Diamond Head Vacation Rentals – Scenic Escapes Near the Crater & Coastline
Diamond Head vacation rentals offer a peaceful home base near one of Oahu's most iconic landmarks. Enjoy upscale homes and ocean-view condos within walking distance of hiking trails, Waikiki Beach, and Honolulu attractions like Kapiolani Park and Diamond Head Crater.
Nestled between the slopes of the crater and the shoreline, Diamond Head is one of Oahu's most sought-after neighborhoods for a relaxing stay. With a unique mix of tropical charm and elegant residential style, rentals here offer tranquility just minutes from the action of Waikiki.
About Diamond Head Vacation Rentals
Staying near Diamond Head State Monument means you'll wake up just steps from Hawaii's most famous hiking trail. The area is known for its lush landscaping, mid-century homes, and low-rise condos-many with lanais that look out over the Pacific or the iconic volcanic ridge.
Vacation homes here tend to be quiet, stylish, and spacious-ideal for long stays, couples, families, or digital nomads. You'll have quick access to beaches, outdoor activities, and the refined dining scene around Monsarrat Avenue, all while avoiding the hustle of central Waikiki.
Key Features of Diamond Head Rentals
- Walking distance to Diamond Head Crater and hiking trails
- Quiet residential feel with upscale homes and condos
- Ocean views, tropical gardens, and private lanais in many units
- Full kitchens, A/C, fast Wi-Fi, and smart TVs in most rentals
- Access to nearby beaches, parks, and boutique cafés
- Ideal for families, long-term travelers, and active couples
Nearby Attractions & Experiences
Outdoor Adventures
- Diamond Head State Monument – Iconic sunrise hike with panoramic views
- Kapiolani Park – Jogging paths, tennis courts, and a shady escape near the beach
- Queen's Surf Beach – A quieter section of Waikiki Beach great for swimming
Dining & Local Flavor
- Try brunch at local favorites along Monsarrat Avenue
- Walk to beachfront dining at Waikiki's Gold Coast
- Access a wide range of fine dining and local grinds in nearby Honolulu
Why Stay in the Diamond Head Area?
- Less crowded than Waikiki, but still very close
- Stunning natural beauty and peaceful surroundings
- Great for morning hikes, beach days, and working remotely
- Close to Honolulu Zoo, Waikiki Aquarium, and iconic surf breaks
Whether you're an early riser headed for a sunrise hike, a couple looking for a peaceful retreat, or a family wanting to explore both beach and mountain, Diamond Head vacation rentals offer location, space, and serenity. Scroll down to explore available listings and book your stay near this iconic Oahu destination.