Photo by Lisa A Schmidt

Kailua holiday lettings

We found 5,025 holiday rentals — enter your dates for availability

Select from 148 houses, 42 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:29 May - 5 Jun

Image gallery for Luxurious Getaway

Bathroom
9.6 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)

Luxurious Getaway

Honolulu

7% off
Price is £2,002
for 7 nights, 1 apartment
£286 per night
includes taxes & fees
Luxurious Getaway

Find spaces that suit your style

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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:

  • Ala Wai Golf Course (10 mi / 16.2 km)
  • Honolulu Zoo (10.4 mi / 16.8 km)
  • Bay View Golf Course (3.2 mi / 5.1 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)

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)
  • Honolulu Harbor (10.6 mi / 17 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 is near Kailua Beach. This picturesque neighbourhood offers a stunning shoreline that's superb for swimming, sunbathing, and water sports, making it a popular choice for visitors. Here, you will find a variety of properties, ranging from charming beach cottages to more spacious family homes, providing options to suit different preferences.

Another delightful area to explore is Lanikai, renowned for its breathtaking views and tranquil atmosphere. The Lanikai Beach is often regarded as one of the most beautiful beaches in the world, with its soft sand and clear turquoise waters. Staying in this neighbourhood allows easy access to the iconic Mokulua Islands, which are a popular spot for kayaking and paddleboarding.

In both of these areas, you will not only enjoy the natural beauty but also be close to local attractions such as the Lanikai Pillbox Hike, which offers stunning panoramic views of the coast. Additionally, the vibrant local shops and eateries in Kailua town contribute to a charming and relaxed holiday experience.
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, the area around Kailua Beach Park is highly recommended. This picturesque stretch of coastline is known for its soft, white sands and clear turquoise waters, making it superb for swimming, paddleboarding, and sunbathing. Many properties in this vicinity offer amenities such as spacious outdoor decks, barbecues, and beach gear, ensuring a relaxing and enjoyable stay for families and groups.

Another great option is the area near Lanikai Beach, which is often considered one of the most beautiful beaches in the world. Rentals here typically feature stunning ocean views and easy access to the beach. Properties may include features like private swimming pools, lush gardens, and gourmet kitchens, ideal for those looking to enjoy a luxurious beach holiday.

Kailua itself offers a charming town atmosphere with local shops, cafes, and restaurants, making it convenient for guests to explore the local culture and cuisine. The nearby Mokulua Islands also provide opportunities for kayaking and hiking, and many beach rentals are equipped with kayaks or snorkelling gear to enhance your experience.
What is the most popular type of holiday rental accomodation in Kailua?
In Kailua, holiday houses are the most popular type of holiday rental, with around 588 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups looking to enjoy the beautiful Hawaiian surroundings. Additionally, there are approximately 172 apartments, which provide a more compact living option and typically include kitchen facilities and comfortable living areas. For those seeking a quaint experience, around 72 cottages are also available, often located in tranquil settings. While villas and condos are less common, there are still several options for travellers looking for luxury or resort-style amenities.
Are there any family house rentals in Kailua?
In Kailua, Hawaii, family-friendly house rentals are plentiful, with approximately 147 options available to choose from. This charming coastal town is great for families seeking a blend of relaxation and adventure. Many properties boast spacious living areas, fully equipped kitchens ideal for preparing meals, and outdoor spaces for barbecues or simply enjoying the stunning Hawaiian weather.

Neighbourhoods like Lanikai are particularly appealing, offering proximity to the beautiful Lanikai Beach, where families can indulge in swimming, kayaking, and beachcombing. Additionally, the area is close to the picturesque Mokulua Islands, great for a day of exploration.

Kailua also features spacious yards and amenities such as game rooms, which can keep the younger members of the family entertained during downtime.
Can I rent a holiday home with a pool or hot tub in Kailua?
In Kailua, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 81 options to choose from. This picturesque Hawaiian town offers a variety of neighbourhoods where these properties can be found, including the tranquil areas near Kailua Beach and Lanikai Beach, both renowned for their stunning landscapes and pristine waters.

Travellers can expect a range of amenities in these rentals, such as private swimming pools, relaxing hot tubs, and spacious outdoor areas superb for soaking up the sun. Many properties also come equipped with fully stocked kitchens, allowing for home-cooked meals, as well as comfortable living spaces ideal for families or groups.
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 is a variety of pet-friendly house rentals available, with around 19 options to choose from. Many of these properties are situated close to beautiful beaches, such as Kailua Beach and Lanikai Beach, which are ideal for enjoying the sun and surf with your furry friends. The holiday rentals typically come equipped with amenities like spacious backyards, outdoor grills, and fully-stocked kitchens, making them superb for families or groups looking to relax and enjoy the Hawaiian lifestyle.

Kailua is also home to several parks and outdoor spaces that welcome pets, such as Kailua District Park, which features walking paths and open areas for pets to play. Nearby, the Lanikai Pillbox hike offers stunning views and is a great way to explore the area's natural beauty with your pet.
Are there any remote work holiday rentals in Kailua?
In Kailua, Hawaii, there are numerous holiday rentals available for those looking to work remotely, with around 804 options to choose from. This picturesque town offers a tranquil setting with stunning beaches and lush landscapes, superb for combining work and leisure. Many properties come equipped with essential amenities like free Wi-Fi, ensuring reliable internet access for remote work.

Travellers can expect varied accommodations, ranging from spacious villas to charming beach cottages, often featuring dedicated workspaces or comfortable areas suitable for setting up a laptop. Additionally, many rentals provide outdoor spaces where one can enjoy the beautiful Hawaiian weather during breaks.

With nearby attractions like Kailua Beach and the scenic Lanikai Beach, residents can easily unwind after a day of work. The area is also home to local shops and eateries, adding convenience for those seeking a balance between productivity and relaxation. 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 with ease. Many properties also feature outdoor decks or patios, providing lovely spaces to relax and enjoy the tropical weather. Onsite parking is commonly available, adding convenience for those travelling with vehicles. Additionally, rentals often come with essentials such as blenders for smoothies and coffee or tea makers for a refreshing morning brew.
When is the best time to visit Kailua for a holiday rental?
April is a fantastic time to visit Kailua for a holiday rental, as it falls within the lovely peak season from March to May. During these months, the weather is warm and inviting, with average temperatures ranging from 23 to 29 degrees Celsius, making it ideal for beach activities and outdoor adventures.

In Kailua, the stunning beaches, such as Lanikai and Kailua Beach, are superb for sunbathing, swimming, and various water sports. Additionally, this period sees vibrant local events and cultural festivals, which enhance the overall experience of your stay. The lively option invites families, couples, and solo travellers alike to explore the natural beauty and charm of the area.

If you're looking for a more affordable option, consider visiting in October, when the crowds are thinner and the prices for holiday rentals tend to drop. This month offers the chance to enjoy the serene beauty of Kailua while still enjoying pleasant weather for hiking and exploring the lush landscapes.
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, Hawaii, visitors can enjoy a variety of attractions that showcase the area's natural beauty and vibrant culture. The stunning Kailua Beach Park is a must-visit, known for its powdery white sand and crystal-clear waters, superb for swimming, kayaking, and paddleboarding. Nearby, Lanikai Beach offers equally picturesque scenery and is often less crowded, making it a favourite spot for relaxation and beach activities.

For those interested in hiking, the Makapu'u Point Lighthouse Trail provides breathtaking views of the coastline and opportunities for whale watching during the migratory season. The trail is well-maintained and accessible for most fitness levels.

In the heart of Kailua, the local farmers' market is a great place to experience the island's fresh produce, artisanal goods, and local crafts, giving visitors a taste of the community spirit. The quaint downtown area is also worth exploring, with its charming shops, cafes, and restaurants that offer a variety of dining options, from casual bites to fine dining experiences.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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