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!

Guest favorite
A spacious living area features large windows providing an ocean view and natural light. Leather sofas are positioned around a glass coffee table. A wall-mounted TV is displayed above a modern console. A dining set with two chairs is situated near the balcony.
Apartment in Waikiki
4.91 out of 5 average rating, 276 reviews

Ocean view across Waikiki beach/washer dryer/pkng

HALF BLOCK TO BEACH, OCEAN VIEW from every room! Legal transient vacation rental (registration number 87) at prime location in East Waikiki. A stone throw from Waikiki beach, across from Marriott hotel. Ultra speed internet & wifi, Split AC system in every room, full size washer dryer in the unit, double pane windows, one free parking onsite. En-suite bathroom in each bedroom. Beach essentials and family oriented amenities incl. pack n play crib. ABC convenient store at the bottom of building.

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 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, 138 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 favorite
Apartment in Waikiki
4.86 out of 5 average rating, 243 reviews

Waikiki Beach 1.5 blocks away! Free parking space!

Very comfortable 2 bedroom unit with their own attached bathrooms FREE parking space Super close to the beach Easy access in and out of Waikiki Full kitchen with dishwasher Washer and dryer in the unit 1 Main Bedroom with King Bed and bathroom attached 1 Guest Bedroom with Queen Bed and bathroom attached 1 NEW Queen Sleeper Sofa Surf Sun Relax Sunsets Diamond Head Dining Shopping Nightlife Honolulu Zoo Waikiki Aquarium Trash chute Scandia Tower 155 Paoakalani Ave #402 Honolulu HI 96815

Top guest favorite
Condo in Waikiki
4.96 out of 5 average rating, 158 reviews

Take-It-Easy Waikiki Beach Condo

Stay close to Waikīkī Beach, Kūhiō Beach Park and Kapiʻolani Park. Our 2-bedroom 2-bathroom beach pad is in a secure building with free parking. Highlights include a balcony with dining area, full kitchen, beach gear, kids accessories and a washing machine/dryer. Find an ABC Store downstairs and great shopping, restaurants and bars nearby - like Tiki's, Lulu’s, Hula’s and Deck. Hosted by Hawaiian Keliʻi and Aussie Ash of Waikīkī Beach Stays. Registration Number: STR #2302

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, 338 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, 363 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.

Guest favorite
A modern bedroom features a spacious plush bed with a textured white duvet, accentuated by soft, ambient lighting. A large wall-mounted TV is visible. A sleek white sofa and a round side table complement the contemporary furnishings, set against a light-toned wood floor.
Apartment in Waikiki
4.94 out of 5 average rating, 103 reviews

Top FL-Luxury Ocean View King Suite-Waikiki Beach~

Elevate your stay experience with this unparalleled luxury coastal oasis - the Ocean View King Suite, perched on the top floor of the Pacific Monarch condos, mere steps from the heart of Waikiki Beach. Every detail of this meticulously renovated, ultra-chic condo has been carefully curated to offer a one-of-a-kind experience, perfect for romantic getaways and special celebrations.

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.

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.