Kailua vacation rentals

We found 88 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Kailua to find one that's perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, like air conditioning and cable TV. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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Find out more about Kailua

Find out more about Kailua

Why visit Kailua

  1. Stunning beaches: Relax on Kailua's pristine shores and soak up the sun on world-renowned beaches.
  2. Outdoor activities: Enjoy kayaking, hiking, and exploring scenic state parks amidst breathtaking landscapes.
  3. Picturesque waterfalls: Discover the beauty of nearby waterfalls, perfect for a refreshing swim or a family outing.
  4. Charming village atmosphere: Explore the quaint shops and local eateries that showcase the spirit of Kailua.
  5. Variety of accommodations: Choose from beach house rentals, condos, and private vacation homes for a perfect stay.

Popular types of accommodation in Kailua

Planning a getaway to Kailua? The next exciting step is selecting your ideal accommodation. Explore a range of popular options, including condos, houses, and apartments. Whether you're looking for beach house rentals in Kailua or Oahu vacation rentals, we’ve got you covered with transparent information and great savings. Let us help you find the perfect place to unwind and enjoy the beauty of Oahu, Hawaii!

  • Condos: The top choice for vacation rentals in Kailua, offering modern amenities and convenient access to the beach.
  • Houses: A popular option for families and groups, providing a home-like atmosphere and privacy.
  • Apartments: Ideal for solo travellers or couples, these rentals offer comfort and accessibility in Kailua.
  • Villas: Luxurious spaces that provide upscale living and stunning views, perfect for a special getaway.
  • Cottages: Quaint and charming, these rentals offer a cozy and relaxed atmosphere for your stay.**

Top attractions in Kailua

Kailua, Hawaii is the perfect destination for outdoor enthusiasts and families seeking adventure. With stunning beaches, scenic state parks, and picturesque waterfalls, there's something for everyone. Whether you're looking to explore the beauty of Kailua, enjoy sightseeing, or simply unwind on a Hawaiian vacation, this charming locale offers a blend of romance and excitement. Don't miss the chance to immerse yourself in the natural wonders that Kailua has to offer during your visit!

  1. Haleakala National Park: Experience breathtaking scenery and outdoor adventures in this vast national park, located 19.3km from Kailua. The stunning volcanic landscapes and diverse ecosystems offer hiking trails that showcase the unique beauty of Maui.
  2. Maui Garden Of Eden - Botanical Gardens & Arboretum: Just 4.8km away, this enchanting botanical garden is perfect for families and couples alike. Wander through lush gardens filled with exotic plants, vibrant flowers, and serene walking paths.
  3. Twin Falls: Located 3.2km from Kailua, these picturesque waterfalls invite adventure seekers and romantics. Enjoy a refreshing dip in natural pools or relax amidst lush greenery, creating unforgettable memories.

Things to do recommended for couples

For a romantic getaway in Kailua, indulge in wellness treatments at Ho'omana Spa Maui or Enlighten Up Massage, both 11.3km away, or visit Maui Spa Retreat, 12.9km away. Experience relaxation and rejuvenation together, creating unforgettable memories in this beautiful Hawaiian paradise.

Things to do recommended for families

During your family vacation in Kailua, explore the wellness vibes at Haiku Park and Puaʻa Kaʻa State Wayside Park, both offering relaxing experiences. For some adventure, head to Science City, where fun-filled arcade games await everyone in the family.

Things to do recommended for groups

Experience thrilling outdoor adventures with your group in Kailua! Enjoy a scenic bike ride with Haleakala Bike Company, hike the beautiful Waikamoi Ridge Trail, or play a round of golf at Pukalani Country Club, all within a short drive from Kailua.

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

When planning your trip, whether you're travelling with a group, your family, or pets, or seeking extended stays, it's important to prioritise your preferences. 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 amenities like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kailua with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kailua: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Kailua: If you're seeking vacation rentals with 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 rental options. Also, think about including features such as a parking spot, a well-equipped kitchen, or a private pool in your search.

Where to stay in Kailua

Kailua, Hawaii, is a tropical paradise perfect for outdoor adventures and family vacations. With its serene beaches and lush landscapes, visitors can explore the beauty of this charming village and nearby regions. Enjoy kayaking on the crystal-clear waters, basking in the sun, or taking romantic strolls along the shore. Whether you're seeking relaxation or adventure, Kailua offers a unique blend of experiences that will leave you enchanted and eager to return.

  • Huelo: Nestled a mere 1.3km from Kailua, Huelo offers visitors a serene escape into nature. This charming village is perfect for those seeking outdoor adventures and beautiful scenery. Enjoy a delightful beach experience along the coast, or explore the nearby botanical gardens for a peaceful afternoon. Huelo also features shopping centres and recreational areas, making it an ideal spot for relaxation and exploration. Whether you're lounging on the beach or wandering through local shops, Huelo provides a unique blend of tranquility and excitement.
  • Ulumalu: Located 6.4km away from Kailua, Ulumalu is a haven for adventure seekers and outdoor enthusiasts. The village boasts stunning scenery and an array of activities, including hiking trails that wind through lush landscapes and pristine campgrounds perfect for a weekend getaway. Visitors can explore the nearby national state park, where awe-inspiring vistas and diverse wildlife await. With its excellent recreational areas and breathtaking beaches, Ulumalu is an ideal destination for those looking to immerse themselves in the natural beauty of Hawaii.
  • Keanae: Just 8.0km from Kailua, Keanae is a delightful village that caters to families and adventure lovers alike. This picturesque location is rich in natural beauty, featuring stunning beaches and an array of outdoor activities. Families can enjoy urban parks and the local botanical garden, providing a perfect setting for a day of exploration and fun. Keanae's unique charm and vibrant atmosphere make it a must-visit destination for anyone looking to experience the best of Hawaii's outdoor lifestyle.

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 from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January70.7°F (21.5°C)Light RainMostly SunnySlightly HighSlightly High
February70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
March70.3°F (21.3°C)Light RainMostly SunnySlightly HighAverage
April71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
May72.9°F (22.7°C)Light RainMostly SunnyAverageSlightly Low
June73.6°F (23.1°C)Light RainMostly SunnyAverageAverage
July74.8°F (23.8°C)Light RainMostly SunnyAverageAverage
August75.4°F (24.1°C)Light RainMostly SunnySlightly LowAverage
September75.7°F (24.3°C)Light RainMostly SunnySlightly LowSlightly Low
October75.6°F (24.2°C)Light RainMostly SunnySlightly LowSlightly Low
November73.8°F (23.2°C)Light RainMostly SunnyAverageAverage
December71.8°F (22.1°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next getaway? It’s a great idea to be flexible with your travel dates, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new adventures, pick up right where you left off, or manage and arrange your travel plans. You can easily access properties you've saved or booked in the sections labelled Potential, Upcoming, or Current Trips. To explore and utilize Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Kailua getaway

Experience the unique character of Kailua with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Kailua

Are you looking for things to do while you're in town? Venture out of your vacation home and experience everything that makes Kailua a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Ho'omana Spa Maui (6.6 mi / 10.6 km)
  • Maui Spa Retreat (7.8 mi / 12.5 km)
  • Pukalani Country Club (9.5 mi / 15.3 km)
  • King's Highway (15.8 mi / 25.4 km)
  • Haleakala Bike Company (6.9 mi / 11.2 km)
  • Enlighten Up Massage (7.4 mi / 11.9 km)

Exploring the natural features in Kailua

Whether you're an outdoor enthusiast or just want to take in the scenery, Kailua is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Twin Falls (2 mi / 3.2 km)
  • Garden of Eden Arboretum (3 mi / 4.8 km)
  • Maui Garden Of Eden - Botanical Gardens & Arboretum (3.2 mi / 5.1 km)
  • Haiku Park (7.3 mi / 11.8 km)
  • Hookipa Beach Park (9.5 mi / 15.3 km)
  • Kuau Bay Beach (10 mi / 16.1 km)

How to get to and around Kailua

The nearest airport is in Kahului Airport (OGG), located 14.3 mi (22.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Hana, HI (HNM), which is 14.8 mi (23.9 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Kailua?
The average price for a vacation rental in Kailua depends on a number of factors, such as property type, season and length of stay. Whether you’re searching for a sprawling house with room for friends and family or a quaint cabin that’s perfect for two, just add your dates of travel to see some great-value stays.
How much does it cost to rent a beach house in Kailua?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside vacation rental. Put in your Kailua travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want.
What are the top attractions for families in Kailua?
Treat the kids to a good time at these cool family-friendly attractions in Kailua:

  • Twin Falls
  • Haiku Park

How old do you have to be to rent a vacation rental in Kailua?
We advise checking with the Kailua vacation property you’re considering on Vrbo as the age limit differs. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Kailua for?
The length of time you can rent a vacation rental in Kailua is down to the property. Simply enter your preferred dates to view a list of options offering extended stays. With a range of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to discover somewhere perfect to call your home away from home in Kailua.

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