Kailua vacation rentals

We found 4,888 vacation rentals — enter your dates for availability

Select from 164 houses, 57 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 14 - Nov 21

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

10% off
Price is CA $4,222
CA $39,291 total
includes taxes & fees
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

  1. Stunning Beaches: Enjoy the beautiful beaches of Kailua, perfect for sunbathing, swimming, and beach activities.
  2. Outdoor Adventures: Engage in various outdoor activities like kayaking, hiking, and stand-up paddleboarding in scenic locations.
  3. Charming Kailua Town: Explore the vibrant town filled with local shops, art galleries, and delightful cafes.
  4. Family-Friendly Activities: Discover family-oriented attractions and relaxing spots ideal for all ages.
  5. Cozy Accommodations: Choose from a range of vacation rentals, including charming beach bungalows and private homes.

Popular types of accommodation in Kailua

Planning a getaway to Kailua? You're in for a treat! Discover the charm of this stunning destination with a variety of vacation rentals to suit your needs. From cozy beach bungalows and condos to spacious houses and apartments, Kailua offers the perfect base for your adventures. Experience the beauty of Oahu while enjoying a comfortable stay with our transparent and reliable vacation rental options.

  • Condos: The top choice for visitors to Kailua, offering modern amenities and convenient locations near the beach.
  • Houses: A popular option for families and groups, providing spacious living and a home-like atmosphere.
  • Apartments: Ideal for solo travellers or couples seeking comfort and accessibility in a compact space.
  • Villas: Luxurious accommodations with stunning views, perfect for those wanting an upscale experience.
  • Cottages: Quaint and charming, these provide a cozy retreat amid the natural beauty of Kailua.**

Top attractions in Kailua

Kailua, located in Honolulu County, is perfect for outdoor adventures and family beach vacations. Visitors can enjoy stunning beaches, scenic bays, and modern educational institutions, making it an ideal destination for those seeking relaxation and picturesque views. With a variety of attractions that cater to different interests, Kailua promises memorable experiences for all travellers looking to immerse themselves in Hawaii's natural beauty.

  1. Lanikai Beach: Renowned for its soft, powdery sand and crystal-clear waters, Lanikai Beach offers a tranquil paradise perfect for sunbathing, swimming, and paddleboarding. The picturesque backdrop of the Mokulua Islands adds to its charm, making it a must-visit for beach lovers.
  2. University of Hawaii at Manoa: This vibrant campus showcases modern architecture and lush landscapes, offering a unique blend of city vibes and rich cultural experiences. Explore its art galleries, botanical gardens, and diverse student activities.
  3. Kaneohe Bay: A stunning bay known for its breathtaking scenery and outdoor activities. Enjoy kayaking, snorkeling, or simply relaxing on its serene beaches while taking in views of the lush mountains surrounding the bay.

Things to do recommended for couples

For a romantic getaway in Kailua, indulge in a fun evening at Glow Putt Mini Golf, just 6.4km away, or unwind at the luxurious Country Club, located 12.9km from the heart of Kailua. Both spots promise a memorable experience for couples!

Things to do recommended for families

Families visiting Kailua can unwind at Kaiona Beach Park, enjoy the serene Waʻahila Ridge State Recreation Area, and relax at Kawaikui Beach Park. Each location offers a perfect blend of wellness and family-friendly activities, making for a memorable Hawaiian getaway.

Things to do recommended for groups

Experience the thrill of golf at the Kaneohe Klipper Golf Course, hike the scenic Lanikai Pillboxes Trailhead for breathtaking views, and immerse yourselves in culture at the Hawaii Theater, located 16.1km away, perfect for an entertaining evening with family and friends.

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

If you're planning a trip with a group, family, pets, or seeking extended stays, it's essential to prioritize your preferences when filtering options. Here are some helpful booking tips for Vrbo.

  • Traveling to Kailua with a group: Think about how many bedrooms you require, along with features 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: Travelling with young children can present its own set of challenges. 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, a family vacation isn't truly complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels 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 rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Kailua

Kailua offers an idyllic escape for those seeking outdoor adventures and family-friendly experiences. With its stunning Kailua Bay, vibrant Kailua Town, and charming beach bungalows, visitors can immerse themselves in a relaxing atmosphere filled with art and recreation. Whether you're exploring the picturesque beaches or embarking on exciting excursions, Kailua promises a memorable vacation that perfectly blends relaxation and adventure.

  • Lanikai: Nestled along the eastern coast of Kailua, Lanikai is renowned for its stunning beach and vibrant outdoor activities. Visitors are drawn to its picturesque white sand beaches and clear turquoise waters, making it perfect for swimming, kayaking, and sunbathing. The renowned Lanikai Pillbox Hike offers breathtaking views of the Mokulua Islands and is a must for adventure seekers. Families can enjoy picnics at the nearby urban park, creating lasting memories surrounded by natural beauty.
  • Kalama Tract: Located a short distance from Kailua, Kalama Tract is a charming neighbourhood that balances outdoor fun with urban conveniences. This area is perfect for families, offering access to golf courses and shopping centres where you can find everything from local boutiques to larger retail stores. The nearby beaches and urban parks provide ample opportunities for relaxation and recreational activities, making it an ideal spot for both leisure and adventure.
  • Enchanted Lake: Enchanted Lake is a delightful community close to Kailua that offers a blend of outdoor experiences and urban amenities. Ideal for families, this neighbourhood features access to golf courses and shopping centres, ensuring that there's something for everyone. The picturesque lake itself is perfect for leisurely strolls or picnics, while the proximity to pristine beaches and urban parks invites visitors to explore and unwind in a serene 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.

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 simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often allows for significant 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 Trip Board offers a user-friendly platform for planning your travels. Whether you're starting a new adventure, resuming an existing one, or organizing your itinerary, you'll find it all in one place. Your saved or booked properties will be neatly categorized under Potential, Upcoming, or Current Trips for easy access. To begin using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Kailua

The island views and surrounding scenery provide a peaceful ambiance to your vacation 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-sees in the area. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Kailua

Do you want to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kailua a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Kaneohe Klipper Golf Course (3.4 mi / 5.5 km)
  • Honolulu Zoo (10.4 mi / 16.8 km)
  • Ko'olau Golf Club (3.6 mi / 5.8 km)
  • Waialae Country Club (9.4 mi / 15.1 km)
  • Ala Wai Golf Course (10 mi / 16.2 km)
  • Mamala Bay Golf Course (13.9 mi / 22.3 km)

Exploring the beaches and other natural features in Kailua

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Kailua. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Waikiki Beach (10.4 mi / 16.8 km)
  • Kalama Beach Park (0.2 mi / 0.3 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

Travelers enjoy Kailua for its snorkeling. If you're planning a vacation around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 78°F.

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 most highly recommended area to stay is the charming neighbourhood of Lanikai. This picturesque locale is well-known for its stunning beaches, particularly Lanikai Beach, which boasts powdery white sand and crystal-clear waters, making it a great spot for swimming, kayaking, and paddleboarding. Additionally, the nearby Mokulua Islands offer opportunities for a scenic boat trip or a leisurely swim.

Another appealing option is the Kailua Town area, which provides a vibrant atmosphere with an array of shops, cafes, and restaurants. Here, you can enjoy the local culture and cuisine, as well as visit attractions like the Kailua Farmers Market, where you can sample fresh produce and artisanal goods. The town is also conveniently located near Kailua Beach Park, a popular destination for sunbathers and water sports enthusiasts alike.
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 travelling 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.
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, the most desirable areas are along Kailua Beach and Lanikai Beach, both renowned for their stunning turquoise waters and soft, white sands. Properties located near Kailua Beach Park offer easy access to the beach and often come with amenities such as outdoor showers, large lanais for dining and relaxing, and beach gear like kayaks or paddleboards. Many homes in this area are family-friendly, featuring spacious living areas and fully equipped kitchens, superb for preparing meals after a day in the sun.

Lanikai, known for its picturesque scenery and tranquil atmosphere, has some exquisite beachfront properties. Here, travellers can find luxury rentals that may include private pools, expansive decks with ocean views, and direct beach access. These homes often come with modern conveniences such as air conditioning, high-speed internet, and outdoor barbecue facilities, making them ideal for both relaxation and entertaining. 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 accommodation, with around 150 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or patios, making them ideal for families or groups looking to enjoy the beautiful Hawaiian scenery. Additionally, there are approximately 51 apartments, which provide a more compact option for couples or solo travellers, typically including essentials like kitchenettes and access to shared amenities. Cottages and several villas are also available, offering unique charm and a tranquil setting, while mobile homes provide an alternative, more adventurous lodging experience.
Are there any family house rentals in Kailua?
In Kailua, Hawaii, there are numerous family-friendly house rentals available, with around 163 options to choose from. This beautiful locale is known for its stunning beaches, like Kailua Beach and Lanikai Beach, both of which are superb for family outings. Many of these properties offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play or where families can gather for barbecues.
Can I rent a vacation home with a pool or hot tub in Kailua?
In Kailua, there are a variety of vacation homes available for rent, with around 90 options featuring pools or hot tubs. This picturesque Hawaiian town is known for its beautiful beaches and lush surroundings, making it a fantastic choice for travellers seeking relaxation and adventure. 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. 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 are numerous pet-friendly house rentals available, offering a delightful escape in this picturesque Hawaiian locale. Many of these homes come with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces that often include private gardens or lanai, superb for enjoying the tropical climate.

The area is renowned for its stunning beaches, such as Kailua Beach and Lanikai Beach, both of which are easily accessible from many of the rental properties. These beautiful sandy shores provide ample opportunities for pet owners to enjoy walks along the beach or fun days out with their furry companions.
Are there any remote work vacation rentals in Kailua?
In Kailua, Hawaii, there are plenty of remote work vacation rentals available, with around 217 options to choose from. This vibrant coastal town is not only known for its stunning beaches and lush landscapes but also offers a conducive environment for remote work. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces featuring desks and ergonomic chairs, and often additional comforts like computer monitors and safes for added security. 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 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 vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, along with refrigerators and microwaves for added convenience. Many rentals also feature coffee-making facilities, ensuring that visitors can enjoy a fresh brew to start their day.
When is the best time to visit Kailua for a vacation rental?
April is the most popular month to visit Kailua, as it falls within the peak season from March to May. This period is particularly appealing to travellers seeking a blend of relaxation and adventure, with warm temperatures averaging around 27°C, making it great for outdoor activities like kayaking and hiking. The stunning beaches and lush landscapes of Kailua invite you to explore, offering ample opportunities for sightseeing and enjoying the natural beauty of Oahu.

During this peak season, visitors can immerse themselves in the vibrant local culture, from farmers' markets to beachside events, all while basking in the pleasant tropical climate. The lively atmosphere is complemented by the chance to connect with fellow travellers and locals alike, creating a memorable vacation experience.

If you're looking for a more budget-friendly option, consider visiting in October. This month might not be as bustling as the peak season, but it still offers beautiful weather and a more tranquil environment. You can enjoy the serene beaches and scenic trails without the larger crowds, making it an ideal time for relaxation and reflection amidst nature.
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 variety of attractions that highlight the natural beauty of the area. The stunning Kailua Beach is a major draw, known for its soft sands and crystal-clear waters, making it great for swimming, kayaking, and paddleboarding. Nearby, Lanikai Beach offers breathtaking views and a more tranquil experience, often regarded as one of the best beaches in the world.

For those interested in hiking, the Lanikai Pillbox Trail provides a rewarding trek with panoramic views of the coastline and the Mokulua Islands. The neighbourhood's vibrant local scene includes charming shops and cafes, particularly in the Kailua town centre, where visitors can find unique boutiques and delicious dining options.
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 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 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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