Kailua vacation rentals

We found 4,879 vacation rentals — enter your dates for availability

Select from 165 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:Nov 28 - Dec 5

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

Exterior
10 out of 10 rating
Exceptional
(11 reviews)

Waimānalo Beach Cottages 2 min walk to the beach!

Waimanalo, HI

9% off
Price is $3,639
$25,470 for 7 nights
All fees included
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: Enjoy pristine shores like Lanikai Beach, perfect for sunbathing and water sports.
  • Outdoor Adventures: Engage in activities such as kayaking, paddleboarding, and hiking in lush landscapes.
  • Local Culture: Experience the vibrant Hawaiian culture through local festivals, art, and cuisine.
  • Family-Friendly Atmosphere: Kailua offers numerous parks and family-oriented activities, making it ideal for all ages.
  • Scenic Views: Explore picturesque bays and enjoy breathtaking sunsets that Kailua is known for.

Popular types of accommodation in Kailua

Kailua offers an array of vacation rentals to suit every traveler’s needs. From cozy condos and spacious houses to comfortable apartments, you’ll find the perfect spot to relax. Whether you're seeking Oahu vacation rentals, oceanfront escapes, or house rentals with multiple bedroom units, our platform provides transparent information and great savings. Discover the ideal accommodation for your Hawaiian getaway in Kailua.

  • Condos: The top choice for vacation rentals in Kailua, offering modern amenities and stunning views.
  • Houses: A popular option for those seeking spacious accommodations for families or groups.
  • Apartments: A favored selection for travelers wanting a cozy, independent stay close to local attractions.
  • Villas: Luxurious and stylish, these rentals provide ample space and privacy for a memorable getaway.
  • Cottages: Charming and quaint, perfect for a peaceful retreat amidst the natural beauty of Kailua.**

Top attractions in and around Kailua

Kailua is a perfect destination for outdoor and family beach vacations, offering stunning beaches and scenic views. Popular attractions include the beautiful beaches, picturesque bays, and local colleges. Whether you're seeking adventure or relaxation, Kailua provides a wonderful mix of experiences for travelers looking to enjoy the great outdoors and soak up the sun.

  • Lanikai Beach: Known for its powdery white sand and crystal-clear waters, Lanikai Beach offers a serene escape, perfect for sunbathing, swimming, and kayaking. The picturesque views of the Mokulua Islands enhance its charm.
  • University of Hawaii at Manoa: This vibrant campus features modern architecture and lush landscaping, making it an ideal spot for a leisurely stroll. The university's cultural events and galleries reflect Hawaii's diverse heritage.
  • Kaneohe Bay: A stunning bay surrounded by lush mountains, Kaneohe Bay is perfect for water sports, sailing, and enjoying breathtaking scenery. The tranquil atmosphere invites relaxation and exploration of its natural beauty.

Things to do recommended for couples

Looking for a romantic getaway in Kailua? Enjoy a fun evening at Glow Putt Mini Golf, just 4 miles away, where you can challenge each other in a playful atmosphere. For a touch of luxury, visit the Country Club, 8 miles away, and indulge in a beautiful, serene setting.

Things to do recommended for families

Your family can enjoy a day at Kaiona Beach Park, where relaxation meets fun. Explore the natural beauty of Waʻahila Ridge State Recreation Area or unwind at Kawaikui Beach Park, both offering wellness vibes just a short drive from Kailua.

Things to do recommended for groups

Experience a round of golf at the Royal Hawaiian Golf Club, hike the scenic Lanikai Pillboxes Trailhead for breathtaking views, or shop and dine at Kahala Mall, just 9 miles away, for a perfect mix of entertainment and family fun.

*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

If you're traveling with friends, family, pets, or planning an extended stay, be sure to refine your search based on what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Kailua with a group: Think about how many bedrooms you'll require, as well as additional features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily narrow your search for these options and more on Vrbo.
  • Traveling to Kailua with young kids: Traveling with young kids can be quite a task. It’s important to prioritize their comfort and safety, along with suitable amenities 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 families, a vacation wouldn't feel complete without their beloved furry companion. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels 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 rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Kailua

Kailua, an idyllic Hawaiian town, offers a perfect blend of outdoor adventure and family-friendly fun. With its stunning beaches, vibrant local culture, and lush landscapes, you'll find the best Kailua properties for a relaxing getaway. Explore nearby neighborhoods on Oahu, where romantic excursions and tropical atmospheres await. Whether you're enjoying water sports or simply soaking up the sun, Kailua promises an unforgettable vacation experience.

  • Kaneohe: Located 4 miles from Kailua, Kaneohe is a vibrant city that offers a unique blend of outdoor adventures and family-friendly experiences. Visitors can enjoy thrilling activities like the zipline ropes course and the arcade adventure zone. For those looking to relax, the local beaches and the picturesque bay provide perfect spots for sunbathing and swimming. With a shopping center nearby, travelers can also indulge in retail therapy while soaking in the beautiful surroundings.
  • Lanikai: Nestled near Kailua, Lanikai is a charming neighborhood known for its stunning beaches and outdoor recreational activities. This area is perfect for families and nature enthusiasts, offering access to scenic hiking trails and campgrounds. The picturesque Lanikai Beach, often ranked among the best in the world, beckons visitors for a day of sun and surf. The nearby urban park also provides a lovely space for picnics and leisurely strolls, making Lanikai a must-visit destination.
  • Kalama Tract: Located within the vicinity of Kailua, Kalama Tract is a delightful neighborhood that combines outdoor fun with a city-themed atmosphere. Ideal for families, this area features a golf course for enthusiasts and a shopping center for those looking to explore local shops. The nearby beaches and urban parks enhance the community vibe, providing ample opportunities for both relaxation and recreation. Kalama Tract’s inviting environment makes it a great spot for a memorable family outing.

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

Are you eager to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient way to plan new trips, manage your ongoing travel arrangements, and review your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 best area to stay in Kailua when booking a vacation rental?
When considering a vacation rental in Kailua, Hawaii, the Kailua Beach area is one of the best options. This neighborhood offers stunning views and easy access to the soft sands of Kailua Beach, making it superb for sunbathing, swimming, and water sports. The area is known for its vibrant atmosphere and proximity to popular attractions such as the picturesque Lanikai Beach and the scenic Lanikai Pillbox hike, which provides breathtaking panoramic views of the coastline.

Another great area to explore is the Kalama Beach Park neighborhood. This spot features a lovely park where visitors can enjoy picnics, beach volleyball, and even kayaking. Staying near Kalama Beach Park allows you to immerse yourself in the local community and enjoy a leisurely stroll along the waterfront. Additionally, it provides convenient access to shops and eateries, enhancing your vacation experience.

Both neighborhoods offer a variety of vacation rental properties, ranging from cozy beach cottages to spacious family homes, ensuring you'll find something that suits your needs.
How much does it cost to rent a vacation home in Kailua?
Prices for vacation 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 vacation 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, travelers should focus on the picturesque coastal neighborhoods along Kailua Beach and Lanikai Beach. Kailua Beach, known for its soft white sands and clear turquoise waters, has a variety of vacation rentals that offer amenities such as private beachfront access, outdoor showers, and spacious decks ideal for enjoying the stunning sunsets. Many properties also feature fully equipped kitchens and living areas with large windows that provide breathtaking ocean views.

Lanikai, famous for its beautiful kayak-friendly waters and the iconic Mokulua Islands, offers a selection of upscale beach homes. Here, visitors can expect amenities like swimming pools, lush tropical gardens, and easy access to hiking trails that lead to the Lanikai Pillbox lookout, which offers panoramic views of the coastline. Rentals in this area often include beach gear like kayaks and snorkeling equipment, making it easy to explore the vibrant marine life.

For those interested in local culture, Kailua Town is nearby, where charming shops, cafes, and farmers' markets are located, enhancing the overall experience. Find your rental near the beach in Kailua.
What is the most popular type of vacation rental accomodation in Kailua?
In Kailua, vacation houses are the most popular type of rental, with around 150 available throughout the area. These houses are typically situated in serene neighborhoods, providing a peaceful retreat just a short distance from the stunning beaches and outdoor activities that Kailua is known for. Most vacation houses come equipped with fully furnished kitchens, spacious living areas, and outdoor spaces, such as patios or decks, great for enjoying the island's beautiful weather.

Apartments are also a common option, with about 52 rentals available. These tend to be located closer to local shops and dining, offering travelers the convenience of urban amenities while still being near the beach. Most apartments feature essential amenities like kitchen facilities and comfortable living spaces.

Additionally, there are about 21 cottages available, which offer a quaint and charming alternative for those looking for a more unique stay. Villas and condos are also present, although in smaller numbers, providing more luxurious options for travelers seeking additional amenities and stunning views.
Are there any family house rentals in Kailua?
In Kailua, Hawaii, there are numerous family-friendly vacation rentals available, with around 164 options scattered throughout the area. The locale is celebrated for its stunning beaches, such as Kailua Beach and Lanikai Beach, making it an ideal destination for families seeking a coastal getaway. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for barbecues or enjoying the tropical weather.

Travelers can also find amenities like private pools, game rooms, and quick access to nearby parks, providing ample opportunities for outdoor fun and relaxation. The vibrant town center, with its local shops and restaurants, is just a short drive away, offering additional dining and entertainment options. See all family-friendly rentals in Kailua.
Can I rent a vacation home with a pool or hot tub in Kailua?
In Kailua, there are plenty of vacation homes available for rent that come with pools and hot tubs, with around 87 options to choose from. This beautiful area on the windward coast of Oahu is known for its stunning beaches and lush landscapes, providing an ideal backdrop for relaxation. Many of these rentals are located in residential neighborhoods close to Kailua Beach, where travelers can enjoy both comfort and convenience.

Expect to find amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens in these properties, making them great for families or groups looking to unwind after a day of exploring. Find your rental in Kailua with a pool or a hot tub.
Can I find long-stay vacation rentals in Kailua?
A long-stay vacation rental in Kailua is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Kailua?
In Kailua, there are numerous pet-friendly house rentals available, offering a great combination of comfort and convenience for travelers with pets. Many of these rentals come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces like patios or yards where pets can play.

The area is known for its stunning beaches, including Kailua Beach and Lanikai Beach, both of which are pet-friendly, allowing for enjoyable outings with your furry companions. Additionally, nearby parks, such as Kailua District Park and Lanikai Park, provide ample opportunities for walks and outdoor activities. See all pet-friendly rentals in Kailua.
Are there any remote work vacation rentals in Kailua?
In Kailua, Hawaii, there is a wide selection of remote work vacation rentals available, with around 211 options to choose from. This beautiful coastal town not only offers stunning beaches and a laid-back atmosphere but also provides amenities specifically designed for remote workers. Many properties feature dedicated workspaces, including desks and comfortable office chairs, along with high-speed Wi-Fi to ensure a productive environment. Some rentals even come equipped with additional technology like computer monitors and safe spaces for laptops.

Travelers can enjoy the benefits of working remotely while being close to vibrant local attractions, such as the picturesque Kailua Beach and the scenic Lanikai Beach, known for their soft sands and clear waters. The area also has nearby hiking trails, like the popular Lanikai Pillbox hike, which offers breathtaking views of the coastline. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Kailua vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Kailua with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens equipped with essential appliances like blenders and coffee/tea makers, and outdoor patios for enjoying the pleasant Hawaiian climate.
How early should I book a Kailua vacation rental?
Book your Kailua vacation 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 vacation 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 range of attractions that highlight the area's natural beauty and local culture. Kailua Beach Park is a major highlight, offering stunning sandy shores and clear waters superb for swimming, kayaking, and paddleboarding. Nearby, Lanikai Beach is renowned for its picturesque scenery and is often regarded as one of the best beaches in Hawaii.

For those interested in hiking, the Makapu'u Point Lighthouse Trail provides breathtaking views of the coastline and opportunities for whale watching during the season. The Kailua Town area offers a charming selection of shops, cafes, and local eateries, making it superb for a leisurely stroll after a day at the beach.
Can I change or cancel my Kailua home rental booking on Vrbo?
To find Kailua vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 vacation 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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