Vacation rentals in Diamond Head

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Top-rated vacation rentals in Diamond Head

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Top guest favorite
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
4.92 out of 5 average rating, 177 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 favorite
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, 121 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.

Superhost
A private balcony features a small round table adorned with a colorful mosaic design and two wicker chairs. The view showcases the scenic Waikiki Beach, the shimmering ocean waves, and the lush lagoon bordered by palm trees.
Condo in Waikiki
4.88 out of 5 average rating, 233 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! There’s 2 Ilikai pool iavailable for our guests. Also accepting long term stays at special rates.

Guest favorite
A spacious bedroom is illuminated by natural light, showcasing a beautifully designed king-size bed with crisp white linens and a soft headboard. A large flat-screen TV is mounted on a wooden accent wall. The room features a cozy seating area and direct access to the patio.
Apartment in Waikiki
4.96 out of 5 average rating, 129 reviews

32F-Penthouse Pacific Monarch Studio-Ocean View

Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.

Guest favorite
A contemporary studio is revealed, featuring a spacious bed with neutral bedding and accent pillows. A kitchenette with wooden cabinets, microwave, and countertop is visible, along with a small dining area with two bar stools. The room is complemented by warm-toned walls and a ceiling fan.
Condo in Waikiki
4.91 out of 5 average rating, 422 reviews

Contemporary Waikiki Studio - Steps to the Beach!

Contemporary boutique studio located steps from Waikiki beach, Kapiolani Park, Honolulu Zoo, family-friendly activities, restaurants, nightlife, & public transportation - all within walking distance. You’ll love my place because of the fully equipped kitchenette and comfy bed. Bed & sleeper futon sleeps up to 3 adults comfortably. Beach towels, chairs, boogie board, sand toys & snorkel gears provided. 6/21/26 - See Construction Notice below.

Guest favorite
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.
Apartment in Waikiki
4.87 out of 5 average rating, 420 reviews

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.

Top guest favorite
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
4.85 out of 5 average rating, 339 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

Guest favorite
A private balcony features two aqua-colored chairs overlooking a landscaped park dotted with palm trees. A clear sky adds brightness to the scene, while a glimpse of the ocean can be seen in the distance, providing an inviting setting for relaxation.
Apartment in Waikiki
4.9 out of 5 average rating, 364 reviews

Waikiki Bungalow

YOU WILL BE BLOWN AWAY BY GORGEOUS VIEWS OF WAIKIKI BEACH AND DIAMOND HEAD. THIS MODERN RESIDENCE IS NEWLY RENOVATED AND EXTREMELY CLEAN. LOCATED JUST A FEW STEPS AWAY FROM WAIKIKI BEACH, RESTAURANTS, AND ATTRACTIONS. Unit is located on the third floor of building, upstairs from Hula’s Bar & Lei Stand. There is a potential for bar noise. Unit is priced accordingly. All Taxes and Fees included in price.

Top guest favorite
Condo in Waikiki
4.83 out of 5 average rating, 240 reviews

Studio 2 blocks from Waikiki Beach!

This studio is nestled in the heart of Waikiki—just two blocks from the iconic Duke Kahanamoku Statue and the world-famous Waikiki Beach. Fully renovated in June 2025, the space is all yours to relax and enjoy. Surrounded by shops, restaurants, food trucks, and surf spots, it’s the perfect home base for beach days, surf lessons, exploring Oʻahu, or working remotely—with plenty of aloha.

Guest favorite
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
4.96 out of 5 average rating, 181 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.

Top guest favorite
A raised queen bed is featured, topped with a light quilt and accented by two wall-mounted lamps. Behind the bed, a vibrant wall mural displays an ocean scene with a sunrise and green hills, adding a unique artistic touch to the space.
Apartment in Waikiki
4.88 out of 5 average rating, 210 reviews

Sunsets at The Niihau

GE-165-040-5376-01 TA-165-040-5376-01 STR 415 exp: 1/4/25 TMK#: 2-6-003-013 (CPR: 0026) Studio living in the front with a small private room in the back, bathroom has stall shower. Full kitchen with necessities. You can see the sunsets and Friday night fireworks from every room. Parking for one compact car. Views of park & ocean.

Guest favorite
A view of the shoreline featuring a mountainous landscape, partially covered by green vegetation. The calm water reflects the bright blue sky, with a few white clouds gently drifting overhead. The natural scenery suggests a peaceful coastal environment.
Condo in Waikiki
4.87 out of 5 average rating, 127 reviews

Peaceful cozy comfortable apartment

Wonderful, super quiet, super clean apartment with a parking . Beautiful renovations had been done this year in this cozy one bedroom apartment, new split AC System, washer & Dryer... The bed is a very special, super confortable, with free WIFI-FI TA-203-982-6432-01

Popular amenities for Diamond Head vacation 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.