8 Best Vrbo Vacation Rentals In Diamond Head, Hawaii - Updated 2024

vrbo oahu diamond head
Oishi
Oishi 
Updated
| 5 min read

The perfect spot for both hiking and swimming, Diamond Head is a tourist’s paradise. The 763 feet (33 metres) summit of the 300,000 years-old crater grants a spectacular 360-degree view of the Waikiki Beach and a gorgeous sight of the Pacific Ocean. Waikiki Beach nearby is one of the world’s best beaches and is responsible for welcoming and drawing in tourists in Hawaii. The beach has been a favoured destination for royals and has also been popular among the locals long before tourists started arriving. There are several means of acquiring entertainment in this region in Hawaii. Both the Diamond Head Crater and the beach are tourist spots themselves. So, find the perfect place to stay at the best price from among the Vrbo accommodations in Diamond Head, Hawaii listed below.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 04, 2024.

1. A gorgeous two-bedroom apartment on the seventh floor (from USD 428)

The seventh-floor balcony of this apartment offers incredible views of the Waikiki’s Gold Coast, Diamond Head and the Pacific Ocean. Major tourist attractions like the Kapiolani Park, Waikiki Aquarium, the Outrigger Canoe Club and the Honolulu Zoo are all close to this place. It has a beautifully designed and fully equipped kitchen and the living room is pretty and spacious. There are balconies in each of the bedrooms. A part of the Diamond Head Beach Hotel & Residences, there is a private beachfront area to relax in. Parking is available on the premises.

Stayed at this property?
Honolulu, Hawaii, United States
1.71 km (1.1 mi) from Diamond Head State Monument
condo 4 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
Old drapes/curtains in the Master bedroom
The condo was exactly like the pictures
There was plenty of closet space and the queen size bed was very comfortable
but drawers were difficult to open and close (
It was so nice to spend our down time enjoying the fabulous balcony over looking the ocean
Cleanliness:
It was very clean and tidy
The condo was nicely decorated and clean
But beds were reasonably comfy and bed linens were good
Host:
also the trade winds blowing felt great
our host was easy to work with even with a 4 hour delay to our arrival time
Great property & great location
and I would not hesitate to return for some more R and R Vicki
The information notebook inside the property was the best I have seen We will definitely be returning
Location:
Kaimana beach is just few minutes walk from property
Da Hawaiian Poke Company was our best lunch place and conveniently located by the Safeway
did not fully close Check-in process was a bit convoluted
Loved this location and access to ocean
Perfect location in between Diamond Head and Waikiki Manager Marc and Assistant Mgr David
Read more reviews
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2. A pretty beach house two blocks away from the beach (from USD 125)

This beach house is located at the base of Diamond Head Crater. The apartment, even though on the third floor, offers a wonderful view of Diamond Head, Makiki Mountains and the Waikiki skyline. The interior decor of the place is thoughtfully put together, inclusive of antique furniture, Italian porcelain-tiled floors, Berber carpeting and Roman window shades. It also has a large TV and a 10-speaker surround sound stereo. The bedroom is equally embellished with a crystal lamp, teak and bamboo dressers, a TV, DVD player and several other amenities.

Stayed at this property?
Honolulu, Hawaii, United States
1.21 km (0.8 mi) from Diamond Head State Monument
Apartment 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
the bed and couch are both so comfy and the flat screen tv's and wi-fi work great
the flat screen tvs and then i soundsystem are also a bonus with this beautiful rental
mahalo yokoi can't believe they don't charge more for this beautiful apartment
we had plenty of room with the living area being roomy and a good size bedroom
the apartment is in a quiet residential neighbourhood at the foot of diamond head
Cleanliness:
very clean and bed is soft
everything is very clean and comfortable
it is roomy clean more supplies than expected
great unit clean and great location
loved the place- clean cozy comfortable quiet (a great change from noisy waikiki)
Host:
our host was kind and very helpful
the property owner michelle was very nice responsive and helpful
Location:
great location close to everything
the location was perfect
very good close to the beach
location is great to the beach shopping and public transportation
excellent location - close to: waikiki shops restaurants hotels tourist attractions; park/beach; safeway; starbucks; walmart & costco
Read more reviews
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3. Enjoy Hawaiian artwork at this renovated suite (from USD 300)

Go swimming, snorkelling, or sunbathing along the Gold Coast while staying in this fourth-floor suite. It features a gourmet kitchen. a spa bathroom (with marble inserts), a spacious living room and pretty lighting. Basic toiletries are provided to the guests as well. There are two flat-screen TVs, a Blue Ray DVD and a home stereo system. The nice and spacious balcony with a seating arrangement provides a sparse view of the ocean and the mountains. Complimentary spa amenities, fresh fruits, organic tea, coffee and Hawaiian tropical flowers are what you’re greeted with at your arrival.

Stayed at this property?
Honolulu, Hawaii, United States
1.71 km (1.1 mi) from Diamond Head State Monument
condo 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
the apartment had all the amenities we needed including nice beach towels and full kitchen
the double sized bed is comfortable
there is plenty of space to spread out and relax in the living room/dining room area
the bathroom was great with lots of towel racks
we appreciated too having the well-appointed kitchen (even though we ended up not cooking)
Cleanliness:
it was very clean and well kept
it is clean quiet and well appointed
the condo was perfectly clean and well stocked
the bathroom is clean and the shower was very nice
the condo was as advertised very clean and modern
Host:
wonderful place and great host
donna the owner is a such a wonderful and caring host
donna was very helpful and always contacted me back with any and all of my questions and concerns
donna the owner is great and communicates very well
we found the compiled binder with the best local restaurants and activities very helpful
Location:
and i loved the location
by far the best location on the island
the location is perfectly placed for our needs
the park across the street is great beach easy to walk to - practically next door
great location walking distance from beach parks resturants and shops
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4. An two-storey house in a peaceful historic neighbourhood (from USD 500)

The house has three bedrooms and a study, which can pass off as the fourth bedroom. There is a Weber gas grill and a dining area outdoors in the beautiful backyard. The house flanks two living rooms, a dining space inside, a well-equipped kitchen and a laundry area. The white sand beach is nearby and Waikiki is also a short stroll away. Enjoy a lovely walk along the ocean to reach Waikiki and enjoy all its attractions. The house owing to its central location makes it easy for people to both find solace when required and experience the primary activities of a livelier environment.

Stayed at this property?
Honolulu, Hawaii, United States
1.79 km (1.2 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
The air conditioning upstairs was wonderful
there is plenty of room with bedrooms aircon storage and excellent shower
There is air conditioning in the bedrooms
There is off-street parking although it is tight for
Air conditioners were only in the bedrooms upstairs
Cleanliness:
The house was fully equipped very clean and comfortable
The walls are decorated with the owner's paintings of tropical scenes which adds to the atmosphere
The home is beautiful with large living areas and large bedrooms with two bathrooms and showers
Host:
so memorable Juanita MathewsLondon UK
beach equipment (body boards snorkels flippers
The home was clean and well furnished and the location was wonderful
clean and very nicely decorated Maggie was very helpful in providing useful information for us during our stay
It easily accommodated us all even when some of the other relatives came over for dinner
Location:
It's about a 5 minute walk to a nearby beach and about a 15 minute walk to Waikiki
My parents liked sitting out on the patio
The location of the house was perfect
etc About a 15 minute walk to the main downtown Waikiki area
but it was never a problem for us
Read more reviews
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5. The perfect penthouse with ocean and Diamond Head views (from USD 237)

This penthouse is on the Gold Coast and only a short walk away from the beaches, stores and restaurants of Waikiki. It offers panoramic views of the ocean, Diamond Head and Kapiolani Park. The house features Travertine floors, cherry wood cabinets, African ivory granite tops, a 40-inch HD TV, BlueRay and free WiFi among several other extravagances. Laundry facilities are available here too. The view from this place is magnificent. The kind of peace and seclusion you find here is one of a kind, but it is also close to everything you want to experience in Waikiki. Just rent a surfboard and go surfing, go swimming or sit by the beach with a glass of wine, with some music playing in the background.

Stayed at this property?
Honolulu, Hawaii, United States
1.73 km (1.1 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 2 Guests 0 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
The room itself is cozy with nice views
we had access to the park
You sleep to the sounds of the ocean and the fountain across the street
we thought it was very comfortable
Windows on both sides ot the unit make it feel like a treehouse
Host:
You can see the ocean from every angle looking outward Jan was also easily accessible when we had any questions
I had a wonderful experience
The studio was just right for me and my husband
Jan thank you for sharing your lovely home with us Until next time
The views are amazing I especially enjoyed having all the windows open and feeling the ocean breeze all night
Location:
The location is perfect and I enjoyed walking to the beach
You are far enough away from the nite life noise and close enough to stroll casually for a starbucks coffee and a lovely walk towards The Hula Grill and Dukes and you can even stroll aimlessly towa...
Not only is the location ideal--near enough to enjoy Waikiki but far enough to be quiet and romantic--but the room is beautifully maintained and stocked for a luxury experience in paradise
The room is walkable to restaurants (about a mile to a mile and a half) but we spent a lot of money on Ubers to get to sightseeing things like a luau
It was beyond perfect and loved looking out over the ocean from all windows
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6. A rental right below the Diamond Head's Le'ahi Peak State Monument (from USD 520)

The apartment belongs to the Diamond Head Estate Paradise, which is located just below the Diamond Head’s Le’ahi Peak State Monument. The rental is situated amidst a tropical forest comprising a variety of island birds. Waikiki Beach, Kapiolani Park, Ala Wai Golf Course, the Honolulu Aquarium, Waikiki Shell Amphitheater, Kapiolani Bandstand and the Honolulu Zoo are the famous attractions only a short walk away from this place. There is a gourmet kitchen and shaded balconies with an arrangement for barbecues, and the bedrooms have comfortable and beautiful furnishings.

Stayed at this property?
Honolulu, Hawaii, United States
1.37 km (0.9 mi) from Diamond Head State Monument
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

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7. A gorgeous abode (from USD 275)

Only minutes away from the Pacific Ocean, this beautiful house located on the Gold Coast is perfect for a couple. The interiors of the house are designed with utter precision. The house is so good to look at that staying in it makes for a wonderful treat. It is a one-bedroom apartment, with a spacious drawing room area. The kitchen has granite counter tops and features all the necessary amenities required to curate full meals. Visit the aquarium and the zoo, only minutes away from the place, and enjoy a nice romantic walk by the Waikiki Beach and end the day with a good dinner at one of their best restaurants. Don’t forget to visit the farmer’s market on Saturdays, to pick up some of the fresh local produce.

Stayed at this property?
Honolulu, Hawaii, United States
1.73 km (1.1 mi) from Diamond Head State Monument
condo 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
The bed in the bedroom is incredible
The free parking was appreciated
a lot of closet space a full kitchen and a beautiful shower and bathroom
There are beach chairs and towels and other amenities
The shower is to die for
Cleanliness:
Terri was awesome to connect with
The room was clean and very nice
and there was very limited cooking utensils and dishes)
This is a very well supplied apartment nicely decorated in a quiet part of the city
The unit is very clean and Terri and Calvin are very accommodating Excellent views from the patio area at sunset
Host:
etc to store food
so that helped a lot
We appreciated the opportunity to meet the owner who was very welcoming
Terri and Cal were incredibly welcoming and responsive
Terrific condo for our family of three
Location:
This condo is located in a quieter part of Waikiki which my husband and I preferred within a short walking distance of Sans Souci Beach and the Aquarium A few more blocks gets you into the middle...
lots of room- great place to stay
It was just outside of the busy city but close enough to walk to it also
The building location is exactly what we were looking for: just far enough away from the bustle of Waikiki to be quiet and peaceful but close enough to walk to the fun
This is a great property in a very good location - walking distance to great beaches and Waikiki but far enough away from the hustle and bustle that you can sleep peacefully
Read more reviews
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8. A designer apartment

The 20-storey Colony Surf on the Gold Coast is close to the base of Diamond Head Volcano and located opposite to Queen Kapiolani Park. While the neighbourhood is quiet, lively Waikiki is only a few steps away. The apartment on the eighth floor does not fall short of affording a splendid view of the ocean and the volcano. The bedroom has mahogany furnishings, including an armoire with drawers. There is a separate workspace, a living area with a stereo, a DVD player, a TV and a designer kitchen. Colony Surf also includes a French restaurant, a private sandy beach and two boutique hotels.

Stayed at this property?

1.79 km (1.2 mi) from Diamond Head State Monument
32 reviews   Wifi Available
Apartment 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2
Minimum Nights: 30
Refund Policy :

Top guest reviews
Amenities & Room:
has everything I need with a beautiful view and is right on the beach
The view is well worth the hike
Breezes blowing thru the apartment most of the time
Awaking each morning to beautiful views; seated one way to see the ocean or turning toward the Diamond Head View
I wanted to stay in a part of Waikiki that felt like the old Waikiki I grew up with
Cleanliness:
The views of the ocean and Diamond Head are to die for Roger was great to deal with and the front desk staff in the building were so friendly and helpful
Laundry facilities were inexpensive and easy
Host:
Perfect location beautiful and comfortable with Roger as a gracious host
Wonderfully located extra jumbo studio
Overall a very healing time for me
The dishwasher was a must for any extended vacation
His attentiveness to us was appreciated
Location:
and we took THE BUS at other times
The food and location are FABULOUS
These are all within a short walk from
We cooked some meals and took easy walks to restaurants close by The best part about this condo is the location
its beauty and its people
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
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E komo mai Hawaii

Go on hiking trips or swim under the sun, choose what you may. However, while it is very important to enjoy to the fullest the destination that you’re touring, it is equally important to find the perfect place to stay during your holiday. Make every moment of your stay count and check out these amazing Vrbo accommodations.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Oishi holds a fondness for poetry and music. Her passion for traveling is evident in the numerous articles she has authored for online magazines, covering topics such as women's empowerment,...Read more

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