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House holiday rentals in Diamond Head

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Popular amenities for Diamond Head house rentals

House rentals with a pool

Guest favourite
Home in Waianae
5 out of 5 average rating, 25 reviews

Westside Hawaiian Sanctuary-New Home w/ 24hr Gated

JayRating, 5 stars1 week ago
Charles was the most proactive and responsive host I have ever had on this platform. Extremely pleasant and responded immediately to questions. The home is beautiful and is maintained to perfection. The backyard was my favorite place to sit and take in the beautiful mountains. The gated community was beautiful and felt very safe. The only drawback is that the area outside the community is not as nice. There are not a lot of restaurants and stores in the immediate area. We ended purchasing groceries at a store Charles recommended and cooked our dinners and breakfast at home. Saved a lot of money that way. Overall this was great home base for our adventures around the island.
Guest favourite
Home in Makaha Valley
4.98 out of 5 average rating, 56 reviews

Kalo Homes ~ Mauka to Makai

TimothyRating, 5 stars1 week ago
This place was AMAZING and the hosts were incredible to work with! I can't say enough positive things about our entire stay here. Kerstan and Jerelle definitely made our stay memorable and their hospitality stood out beyond our expectations. The house was beautiful and in a gorgeous location with amazing views. Their recommendations on restaurants and things to do or see were spot on. They were very thoughtful and inclusive with all of the items they had on hand as well. I can't explain the beauty of the location, quietness of the neighborhood and overall experience enough. Absolutely breathtaking!
Home in Waianae
5 out of 5 average rating, 14 reviews

Ocean Views Serene Vacation Escape Home Near Beach

DeriseRating, 5 stars1 month ago
This was a beautiful home with a beautiful view. It was in a gated, newer community that offers a gym and pool. Also a peaceful, quiet neighborhood. The maintenance did come to take the garbage out on our first day there and they forgot to close our door so when we returned home late that day, our door was wide open. The host answered our call and was responsive immediately and changed the code for extra security. There was extra comfort knowing it was in a small gated community and none of our things were misisng but it was definitely a big scare at first. Other than that, which I believe was a rare occurence, we truly enjoyed our stay in this beautiful home.
Home in Waianae
4.88 out of 5 average rating, 41 reviews

Vacation Home in Secluded Makaha Valley Near Beach

VignanRating, 5 stars3 weeks ago
Beautiful backyard with a private hot tub and views. I highly recommend this home 😍
Superhost
Home in Waianae
4.92 out of 5 average rating, 37 reviews

Pakele Oahu by AvantStay | 5 Min to Makaha Beach

MaggieRating, 5 stars2 weeks ago
AvantStay Oahu was amazing throughout my booking process, leading up to my stay and throughout my stay in the rental home. The private community where the rental home is located is absolutely beautiful, and the security guards were very helpful at the gate leading into the gated community. The home was clean, beautiful and offered the accommodations and space that my family needed!
Guest favourite
Home in Makaha Valley
4.91 out of 5 average rating, 111 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

AbhayRating, 5 stars1 month ago
Good place, modern, and had a nice view from the yard of the natural beauty. lots of toys to take to the beach and in a nice gated community
Guest favourite
Home in Makaha Valley
4.96 out of 5 average rating, 135 reviews

Kalo Homes - Makaha's Hidden Gem

JeremyRating, 5 stars1 week ago
In one word, AMAZING!!! Everything was exceptional, the only negative thing I can say is that now I have to buy a new bed at home because the bed at this place was incredible. The home was exactly as advertised, the views of the ocean were sensational. There were even extras for the beach such as coolers, snorkels, umbrellas, boogie boards and much more. Friendly and responsive hosts were there for us, even before we needed them. As long as you know where you are staying and are prepared for the drive, this place is a premium slice of heaven in heaven. Thank you for being part of our adventure.
Guest favourite
Home in Kapolei
5 out of 5 average rating, 8 reviews

Modern Family Beach Villa near shops and dining

EdwardRating, 5 stars2 days ago
Such an amazing stay that my family had in Hawaii, especially with the comfort and peace that we had each minute while in the home. From the secure access into the house to the comfort throughout we felt right at home. The home is a newer condo/villa with nine other units in the same cul de sac and many others in the area. The villas did have a pool although our family did not use them. There are four lagoons nearby with easy access for calm swimming. There are not many food options in the area as this is really away from the main city, and nestled in a mixed villa/resort campus.

Weekly house rentals

Superhost
Home in Kailua
4.86 out of 5 average rating, 427 reviews

Kailua Beach Park - 1 BR Cottage

ShawnRating, 5 stars4 days ago
This has to be the best location in Kailua, hands down. We’ve stayed in both of the units (which are adjacent) hosted by Brooke now. Both units are great and we can’t wait to come back. My only tip would be to rent a compact or sub-compact sized vehicle so that it makes parking as easy as possible.
Guest favourite
Home in Honolulu
4.98 out of 5 average rating, 105 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

MOMOKARating, 5 stars2 weeks ago
It was a very nice inn suitable for a first time in Hawaii.The view from the veranda was of course comfortable, and the kitchen, living room, and bed were all comfortable, and we were able to spend time as if it were our own home. I want to stay again!Thank you! Mahalo!
Superhost
Home in Honolulu

Beautiful Lagoon Tower by Hilton- 2bd villa

AliciaRating, 5 stars5 months ago
The location of this place was amazing. As a family we have always stayed further down closer to the zoo but this location really does have it all. The beaches are amazing, everything is still easily within walking distance and the Hilton property really does have it all. The suite we stayed in was clean, great AC and lots of space for a family of 4. The kitchen could use a few more items to cook with. We went over Christmas and tried to eat in a bit more than usual and had to be VERY creative with our cooking because of what the kitchen had to offer. We throughly enjoyed our stay and you know it’s been a great vacation when you’re sad to leave!
Superhost
Home in Kailua
4.78 out of 5 average rating, 76 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

KelseyRating, 5 stars2 months ago
We loved this place! It was definitely one of the more reasonable cost rentals in the Lanikai neighborhood but it didn’t disappoint. A few things of note: - the appliances are high end KitchenAide and Bosch. The cooktop is a two burner induction that you can put away when not in use. Toaster oven as well. Compact dishwasher and fridge is a one drawer fridge/ one drawer freezer that fits under counter - ample beach towels. Also beach chairs and umbrellas. - the pool was wonderful - less than 10 min walk to Lanikai Beach - do the pillbox hike up the ridge behind you if you want a good workout! We loved our week here. Always planned to cook out on the Weber grill but didn’t end up doing so. The patio was awesome at the end of each day and for morning coffee. Neighborhood was safe. Met the pest control guy and the pool guy while we were here- both really friendly. Would definitely choose this place again.
Guest favourite
Home in Kailua
4.96 out of 5 average rating, 28 reviews

Large Kailua Beach Home - Steps To The Beach!

EricRating, 5 stars4 days ago
We would highly recommend Cary’s place and will definitely come back! It is spacious, comfortable, well stocked, and in a great location. It’s Literally 1 block from one of the best beaches in the world. The house itself is large and comfortable, with dining tables, couches , 3 bathrooms etc. the house is really well stocked - everything to cook, AC units everywhere, and so many beach toys (wagons, chairs, umbrellas, boogie boards, etc). Cary was also super responsive and helpful even with restaurant and other recommendations. The house could use a few minor maintenance repairs but nothing significant.
Superhost
Home in Honolulu
5 out of 5 average rating, 4 reviews

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha

EricaRating, 5 stars11 months ago
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!!
Guest favourite
Home in Kailua
4.9 out of 5 average rating, 309 reviews

Kailua Beach Park - 2 BR Cottage

LindaRating, 5 stars2 weeks ago
Brooke’s place was perfect for my partner and I plus daughter and niece. We were able to cook in the kitchen with sharp knives other good kitchen amenities but also appreciated that there were plenty of dining out options very close by. Kailua and adjacent beaches are clean, friendly and beautiful! It felt safe for the teenagers to spend hours on their own. All around great experience with Brooke being very easy to reach and helpful with recommendations for hikes, shops and restaurants.
Guest favourite
Home in Honolulu
4.85 out of 5 average rating, 47 reviews

24 fl Studio- Oahu Oasis; 1 King Bed

KeniaRating, 5 stars3 weeks ago
This location is just perfect. My tip to avoid paying the expensive parking in the building is to drive around the place looking for a street parking. We found street parking almost everyday, walking time around 15min. It is small but it has all you need :)

Private house rentals

Superhost
Home in Kailua
4.86 out of 5 average rating, 427 reviews

Kailua Beach Park - 1 BR Cottage

ShawnRating, 5 stars4 days ago
This has to be the best location in Kailua, hands down. We’ve stayed in both of the units (which are adjacent) hosted by Brooke now. Both units are great and we can’t wait to come back. My only tip would be to rent a compact or sub-compact sized vehicle so that it makes parking as easy as possible.
Guest favourite
Home in Honolulu
4.98 out of 5 average rating, 105 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

MOMOKARating, 5 stars2 weeks ago
It was a very nice inn suitable for a first time in Hawaii.The view from the veranda was of course comfortable, and the kitchen, living room, and bed were all comfortable, and we were able to spend time as if it were our own home. I want to stay again!Thank you! Mahalo!
Superhost
Home in Honolulu

Beautiful Lagoon Tower by Hilton- 2bd villa

AliciaRating, 5 stars5 months ago
The location of this place was amazing. As a family we have always stayed further down closer to the zoo but this location really does have it all. The beaches are amazing, everything is still easily within walking distance and the Hilton property really does have it all. The suite we stayed in was clean, great AC and lots of space for a family of 4. The kitchen could use a few more items to cook with. We went over Christmas and tried to eat in a bit more than usual and had to be VERY creative with our cooking because of what the kitchen had to offer. We throughly enjoyed our stay and you know it’s been a great vacation when you’re sad to leave!
Superhost
Home in Kailua
4.78 out of 5 average rating, 76 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

KelseyRating, 5 stars2 months ago
We loved this place! It was definitely one of the more reasonable cost rentals in the Lanikai neighborhood but it didn’t disappoint. A few things of note: - the appliances are high end KitchenAide and Bosch. The cooktop is a two burner induction that you can put away when not in use. Toaster oven as well. Compact dishwasher and fridge is a one drawer fridge/ one drawer freezer that fits under counter - ample beach towels. Also beach chairs and umbrellas. - the pool was wonderful - less than 10 min walk to Lanikai Beach - do the pillbox hike up the ridge behind you if you want a good workout! We loved our week here. Always planned to cook out on the Weber grill but didn’t end up doing so. The patio was awesome at the end of each day and for morning coffee. Neighborhood was safe. Met the pest control guy and the pool guy while we were here- both really friendly. Would definitely choose this place again.
Guest favourite
Home in Kailua
4.96 out of 5 average rating, 28 reviews

Large Kailua Beach Home - Steps To The Beach!

EricRating, 5 stars4 days ago
We would highly recommend Cary’s place and will definitely come back! It is spacious, comfortable, well stocked, and in a great location. It’s Literally 1 block from one of the best beaches in the world. The house itself is large and comfortable, with dining tables, couches , 3 bathrooms etc. the house is really well stocked - everything to cook, AC units everywhere, and so many beach toys (wagons, chairs, umbrellas, boogie boards, etc). Cary was also super responsive and helpful even with restaurant and other recommendations. The house could use a few minor maintenance repairs but nothing significant.
Superhost
Home in Honolulu
5 out of 5 average rating, 4 reviews

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha

EricaRating, 5 stars11 months ago
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!!
Guest favourite
Home in Kailua
4.9 out of 5 average rating, 309 reviews

Kailua Beach Park - 2 BR Cottage

LindaRating, 5 stars2 weeks ago
Brooke’s place was perfect for my partner and I plus daughter and niece. We were able to cook in the kitchen with sharp knives other good kitchen amenities but also appreciated that there were plenty of dining out options very close by. Kailua and adjacent beaches are clean, friendly and beautiful! It felt safe for the teenagers to spend hours on their own. All around great experience with Brooke being very easy to reach and helpful with recommendations for hikes, shops and restaurants.
Guest favourite
Home in Honolulu
4.85 out of 5 average rating, 47 reviews

24 fl Studio- Oahu Oasis; 1 King Bed

KeniaRating, 5 stars3 weeks ago
This location is just perfect. My tip to avoid paying the expensive parking in the building is to drive around the place looking for a street parking. We found street parking almost everyday, walking time around 15min. It is small but it has all you need :)

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