Kailua Vacation Rentals, Hawaii: house rentals & more

Select from 186 houses, 59 apartments, and other vacation rentals to find the perfect place for your stay in Kailua. Vacation rentals provide the best amenities for your family, friends, or furry companion, like air conditioning and WiFi. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Kailua Beach

Find the best place to stay - Kailua

Unforgettable Beach Trip! 2 Spacious Units with Kitchenettes, City View!

Sleeps 10 · 2 bedrooms · 2 bathrooms

Top rated rentals - Kailua

A Slice of Heaven

We had a fabulous time. The property was beautiful, clean and just steps from the beach. Vicki, the property host, was so nice and helpful. Sunrises are amazing and this location is perfect to take in all the sights that Oahu has to offer.

Louise U.

Stayed Sep 2023

Tree House in the Banyon Tree

Quite the find! The beautifully designed house, its proximity to the beach and to the restaurants and stores in Kailua town far exceeded the positive comments in the previous reviews. The welcome of the hostess, and the care that she took to make sure we were comfortable, and familiar with our surroundings was a great experience of aloha! The house had everything we needed: comfortable bed and linen, a well equiped kitchen, and a washer and dryer--plus private outdoor spaces that include a balcony and an outdoor shower. Add to this, the fact that Kailua beach is literally 110 steps from the house (yup we counted it) and we ended up with a stay which was a sweet taste of paradise. Looking forward to our next stay!

William K.

Stayed Sep 2023

A total DREAM!

The stay and location was 100% a dream!!!! It was less than a minute walk to the beach which was mostly secluded! The place was just perfect enough for a couples getaway. The cleanest stay I have ever done, not a sight of cobwebs or dust in sight! The rental had everything you could think of up to beach chairs, shade umbrella, and even body surf boards! We did the last weekend of our stay in Waikiki but regretted it as this location was equivalent in price and was a better choice. Will be returning again and booking in the future!!! The rental is within walking distance to town which had a variety of local restaurants, coffee shops, and farmers market location which was perfect for trying local cuisines and delicacies! This stay made this trip a trip of a life time and extremely happy!!!

Gloria B.

Stayed Sep 2023

Amazing property and great location!

We recently stayed here for our family vacation and our wedding. When I say this house is perfect for large families, I mean it was perfect. Our boys had the bunk room and had such a fun time. The girls each got their own room along with one other bedroom in the main house. My brother and his significant other had the apartment upstairs of the pool house and my now Husband and I used the downstairs of the pool house. I felt that this was the perfect home to be able to celebrate and hang out together, yet all still have some privacy. The kitchen was well stocked, and the home is close to grocery stores which was very nice as we cooked a lot at the house. I really appreciated that there was plenty of dishwasher detergent, dish soap, kitchen towels, shampoo/conditioner etc. We left a lot of things behind for the next tenants and you can tell others did too as it was very well stocked with seasonings, etc. The home has a ton of pool and house towels which was also a huge benefit. We had a total of 12 people at the house and never ran out of towels. I did a couple loads of towels throughout the week but always had plenty of towels while doing laundry. For those who travel in large groups.... you will understand the value in that. I also felt that the Owners were amazing to communicate with and very responsive. They even sent me a text the day we arrived to check in and ensure everything went well. If the opportunity presented itself again, I would absolutely stay here again.

Angela C.

Stayed Aug 2023

Kailua Retreat and Relaxation

We had a relaxing stay at this beautiful house and location. Having access to a private pool, the covered lanai and the beautiful sandy shores of Kailua beachfront steps away really enhanced our retreat in paradise. Sue was the perfect hostess and welcomed us with a yummy basket of local treats which we throughly enjoyed. She was very accommodating and communication was seamless. We loved the layout of the house and used the beautiful kitchen to cook our meals. We look forward to staying again when we return to Kailua. Mahalo Sue and Peter for your hospitality.

Kathy L.

Stayed Aug 2023

Magical property, wonderful stay

Our family had such a wonderful stay in this amazing property. The grounds, gardens, and home are truly a tropical retreat. Location was perfect - short walk to the beach and even closer access to the ocean. The home is very nicely decorated, everything was fresh, clean and comfortable, and the house had everything we needed. We were truly sad to leave. Kalani was an amazing host. We’ve had many stays at vacation homes and this was by far our best experience. We look forward to returning!

Agnes K.

Stayed Jul 2023

Absolutely Wonderful House in Kailua

We had the pleasure of staying Summer 2023 in this amazing property. This 2-level home was perfect for our family of 5. It has 3 bedrooms, 3 bathrooms, dining room, living room, a well-appointed full kitchen, a huge lanai and several other niceties. From the refreshing infinity pool & hot tub to enjoying sunrises/sunsets on the stunning lanai, this place was such a treat. Added bonuses were the awesome pool table in the living area where epic tournaments took place between the adults after the kids went to bed. Location was ideal. We rented a car and downtown Kailua as well as all the beautiful local beaches were a very short drive away. Grocery shopping & local restaurants were conveniently just minutes away by car. It’s also worth mentioning that the host for this property is such a nice guy. He was always accessible and extremely accommodating. He helped curate a truly perfect stay for us. We definitely look forward to returning back to this exquisite VRBO!

Justin L.

Stayed Jun 2023

Great stay in paradise!

Can’t beat location on this side of the island! Minutes from beach and local restaurants! Wonderful host! Nice accommodations!

Lisa E.

Stayed Jun 2023

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Delight in the waterfront landscape of Kailua

The island views and surrounding scenery provide a peaceful ambiance to your vacation home in Kailua. This city's kayaking, coral reefs and hiking draw many visitors. There are plenty of places to find the perfect souvenir including Ala Moana Center, Waikiki Beach Walk and International Market Place. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Kailua

Do you want to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kailua a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Ala Wai Golf Course (10 mi / 16.2 km)
Honolulu Zoo (10.4 mi / 16.8 km)
Kaneohe Klipper Golf Course (3.4 mi / 5.5 km)
Ko'olau Golf Club (3.6 mi / 5.8 km)
Waialae Country Club (9.4 mi / 15.1 km)
Mamala Bay Golf Course (13.9 mi / 22.3 km)

Exploring the beaches and other natural features in Kailua

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Kailua. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

Waikiki Beach (10.4 mi / 16.8 km)
Pearl Harbor (15.3 mi / 24.6 km)
Kalama Beach Park (0.2 mi / 0.3 km)
Kailua Bay Beach (0.8 mi / 1.2 km)
Kailua Beach (0.9 mi / 1.4 km)
Lanikai Beach (1.7 mi / 2.7 km)

Seasonal weather averages in Kailua

Travelers enjoy Kailua for its snorkeling. If you're planning a vacation around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 79°F.

Transportation to and around Kailua

The nearest airport is in Daniel K. Inouye Intl. Airport (HNL), located 12.6 mi (20.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kapolei, HI (JRF-Kalaeloa), which is 22.2 mi (35.7 km) away.