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.
Fabulous Ocean & Diamond Head View with 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...
The Windsor 3802 Luxury 2 Br/2 Ba Ocean View / Diamond head / City lights
STUNNING DIAMOND HEAD VIEWS! 10 minutes walk to WAIKIKI BEACH. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.WINDSOR BUILDING HAS A BEAUTIFUL LOBBY, GYM, POOL, BBQ AREAS, PUTTING GREEN AND THE AMAZING SKY TERRANCE...
Diamond Head Penthouse 2bed/2bath Kitchen & Parking in heart of Waikiki.
Minimum 30 day rental. Light and fresh beach Penthouse condo in the heart of Waikiki. Enjoy Diamond Head and ocean views from the large breezy lanai. Walk 3 min to shopping or 5 min to the boards and beach essentials provided! Relax in a stylish living room with WiFi,...
Gorgeous Ocean & Diamond Head Views! Waikiki, FREE Parking!!
One of a kind nearly 3000 SF (280 SQ/M) high floor custom condo with one of the best views in Waikiki. Located a mere 5 minute walk to beach and across from the world famous Hilton Hawaiian Village, this truly unique and newly remodeled unit offers unparalleled luxury...
Waikiki Ocean & Diamond Head View Corner Unit 35th floor by Convention Center
This corner unit studio has 180 Degree views of the ocean, Diamond Head, Ala Wai Canal, sunrise and Manoa valley and mountain. Studio has full kitchen, free wifi, wall mount TV, and AC. Wonderful panoramic views of Waikiki.Building amenities include: pool, BBQ, hot tub,...
Ocean & Diamond Head Exclusive Panoramic PH Condo w/Parking & Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Waikiki Landmark high rise is located at 1888 Kalakaua Ave. on the main strip of Waikiki. Situated in...
Ocean & Diamond Head View Condo at Waikiki+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...
Executive Gold Coast Oceanfront Suite: Diamond Head Views, Amazing Seaside Pool
Prices start at $7,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.This exquisitely decorated two bedroom Coral Strand suite provides nearly 360 degree panoramic views along the Gold Coast beyond Waikiki Beach and...
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
**Looking for other accommodations, please view my other unit located in the same building #2824127**This unit is located on a high floor of the Waikiki Sunset with sweeping Diamondhead, ocean, coastline, and park views, this condo offers 2 bedroom (one queen bed and...
Stunning High Floor Waikiki Landmark with Mountain & Diamond Head Views!
The Landmark is Waikiki's premier condominium. The Waikiki Landmark is close to the convention center and the famous Hilton Hawaiian Village. The timeless elegance of the architecture comprises a pair of triangular towers; the Makai Tower (ocean) and Mauka Tower...
Sky Ala Moana 43rd fl PENTHOUSE Ocean & Diamond head view 1 Parking
-Luxurious Penthouse Retreat in the Heart of HonoluluIndulge in the ultimate urban oasis with our luxurious 43rd-floor penthouse condo, perfectly situated in the vibrant Ala Moana Center area between Waikiki and Kaka'ako. This prime location offers unparalleled...
Iconic Diamond Head and Ocean View in Waikiki!
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...
Spectacular Diamond Head and Ocean View! Best location in Waikiki!
You'll love our 2 bedroom 1 bath unit on a high floor with the best views in Waikiki.Located a short 5 min walk to the beach and across from the world famous Hilton Hawaiian Village.Whether seated in the living room or relaxing in bed you'll be treated to a breathtaking...
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...
Waikiki Sunset 2BR - DIRECT Diamond Head View!
The best Diamond Head view in all of Waikiki is yours to behold from this immaculate, beautifully furnished and well-appointed condominium. This is for you, the guest who appreciates quality and value.A spectacular, direct Diamond Head view, Hawaii's most famous...
Diamond Head Surf House: Gold Coast Oceanfront Home w/AC & Gorgeous 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.Completely immerse yourself into the island...
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...
Top Remodel of a gorgeous Diamond Head Oceanfront Lanai Condo - Sleeps 4
Legally permitted vacation rental - 2947 Kalakaua Ave 968115Stunning Gold Coast Diamond Head Condo fully remodeled over a two year period.Perfectly situated on Hawaii's Gold Coast, this beautiful home has been treated to nothing but the best with care and attention to...
@ Marbella Lane -Coastal retreat near Diamond Head
Summary:Enjoy this tastefully decorated studio with lots of natural light and cool ocean breezes. This unit has a private lanai, great for enjoying your morning coffee or afternoon tea, and has a great view of Diamond Head, Kapiolani Park and across-the-street water...
Beautiful Ocean and Diamond Head Views 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...
Spectacular Diamond Head and Ocean Views! Free Valet Parking, Wi-Fi, Pool!
Waikiki Beach Tower #3602 – 2470 Kalakaua Ave.This spacious, centrally air-conditioned two-bedroom, two-bath condo (1025 square feet plus large lanai with table and chairs) has one of the most breathtaking panoramic ocean views in Waikiki, plus an unobstructed Diamond...
Fabulous Diamond Head and Ocean views from this two-bedroom penthouse suite!
Waikiki Sunset #PH3807 – 229 Paoakalani Ave. (7-Night Minimum)This beautiful 38th floor penthouse suite boasts dramatic unobstructed ocean and Diamond Head views! The spacious 1308 square feet of modern design is cooled by energy-efficient central air conditioning and...
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...
Newly Renovated Sweeping Ocean and Diamond Head View Waikiki Condo
Sweeping view of Ocean and Diamond Head from beautiful 1 bedroom sparkling just renovated condo unit in the Waikiki Sunset Hotel! The location is perfectly located just 2 short blocks to the main area of Waikiki beach, International Marketplace, the best shopping and...
Great for Families! Partial Ocean/Canal/Diamond Head Views! Pool, Wi-Fi, Prkg
Fairway Villa #2217 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Your Home Away from Home! Enjoy this recently remodeled contemporary two-bedroom, two-bath condo (723 sqft plus 151-sqft lanai) with great views! Sleeps up to...
Ocean & Diamond Head Vu; Full Kitchen; Free Wifi; 2 min. walk to the beach
Legally permitted rental - 2450 Koa Ave #92Located in the heart of Waikiki steps from the beach, at The Seashore. On the 9th floor of a 10 floor building, near the Hyatt Regency and the Duke Kahanamoku statue. This beautifully and comfortably furnished ocean and Diamond...
Amazing views of Diamond Head, Waikiki Beach, and the Pacific Ocean!
UNBELIEVABLE VIEWS!: This 2 BR condo is on the 35th floor of the Waikiki Sunset. It offers unmatched views of Diamond Head and Waikiki Beach. No expense was spared in this condo's remodel. Bold granite highlights the custom cabinetry and stainless appliances. Designer...
Base of Diamond Head, Full Ocean View, 8th Floor, Private, 6 month special
Book 'em, Danno30 Night minimum booking is required. Available Oct 1-Nov 30, 2025 and June 1-Nov 30 2026.Experience TRUE ALOHA in this condo that was home to James MacArthur, the original Danno of Hawaii Five-0, and is still owned by the MacArthur family. This premiere...
Hale Makai at Diamond Head – Oceanfront Estate
We want to inform our valued guests that there is ongoing construction next door to Hale Makai at Diamond Head. This construction is expected to last into 2026. We apologize for any inconvenience and appreciate your understanding in this matter.This Diamond Head...
OCEANFRONT PROPERTY DIAMOND HEAD BEACH HOTEL unit 704
Newly remodeled studio unit at the Diamond Head Beach Hotel and Condominiums located at the Gold Coast area. Very friendly building located on the ocean with outdoor space for watching sunset and sunbathing. Laundry facilities available downstairs. Parking in the...
LUCKY YOU! Breathtaking Ocean and Diamond Head Views! Steps to Beach!
Waikiki Beach Tower #2302 – 2470 Kalakaua Ave.This spacious, centrally air-conditioned two-bedroom, two-bath condo (1025 square feet plus large lanai) has a breathtaking unobstructed panoramic ocean view! Photos do NOT do this beautiful vacation rental justice! Sleeps...
Diamond Head Views! Freshly renovated! A/C, Parking and Wi-Fi Included!
Waikiki Banyan #2603-T1 – 201 Ohua Ave.Fresh and modern, you'll love the feel of this contemporary one-bedroom air-conditioned suite (533 sq.ft. plus lanai with table and chairs) with NEW furnishings and window coverings throughout at Waikiki Banyan! 4-person max.The...
20th Floor, Quiet End of Waikiki, Beachfront with Diamond Head View!
Colony Surf #PH6 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)NEW TO OUR INVENTORY! You'll fall in love with the amazing Diamond Head and ocean views from this 540 sqft 20th floor...
Diamond Head View Rare Condo at the Waikiki Banyan by the Beach with Parking
Book with confidence! This property is professionally managed by Ali'i Beach Rentals.8/31/22: BUILDING: The pool and hot tubs are tentatively scheduled to be closed for repairs, roughly April–August 2023. Timeframe subject to change without notice.ENHANCED PROTOCOLS :...
Stunning Ocean and Diamond Head View Luxury Condo
This is a beautifully appointed 2 bedroom 2 bath condo with approximately 1170 square feet of living space and 1 parking stall on the convenient lobby level. This unit is on the 41st floor (one floor below the penthouse) of one of Waikiki's best buildings and has...
GORGEOUS Ocean and Diamond Head Views! Close to beach! A/C, Wi-Fi, Parking!
Waikiki Sunset #2910 – 229 Paoakalani Ave.NEW TO OUR INVENTORY! Enjoy BREATHTAKING colorful blues of the Pacific Ocean and the lush greenery of Diamond Head and Kapiolani Park from this 29th floor, 1-bedroom condo (534 sf interior plus 67 sf lanai) with central...
Modern 2BR w/Diamond Head view, beach, FREE parking, king bed, pool, gym,& more!
Two bedroom condo with beautiful Diamond Head view in the heart of Waikiki, with full kitchen, living room, and balcony(lanai). Bedroom one features king bed, and small desk/workspace. Bedroom two features two twin beds. Sofa pulls out into a bed in the living room....
Unobstructed Diamond Head and Ocean Views!
Waikiki Banyan #3511-T1 – 201 Ohua Ave.Unobstructed panoramic views of Diamond Head, the Pacific Ocean, and the Gold Coast from this 35th floor unit! Modern and contemporary, this air-conditioned condo has tasteful Hawaiian touches, 533 sq.ft. plus lanai with table...
Pacific Monarch Top Floor Condo with Ocean, Diamond Head and Mountain Views!
Step into your own slice of paradise in this beautifully appointed 23rd-floor retreat at Pacific Monarch. Designed for those who crave both luxury and the relaxed spirit of island living, this one-bedroom escape offers a serene atmosphere with stunning views of...
Amazing 2 Bdrm Penthouse with Sea, Diamond Head and Ala Wai Views with Parking.
This magnificent 2 bedroom penthouse apartment has sweeping ocean and Diamond Head views that will enchant you. From the garden feature at the apartment entrance to the granite bench tops, top quality kitchen appliances, leather lounge suite and stone work in the...
Gorgeous Diamond Head Penthouse Studio Stunning views, Private Balcony.
Legally permitted vacation rental - 2947 Kalakaua Ave, Penthouse 5Stunning style with incredible Ocean & Diamond Head views.The care and attention to detail our owners put in, bringing their pride and joy on Hawaii's Gold Coast to fruition shows in every corner of this...
A 'Spa feel' at the Diamond Head Beach Hotel
Legally permitted vacation rentalDiamond Head Beach Hotel🕉2947 Kalakaua Ave 303⚕⚕For your health and safety⚕⚕We utilize additional Sterilization procedures between reservations.Whether for business or pleasure the delightful attention to detail...
Charming Studio Apartment with WiFi, AC in beautiful Diamond Head Beach Park!
Enjoy a peaceful stay at this wonderful studio apartment on the Gold Coast. The space features a queen bed and open floor plan. The bathroom includes bath and shower combo. In the additional living space, there's a comfy sofa bed for extra guests. Fall in love with this...
14th Floor Penthouse On Hawaii's Gold Coast At The Diamond Head Beach Hotel
Legally permitted vacation rental❤2947 Kalakaua Ave 1401⚕⚕For your health and safety⚕⚕We utilize additional Sterilization procedures between reservations.⬆Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head...
2Bed/2Bath Penthouse Ocean/Diamond Head views, near Convention Center
You'll be sitting on top of the world at this spacious 2-bedroom, 2-bath Penthouse with an open living room and fully-equipped kitchen.The jaw-dropping 270-degree view includes Diamond Head, a sweeping ocean view, the Ala Wai Canal, the Ala Wai golf course, Ft DeRussy...
Just Renovated!! Spectacular Ocean & Diamond head View w/ Free Parking!
Recently Renovated! (?)
Casa de Makalei – Diamond Head Vacation Home
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.Set alongside Oahu's Iconic Diamond Head this...
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Aloha to paradise, this studio is cozy, Charming, Comfortable and locate on a high floor with a panoramic ocean and diamond head view. We are located across the street from Fort Derussy Park and Hilton Hawaiian Village Resort. You are only a short walk to the beach, the...
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...
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...