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.
Kahala Seaside: Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa!
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kahala Seaside, a spacious...
Honolulu Condo for Rent Steps to Kahala Beach
Ask owner about available dates/rates. The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful and spacious studio with 1...
Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise
Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to...
Crutchfield Estate - Charming Historical Home in Honolulu
This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new refrigerator and dishwasher. Morning...
Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood
Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis. Please inquire about...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Pili Pono by GatherExperience the...
Kahala Oceanside – Coastal Sanctuary with Panoramic Views
Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the endless attractions of...
Island Adventure: Minivan Rental, Contact Us
Mahalo is the Hawaiian word for thanks, and a feeling of profound gratitude is what inspired this beautiful home. From the moment you arrive at Hale Mahalo, you’ll understand why. This lovely 3-bedroom, 3-bathroom home is a tribute to the stunning beauty of its...
Fabulous, Renovated Large 3BR Condo on Kahala Beach
Welcome to our newly renovated slice of paradise at Kahala Beach! Nestled in one of the most sought-after neighborhoods in Honolulu, this spacious 3-bedroom, 2-bathroom property promises a luxurious escape for your Hawaiian getaway.Step inside and be greeted by a...
Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach
Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...
Kahala Breeze: Modern Tropical Home with Pool & Private Yard
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Experience the laidback luxury and authentic...
Ho'okipa Villa: Historic Home + Guest Cottage in Kahala
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Kahala Luxury Living Welcome to Ho'okipa...
Cottage with Private Salt Water Pool
30 night minimum This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu coast. Also, in very short...
Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kahala Cottage by Gather, your...
Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath
Minimum rental period of 30 days, Rental included Electric, Water, Cable WiFi Clean the yard twice a month and clean the swimming pool every Tuesday and FridayUpscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.Spacious beachfront estate is situated on lush tropical grounds,...
Hale Mahie by Gather: Spanish Colonial Historic Home w/ Ocean Views & AC
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.A 10-minute walk from Waikiki, discover your...
Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Let your dream tropical vacation begin when...
BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!
~Breezy Spacious and Welcoming Vacation Home~This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the lanai. Situated only 2 miles...
Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!
Waikiki Sunset #2503 – 229 Paoakalani Ave.NEW TO OUR INVENTORY! Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, free Wi-Fi, and free on-site...
Spacious Family Home With Gorgeous Sunset Views of Diamond Head
This is a truly a local style experience property and the area of Kahala is full of the best of the best of locations on the Island of Oahu with everything close by: City Life , Awesome Beaches , Great Dinning , Tropical Hiking Trails & Views Galore , Look at the Famous...
KAHALA BEACH APARTMENT
FORGET YOUR WORRIES IN THIS SPACIOUS AND SERENE SPACE. THIS MODERN RESIDENCE IS NEWLY RENOVATED AND EXTREMELY CLEAN. LOCATED ON THE BEAUTIFUL KAHALA BEACH. UNIT OFFERS PRIVATE OUTDOOR PATIO WITH SEATING AND DINING TABLE TO HELP YOU ENJOY THE TROPICAL BEAUTY OF THE...
Right on the beach near Diamond Head and 4 miles from Waikiki!
On the beach, in a coveted luxury resort location are the Kahala Beach condos, adjacent to the Kahala Hotel, the only 5-star Hawaiian destination. Secure, with 24/7 guards, keyed building access, and a private underground parking garage. Sited on an idyllic cove beach,...
Kahala Beachfront Unique Bohemian Home
($99- Clean Fee special for Spring bookings, please inquiry. Car/ Suv Available at discounted rate- pls inquire)A relaxing escape in this abode situated in the coveted Kahala, tucked away for your enjoyment . ENTIRE High end condo-home for rent (2bedroom 2bath) with a...
Breezy Ocean View Waikiki Condo with Free Parking!
The pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation project.Waikiki Banyan Ocean View Corner Condo comes with a fully equipped kitchen, which includes a...
Kahala Beach #446 Vacation Rental
This highly desirable top-floor unit overlooks the lovely koi pond and provides the best views of the sky and stars. The lanai is oriented to the afternoon sun and sunset. Importantly, its top floor position makes it one of the most quiet apartments at Kahala Beach....
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Luxury, Privacy, and Grand-Scale Elegance at...
Kahala Zen by Gather: Spacious 5BR Modern Oasis w/ Studio & Lush Garden
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kahala ZenNestled in the...
Kahala Beachside Villa: Lux Condo w/ Pool, Balcony Views & Beach Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Escape to paradise at Kahala Beachfront Villa...
BEACHFRONT - 2bdrm 2 bath, fine art, contemporary design in luxury building.
Next to world-class Kahala Resort, 24 hr security on Kahala Beach. Condo offers 5G internet, central AC, one covered parking, washer/dryer, linens, full open kitchen, 3 flatscreen TVs, DVD, two bedrooms, two full baths. Access Kahala Resort spa, restaurants, activities,...
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Boasting an extraordinary beachfront location,...
Experience Honolulu, 3BR Home w/ Modern Comfort & Ocean Views
Wake up to stunning Diamond Head views from your private deckPERFECT FOR: Families | Groups | Remote workers | Pet owners | View lovers | Adventure seekersPrime Location:- Diamond Head Beach (2.2 mi, 7 min drive)- Diamond Head hiking trail (5-8 mins drive)- Waikiki...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Find peace and tranquility in your very own...
Kahala Resort Style Home - Aug/Sept 2022
Fabulous Kahala home close to Waialae Country Club, Kahala Beaches, Shopping, and Dining. 5 minutes from Waikiki and downtown! Great home offers privacy that opens up to the huge lanai with pool, spa, and cabana. True indoor/outdoor Hawaiiana living. 2 car garage with...
Relaxing tropical retreat near Diamond Head. Unwind and rejuvenate your senses.
Experience a calming Oasis at the Kahala Beach Apartments. This peaceful retreat is a fully furnished 2 bedroom, 2 bath dwelling located on the 1st floor and has 1 parking stall included. Cool off comfortably with fully integrated air conditioning throughout the space...
One of a Kind Luxury
FEATURED IN ARCHITECTURAL DIGEST MAGAZINE! Are you ready to graduate from the Presidential Suite? Are you looking for the most relaxing vacation accommodation?*Specials not available during Peak Season*This OCEANFRONT CROWN JEWEL – A MODERN DIAMOND HEAD HOME –...
15% Off Summer Special! Luxury Oceanfront Estate: Banyan House 4BD
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Banyan House is Oahu’s most luxurious...
Pet Friendly Guesthouse + Parking
LOCATIONThis is location is absolutely amazing! It's very walkable and safe in the morning, and evening. Walk to Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking trail, Safeway grocery store, restaurants, Starbucks, Jamba Juice, Honolulu Zoo,...
Long term rental near beach in Kahala with Pool
Beautiful house located two blocks from the beach with pool.Five bedrooms, Five baths, fully furnished with internet, cable and utilities included.30 day minimum rental, no exceptions.$46,800/month
Pet Friendly Private Room In Shared Guesthouse
Private Room Rental in Shared GuestHouse Very Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Close to...
Kahala Oasis: 6BR Retreat with Pool, Spa & Near Beach
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Kahala Oasis by Gather, an...
Pet Friendly Private Room In Shared Guesthouse
Private Room Rental in Shared GuestHouseVery Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Close to...
Kahala Lani: Balinese-Inspired Home with Private Pool
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ideal for multi-generational families and golf...
Quiet Town Studio
Quiet town studio, very close to Waikiki, but far enough to get a good night's sleep.We offer a separate, private bedroom and bath, with it's own kitchenette, washer/dryer, front and side sitting areas. The unit has it's own parking in front, with it's own private...