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House vacation rentals in Kailua

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Popular amenities for Kailua house rentals

House rentals with a pool

Home in Waianae
4.75 out of 5 average rating, 16 reviews

Family Vacation Home w/Ocean View at Makaha Valley

KateRating, 5 stars1 month ago
We absolutely loved the unit. Beautiful home with everything we needed for a perfect stay.
Guest favorite
Home in Waianae
5 out of 5 average rating, 24 reviews

Westside Hawaiian Sanctuary-New Home w/ 24hr Gated

NicoletteRating, 5 stars1 month ago
Charles Place was perfect for for my family. The outdoor space was amazing , we sat outside almost every day to enjoy the beautiful weather, view, and we loved the BBQ and fire pit to sit around. All bathrooms were stocked with stuff that you sometimes forget on vacation. The beds were very comfy. Kitchen was very modern. We loved the water filter attached to the sink this made it easy for us to get water at anytime. The space comes along with plenty of beach supplies for 8 people which was very nice. The local beach was only a 5 minute drive from the property. Not a lot of restaurants but honestly the drive around the island was beautiful which distracted you from the drive time. Charles is an amazing responsive host which made it very easy to express any questions we had . We will definitely stay again if we come back to this island. Thanks for the great stay !
Superhost
Home in Waikiki
5 out of 5 average rating, 4 reviews

LAST MIN Lagoon Tower by Hilton- 2 bedroom Aloha

EricaRating, 5 stars10 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!!
Home in Waianae
4.9 out of 5 average rating, 30 reviews

Ocean View Exquisite Home at Cottages at Mauna Olu

KristieRating, 5 stars3 months ago
We loved the house. The backyard was stunning with the mountain and ocean views. The yard was beautiful and the house was clean. Appreciated they had beach items. We would want to stay here again!
Guest favorite
Home in Kahuku
4.93 out of 5 average rating, 15 reviews

Peek-a-Boo Ocean View

JuliusRating, 5 stars3 weeks ago
Alex was very responsive when I needed help with some things. Taught me a trick with the shower. Reading their rule binder gave me a warm welcome vibe. I recommend if you’re staying around for a quick getaway.
Guest favorite
Home in Kahuku
4.94 out of 5 average rating, 33 reviews

Aloha Sunny Turtle Bay - Updated 2 BD + Loft

MeganRating, 5 stars1 week ago
This place as such a beautiful place to stay. We had some of our granddie kiddos and children and it was just perfect. Fantastic location and close to Turtle Bay. It has a beautiful walking path to a beach where we swam with lots of turtles. So many gorgeous beaches and hikes around this area and some yummy food trucks are close by. The place has 3 beach chairs, assorted snorkel gear and beach towels. Joel was super quick and responsive with any questions we asked. We all were so grateful to stay in this absolutely lovely condo! Quick - reserve your time here 😊
Guest favorite
Home in Ewa
5 out of 5 average rating, 6 reviews

Modern Family Beach Villa near shops and dining

AndreaRating, 5 stars1 month ago
A comfortable home that is perfect for a family with kids who want to stay near the beach and away from the bustle of Waikiki. We enjoyed having easy access to the lagoons and marina in Ko Olina and the house was a good home base for adventures around Oahu. The information provided was useful and our co-host was quick to respond and helpful when we had questions.
Top guest favorite
Home in Waianae
5 out of 5 average rating, 22 reviews

Island Retreat: 2 Master Suites|Ocean & Mtn Views

TounetaRating, 5 stars2 weeks ago
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

Guest favorite
Home in Waianae
4.97 out of 5 average rating, 70 reviews

Makaha Hale - New 3 BR Home

MinnieRating, 5 stars3 weeks ago
We had a wonderful stay at Melissa’s home in Makaha Valley! The house was clean, well-maintained, and had everything we needed—including thoughtful touches like toys for our baby, which made a big difference for our family. Melissa was incredibly responsive, friendly, and helpful throughout our stay. The location is peaceful and private, set within a secure gated community. It’s perfect for families with young children who are looking to relax and enjoy a slower pace. While most tourist attractions are about a 40-minute drive away, the setting more than makes up for it if you’re not planning to be out all day. Overall, we felt very comfortable and well taken care of. Would definitely recommend for families looking for a quiet, kid-friendly getaway (away from the hustle and bustle of touristy areas) on Oahu!
Guest favorite
Home in Waianae
4.98 out of 5 average rating, 41 reviews

Ocean and Mountain View/ Gardener’s Dream Gateway

LukeRating, 5 stars1 month ago
Our family considers this house a home away from home. Any and everything you need is available and the owner is super helpful/responsive. We love staying here and will on each of our trips. So far we have spent 18 days there through 2 separate vacations and would choose it every time over any other spot.
Guest favorite
Home in Waianae
4.94 out of 5 average rating, 88 reviews

3BR New Construction w/Mt views, Close to Beach

JulieRating, 5 stars2 weeks ago
My family felt right at home it was a beautiful place with the most beautiful beach nearby to swim at. We had a 4 months old baby with us so it was wonderful to have a crib and change of sheets available for the baby along with beach toys such as snorkeling gear and boogie boards. Lots of towels available and comfortable beds. Thank you for such an amazing and comfortable stay.
Guest favorite
Home in Waianae
4.98 out of 5 average rating, 57 reviews

Ocean View Oasis- Gated Luxury w/comm pool/spa/Gym

MichelleRating, 5 stars2 weeks ago
Seven of us stayed at this home nestled in the beautiful Makaha Valley. The home had everything we needed and more and all was of excellent quality. Cynthia provided laundry baskets in each bedroom which was an unexpected nice touch. Also, Pantene hair products and body wash in the bathrooms. On our arrival we were greeted by neighborhood chickens which we all enjoyed. The lanai outside had comfortable seating for our entire group and we used the gas grill several times. We woke to the sound of birds and frequently saw toads or large frogs. It felt like being in a nature preserve. The gated community felt very safe and was nice to walk around. It adjoins the Makaha Valley golf course which a couple of our group took advantage of multiple times. The beach is a short drive away. Our favorite spot was close to a restaurant with a great ambiance, the Beachouse at 608. Our stay at Cynthia’s place provided the relaxing environment that we all needed. We would stay here again
Guest favorite
Home in Hauula
5 out of 5 average rating, 19 reviews

Ocean View Vacation Home

Kyle And AjaRating, 5 stars2 months ago
This was our first time visiting Oahu as a family. The hosts were friendly and we enjoyed having the space to ourselves with a washer and dryer on site. We do appreciate how clean things were and the beach accessories that were available to use under the stairs. Plenty of beach towels, and bedding and we loved the location. You can also vaguely see the ocean from the kitchen window. Things to consider -windows need to be shut and locked while away. By the time we returned and opened windows by 6pm it was too hot to cook dinner and there was little breeze to cool the space. We made sure to pick up something to eat prior to returning. We were warmer than we liked sleeping at night but survived -don’t sleep with windows open if sensitive to noise. There’s a rooster that goes off throughout the night. -The Airbnb is the bottom floor of a house so you do hear footsteps occasionally, and the parking is up a tight, narrow driveway on a hill which accommodates one car at a time up and down
Guest favorite
Home in Kahuku
5 out of 5 average rating, 23 reviews

"Coconut Crest Cottage"

FrancesRating, 5 stars2 weeks ago
Perfect stay for our vacation, with plenty of room for our party of 5! Couldn’t have been a better location for our day to day activities!
Guest favorite
Home in Waianae
4.82 out of 5 average rating, 51 reviews

Ocean Escape by AvantStay | Brand New |Ocean Views

JonathanRating, 5 stars1 week ago
Lovely vista of mountains, can see the ocean. Local dining options are somewhat limited. Driving to/from the Honolulu area was a bit of a slog. There is a decent supermarket nearby.
Guest favorite
Home in Waianae
4.96 out of 5 average rating, 55 reviews

Premium home with stunning ocean & mountain views

TimRating, 5 stars2 weeks ago
Mauna Olu is a new gated development. This house is in the main grouping of houses quite close together, but the garden is very nice and the views of the mountains are awesome. The guards are sticklers for showing parking pass, but quite friendly. The clubhouse has an excellent gym (sparkling new equipment), and sadly the pool was not yet open when we were there but should be soon. Beds very comfy, a/c worked well, and good night's sleep was assured!

Private house rentals

Home in Waianae
4.8 out of 5 average rating, 15 reviews

5b2ba historical place w/no st.lights&no neighbors

VicenteRating, 5 stars2 months ago
Truly a secluded place with little to no neighbors and large enough for my family of Seven. Beautiful lighting especially at night. Hardly no AC needed as quiet as it was, could leave the windows completely open and with a fan. Kitchen needs a little more amenities for a full Airbnb experience, but provided enough to get by. Neighborhood was quiet. I think we made the most ruckus, but truly a nice little home away from home. A little further away than we anticipated from the bigger cities but easily manageable with a rental. Close to Disneys Aulani and 4 seasons!
Superhost
Home in Waianae
4.84 out of 5 average rating, 80 reviews

Brand New 4BR Home! Ocean and Mountain View!

AshleyRating, 5 stars1 month ago
Rajani’s place was absolutely beautiful to stay at for our family group of 11. It was exactly as described and pictured but more beautiful! The scenery was stunning and amazing to wake up to breathtaking views every morning. Rajani was very communicative, responsive and helpful the entire trip. She wished us a great day almost daily. We really enjoyed our stay at this very clean, spacious home. Thanks for making our vacation to Hawaii from California one to remember. We would definitely stay again in the future and hope to soon. Thank you.
Home in Laie
4.78 out of 5 average rating, 32 reviews

Hale Mahina Beach House

ScottRating, 5 stars2 months ago
Nice beach house. Little busier road than expected to get to the beach, but liked the access to the nice beach and easy access to local attractions.
Superhost
Home in Waianae
4.29 out of 5 average rating, 31 reviews

Modern Waianae Home w/ Mountain & Valley View

PaulRating, 5 stars11 months ago
House is just as pictured and in the beautiful Makaha Valley. Very seamless check in process and house is nice and clean. Wouldn't hesitate to stay again
Home in Ewa
5 out of 5 average rating, 6 reviews

Golf Course View - 2 Bed and 2.5 Bathrooms

TinaRating, 5 stars2 weeks ago
This was a great place to stay. Others had mentioned the airplane noise but we slept perfectly without a bother. The patio was enjoyable to sit and relax. If I could request anything it would be a washer and dryer, but other than that it was good. Very friendly and was helpful.
Guest favorite
Home in Mililani
4.83 out of 5 average rating, 18 reviews

Cozy Guesthouse Central Oahu

TimRating, 5 stars3 weeks ago
The place was great, host communication was great. Lots to do in the area. Nice and private and clean. 10/10 would recommend.
Top guest favorite
Home in Hauula
5 out of 5 average rating, 18 reviews

Mauka Sunrise, Walk to Hau‘ula Beach & Trails, A/C

EvetteRating, 5 stars1 week ago
Wonderful, relaxed, peaceful place. Home thoughtfully supplied with tons of beach towels, beach chairs, snorkel masks, guidebooks, etc, everything you need for a fun getaway. If you like hiking, do not miss the Hau’ula Loop trail two blocks up the road— fantastic well-maintained trail with varied terrain and stunning mountain views. Our favorite beach in the area was at Mālaekahana State Recreation Area (near Goat Island), 4 miles up the highway. We went there 3 times and saw many sea turtles every time!
Home in North Shore
4.81 out of 5 average rating, 279 reviews

Haleiwa Dream Location

KristinRating, 5 stars3 weeks ago
Great place to stay on the north shore of Oahu. Carols place is roomy and clean and had everything we needed. Loved being able to use the bikes. Gorgeous beach just a short walk from the place.

Quick stats about house rentals in Kailua

  • Total rentals

    190 properties

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

Destinations to explore

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