Kailua holiday lettings

We found 4,986 holiday rentals — enter your dates for availability
Select from 141 houses, 38 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.

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Kailua

  • Stunning beaches: Relax on the soft sands of Kailua Beach and Lanikai Beach, both renowned for their clear turquoise waters and idyllic settings.
  • Outdoor adventures: Hike the scenic trails of the nearby Olomana Mountains, offering breathtaking views of the coastline and lush landscapes.
  • Paddleboarding: Enjoy paddleboarding in the calm waters of Kailua Bay, perfect for both beginners and experienced enthusiasts.
  • Botanical gardens: Explore vibrant local botanical gardens that showcase Hawaii's unique flora and provide tranquil spaces for relaxation.
  • Charming local town: Experience the laid-back atmosphere of Kailua's town centre, featuring local shops, cafes, and cultural experiences.

Popular types of accommodation in Kailua

Nestled in the stunning landscapes of Honolulu County, Kailua offers a perfect blend of relaxation and adventure. Visitors can explore the beautiful beaches, such as Lanikai and Kailua Beach, renowned for their soft sands and turquoise waters. Enjoy hiking the scenic trails of the nearby Olomana Mountains or paddleboarding in the calm bay. For your stay, popular accommodation choices include condos, private holiday homes, and well-equipped apartments, ensuring a comfortable retreat after a day of exploration.

  • Condos: These modern, often spacious units are the most sought-after choice for visitors, offering stunning views and convenient amenities.
  • Houses: Ideal for families or groups, these homes provide a home-like atmosphere with added privacy and comfort.
  • Apartments: A practical option, these self-contained spaces are perfect for couples or solo travellers seeking convenience.
  • Villas: Luxurious and often expansive, villas provide an upscale retreat with beautiful surroundings.
  • Cottages: Charming and quaint, cottages offer a cosy escape with a touch of local character.**

Top attractions in and around Kailua

Kailua, located in Honolulu County, Hawaii, is a picturesque destination ideal for outdoor and family beach vacations. Visitors can enjoy the stunning Kailua Beach, known for its soft sands and clear waters, as well as explore the scenic bay and vibrant botanical gardens. This charming town offers a perfect blend of relaxation and cultural experiences, making it an excellent spot for those seeking adventure and natural beauty in a tranquil setting.

  • Lanikai Beach: Known for its stunning turquoise waters and soft, white sand, Lanikai Beach offers the quintessential Hawaiian beach experience. It's perfect for sunbathing, swimming, and kayaking, with a serene atmosphere that invites relaxation.
  • Kaneohe Bay: Just 5km from Kailua, this picturesque bay features breathtaking scenery and outdoor activities like snorkelling and paddleboarding, making it ideal for nature lovers and adventure seekers.
  • Ho'omaluhia Botanical Garden: Located 6km away, this expansive garden showcases lush tropical landscapes, tranquil walking paths, and romantic spots, perfect for families and couples alike.

Things to do recommended for couples

Looking for a romantic getaway in Kailua? Enjoy a sunset picnic on the stunning Lanikai Beach, or take a leisurely kayak ride to the beautiful Mokulua Islands. Don't miss a stroll through the charming town for local shops and dining experiences perfect for couples.

Things to do recommended for families

Families visiting Kailua can enjoy a day at the stunning Kailua Beach, where children can play in the gentle waves, and explore the lush landscapes of Lanikai Pillbox Hike for breathtaking views. Don't miss the vibrant local markets for unique souvenirs and delicious Hawaiian treats.

Things to do recommended for groups

Groups visiting Kailua can enjoy a thrilling day of kayaking to the picturesque Mokulua Islands, followed by a relaxing afternoon on the stunning Lanikai Beach, known for its soft sands and clear waters. Don’t miss out on local food trucks for a taste of Hawaiian cuisine.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Regardless of whether you are travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Kailua with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kailua with young kids: Journeying with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Kailua: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely 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 right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Kailua

Kailua, nestled in Honolulu County, Hawaii, is a picturesque haven perfect for outdoor and family-friendly vacations. With its stunning beaches and vibrant local town, visitors can enjoy a relaxed tropical atmosphere. From exciting excursions to tranquil moments by the shore, Kailua offers a delightful blend of experiences. The pleasant weather year-round enhances the charm, while the local amenities ensure a comfortable stay, making it an ideal destination for those seeking both adventure and relaxation.

  • Kaneohe: Located approximately 6km from Kailua, Kaneohe is a vibrant city that offers an array of outdoor adventures and leisurely beach experiences. Renowned for its family-friendly atmosphere, visitors can enjoy thrilling activities such as ziplining at local adventure parks or having fun at the arcade adventure zone. Golf enthusiasts will find several picturesque courses to enjoy. Among the highlights are the beautiful beaches and urban parks, perfect for a day of relaxation or family picnics. With its stunning views of the Ko'olau mountains, Kaneohe is an inviting destination for those seeking both excitement and natural beauty.
  • Lanikai: Nestled in the vicinity of Kailua, Lanikai is a picturesque neighbourhood famed for its pristine beaches and outdoor recreational opportunities. This area is ideal for families looking to immerse themselves in nature, with access to scenic hiking trails that lead to breathtaking views of the ocean and the Mokulua Islands. The sandy shores of Lanikai Beach are perfect for sunbathing and swimming, while the nearby campgrounds offer a chance to connect with nature. With its tranquil atmosphere and stunning landscapes, Lanikai is a dreamy spot for relaxation and adventure alike.
  • Kalama Tract: Located in close proximity to Kailua, Kalama Tract is a charming neighbourhood that blends outdoor enjoyment with a bustling city vibe. Families will appreciate the variety of amenities, including shopping centres and malls, where one can find everything from local goods to international brands. The area is also home to inviting campgrounds, perfect for a family outing or a weekend getaway. With easy access to beautiful beaches and urban parks, Kalama Tract offers a delightful mix of leisure and fun for visitors looking to explore the best of what Kailua has to offer.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageAverage
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 LowSlightly Low
December74.5°F (23.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform for you to plan new journeys, continue from where you last stopped, or manage your existing arrangements. You can easily access the properties you've saved or reserved, organised into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please 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 Walk 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)
  • Waialae Country Club (9.4 mi / 15.1 km)
  • Waikele Golf Club (17.1 mi / 27.6 km)
  • Ewa Beach Golf Club (17.3 mi / 27.9 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)
  • Lanikai Beach (1.7 mi / 2.7 km)
  • Honolulu Harbor (10.6 mi / 17 km)
  • Diamond Head (10.6 mi / 17 km)
  • Kalama Beach Park (0.2 mi / 0.3 km)
  • Kailua Bay Beach (0.8 mi / 1.2 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.

More holiday ideas