
Diamond Head vacation rentals
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Top-rated vacation rentals in Diamond Head
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Diamond Head houses

SS75 Waikiki 2450 Koa Ave Honolulu
I have stayed in this property once before and loved it then too. However this time - I had to make a last minute booking as other air bnb accom fell through on the day and was stuck. The team were incredible, so responsive, had me sorted and in within 2 hours of first reaching out. Do not spend your money staying at old run down hotels on the beach, the view from the balcony alone here is worth it, music playing at the cafe downstairs, palm trees swaying against the beach all visible from the balcony and from the bed. Has everything you need - drip coffee for the morning, can fit ice in the freezer for some lazy sunset balcony drinks, comfortable bed (I always travel with my own pillow so can’t comment on the pillows), air con worked beautifully. Location cannot be beaten one block from pretty much everything. Do yourself a favour, don’t read any more reviews, book this place and happy happy Hawaiian holidays.

Waikiki Gem, Stunning Ocean View, Parking Included
Charlie’s place is really special — corner unit with an incredible view. It feels like you’re staying in a fancy hotel almost. It was also very clean and well taken care of, an easy to use keurig and it’s so lovely to sit out on the patio in the morning. Charlie was also very communicative and responsive (though we ran into no issues!). Highly recommend!

Manoa Cottage with Diamond Head Lanai View
We had a great stay in this Manoa Valley home. The house was spacious, airy, and perfect for our group of four. Two bedrooms had working ACs; the one in the main living area didn’t, but opening windows/doors or using bedroom ACs worked well. Two bathrooms were a big plus! Shampoo, conditioner, and body wash were provided—very convenient. The washer and dryer in the unit were amazing, and having beach toys to borrow was a fun bonus. Parking was easy and convenient, right next to the house. Hosts Eric and Miranda were friendly and quick to respond. The large couch in the living room isn’t a sleeper sofa but was fine to sleep on, with extra linens available. The only downside was the floor cleanliness—our feet got dirty fast despite the no-shoes rule. A better clean before arrival would make a big difference. Otherwise, a really comfortable, well-equipped place—we’d happily return!

Spacious Quiet Corner Studio - Minutes to Beach
We love this super clean, quiet, safe corner unit. The view is unique: from this apartment, we can see the ocean, the Ala Wai canal, the Fort DeRussy beach park. This location is super convenient, bus route 8 and 20 are enough to take us to any popular places on Waikiki, and the bus stop is just right across the street from the hotel. Communication with our host Albert is prompt and very informative. Definitely we want to stay here again! Thank you Albert!

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai
We had a great stay in Lanikai! Very walkable. Our toddler was very happy on the memory foam pull out couch. I could see it harder with older kids or another couple as the bathoom is attached to the main bedroom. Like other reviewers, we did notice mosquitos after heavy rain, but otherwise it was not an issue. The pool was much bigger than I was expecting and had a nice shallow/deep end split. We would stay again!

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha
Hilton Village is easy. Has everything you could need or want so you don’t spend time driving all over in Honolulu traffic! We wanted to arrive and park it! This place allowed us to do just that!!

Charming Cottage Home near Waikiki
I lived here temporarily for about 7 months and really enjoyed the life outside of Waikiki, while also being very close to everything. Kapahulu is wonderful and Kaimuki is also one of my favorite spots on O’ahu. The house had everything I needed to live a “normal” life, IE laundry, kitchen supplies, amenities, etc.
Diamond Head beach vacation rentals

New Reno! Direct Oceanfront @ Waikiki Beach Tower
This place was gorgeous, Shawn was very responsive, answered with in 30 minutes. He was accommodating, when I told him I had a 2 year old traveling with us he provided a pack and play and a high chair. We didn't do any cooking there however if we wanted everything was there. The location is PERFECT for the beach.The view was stunning. The porch furniture was comfortable for hanging out and watching the sunset I would recommend this place. and next time we are here I would rent it again. Thank you Shawn!

Waikiki Shore - Beachfront
Place was great especially if you are wanting to stay in Waikiki area. Easy to get inside. The place was clean and had a washer/dryer which is nice. There were beach chairs available (we didn’t use them) If you have a car or rent one, parking is extremely expensive around the area. There is limited parking at unit, which was communicated as “first come first serve” but we found garage was under construction and had been since October and all parking was taken by residents so nothing was available. The water was shut off on our last day from 9-12 which wasn’t communicated with us prior to arriving. Overall, great place to stay but communication about amenities that were not available at time of booking or time of stay would have been appreciated.

0.1 mile to Beach 2B+Den/2B/6 Beds/Parking /condo
Great location, great space (especially for what you normally find in Waikiki), great for families, plenty of amenities provided. Kelly was super responsive. Would definitely recommend.

Seabreeze Studio (Legal Rental)
Great condo, great location. I really enjoyed my stay and even extended another day. Will look to book again my next visit.

Beautiful Waikiki Apartment Free Parking*
Very clean place! As you enter the room its smell good and clean, everything looks good and nice The host are very nice and responsive

Escape to the Beach in 2 blocks
The location of this place is perfect walking distance to the beach and is literally in the heart of Waikiki! It was clear when we checked in that this place is newly remodeled. The building itself resembles Waikiki of the 90s and 2000s, but the unit is so modern! we had no issues with check in or parking. In fact, the parking is A ++++, considering that parking is $48/night if it isn't included in the rate. Definitely an added plus since parking rates in Waikiki are ridiculous! This place had all the essentials equipped with kitchen needs, extra beach towels, beach chairs, wagon and beach umbrellas. Additionally, the communication was clear and smooth! They really made it a point for us to communicate without long wait times. Lastly, the AC was strong and they provided x2 extra room fans for added comfort! Thank you Avery and Ericka! We appreciate your hospitality and will stay here again when available 💯! Mahalo 😎🤙🏽

Ocean View w/ 2 private balconies; Steps to Beach
Our family loved ryan’s place! We were apprehensive about staying in the city but his place with the view made our stay better than expected. (I could enjoy my coffee with all the sounds of the birds) The added bonus of the many beach supplies made our trip with kids so much easier! Would recommend and stay again! 10/10

Ocean Front Spectacular Condo
The building (interior and exterior) are a little dated, and could use a refresh. BUT the location is amazing and the view is stunning. We arrived on a there was an annual parade - we had no idea, but there was so much traffic and road closures making it a little hectic getting to the building - but I managed to run out to speak with one of the attendants, and he came and helped us through the traffic to park. From then on, it everything was a breeze. Check in was easy, car valet, they brought up all of our luggage. We got to see the fireworks that evening that was part of the parade celebration from our balcony. The private walkway to the beach was amazing from the hotel and we felt comfortable letting our kids go back and forth on their own. Eating breakfast on the balcony with the amazing views was one of our favourite things. The location is amazing to be able to just walk to the beach in a minute or two, and anything you need is walkable.
Diamond Head beach houses

Ko Olina: Book Now! Car Available!
Our family of 8 absolutely loved Courtney's rental. I don't think it could have been in a better location. It is with in walking distance of all the lagoons, local shops, golfing and it's a quick drive to grocery stores. The house was very clean, beds were comfortable, instructions were clear and the check in/out process was a breeze. Our only cons were there were only 2 beach towels, no spices and the trash under the sink was way too small for the 8 of us. We are seasoned Air bnbers so we did pack a few of things we knew we would need like laundry pods, paper towels and a few smaller items but coming from the East Coast we were only checking 1 bag and didn't bring any spices, beach towels or dish & dishwasher soap. Island Country Market (SAVE YOUR RECEIPTS and get those free items!), Safeway, Target and Walmart are really just a short drive to grab what was needed so it wasn't a big deal but just be prepared to need these items. We absolutely can not wait to go back. Aloha.

Paradise Getaway Only 2-Min Drive From The Beach!
This place was perfect for our quick stay for a funeral that was at the bay 4 minutes away. The house was well equipped, comfortable and clean. The back porch was a great place to relax after a long day at the beach. The AC was a refreshing change after a hot day. Oh and the beds were super comfortable. We would highly recommend.

One of a kind Beach front 2brm ocean and mnt views
The high rating, general feel of the pics, and reviews of this listing are SPOT ON. What a lovely cottage-y home base for those wanting a safe, private, beautiful, off-the-beaten-on-the-authentic-North-Shore-path vibe. The beach and view of the Pacific Ocean are world-class. 10-minute, beautiful, quiet drive to the charming beaches, shopping, and dining centers dotting the oceanfront highway heading east. Lots of active things to do in the area. Decor and kitchen are high-end. Hosts quick to respond and hospitable. North Shore waters are mostly not for families with small children who want to swim and snorkel, and this spot is no different. Our only wish: upgrade the mattresses. It’s like Goldilocks, but with only two we never got to the “just right” part. ☺️ Whomever snags this reservation, think you’ll be blown away!

Kailua Beach Park - 2 BR Cottage
Lovely spot right across from the beach park. Easy walk to stores, restaurants and kayak rentals. So much more peaceful than Waikiki, wish we would have spent the whole vacation here, instead of the nights in Honolulu.

Relax Hawaiian Style
This place was terrific for us. It is situated in a lovely neighborhood that is quiet. The house is immaculate and spacious with up-to-date bathrooms. Easy in and out; parking on site and easy; close to shopping and places to shop/ eat. Access to highways to get back to Honolulu or to outings on the North Shore or wherever. Great place!

"HALE HONU" North Shore Beach House
This is the second time staying here. We love staying at this house. It is close to all of the things that we like to do on the east and north shores. Right on the beach with a shed full of beach equipment and a kayak to use as well. Walking distance to food trucks to the north and a food truck, market, and coffee shop to the south. Just five miles south of the Polynesian Cultural Center. Can’t wait to get back to the island.

Modern Family Beach Villa near shops and dining
This is a fantastic townhouse for a family to stay! It is extremely close to the lagoons which we drove daily 2 mins away. We found it a little far to walk. We forgot our stroller at home and were so grateful when we arrived they had one! They have tons of beach items for the kids to use and chairs. The beds were super comfortable! The pool was fantastic to use when making dinner on the bbq. It was a great stay and would love to stay again!

Serenity Beachfront Cottage- NUC No 90/TVU-0326
Could not ask for a better location. Having the gorgeous beach literally in the backyard is just amazing. The accommodations themselves were clean, comfortable and accurately described, could use some updating, however we would 100% stay here again for the location. Loved our stay and would recommend.
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