Kailua Beach featuring swimming, a beach and landscape views

Kailua holiday rentals

We found 4,884 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

September 2025

October 2025

Select from 161 houses, 54 apartments and other holiday rentals to find the perfect place for your stay in Kailua. Holiday rentals provide the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Kailua

Showing deals for:19 Dec - 26 Dec

Exceptional

(11 reviews)

Waimānalo Beach Cottages 2 min walk to the beach!

Waimanalo, HI

8% off

for 7 nights, 1 cottage

AU$6,130 per night

includes taxes & fees

Full kitchen, queen size sofa sleeper and dining table with chairs

Exceptional

(7 reviews)

Coastal Chic Condo with Ocean View & Full Kitchen

Honolulu, HI

7% off

for 7 nights, 1 apartment

AU$743 per night

includes taxes & fees

Beach side swimming pool. Another wadding pool for suntanning on 2nd floor.

Exceptional

(137 reviews)

Next to Ocean, 120/nt. monthly rate May 1 - Oct 31, fully renovated condo

Honolulu, HI

8% off

for 7 nights, 1 apartment

AU$440 per night

includes taxes & fees

Exceptional

(42 reviews)

@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel

Honolulu, HI

15% off

for 7 nights, 1 apartment

AU$493 per night

includes taxes & fees

Exceptional

(267 reviews)

Oceanfront Waikiki/Ilikai Condo with stunning ocean views and free parking

Honolulu, HI

7% off

for 7 nights, 1 apartment

AU$570 per night

includes taxes & fees

Exceptional

(180 reviews)

Waikiki Beach ocean view studio with pool access right on the white sand beach.

Honolulu, HI

7% off

for 7 nights, 1 apartment

AU$637 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Kailua

Lanikai Beach

Find the best place to stay - Kailua

Premier Host

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

Sleeps 3 · 2 bedrooms · 2 bathrooms

Best part of Kailua Beach just across the road...

Premier Host

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

Sleeps 5 · 2 bedrooms · 2 bathrooms

House is located at the end of the driveway

Premier Host

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Top rated rentals - Kailua

The path to the beach gate is right out from your private garden...

Premier Host

Thrilled with our stay

Thank you Cheri and Scott for your kind hospitality during our wonderful weeks in your garden bungalow. The updated kitchen facilities were excellent and we loved sitting in the garden room and feeling like we were right in the middle of your Hawaiian paradise

Debbie C.

Stayed July 2024

Premier Host

Perfect

This was the perfect property and place for us to begin our Hawaiian stay. We moved away from Kailua six years ago and it was our first visit back. The view of Kailua beach and the ocean from the room's window is gorgeous. Waking to the sound of the waves crashing is wonderful. The unit was immaculate. The bed was very comfy, and the shower was also very good. Communication with the owner, Shari, is excellent. We highly recommend this beautiful little slice of heaven on earth. Aloha.

Jim and Sharon B.

Stayed Apr 2024

Premier Host

The perfect holiday home!!!

My wife and I flew in from Australia with our son and spent a week at Kaimalino Kai with my mother and grandmother. It is such an amazing house. Great location with stunning views, a beautiful heated pool, tons of room and very comfortable furnishings. The kitchen is extremely well stocked with cookware, plates and cutlery so meals at home were convenient for us. Laundry was also easy as the house has a large washer and dryer. Probably the best holiday home we’ve ever rented, seems like they’ve thought of everything that someone would or could need. The pictures don’t do the house justice, it’s absolutely stunning! Can’t recommend it enough for a small family getaway. Considering we ranged in age from 18 months to 80 years old, and we all were comfortable and super happy with everything the house had to offer, pretty much says it all. Richard the owner was a pleasure to deal with, as was Ramon and Lianne the property managers. Really hope we can come back for another holiday, Thanks for everything!

Mario M.

Stayed May 2019

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Delight in the waterfront landscape of Kailua

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Kailua. This city's kayaking, coral reefs and hiking draw many visitors. Ala Moana Center and Waikiki Beach are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Kailua

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

Kaneohe Klipper Golf Course (3.4 mi / 5.5 km)
Ala Wai Golf Course (10 mi / 16.2 km)
Honolulu Zoo (10.4 mi / 16.8 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 an outdoor enthusiast or just want to spend some time taking in the scenery, Kailua is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Waikiki Beach (10.4 mi / 16.8 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)
Bellows Field Beach Park (3 mi / 4.8 km)

Seasonal weather averages in Kailua

Travellers enjoy Kailua for its snorkelling. If you're planning a holiday around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 26°C.

Transport to and around Kailua

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Kailua?

Based on our research, houses are the most desirable holiday home type in Kailua. But naturally, everyone's idea of an epic stay isn't going to be the same. Stayz has holiday homes of all shapes and sizes, so you're sure to discover your perfect match.

How much does it cost to rent a holiday home in Kailua?

Different things affect what you'll pay for your holiday home in Kailua, such as the season, length of stay and type of property. But, all of our holiday homes have something in common — incredible value. Just add your travel dates to find your perfect match.

How much does it cost to rent a beach house in Kailua?

When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Kailua travel dates to see all your options on Stayz. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your beach house.

What are popular home amenities in Kailua?

Some of the most popular home amenities people search for in Kailua are a sauna, a barbecue grill and ski-in/ski-out facilities. Whether you're holidaying with family, pals or even pets, Stayz holiday properties feature the best amenities for fun and relaxation with the people that matter most.

What are the top attractions for families in Kailua?

There are lots of amazing things to do and see with the family in Kailua, such as:

Kailua Beach
Lanikai Beach
Waimanalo Beach

Can I find two-bedroom holiday homes in Kailua?

Kailua has 28 two-bedroom holiday homes to choose from. Discover a holiday home with all the comfort and privacy you're looking for at a price that's hard to resist on Stayz.

Are there holiday homes with WiFi in Kailua?

Kailua has 91 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to catching up on social media, these Stayz homes make it a cinch to go online.

How old do you have to be to rent a holiday home in Kailua?

The minimum age requirements can vary across properties on Stayz, so look at the rules of the holiday home in Kailua you want to book. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Kailua for?

The amount of time you can stay in a Kailua holiday home for depends on the property. Simply put in your travel dates to find available options offering longer term stays. They include the things you need to make your extended getaway more enjoyable like kitchens and yards. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.