
House holiday rentals in Diamond Head
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Top-rated house rentals in Diamond Head
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Popular amenities for house rentals in Diamond Head
House rentals with a pool

Westside Hawaiian Sanctuary-New Home w/ 24hr Gated
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.

Kalo Homes ~ Mauka to Makai
We flew into Oahu to attend a family function at Makaha beach. Location was perfect, less than 10 minutes away from the function. Self Check-In was easy. There was more than enough room for our family of eight. All beds were comfortable. 2 1/2 bathrooms was a + for 8 people. The kitchen is well equipped. The backyard was awesome. It’s been a minute since I’ve sat under the Makaha stars✨. It gets pretty warm on the westside, but every room has its own split system unit which is nice. Overall this is one of the best places I’ve stayed in. Makaha “No ka`oi” 🤙🏽. Mahalo Kerstan for your hospitality. I highly recommend 💯

Vacation Home in Secluded Makaha Valley Near Beach
Beautiful backyard with a private hot tub and views. I highly recommend this home 😍

@ Marbella Lane - Stunning Gem w/ MT & Ocean Views
Stella’s home was absolutely lovely and had everything we needed. We had a small issue with the booking at first, but Stella handled it promptly and professionally. Check-in was smooth, and she continued to provide excellent care throughout our stay. I truly hope future guests feel confident booking this home—it’s a peaceful, well-managed place to stay.

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

Kalo Homes - Makaha's Hidden Gem
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.

Modern Family Beach Villa near shops and dining
Great spot for a group of five—just the right amount of space and everything we needed. We had a small issue with the Wi-Fi, but the host was super quick to help and got it sorted fast. The area is beautiful, the place was clean, and check-in was super easy. Would definitely recommend!

Island Retreat: 2 Master Suites|Ocean & Mtn Views
My family and I thoroughly enjoyed our stay. The house is spacious and comfortably fit the 9 of us. The home has all of your basic needs and the garage is equipped with all of your beach essentials. The neighborhood was quiet and the view was immaculate. Being surrounded by serene mountain views and an ocean view from the backyard felt like a fairytale. We flew in to attend a graduation and Justin was gracious enough to allow our extended family to come over for dinner. It was nice to be able enjoy a meal with our entire family in the comfort of what felt like our home away from home. Justin and his team were gracious, responsive, and accommodating. I highly recommend this place if you have a large family and want to be in a comfortable space. However, some downsides include being in a somewhat remote area. You’ll have to drive at least an hour to reach some of the more popular parts of the island, so keep that in mind when it comes to planning.
Weekly house rentals

Kailua Beach Park - 1 BR Cottage
Our second time staying here . We love the location. It’s reasonably priced compared to some other air bnbs. Cant go wrong with being across the beach. It’s small and quaint and nothing crazy and perfect for our fam

Waikiki Gem, Stunning Ocean View, Parking Included
I had a great stay at this beautiful apartment! The space was clean, well-maintained, and exactly as described. Check-in was super easy with clear instructions provided ahead of time. Charlie was communicative and helpful throughout the stay. I would definitely recommend this place and would happily stay here again! Mahalo nui!

Beautiful Lagoon Tower by Hilton- 2bd villa
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!

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai
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.

Large Kailua Beach Home - Steps To The Beach!
We had a great stay in Kailua! The house is very comfortable, and it’s only a couple minutes walk to the Kalamas beach access. When not at the beach (with the chairs, towels, boogie boards, and toys provided) or eating Island Snow, the kids loved playing in the yard and the play room, and watching movies in the living room. We ended up staying mostly in Kailua and Lanikai for beaches, shopping, and restaurants, with one morning at the botanical gardens in Kaneohe and one at Haunama Bay, and an afternoon at Bishop Museum after check-out. We’d love to stay here again, in this well-appointed and clean house with hosts who responded to our questions and provided clear guidance on the check-in and check-out process.

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!!

Kailua Beach Park - 2 BR Cottage
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.

Serenity Beachfront Cottage- NUC No 90/TVU-0326
Idyllic location, comfy and cozy, private sanctuary of a home and beach while still walking/biking distance to lovely local markets, food, book stores, etc. Misty Ann was such a responsive and helpful host, went above and beyond for us! She had boogie board, beach chairs, sand toys available; my young daughters and I had a wonderful time, and would return back and recommend 1000%.
Private house rentals

Kailua Beach Park - 1 BR Cottage
Our second time staying here . We love the location. It’s reasonably priced compared to some other air bnbs. Cant go wrong with being across the beach. It’s small and quaint and nothing crazy and perfect for our fam

Waikiki Gem, Stunning Ocean View, Parking Included
I had a great stay at this beautiful apartment! The space was clean, well-maintained, and exactly as described. Check-in was super easy with clear instructions provided ahead of time. Charlie was communicative and helpful throughout the stay. I would definitely recommend this place and would happily stay here again! Mahalo nui!

Beautiful Lagoon Tower by Hilton- 2bd villa
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!

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai
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.

Large Kailua Beach Home - Steps To The Beach!
We had a great stay in Kailua! The house is very comfortable, and it’s only a couple minutes walk to the Kalamas beach access. When not at the beach (with the chairs, towels, boogie boards, and toys provided) or eating Island Snow, the kids loved playing in the yard and the play room, and watching movies in the living room. We ended up staying mostly in Kailua and Lanikai for beaches, shopping, and restaurants, with one morning at the botanical gardens in Kaneohe and one at Haunama Bay, and an afternoon at Bishop Museum after check-out. We’d love to stay here again, in this well-appointed and clean house with hosts who responded to our questions and provided clear guidance on the check-in and check-out process.

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!!

Kailua Beach Park - 2 BR Cottage
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.

Serenity Beachfront Cottage- NUC No 90/TVU-0326
Idyllic location, comfy and cozy, private sanctuary of a home and beach while still walking/biking distance to lovely local markets, food, book stores, etc. Misty Ann was such a responsive and helpful host, went above and beyond for us! She had boogie board, beach chairs, sand toys available; my young daughters and I had a wonderful time, and would return back and recommend 1000%.
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- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kepuhi Beach
- Mālaekahana Beach
- Lanikai Beach
- Kualoa Ranch
- Mākoa Beach
- Honolulu Zoo
- Banzai Pipeline
- Hanauma Bay
- Kapalaoa Beach
- Ala Moana Beach Park
- Kaupoa Beach
- White Plains Beach
- Pyramid Rock Beach
- Wet 'n' Wild Hawaii
- Kalama Beach
- Makao Beach
- Diamond Head Beach Park
- Sans Souci Beach
- Bishop Museum
- Mahakea Beach
- Waimea Valley