Diamond Head Vacation Rentals
Diamond Head vacation rentals place you just steps from one of Hawaii's most iconic natural wonders. Whether you're seeking a luxury oceanview condo or a hillside home with privacy and charm, these rentals offer easy access to Waikiki Beach, surfing, hiking, and world-class dining.
Located along Oahu's scenic Gold Coast, vacation rentals near Diamond Head Crater offer a peaceful retreat minutes from the action of Waikiki. Choose from beachfront villas, modern high-rise condos, or tropical hideaways with panoramic views of the Pacific and the famous volcanic cone.
Popular with couples, digital nomads, and families alike, these rentals provide the ideal blend of adventure and serenity. Spend your days hiking the Diamond Head trail, snorkeling at nearby beaches, or strolling to Kapiolani Park and Honolulu Zoo. Many properties also include private lanais, gourmet kitchens, air conditioning, and reserved parking.
Key Features of Diamond Head Rentals
- Walkable to Waikiki Beach and Diamond Head trail
- Oceanview lanais and sunset-facing balconies
- Upscale condos and private homes in the Gold Coast area
- Close to Honolulu Zoo, Kapiolani Park, and farmers markets
- Peaceful setting minutes from shopping, dining, and nightlife
- Ideal for couples, families, and longer stays
Not finding availability here? Browse more nearby options in Ala Moana, Honolulu, or Waikiki for additional oceanfront escapes.
Extended Stay Panoramic Ocean & Diamond Head Views
Our unique quality listing features panoramic ocean and Diamond Head views overlooking Fort DeRussey park. Great location. Furnished as high end luxury recluse. Parking, wifi, cable, etc. You'll love it! We're looking for guest who would like to stay for 4-6 weeks or...
A Gem of a Studio at The Diamond Head Beach Hotel
Legally permitted vacation rental - 2947 Kalakaua Ave HI 96815A delightful well loved studio on Honolulu's Gold Coast nestled under Diamond Head.A comfortable Queen bed and a separate sleeper sofa in case it's needed await in this beautiful Diamond Head Beach Hotel...
Modern 43rd Floor 1BD - Views of Panoramic Ocean & Diamond Head!
Perfect 1 bedroom in 43rd floor. You may view 180 degree panoramic ocean view from the living room!!As you enter, you will find the fully equipped contemporary kitchen perfectly matching the whole design of the unit.In the living room, you will find designer furniture:...
Diamond Head View at Waikiki Sunset w/ Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Garden Cottage Unit B - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Vintage Hawaiian décor -- including lovely teak furniture and vibrant pops of color --...
Panoramic Diamond Head Ocean View Spacious Home
Charming Comfortable, Affordable dwelling boasts 3 Bedrooms with 2 1/2 bathrooms and front loading high energy smart stack washer/dryer laundry facility in the 1/2 bath. Two of the bedrooms have California king size beds and 1 has a Queen size bed. Each bedroom has a...
Diamond Head Location, Spacious, Super Clean, King One Bedroom Suite Sleeps Four
Legally permitted vacation rental - 2947 Kalakaua Ave #603** For your health and safety, we utilize additional Sterilization procedures between reservations.New floors, upgrades and fully repainted May 2020My place is close to the Ocean and nestled beneath the Diamond...
Remodeled in 2022, Diamond Head 2 Bedroom Oceanfront condo
Legal Vacation Rental - 2947 Kalakaua Ave #601Gorgeous blue ocean view from your Lanai. Restful sleep in this two bedroom large suite, with full kitchen and shower/tub combo. This condo provides quiet yet you are only 5 minutes away from the night life. Superb 'postcard...
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,...
FREE Parking - Diamond Head & Ocean View Studio with Pool - Sleeps 4
Legally permitted vacation rental.1850 Ala Moana Blvd #1124This comfortable studio suite at The Palms Waikiki offers 2 queen bed to accommodate up to four guests.With a view of Diamond Head crater in the distance, ocean views to the South we are nestled just West of the...
Amazing High Floor 1bd/1ba with Diamond Head Views at the Waikiki Banyan 2901 T1
Aloha and welcome to your beautiful new home-away-from-home with enchanting views of the Koolau mountains and Ala Wai golf course.This 29th floor corner unit of the Waikiki Banyan has been completely remodeled with brand new wood laminate flooring, countertops,...
Stylish Oasis w/ Great Ocean and Diamond Head Views + Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Ocean and Diamond Head view suite w/balcony
Legally permitted rental - 134 Kapahulu Ave #408** For your health and safety, we utilize additional Sterilization procedures between reservations.Ocean and Diamond Head view suite at the Waikiki Grand - Kitchenette with electric cook top, microwave and regular size...
Stunning! Diamond Head Oceanfront Lanai Condo - Sleeps 5
Legally permitted vacation rental - 2947 Kalakaua Ave #201A Spacious Condo with incredible Ocean views from our private oversized Lanai.Fitted with a new kitchen in March 2021 along with new living room furniture and 2 new comfortable Queen beds in the bedroom- We are...
Beautiful Oceanfront Home - Fantastic Views of Waikiki and Diamond Head!
Enjoy the island lifestyle in this beautiful beach house that sits on the Pacific Ocean. Relax on the lanai and look out at the waves as the sea turtles pop their heads up for air. As you swing on the lanai with a cup of coffee, take a breath of the morning fresh air as...
Two Hawaiian cottages with Diamond Head views - walk to Waikiki
Garden Cottage A & B - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for groups who want both togetherness and privacy, this pair of vintage-inspired Hawaiian...
Ocean/Diamond head view condo at Waikiki Banyan. Free Parking! Centrally located
Welcome to your perfect island getaway at the Waikiki Banyan! This 1-bedroom, 1-bathroom condo comfortably sleeps up to 4 guests and features stunning ocean views and an iconic view of Diamond Head from your private lanai. Whether you're enjoying your morning coffee or...
Ocean & Diamond Head Views! Full Kitchen, Lanai, 1 Free Parking! Sleeps 6
Waikiki Sunset #2514 – 229 Paoakalani Ave.Popular 2-bedroom, 1-bath condo (604 sf plus 56-sf lanai, sleeps 6) positioned on the 25th floor in the preferred corner end suite stack with central A/C and spectacular views of Diamond Head, Kapiolani Park, and the Pacific...
Iconic Diamond Head! Great for Family!
Waikiki Sunset #1414 – 229 Paoakalani Ave.Enjoy a fabulous view of majestic Diamond Head from this 14th floor, two-bedroom, one-bath condo with central AC (604sf plus lanai with table and chairs). 6-person max!Just 10-minute walk to the best swimming and surfing beach...
Diamond Head Ocean Views! Parking/Wifi included
Panoramic views of Diamond Head Crater and the ocean is the WOW factor to this unit on the 31st floor in the Royal Kuhio!Newly upgraded bathroom to a “luxury 5 star spa”. Also the unit has “washer/dryer combination”.The spaceOpen floor plan featuring a "pocket...
Breathtaking Diamond Head and Sunrise Views!
Ohua #7E – 250 Ohua Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll create wonderful vacation memories in this beautiful vacation rental with breathtaking Diamond Head views! 6-person max.Small pool on property. Close to world-class...
Just Renovated!! Spectacular Ocean & Diamond head View w/ Free Parking!
High Floor 1 Bedroom with the Spectacular View!!You can feel time goes by slowly and leisurely while you enjoy your stay in this unitThis room features full kitchen, large bath, High Speed Wi-Fi, and Television.In the morning, observe Waikiki waking up and the clouds...
Amazing Diamond Head and Ocean Views, Prime Location-Free High Speed Wifi
The studio is located just steps away from the broadest and sandiest beach in Waikiki, world class shopping and dining.The unit is remodeled, fully equipped studio condo with one full bath. Comfortable Queen size bed and mattress to ensure a good night’s sleep after a...
Stunning High-Floor Unit with Spectacular Ocean, Diamond Head, and Waikiki Views
Welcome to Waikiki Landmark, where paradise meets luxury living. Come stay at this stunning high-floor views of the Ocean, Diamond Head, and Waikiki. This exquisite 2-bedroom, 2-bathroom unit with 1 parking spot embodies the essence of island living. Located at the...
Recently Updated, Diamond Head Studio w/ Gr8 Ocean Views
Legal Vacation Rental - Diamondhead Beach Hotel2947 Kalakaua Ave #1005** For your health and safety, we utilize additional Sterilization procedures between reservations.2 Double Beds, Microwave, Fridge, Coffee, Pacific Ocean and Diamond Head ViewsPeace and tranquility...
Comfortable Spacious and Modern - PLUS Just 1min to Beach with Diamond Head View
Legally permitted rental - Waikiki Grand Hotel®134 Kapahulu Ave #516⚕For your health and safety⚕ we utilize additional Sterilization procedures between reservations.❤This is actually one of my favorite suites at the Waikiki Grand Hotel®, not only for the price...
Ocean & Diamond Head Views 8th floor with Balcony
Legally permitted short term rental⛰134 Kapahulu Ave 811⛰⚕For your health and safety⚕ we utilize additional Sterilization procedures between reservations.Gorgeous Balcony Suite with Incredible Views, in a Prime location.My place is close to Waikiki Beach and...
Ocean & Diamond Head Views - Near Beach - Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Diamond Head and Ocean View Waikiki Sunset with Free Parking! (WS06)
Be Cool... This is my own Hawaii!! Monochromatic! Ocean and Diamond Head View!!This renovated 1 bedroom will provide you the perfect vacation!!As you arrive at Waikiki Sunset, you will be met with the modern monochrome design of your homey living room. Here, you can...
Romantic Waikiki Banyan 2513 with Ocean and Diamond Head Views and Free Parking!
Waikiki Banyan 2513 Dancing in the Moonlight Ocean and DH Views and Free Parking!This cheerful and calming Honeymoon Suite is located on the 25th floor facing east with awesome Ocean, Diamond Head & Coco Head Views. This is a large one bedroom corner unit that has been...
Centrally Located 2 BDRM 2 bath Condo w/City, Diamond Head & Ocean Views
Aloha and Mahalo from Waikiki! This property is a 30 day minimum rental at The Windsor. Centrally Located near the main Waikiki strip and in one of the most convenient areas of Oahu. Featuring a fully equipped kitchen ready for you to cook, and great views from your...
Amazing Ocean and Diamond Head Views
Breathtaking ocean view while also being able to see Diamon Head! This beautiful condo in Waikiki Sunset boasts the comfort of central AC while bringing you right to the beach.. With close proximity to the beach shopping and restaurants it is a perfect place for your...
37th Floor Newly furnished @ Island Colony Diamond Head & Partial Ocean View
High floor, Newly furnished Condo at Island Colony IC3711Island Colony is a few steps away from the building is a large concentration of shopping centers, such as Waikiki Shopping Plaza, BeachWalk, and the International Marketplace.There is truly no end to the stores to...
Diamond Head View! Fully Renovated! Free Parking! Close to Beach!
Waikiki Banyan #1903-T1 – 201 Ohua Ave.You'll fall in love with this contemporary one-bedroom suite (533 sf + 67-sf private lanai), fully renovated in 2024, at the repeat-guest favorite Waikiki Banyan! Enjoy the vibrant greens and blues of the gorgeous Diamond Head,...
Royal Kuhio 1606 - Spacious Studio w/ Diamond Head and City Views in Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1606, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 444 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
Diamond Head & Ocean View - Free Parking - Walk to the beach.
TA/GE-080-509-7472-011990/NUC-0827 for TMK 260250050267(formerly NUC 90/TVU-1617 )Comfortable family apartment at Waikiki.High floor. Ocean and Diamond Head View.1 block from the beach, located near restaurants and shops.Equipped kitchen.Free WiFi.Free parking for one...
Spectacular Ocean & Diamond Head View 2 Bedroom Condo w/ Free Parking! by Koko Resort Vacation Rentals
Spectacular Ocean & Diamond Head View 2 Bedroom Condo w/ Free Parking! This cozy 2 bedroom 31st floor condo with gorgeous ocean and Diamond Headviews is only 2 blocks away from the world-famous Waikiki Beach. This condocomes with a fully furnished kitchen which includes...
Royal Kuhio 1706 - Spacious Waikiki Studio w/ Stunning Diamond Head & City Views
HEART OF WAIKIKI - ROYAL KUHIO 17th floor FREE WIFI! 1 bed 1 bath sleeps 4 ※Parking is available at $30/night upon request and advanced payment is required. Please request parking via email at least three (3) business days in advance. - Located in Heart of Waikiki...
Waikiki Banyan - Diamond Head/Ocean View, Walk to Beach. Under new mgmt.
We're pleased to announce this unit is now under new management, ensuring a higher standard of cleanliness with a reputable cleaning companyWalk to Waikiki beach, zoo, aquarium, restaurants, shops and many other Waikiki attractions in this newly renovated unit with two...
High-Floor Beachfront Colony Surf Condo w/ Sunset Views, Diamond Head Gold Coast
Wake up to turquoise Kaimana Beach and fall asleep to fiery Hawaiian sunsets. Located on the 12th floor of the iconic Colony Surf, this 1-bedroom suite delivers true “live like a local” comfort with resort-level amenities.There is no air conditioning, so please...
High-Floor 1BR in Waikiki – Diamond Head View, Free Parking, Walk to Beach & Attractions
Nestled on High Floor, this One-Bedroom unit with Free Parking included (max 6’) offers Unique Moments of Rest and Fun for an Unforgettable Stay in the Island. Total of 3 Beds: 2 Full in Bedroom and 1 Queen Sofabed in Living Room, sleeps up to 4 guests. From your own...
Welcome to magnificent views of Diamond Head, Ala Moana Beach!
Located in Honolulu, this condo lets you experience it all. Fans of nature and the outdoors will love being 13 minutes by foot from Ala Moana Beach Park and 12 minutes from Magic Island. Ala Moana Center is an easy 9-minute walk away and Hawaii Convention Center is also...
Cozy historic home in Manoa Valley, view of Diamond Head, walk to UH
Private home in a quiet historic neighborhood in Manoa Valley. This hidden gem is tucked away on a quiet little road, surrounded by greenery. Above the city with picturesque view of Diamond Head and mountainside rainbows in the day and view of Waikiki City lights and...
Amazing 1 BDRM Ocean and Diamond Head View Condo w/Parking/Washer/Dryer
Aloha and Mahalo from Waikiki! This property is a 30 day minimum rental at the Chateau Waikiki and is professionally managed by Happy Vacations. Very convenient and affordable condo, with Ocean and City Views! Friday night fireworks from the Hilton Hawaiian Village....
Monthly- Chateau Waikiki 3513 2 Bedroom Ocean / Diamond Head
PANORAMIC OCEAN / Diamond Head VIEWS, 10 Minute Walk to Beach, 2 Bed Room, Furnished. No smoking condo. 2 Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 2 Month Minimum / contact Agent.Spectacular ocean, volcano, mountain and town views from...
Upgraded Luxury Diamond Head Waikiki Condo Amazing Location--FREE Parking
MINIMUM 90 DAY RENTAL: Monthly Rate Available. CLEAN and beautifully upgraded /remodeled open concept- comfortable/ quiet / breezy - 1 bdrm (King Bed, walk-in closet, w/black-out curtains)/1 bath w/Diamond Head View and 1 1/2 blocks to famous Waikiki Beach. Fully...
Diamond Head/Waikiki Surf Shack Lanai Unit
Be our guest at this sweet island getaway on a quiet cul-de-sac near the base of Diamond Head. Less than 20-minute walk (or 5-minute drive) to Waikiki Beach. Wonderful neighborhood with a great local vibe and delicious dining options on Monsarrat Avenue, all within a...
Diamond Head Hale | Steps to Sand
Listed as one of Hawaii's historic properties, enjoy some of the best that island living has to offer in this fully furnished 4-bedroom, 3-bathroom Diamond Head Hale. Natural light, refreshing ocean breezes, and hardwood floors flow through this home. 3 bedrooms and 2...
Kaimana Beach Penthouse by Gather: Luxury Ocean & Diamond Head Views
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 Kaimana Beach Penthouse by Gather,...
Penthouse Condo with Ocean & Diamond Head Views at The Windsor
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This property is new to our inventory, so reviews are on the way! Rest assured, it has been carefully...