Discover a selection of 5,000 vacation rentals in Kailua, HI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $109 per night, and houses and cottages are popular options for a stay in Kailua. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Kailua
Destination guide

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.

Things to do

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.

Natural features

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.

How to get there

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.

What are the top vacation rentals in or near Kailua?

Whether you're organizing your next big adventure with friends or a romantic trip with your sweetheart, one of these top vacation rentals in Kailua is sure to entice you:

  • "Kailua Beachside - 5 - Bedroom": This Pacific States property comes with 5 bedrooms and is highly rated among guests. Amenities such as cookware, dishware and utensils and golf help make your stay a memorable one.
  • "Licensed Short Term Rental Beach Front": Stay at this option in Honolulu County and make use of a hair dryer, lowered locks and more. It has 5 bedrooms to accommodate your family and friends.

For even more great options, use the search bar at the top of the page to find the perfect Kailua vacation rental for you.

What are the best tiny house vacation rentals in or near Kailua?

Punching above its weight when it comes to character and ingenuity, a tiny house vacation rental in Kailua offers a front-row seat to big adventure. Close down your laptop and switch your focus to nature at one of these compact stays:

  • Take a few days off to reenergize at "Tiny House Best Location In Kailua". Located in Honolulu County, nearby birdwatching activities and a fridge are just a couple of the amenities included here.
  • Alternatively, make yourself at home at "New Tiny House Big Yard Fruit Trees Fire Pit Ocean Views Beach Gear". Situated in Honolulu County, this tiny gem comes with nearby ecotour services and a washing machine.

What are the top-rated vacation rentals for weekend getaways in or near Kailua?

There's nothing better than a quick break to revive your spirits. Pack your overnight bag and get cozy in one of these enticing weekend getaways in and near Kailua:

  • Escape the daily grind at "Kailua Beachside - 5 - Bedroom", which is around 1 mile to the southeast of central Kailua. There's lots of adventure and nature to uncover here. Try some windsurfing and cycling or simply explore the sights of One'ula Beach and Pokai Bay Beach Park.
  • Alternatively, get into vacation mode at "Beautiful Oceanfront Home Pool". Approximately 25 miles northwest of Kailua, fun activities around here include horse riding and snorkeling. Rather see the sights? Find time in your schedule for Crouching Lion and Ulehawa Beach Park.

Can I find studio apartments for rent in and around Kailua?

Studio apartments are a simple yet stylish pick, perfectly suited for traveling sweethearts or solo stays. Spend your days familiarizing yourself with the area and your nights resting up in your comfy hideaway. The following options in or near Kailua are guaranteed to please:

  • Enjoy some time out on your own or take a few pals to "Sandy Beachfront /direct Oceanfront - Allowed One Rental Per 30 Day Period". You'll have lots of amenities at your disposal, including a resort and tennis.
  • "Charming Ocean Front/ Beach Front" is another superb stay, offering all you could want for a dream Kailua vacation. Some amenities here include internet services and beach sun loungers.

Can I find short term rentals in or near Kailua?

Whether you're after a compact apartment for you and a pal or a townhouse with space for the whole family, short-term rentals are easy to find in and around Kailua. These retreats make the perfect base for a whirlwind visit:

  • If you can only spare a few nights, "Luxury Beachfront Ocean Villa 217 With Newest Interior Remodel Turtle Bay Resort" is an excellent choice. It's close to central Kailua, so you'll be within easy reach of all the top sights.
  • Alternatively, spend a couple of relaxing nights at "Large Corner Condo In Beach Tower Steps To Beach". This conveniently located property makes exploring the local sights easy.

What are the best romantic weekend getaways in or near Kailua?

Forget about flowers and chocolates. Sometimes all you need is to get away for a weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Kailua that would make Cupid envious. Here are some to tempt you:

  • Located around 25 miles from Kailua, "Sandy Beachfront /direct Oceanfront - Allowed One Rental Per 30 Day Period" is the ideal place for adoring couples. Beauty services and a fireplace are among the many amenities here.
  • Another place where you can spend a few dreamy days together is "Charming Ocean Front/ Beach Front". Around 20 miles from Kailua, beauty services and beach sun loungers add to the atmosphere here.

What are the best large group vacation rentals in or near Kailua?

Big groups mean gigantic fun. They also mean finding someplace that'll comfortably fit your whole crew. Check out our large group vacation rentals in or around Kailua and get your loved ones together under one roof:

  • There's plenty of space to sprawl out at "Licensed Short Term Rental Beach Front". Around 1 mile north of Kailua, this welcoming retreat has 5 bedrooms sleeping up to 14 guests. Amenities include an ocean view and a nearby waterfront.
  • "Large Beachfront 5 Bedroom Home" is another option that'll fit the whole crew. It's around 20 miles to the northwest of Kailua, has 5 bedrooms and welcomes up to 20 guests. A beach view and an ocean view are among the things designed to make your visit even more memorable.

What are the best houses for rent with a pool in or near Kailua?

A pool is often a must-have amenity when deciding where to stay on vacation, especially if you're taking the kids. Check out these houses with a pool in or near Kailua and spend your days splashing around:

  • Get your vacation on at "Waimea Point Oceanfront House - - With Air Conditioning", where your biggest priority will be pool time. Amenities including a barbecue grill and a nearby bay help make this escape a favorite with guests.
  • Spend lazy vacation days splashing about or simply unwinding by the water at "Beachfront Palaypa - Former Mission House". This property is also a firm favorite and comes with on-site watersports, a fridge and more.

Not sure how to pack your bags for your Kailua escape? This enticing destination has a tropical savanna climate. In the summertime, expect average temperatures of between 75 ºF and 80 ºF. Scroll through our range of Kailua vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Kailua?

You love your family dearly, but that doesn't mean you need to pack together like sardines on your getaway. Take no chances and book a large family vacation rental in or around Kailua where you can spread out and relax:

  • Make lifelong memories at "Kailua Beachside - 5 - Bedroom". With 5 bedrooms sleeping up to 10 people, this roomy retreat is around 1 mile southeast of Kailua. There are lots of amenities to make use of here, such as a separate dining area and cable/satellite TV services.
  • Another family escape is "Beautiful Oceanfront Home Pool". Around 25 miles northwest of Kailua, it comes with 4 bedrooms, room for up to 8 guests, a travel crib and cable/satellite TV services.

What are the best large houses to rent with indoor pools in or near Kailua?

Take a dip anytime you like when you stay at one of our large rental houses with an indoor pool. Slip on your swimsuit and consider these escapes in or near Kailua that boast this premium perk:

  • Book a few days or more at "Wifi, View Mountain, Fitness, Swimming Pool" and spend your days kicking back poolside. This roomy rental has 3 bedrooms that sleep up to 7 guests and a host of other impressive amenities. Ski-in/ski-out facilities and a kitchen are among them.
  • Alternatively, treat your gang to a stay at "Beautiful Island Beach Home, Steps To Beach. Make Memories", which has 3 bedrooms and caters for up to 8 guests. Along with that chic pool tucked away inside, a swimming pool and mountain views will keep everyone comfortable and happy.

Use the search bar at the top of the page and adjust the filters to find more impressive Kailua vacation rental options for your next big getaway.