Kailua vacation rentals

We found 4,811 vacation rentals — enter your dates for availability

Select from 160 houses, 58 apartments, and other vacation rentals to find the perfect place for your stay in Kailua. Vacation rentals provide the best amenities for your family, friends, or furry companion, like air conditioning and WiFi. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Kailua

Showing deals for:Aug 1 - Aug 8

Find out more about Kailua

Find out more about Kailua

Why visit Kailua

  1. Stunning Beaches: Enjoy the breathtaking beauty of Kailua Beach and Lanikai Beach, perfect for sunbathing, swimming, and water sports.
  2. Outdoor Adventures: Engage in activities like kayaking, hiking, and snorkeling in the area's scenic bays and lush landscapes.
  3. Family-Friendly Atmosphere: Experience a welcoming environment with parks and safe beaches, ideal for families and children.
  4. Cultural Immersion: Discover local culture through vibrant community events, markets, and traditional Hawaiian experiences.
  5. Charming Accommodations: Choose from a variety of cozy vacation rentals, from beachside condos to quaint cottages.

Popular types of accommodation in Kailua

If you're looking for the perfect getaway in Kailua, you have plenty of great options. Our most popular accommodations include cozy condos, spacious apartments, convenient apart-hotels, and charming studio cottages. Whether you prefer a sleek apartment, a comfortable Kailua motel, or a welcoming house, you'll find a variety of choices to suit your needs. Enjoy your stay with transparency and reassurance while making unforgettable memories in beautiful Kailua!

  • Condos: The top choice for visitors to Kailua, condos offer modern amenities and convenient locations close to the beach.
  • Apartments: A favored option among travelers, apartments provide a comfortable and home-like feel, perfect for longer stays.
  • Houses: Ideal for families or groups, these homes allow for a more personalized and spacious experience.
  • Villas: Luxurious and spacious, villas offer stunning views and upscale living for a premium getaway.
  • Cottages: Quaint and charming, cottages provide a cozy atmosphere for a relaxing retreat.**

Top attractions in Kailua

Kailua is the perfect destination for outdoor enthusiasts and families seeking a beach vacation. With stunning beaches, scenic bays, and vibrant urban parks, there's a wealth of attractions to explore. Whether you're looking to soak up the sun, engage in outdoor activities, or immerse yourself in the local culture, Kailua offers something for everyone. Make your trip unforgettable by discovering the natural beauty and unique experiences this charming area has to offer.

  1. Waikiki Beach: Famous for its golden sands and vibrant atmosphere, Waikiki Beach offers stunning views, surf opportunities, and beach activities, making it a quintessential Hawaiian experience.
  2. Waikiki Beach Walk: This lively esplanade features shops, restaurants, and entertainment options, perfect for families and couples seeking a romantic evening while enjoying the outdoors.
  3. Honolulu Harbor: With breathtaking scenery and a lively maritime vibe, Honolulu Harbor is ideal for scenic strolls, photography, and soaking in the beauty of the ocean.

Things to do recommended for couples

Experience romance in Kailua with a concert at Waikiki Shell, just 11 miles away, or enjoy a fun-filled evening at Glow Putt Mini Golf, 4 miles from your stay. For a touch of luxury, visit the exclusive Country Club, located 8 miles away. Your perfect getaway awaits!

Things to do recommended for families

Families visiting Kailua can relax at Kaiona Beach Park, only 6 miles away, or explore the scenic trails at Waʻahila Ridge State Recreation Area, 8 miles from town. For sports enthusiasts, Aloha Stadium, located 13 miles away, offers an exciting atmosphere suitable for the whole family.

Things to do recommended for groups

Explore the vibrant Ala Moana Center for shopping and entertainment, tee off at the scenic Royal Hawaiian Golf Club, or embark on an adventurous hike at Lanikai Pillboxes Trailhead for stunning views. These activities promise a memorable group experience in Kailua.

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

When traveling with a group, family, pets, or planning for extended stays, it's important to set your priorities when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Kailua with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Kailua with young kids: Traveling with young kids can be a bit daunting. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your trip.
  • Taking your pets with you to Kailua: For many families, a vacation wouldn't feel complete without their furry companions. If you relate to this, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Kailua: If you're in search of vacation 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in Kailua

Discover the tropical paradise of Kailua, where stunning Hawaiian beachfronts meet a family-friendly atmosphere. Enjoy outdoor adventures, romantic sunsets, and relaxing days by the ocean. From vibrant local excursions to the serene beauty of the nearby neighborhoods, your travel experience in Kailua will be filled with unforgettable moments and the essence of island life. Get ready to explore the best of what this charming destination has to offer!

  • Honolulu: Honolulu, located 10 miles from Kailua, is the vibrant capital city of Hawaii and a hub for outdoor, family, and beach experiences. Visitors flock to its stunning beaches, including the famous Waikiki Beach, offering a perfect spot for sunbathing, swimming, and surfing. The city is also home to a variety of shopping centers and malls, making it easy to find souvenirs and local crafts. Don't miss the iconic landmarks such as Diamond Head and Pearl Harbor, where you can immerse yourself in the rich history and culture of Hawaii while enjoying breathtaking views.
  • Waikiki: Approximately 10 miles from Kailua, Waikiki is a lively neighborhood known for its beautiful beaches and vibrant atmosphere. It attracts families and travelers of all ages seeking outdoor adventures, from surfing lessons to beach volleyball. Waikiki boasts an array of shopping options, from high-end boutiques to local markets. The area is rich in attractions, including the Honolulu Zoo and the Waikiki Aquarium, making it an ideal destination for family outings. As the sun sets, the beachfront transforms into a lively scene with restaurants and entertainment, perfect for a fun evening out.
  • Kaneohe: Just 4 miles away from Kailua, Kaneohe is a picturesque city offering a mix of outdoor activities and family-friendly fun. Adventure seekers can enjoy a zipline ropes course or explore the arcade adventure zone, while those looking for relaxation can visit the serene beaches and parks in the area. Kaneohe is known for its stunning scenery, including the majestic Ko'olau Mountains, providing a beautiful backdrop for outdoor picnics and hikes. The welcoming community atmosphere makes it an excellent location for a day trip filled with adventure and exploration.

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 HighSlightly High
April74.1°F (23.4°C)No Rain (Dry)Mostly SunnySlightly HighSlightly Low
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 LowAverage
November76.5°F (24.7°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
December74.5°F (23.6°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. It's truly rewarding to take on the planning role! By becoming a member of our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash™ on eligible reservations. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your journeys. You can create new trips, continue from where you last left off, or manage your travel plans all in one place. Your saved or booked properties are neatly organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The laid-back Kama’aina lifestyle in Kailua

Called Kailua Town by residents, Kailua is a buzzing beach community where a laid-back lifestyle is the rule. If turquoise water and white sand on Oahu’s windward coast aren’t enough for you, jump into trendy boutiques, stop off at popular eateries, and hang out with the kama’aina (locals) at the Thursday evening farmers’ market. Distinctive ingredients put a twist on the island cuisine here, and unique boutiques offer treasures to commemorate your stay in any one of the Kailua vacation rentals.

An Aloha adventure in Kailua

Water is the watchword here, and Lanikai Beach or Kalama Beach Park, the Kawai Nui Marsh wetlands, or Maunawili Falls may just float your boat. From stunning sunrises to spectacular sunsets, the 1-mile Lanikai Pillbox hike offers a sweeping panoramic view of land and sea from concrete bunkers, built between WWI and WWII as part of Oahu’s coastal defense system. And, within a stone’s throw of the shore, Moku Nui, Moku Iki, and Flat Island are a meditative mantra to while away the hours on the silky soft sand of Kailua Beach. Experience all the warmth and hospitality of the Aloha spirit at family-friendly Kailua vacation rentals.

Land and sea is all you need in Kailua

Surf, kitesurf, windsurf, or kayak are the best ways to explore this area. Kailua Beach is a reef-protected bay where beauty and safety reign supreme, so swimming and snorkeling are stress-free. Head out for a hike or a round of golf in this lush, green paradise. Take a picnic blanket, and enjoy local favorites as you listen to live music at the Kailua Farmers’ Market. If you’re a fan of the slower island pace, Kailua has the small-town vibe that delivers an authentic Hawaiian experience. Kailua vacation rentals offer the calm you crave and the family fun you want.

A tropical paradise in Kailua

With an annual average temperature of 71°F, inching up to 80 or so in summer, any season is a good time to visit Kailua. Lush and tropical, passing showers in winter months won’t dissuade you from hanging loose under the sun, and coastal trade winds will temper any high humidity in summer. Keep in mind that high season in Hawaii runs from mid-December through March or mid-April, since snowbirds from colder climes like to wing their way to paradise at that time, though Kailua is still somewhat of an Oahu hideaway.

Kailua—a natural beauty

Located on the leeward side of the Nu’uanu Pali peak, crescent-shaped Kailua Bay is sheltered from the hustle and bustle of Honolulu. Crystal blue water and silky white sand invite visitors to come and stay awhile. Meaning heavenly sea in Hawaiian, Lanikai Beach is another mile-long stretch that is a favorite of many locals. Once the center of life for early Kailuans, the Kawai Nui Marsh is a protected wetland, providing a habitat to many wildlife species, and a peaceful trail. Hike in Maunawili Falls are the most accessible in Oahu and cascade 15 to 30 feet into a cool mountain pool.

Transportation to and around Kailua

The nearest airport is in Daniel K. Inouye Intl. Airport (HNL), located 12.6 mi (20.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can 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 vacation rental accommodation in Kailua?
The most desirable types of vacation rentals in Kailua are cottages. Looking for something different? Vrbo has numerous options to match the unique needs of our guests, so you’ll see properties in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — lock in yours today.
How much does it cost to rent a vacation rental in Kailua?
Length of stay, property type and season are some factors that can affect the price of a vacation home. Simply click on your travel dates to find your perfect escape. From cozy country cottages to expansive luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Kailua?
Prices for beach houses in Kailua can vary depending on the size and type of the property and when you’re traveling. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to tailor your search results by ratings, nearby activities and more.
What are popular rental amenities in Kailua?
When it comes to rental amenities that people search for in Kailua, a barbecue grill, an ocean view and a water view rank highest. With Vrbo vacation homes, you’ll find options to suit your taste and style, whether you’re going on a vacation with family, friends or even pets.
What are the top attractions for families in Kailua?
Keeping the kids occupied during your vacation in Kailua is a snap with these leading family-friendly attractions:

  • Kaneohe Klipper Golf Course
  • Lanikai Beach
  • Kailua Beach

Can I find two-bedroom vacation rentals in Kailua?
Kailua has 46 two-bedroom vacation rentals to choose from. Discover a vacation home with all the comfort and privacy you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Kailua?
Kailua has 128 vacation rentals with WiFi, so you can stay connected during your trip. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to checking emails, these Vrbo homes make it a breeze to get online.
How old do you have to be to rent a vacation rental in Kailua?
The minimum age permitted can vary across properties on Vrbo, so be sure to check the rules of the vacation rental in Kailua you’re considering. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Kailua for?
The length of time you can book a vacation rental in Kailua varies according to the property. Simply enter your chosen dates to look at a list of options offering extended stays. With loads of creature comforts such as washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to get a terrific place to call your home away from home in Kailua.
Does Vrbo offer discounts for vacation homes in Kailua?
On Vrbo, we’ve got plenty of fantastic discounts and bargains for Kailua. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re after a weekend retreat or an extended escape, Vrbo offers options for all budgets and styles.

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