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
4.91 out of 5 average rating, 176 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, 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.

Top guest favorite
Apartment in Waikiki
4.93 out of 5 average rating, 332 reviews

500 feet to Waikiki beach/washer dryer/parking

Legal transient vacation rental (registration number 86) at a prime location in East Waikiki. HALF BLOCK TO BEACH, a stone throw from best part of Kuhio beach, across from Marriott Hotel, walk to zoo and Kapiolani park. SPLIT AC in EVERY ROOM, full size WASHER DRYER in unit, Ultra speed internet, double pane windows, one free extra large parking stall onsite that can fit a big SUV or minivan. En-suite bathroom in each bedroom. Beach essentials and family oriented amenities incl. pack n play.

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, 137 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
4.94 out of 5 average rating, 148 reviews

9A Cozy Waikiki 1BR | Steps to Beach | Ocean View

Excellent location in the heart of Waikiki, just a 3-minute walk to Waikiki Beach. This 9th-floor unit features a balcony with partial ocean view, 1 adjustable Beautyrest queen bed, 1 queen sofa bed, 1 bath, full-size kitchen, 2 window A/Cs, high-speed WiFi, 2 smart TVs (70” & 55”), and cold-water bidet. Restaurants, shopping, beaches, surfing, nightlife, and endless Waikiki activities are all just steps away, with the convenience of easily returning to relax anytime during your stay.

Top guest favorite
A bright studio apartment features large windows with views of the ocean and city. A plush queen bed is positioned alongside a sofa bed and a dining table with chairs. Soft curtains frame the windows, while a ceiling fan adds comfort to the airy space.
Condo in Waikiki
4.93 out of 5 average rating, 179 reviews

Cozy Ocean View Retreat Steps from Waikiki Beach

Book in the heart of Waikiki on a high floor with ocean views, a TWO MINUTE walk to the main beach & shops! Paradise is calling! Enjoy a cup of coffee while taking in the sweeping partial ocean, mountain, and city views. Our private and airy studio boasts a plush queen bed, firm twin sofa bed (recommended for a guest 5'9 or under), full bath & kitchenette. High-speed internet for streaming your favorite movies or catching up on remote work life. Reserve now before we're fully booked!

Superhost
A modern kitchen space with a stove and cooking area is visible, leading into a spacious living area. Large windows overlook the Pacific Ocean, providing sweeping views. A comfortable seating area includes a gray sofa and light rug, while a small dining space is also present.
Apartment in Waikiki
4.86 out of 5 average rating, 106 reviews

Top FL-Grand Ocean View Suite-Waikiki Beach

This fully upgraded ocean view suite boasts a sophisticated and modern design with top-of-the-line finishes. Up on the 31st floor, you'll enjoy breathtaking views of the Pacific Ocean and Diamond Head from the expansive windows throughout the unit. The Pacific Monarch building is well-known for its unbeatable central location. From here, you'll be minutes away from all of Waikiki's top attractions, including world-class restaurants, high-end shopping, and pristine beaches.

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, 337 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.

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.