diamond Head

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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.
Condo in Waikiki
5.0 out of 5 average rating, 90 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
Condo in Waikiki
5.0 out of 5 average rating, 13 reviews

New! Renovated 17F Luxe Ocean View |Walk to Beach

🌺 Welcome to Your Waikīkī Getaway! 🌴 Experience a newly renovated private Waikīkī condo in the Pacific Monarch Hotel. Enjoy ocean, city, and Diamond Head views from your lanai. This bright studio features a full kitchenette, King bed, Queen sleeper sofa, and hotel amenities like Waikīkī's highest rooftop pool, all without resort fees. Just 2 blocks from Waikīkī Beach, with dining and shopping steps away. Comfortably sleeps 4, perfect for couples or small families seeking a prime Oahu getaway.

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.
Condo in Waikiki
4.91 out of 5 average rating, 174 reviews

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!

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.
Apartment in Waikiki
4.95 out of 5 average rating, 115 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.
Apartment in Waikiki
4.99 out of 5 average rating, 130 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!

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.
Apartment in Waikiki
4.94 out of 5 average rating, 84 reviews

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.

Guest favourite
Apartment in Waikiki
5.0 out of 5 average rating, 8 reviews

12th Floor Ocean View - 5 min to Waikiki Beach

✨Ocean View Lanai in the Heart of Waikiki! Welcome to this beautifully furnished 1-bedroom suite at Pacific Monarch, just one block from Waikiki Beach! Perfect for couples, small families, and remote workers, this island retreat offers stunning ocean views, resort-style amenities, and unbeatable walkability to Waikiki’s best dining, shopping, and attractions. Relax, recharge, and experience paradise in one of Oahu’s most vibrant locations, right in the heart of it all. ✨

Top Guest favourite
Apartment in Waikiki
5.0 out of 5 average rating, 23 reviews

Corner Condo | Near Waikiki Beach | Free Parking

High-floor corner condo just steps from Waikiki Beach! Enjoy cool island breezes in this corner unit with a private lanai (balcony) and ocean view. Includes free parking, a fully equipped kitchen, Queen-size bed, and full-size sofa bed. Stay connected with free high-speed Wi-Fi, plus coin-operated laundry on every floor. Located in the popular Waikiki Banyan, close to beaches, dining, and shopping. Instant Book available — perfect for a relaxing Waikiki getaway! 🌴

Top Guest favourite
A lanai provides a scenic view of Diamond Head and the ocean. Glass doors allow natural light into the space. Outdoor seating is available for relaxation, with a light-colored chair positioned near the railing. The surrounding high-rise buildings contribute to the urban backdrop.
Apartment in Waikiki
5.0 out of 5 average rating, 82 reviews

Diamond View from Waikiki Banyan

Nestled steps away from world-famous Waikiki Beach, this newly renovated condo offers sweeping panoramic views of Diamond Head. Enjoy morning coffee in bed or evening cocktails on the lanai with some of the most stunning views Waikiki has to offer! The Waikiki Banyan is one of Honolulu’s most sought after addresses and offers a quieter side of Waikiki while still withinwalking distance to the beach, Kapiolani Park, and Kalakaua Avenue. Free parking space included!

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, 329 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
Apartment in Waikiki
4.96 out of 5 average rating, 26 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.

Guest favourite
A modern living area is illuminated by natural light from large glass doors leading to a balcony. The space features a curved gray sofa and a wall-mounted TV, with a backdrop of a serene ocean view visible through the doors.
Apartment in Waikiki
4.95 out of 5 average rating, 174 reviews

High FL-Upscale Ocean View w/ Easy Beach Access~

Situated in one of the most vibrant neighborhoods in all of Waikiki, you'll be within steps away from many local restaurants, and shopping plazas. Most importantly, a quick 2 min walk to Waikiki beach, surrounded by cultural activities such as surf lessons and rentals. This stunning apartment is truly one of a kind, and it's the perfect choice for couples & memorable occasions.

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.