Vacation rentals in Diamond Head

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Top-rated vacation rentals in Diamond Head

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Guest favorite
Condo in Waikiki
4.87 out of 5 average rating, 113 reviews

Sunny Waikiki 2Bd/2Bth Corner Unit, 1 Min to Beach

NOW w/ AIR CONDITIONING! Sunny, breezy 2 bed 2 bath condo in the heart of vibrant Waikiki. 8th fl corner unit w/ secure entrance. FREE PARKING +laundry in unit. 1 min walk to ocean. Endless options for activities, restaurants + entertainment surround in short walking distance. Mini-store w/ essentials, food drink + beach supplies right downstairs, coffee shops on the corner. Wake up and enjoy Diamond Head view from your private lanai, then take advantage of all the fun Waikiki has to offer!

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!

Superhost
The kitchen features sleek appliances and a granite countertop with bar seating for three. Modern white cabinetry contrasts with the dark tiles, while a light fixture hangs above. The space is illuminated by natural light from an adjoining room.
Condo in Waikiki
4.84 out of 5 average rating, 292 reviews

Bright & Breezy Condo at Beach w/ Free Parking!!

Fully furnished 2 bedroom, 2 bath condo one block from the beach with lots of breeze, sunshine, and a gorgeous view of Diamond Head. You can't beat the location with all the shopping, restaurants, bars, and night life of Waikiki at your fingertips. Please note: The unit is on the 10th floor and there is only one elevator. Like many older Waikiki buildings, it can occasionally be out of service. Exact Location: 155 Paoakalani Ave, #1003, Honolulu, HI 96815 Honolulu STR License: 2211-CCH-0501

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, 120 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.

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 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
4.82 out of 5 average rating, 239 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 cozy seating area is highlighted by a green sofa adorned with a decorative pillow featuring a flowered design. A small side table with a potted plant is positioned nearby, and wall art displaying a tropical motif adds visual interest to the space.
Condo in Waikiki
4.91 out of 5 average rating, 213 reviews

Fall Promos! 1.5 Blocks to the beach Pool+hot tub

✔ 1.5 Blocks to the Beach front ✔ Located on Kuhio Ave. surrounded by shops + restaurants ✔ Pool + Hot Tub + Ko Tiki Terrace Restaurant in the Condo ✔ New AC ✔ Fully outfitted Kitchenette ✔ Free Fast Wifi ✔ Flat Screen TV with Cable TV ✔ Queen Bed ✔ Beach Towels ✔ On site parking (paid)

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.