Kailua holiday lettings

We found 4,912 holiday rentals — enter your dates for availability

Select from 160 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:26 Dec - 2 Jan

Image gallery for Waimānalo Beach Cottages 2 min walk to the beach!

Exterior
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

Waimānalo Beach Cottages 2 min walk to the beach!

Waimanalo, HI

7% off
Price is £22,990
for 7 nights, 1 cottage
£3,284 per night
includes taxes & fees
Waimānalo Beach Cottages 2 min walk to the beach!

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Find out more about Kailua

Find out more about Kailua

Why visit Kailua

  • Stunning beaches: Kailua Beach Park offers pristine sands and turquoise waters, perfect for sunbathing and swimming.
  • Outdoor activities: Enjoy kayaking, paddleboarding, and hiking, providing both relaxation and adventure.
  • Charming local neighbourhoods: Explore the quaint shops and eateries that reflect the island's laid-back lifestyle.
  • Family-friendly atmosphere: Kailua is ideal for families, with safe beaches and numerous parks for children to play.
  • Varied accommodation options: Choose from delightful holiday rentals, including condos and private homes near the beach.

Popular types of accommodation in Kailua

You've chosen Kailua for your holiday, and now it's time to find the perfect place to stay. Whether you're looking for charming condos, houses, or spacious apartments, Kailua offers a variety of delightful holiday rentals. With an array of options available, you're sure to discover the ideal accommodation that suits your needs. Explore our selection of holiday rentals in Kailua and make your stay in this stunning Hawaiian paradise memorable.

  • Condos: The top choice for holidaymakers in Kailua, offering modern amenities and stunning views.
  • Houses: A popular option for families or groups, providing a homely atmosphere and privacy.
  • Apartments: Ideal for those seeking a convenient and compact living space during their stay.
  • Villas: Luxurious and spacious, perfect for a lavish getaway with friends or family.
  • Cottages: Charming and quaint, these accommodations offer a cozy retreat in a picturesque setting.**

Top attractions in and around Kailua

Kailua, a delightful destination in Honolulu County, is perfect for outdoor and family beach holidays. Visitors can enjoy the stunning Kailua Beach Park, alongside other scenic spots like the bay and local modern colleges. With a focus on beach and outdoor experiences, Kailua offers a variety of attractions that cater to both relaxation and adventure, making it an ideal location for a memorable getaway.

  • Lanikai Beach: Renowned for its stunning white sands and crystal-clear waters, Lanikai Beach offers a quintessential tropical experience. Ideal for sunbathing, swimming, and kayaking, it’s a perfect spot for relaxation amidst breathtaking views of the Mokulua Islands.
  • University of Hawaii at Manoa: This vibrant campus boasts a blend of modern architecture and lush landscapes. Immerse yourself in the university's lively atmosphere, explore its art galleries, and enjoy the diverse cultural events that reflect Hawaiian heritage.
  • Kaneohe Bay: A picturesque bay surrounded by lush mountains, Kaneohe Bay offers various outdoor activities like snorkelling and kayaking. Experience the stunning scenery and vibrant marine life, making it a paradise for nature lovers and adventure seekers.

Things to do recommended for couples

Looking for a romantic getaway in Kailua? Enjoy a fun-filled evening at Glow Putt Mini Golf, just 2.5km away, or indulge in luxury at the nearby Country Club, located 5.0km from your base. Perfect for couples seeking adventure and relaxation alike!

Things to do recommended for families

Families in Kailua can enjoy a relaxing day at Kaiona Beach Park, explore the scenic Waʻahila Ridge State Recreation Area, or unwind at Kawaikui Beach Park, all offering wonderful wellness vibes and suitable activities for children.

Things to do recommended for groups

Gather your group for a round of golf at Kaneohe Klipper Golf Course, hike the scenic Lanikai Pillboxes Trailhead for breathtaking views, or enjoy shopping and entertainment at Kahala Mall, just 5.6km away from Kailua.

What do I need to keep in mind when booking a vacation in 'Kailua

When planning your trip, whether you're journeying with friends, family, your pets, or seeking extended stays, be sure to apply the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Kailua with a group: Think about how many bedrooms you require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Kailua with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Kailua: For many, a family holiday isn’t truly complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kailua: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Kailua

Kailua, an idyllic Hawaiian town, offers a perfect blend of relaxation and adventure for families and couples alike. With stunning holiday homes near the beach, you can soak in the tropical atmosphere while exploring the charming Oahu neighbourhoods. Whether you’re seeking excursions or a serene spot to unwind, Kailua's exquisite selection of outdoor activities and picturesque scenery ensures a memorable getaway.

  • Kaneohe: Located merely 2.5km from Kailua, Kaneohe is a vibrant city known for its stunning outdoor experiences and family-friendly activities. Visitors can enjoy a thrilling zipline ropes course or spend an entertaining day at the arcade adventure zone. Kaneohe is also home to shopping centres that cater to all needs. The picturesque bay and local beaches provide a perfect backdrop for relaxation and water activities, making it an ideal destination for families seeking adventure and leisure.
  • Lanikai: Nestled around Kailua, Lanikai is a charming neighbourhood renowned for its idyllic beaches and outdoor pursuits. This picturesque area invites visitors to explore its scenic hiking trails, which lead to breathtaking views of the coastline. The local campground offers a unique camping experience, allowing families to immerse themselves in nature. Lanikai Beach, with its soft sands and crystal-clear waters, is a highlight, while the nearby urban park provides a lovely spot for picnics and leisurely strolls.
  • Kalama Tract: Situated close to Kailua, Kalama Tract offers a delightful blend of outdoor fun and city-themed experiences. Golf enthusiasts will appreciate the well-maintained golf courses, providing a great day out for families. The local shopping centres are perfect for those looking to indulge in some retail therapy. With access to beautiful beaches and urban parks, Kalama Tract is an excellent choice for visitors seeking both relaxation and recreation in a vibrant community setting.

Best time to go to Kailua

If you're planning a trip to Kailua, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January73.4°F (23.0°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.7°F (22.6°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.9°F (22.7°C)Light RainMostly SunnySlightly HighAverage
April74.1°F (23.4°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May75.6°F (24.2°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
June77.0°F (25.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High
July77.9°F (25.5°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
August78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
September78.8°F (26.0°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
October78.3°F (25.7°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
November76.5°F (24.7°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December74.5°F (23.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings. Moreover, opting for a longer stay often results in even greater discounts. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or review and organise your travel plans. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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 best area to stay in Kailua when booking a holiday rental?
When considering a holiday rental in Kailua, Hawaii, a popular area to stay in is the picturesque Lanikai neighbourhood. Known for its stunning beaches and turquoise waters, Lanikai offers a serene atmosphere that is great for relaxation. The famous Lanikai Beach, often hailed as one of the best beaches in the world, provides opportunities for swimming, kayaking, and sunbathing. Additionally, the Lanikai Pillboxes hike offers breathtaking panoramic views of the coastline and the Mokulua Islands, making it a must-do for outdoor enthusiasts.

Another excellent choice is the Kailua Town area, which boasts a vibrant local vibe with an array of shops, cafes, and restaurants. Staying in Kailua Town means you're just a short distance from the beautiful Kailua Beach, which is ideal for both water sports and leisurely beach strolls. This neighbourhood has a variety of holiday rental properties, with many options available that cater to different budgets and preferences.
How much does it cost to rent a holiday home in Kailua?
Prices for holiday rentals in Kailua vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kailua to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Kailua holiday house rentals?
You can find great discounts on house rentals in Kailua on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Kailua?
For renting a beach house in Kailua, Hawaii, the area along Kailua Beach is highly recommended. This picturesque stretch features soft, white sand and crystal-clear waters, making it a prime location for beachside accommodations. Many properties in this area offer amenities such as spacious outdoor decks with stunning ocean views, private access to the beach, and fully equipped kitchens, ideal for travellers seeking a relaxing seaside getaway.

Additionally, the Lanikai Beach neighbourhood, known for its stunning sunrise views and tranquil waters, presents a variety of holiday rentals, including charming beachfront cottages and luxurious villas. These properties often boast amenities like private gardens, outdoor showers, and access to water sports equipment such as kayaks and paddleboards, allowing guests to fully immerse themselves in the coastal lifestyle.
What is the most popular type of holiday rental accomodation in Kailua?
In Kailua, holiday houses are the most popular type of rental accommodation, with approximately 150 available throughout the area. These properties are often situated in peaceful neighbourhoods, close to beautiful beaches such as Kailua Beach and Lanikai Beach, making them ideal for those looking to enjoy the sun and surf. Most holiday houses come with amenities like fully equipped kitchens, spacious living areas, and outdoor patios or decks, great for relaxing after a day of activities.

Apartments are also a popular choice, with around 51 options available, typically offering a more compact and affordable stay while still providing essential amenities including kitchen facilities and comfortable living spaces. Additionally, there are about 22 cottages scattered across Kailua, which offer a quaint and charming atmosphere, often surrounded by lush gardens.
Are there any family house rentals in Kailua?
In Kailua, Hawaii, there are plenty of family-friendly house rentals available, with around 163 options to choose from. This beautiful area is known for its stunning beaches and vibrant community, making it a fantastic choice for families. Many properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can enjoy playtime. Additionally, amenities such as Wi-Fi and air conditioning are commonly included to ensure a comfortable stay.
Can I rent a holiday home with a pool or hot tub in Kailua?
In Kailua, there are many holiday homes available for rent that feature pools or hot tubs, with around 90 options to choose from. This picturesque coastal town on the island of Oahu offers a range of neighbourhoods where these properties can be found, including the serene Lanikai area, known for its stunning beaches and tranquil atmosphere, as well as the vibrant Kailua Beach neighbourhood, which is great for outdoor enthusiasts.
Can I find long-stay holiday rentals in Kailua?
A long-stay holiday rental in Kailua is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Kailua?
In Kailua, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. These properties often come equipped with amenities such as spacious gardens, outdoor patios, and fully stocked kitchens, allowing for a comfortable stay. Many rentals are located close to the beautiful beaches of Kailua, where you can enjoy sunbathing and swimming, and some even offer easy access to pet-friendly areas.
Are there any remote work holiday rentals in Kailua?
In Kailua, Hawaii, there are numerous remote work holiday rentals available—around 217 options to choose from. This vibrant coastal town is known for its stunning beaches and lush landscapes, providing an inspiring backdrop for remote work. Many rentals offer amenities tailored for working professionals, such as high-speed Wi-Fi, dedicated office spaces, and comfortable desks and chairs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kailua holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Kailua with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Kailua?
In Kailua, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, along with refrigerators and microwaves for added convenience. Many rentals also feature coffee-making facilities, ensuring that visitors can enjoy a fresh brew to start their day.
How early should I book a Kailua holiday rental?
Book your Kailua holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kailua?
In Kailua, visitors can enjoy a variety of attractions that showcase the area's natural beauty and local culture. One of the main highlights is Kailua Beach, renowned for its soft sand and clear waters, great for swimming and kayaking. The nearby Lanikai Beach is equally picturesque, often praised for its stunning sunrises and the iconic Mokulua Islands just offshore, making it an ideal spot for a day of relaxation or water sports.
Can I change or cancel my Kailua home rental booking on Vrbo?
To find Kailua holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Kailua holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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