Kailua vacation rentals

We found 5,167 vacation rentals — enter your dates for availability

Welcome to Kailua, where stunning beaches meet lush landscapes, creating an idyllic paradise for travelers seeking both adventure and relaxation. With the soft sands of Kailua Beach and the serene beauty of Lanikai, your days can be filled with sunbathing, kayaking, and exploring vibrant botanical gardens. Ideal for families and groups, our diverse vacation rentals—from cozy condos to luxurious villas—provide the perfect home base for creating unforgettable memories amidst this Hawaiian gem. Experience the comfort and convenience of a vacation rental, where you can unwind and enjoy all the space and amenities you need for a truly memorable getaway.

Holiday rentals with weekly discounts - Kailua

Showing deals for:Dec 11 - Dec 18

Room
Interior
Bedroom
Pool and hot tub
Wonderful
(10 reviews)

1BR Ocean/Sunset View w/Parking

Honolulu

9% off
$267
$1,872 for 7 nights
All fees included
1BR Ocean/Sunset View w/Parking
Property grounds
Private kitchen
Living area
Interior
Wonderful
(18 reviews)

Ocean View Mid Waikiki 1 Block to the Beach

Honolulu

8% off
$778
$5,448 for 7 nights
All fees included
Ocean View Mid Waikiki 1 Block to the Beach
Dining
Pool
Property grounds
Room
Exceptional
(10 reviews)

Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!

Honolulu

8% off
$304
$2,130 for 7 nights
All fees included
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!
The lobby of the Ilikai
Second floor pool
Behind the Ilikai
Enjoy your view of Honolulu while sipping coffee or tea on your lanai! (balcony)
Exceptional
(5 reviews)

Waikiki - Resort amenities for condo prices, just steps from the beach!

Honolulu

13% off
$320
$2,240 for 7 nights
All fees included
Waikiki - Resort amenities for condo prices, just steps from the beach!
Room
Exterior
Pool
Fitness facility
Very Good
(17 reviews)

Beautiful Remodeled Studio with canal, city and mountain views

Honolulu

8% off
$138
$963 for 7 nights
All fees included
Beautiful Remodeled Studio with canal, city and mountain views
Room
Interior
Dining
Pool
Very Good
(9 reviews)

Entire condo in Waikiki - Ocean View 2 BR & 4 bed

Honolulu

9% off
$248
$1,738 for 7 nights
All fees included
Entire condo in Waikiki - Ocean View 2 BR & 4 bed
Cottage Waikiki. Central AC .
Pineapple Cottage # 2
On-site Swimming pool!
Pineapple Cottage #2
Exceptional
(6 reviews)

Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available

Honolulu

8% off
$242
$1,697 for 7 nights
All fees included
Queen beds, oceanview, 2 min walk to beach, central AC, Parking is available
Front of the Building View
Koi Pond in Lobby  Unit is in Tower 1 Makai
Lobby
Property grounds
Exceptional
(102 reviews)

⛱ Ocean Escape - Your Perfect Spot! Clean, Ocean View, 5 min walk to Beach, Prkg

Honolulu

7% off
$359
$2,515 for 7 nights
All fees included
⛱ Ocean Escape - Your Perfect Spot! Clean, Ocean View, 5 min walk to Beach, Prkg
Living area
Pool
Outdoor dining
Private kitchen
Exceptional
(47 reviews)

Newly Renovated Waikiki Condo 2 blocks to the Beach! Free parking.

Honolulu

8% off
$272
$1,905 for 7 nights
All fees included
Newly Renovated Waikiki Condo 2 blocks to the Beach! Free parking.
Spa
The views of coastline from your lanai.
Exterior detail
Outdoor dining
Exceptional
(218 reviews)

Direct Oceanfront Waikiki! Parking at Waikiki Shore included!

Honolulu

8% off
$663
$4,644 for 7 nights
All fees included
Direct Oceanfront Waikiki! Parking at Waikiki Shore included!
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Find out more about Kailua

Why visit Kailua

  • Stunning Beaches: Kailua Beach is renowned for its soft sand and picturesque views, perfect for sunbathing and swimming.
  • Outdoor Adventures: The area offers a variety of activities, from kayaking to hiking, catering to adventure seekers and families alike.
  • Scenic Bays and Gardens: Explore the beautiful bays and lush botanical gardens that enhance Kailua's natural charm.
  • Relaxing Atmosphere: Kailua provides a tranquil environment, ideal for romantic getaways or family vacations.
  • Diverse Accommodations: Choose from cozy condos to luxurious villas, ensuring a perfect stay that suits your needs.

Popular types of accommodation in Kailua

Discover the perfect getaway in Kailua with our selection of vacation rentals. From cozy condos and spacious private homes to inviting apartments, we offer a variety of options to suit your needs. Whether you're seeking a luxurious Kailua villa or a charming Lanikai beach rental, you'll find the ideal beach house to create unforgettable memories. Explore our Kailua vacation rentals and enjoy the beauty of Oahu, Hawaii.

  • Condos: The top choice for travelers in Kailua, offering modern amenities and stunning views for a perfect getaway.
  • Houses: A fantastic option for families or groups, these homes provide spacious living and a home-like atmosphere.
  • Apartments: Ideal for solo travelers or couples, these cozy spaces offer convenience and comfort close to local attractions.
  • Villas: Luxurious and spacious, villas are perfect for those seeking a high-end experience with beautiful surroundings.
  • Cottages: Charming and quaint, cottages provide a peaceful retreat with a touch of rustic charm.**

Top attractions in and around Kailua

Kailua, located in Honolulu County, Hawaii, is perfect for outdoor and family beach vacations. Visitors can enjoy stunning attractions like Kailua Beach, known for its soft sand and vibrant scenery. Explore the beautiful bays and botanical gardens in the area, making it an ideal destination for those seeking a mix of relaxation and adventure. Whether you're looking to soak up the sun or explore the local landscape, Kailua offers a variety of experiences for every traveler.

  • Lanikai Beach: Renowned for its powdery white sand and crystal-clear waters, Lanikai Beach offers a serene paradise perfect for sunbathing, swimming, and relaxing with picturesque views of the Mokulua Islands.
  • Kaneohe Bay: Located only 3 miles from Kailua, Kaneohe Bay boasts stunning scenery, ideal for kayaking, paddleboarding, and enjoying vibrant sunsets while surrounded by lush mountains.
  • Hoomaluhia Botanical Gardens: About 4 miles away, this expansive garden features diverse plant species, tranquil walking paths, and scenic picnic spots, creating a romantic and family-friendly atmosphere.

Things to do recommended for couples

For a romantic getaway in Kailua, consider a visit to a luxurious Country Club just 8 miles away. Indulge in the serene atmosphere and enjoy exquisite dining and beautiful surroundings, perfect for creating unforgettable memories as a couple amidst the stunning Hawaiian landscape.

Things to do recommended for families

Families can explore the stunning beaches of Kailua, like Lanikai Beach, perfect for swimming and building sandcastles. Enjoy kayaking to the nearby Mokulua Islands or take a hike up the Lanikai Pillbox Trail for breathtaking views of the coastline.

Things to do recommended for groups

Groups visiting Kailua can enjoy a day at the beautiful Kailua Beach, partake in a fun kayaking adventure to the nearby Mokulua Islands, and savor local flavors at a beachside picnic. Exploring the lush landscapes of Lanikai Pillbox Hike offers breathtaking views for memorable group photos.

*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

When planning your trip—whether you're traveling with a group, spending time with family, bringing your pets along, or seeking extended stays—be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Kailua with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options and more on Vrbo.
  • Traveling to Kailua with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with amenities that suit 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 families, a vacation feels incomplete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kailua: If you're in search of vacation rentals that offer great deals 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Kailua

Kailua, an idyllic Hawaiian town, offers a perfect blend of outdoor adventures and family-friendly activities. With stunning ocean views and a relaxing atmosphere, visitors can explore pristine beaches and lush landscapes. Just a short drive from Honolulu, Kailua serves as a gateway to a tropical paradise filled with excursions, making it an ideal spot for romantic getaways or memorable family vacations. Experience the true essence of Hawaii in this charming coastal community.

  • Kaneohe: Located approximately 4 miles from Kailua, Kaneohe is a vibrant city that offers a rich blend of outdoor activities and family-friendly experiences. Visitors can enjoy exciting venues like the arcade adventure zone and zipline ropes course, making it a great spot for thrill-seekers. Kaneohe is also home to beautiful beaches and urban parks, perfect for a relaxing day in the sun. Whether you’re playing a round of golf or exploring the local landmarks, Kaneohe provides ample opportunities for adventure and leisure.
  • Lanikai: Nestled around Kailua, Lanikai is a picturesque neighborhood renowned for its stunning beaches and outdoor activities. Travelers flock to Lanikai for its breathtaking views and family-oriented experiences, such as hiking trails that lead to scenic overlooks. The area offers convenient access to campgrounds and beautiful family beaches, allowing visitors to immerse themselves in nature. Whether you’re sunbathing on the sandy shores or embarking on an outdoor adventure, Lanikai is the ideal destination for beach lovers and nature enthusiasts alike.
  • Kalama Tract: Kalama Tract, located near Kailua, is a charming neighborhood known for its vibrant community and city-themed experiences. This area is perfect for families looking to enjoy a day out, with shopping centers and malls providing a variety of retail options. Visitors can also find campgrounds nearby, catering to those who wish to experience the outdoors. With its close proximity to beaches and urban parks, Kalama Tract offers a wonderful blend of city life and natural beauty, making it a great addition to your vacation itinerary.

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 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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and organize your bookings. Your saved or booked properties are 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 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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