Some info has been automatically translated. Show original language
Become a host

Vacation rentals in Kailua

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
A covered patio area is viewed, featuring a large umbrella providing shade over a small table. The entrance to the unit is visible in the background, framed by a railing and surrounded by greenery.
Home in Kailua
4.87 out of 5 average rating, 455 reviews

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

Top guest favorite
A serene seascape showcases a calm ocean reflecting vibrant sunset hues of orange and gold. Silhouettes of two distant islands emerge against the colorful sky, while a lone canoe floats quietly on the water, enhancing the tranquil scene.
Guesthouse in Kailua
4.93 out of 5 average rating, 115 reviews

Lanikai Oasis, 2 beds, 5 min walk to the beach!

Located in the most private and peaceful locations on Oahu, our Lanikai cottage is only 5 min from one of the most beautiful beaches in the world. Welcome to Lanikai Oasis, best place for a clean and relaxing vacay in paradise! 5- 10min drive to many restaurants and eateries. The unit has been newly remodeled and is on the base Ohana unit to the main home. Newer appliances, kitchen, bathroom, beds, sectional couch etc for your enjoyment. Tax ID codes, GE-159-110-0416-01 and TA-159-110-0416-01

Guest favorite
A private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.
Condo in Hauula
4.77 out of 5 average rating, 147 reviews

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! This 1 large bedroom has a new king bed, and there is a bed in the living room as well. Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped remodeled kitchen, washer/dryer & private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

Guest favorite
A spacious bedroom features a king bed draped with sheer white fabric, creating an airy ambiance. Two stylish chairs are positioned beside large windows that overlook lush greenery. A natural fiber rug covers the hardwood floor, complemented by a simple wooden bench at the foot of the bed.
Condo in Kahuku
4.93 out of 5 average rating, 250 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)

Guest favorite
A spacious studio suite features a king-size bed centered against a vibrant tropical-themed wall art. A dining area with a glass table and wicker chairs sits adjacent, while a cozy seating area with floral-patterned cushions completes the inviting layout. Ample natural light filters through the windows.
Guest suite in Kailua
4.91 out of 5 average rating, 358 reviews

Kailua Pineapple Studio. Walk to Beach! PERMITTED

Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.

Guest favorite
A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.
Condo in Waianae
4.97 out of 5 average rating, 307 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favorite
A serene view of the expansive saltwater pool, framed by lush greenery and tropical plants. Outdoor furniture is arranged on the wooden deck beside the pool, overlooking the tranquil water and rock features. The ocean can be seen in the distance between the buildings.
Guest suite in Kailua
4.79 out of 5 average rating, 171 reviews

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks

Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

Top guest favorite
A tropical pathway leads from a sandy beach to the bright blue ocean, with gentle waves lapping against the shore. Lush greenery borders the scene, while distant hills are visible on the horizon under a partly cloudy sky.
Place to stay in Kailua
5 out of 5 average rating, 104 reviews

Nai’a Suite at La Bella’s-Walk to Beach-Licensed

La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.

Guest favorite
A private balcony features a small round table adorned with a colorful mosaic design and two wicker chairs. The view showcases the scenic Waikiki Beach, the shimmering ocean waves, and the lush lagoon bordered by palm trees.
Condo in Waikiki
4.9 out of 5 average rating, 198 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Guest favorite
A modern kitchen is featured with light wood cabinetry and natural stone countertops. Three rattan bar stools are positioned at the breakfast bar. Pendant lights with woven shades hang above. Fresh greenery is placed on the counter, enhancing the spacious and airy feel of the room.
Condo in Kahuku
4.93 out of 5 average rating, 215 reviews

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

Guest favorite
Guest suite in Kailua
4.87 out of 5 average rating, 150 reviews

Kailua Rental for Med/Long Term ($1,500/month)

Escape to beautiful Kailua and enjoy our cozy guest suite! Located in a quiet cul-de-sac, this unit provides modern amenities, a new full-sized bed and direct access to your own private lanai. Mountain views, nearby attractions, shopping, dining, and world-class beaches ensure an ideal destination for your next retreat! We welcome minimum stays of 30 days or more. Please contact for inquiry details. * 30 night minimum

Guest favorite
A serene beach scene features soft white sand leading to clear turquoise waters. Gentle waves lap against the shoreline under a bright blue sky with scattered clouds. Lush greenery borders the beach, providing a natural frame to the picturesque landscape.
Guesthouse in Kailua
4.8 out of 5 average rating, 163 reviews

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Popular amenities for Kailua vacation rentals

Self check-inBeachfrontGymBBQ grillLaptop-friendly workspace

Stay near Kailua's top sights

Lanikai Beach

459 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

259 locals recommend

Kailua beach vacation rentals

Guest favorite
Aerial view captures the resort complex positioned along the shoreline, featuring three distinct buildings surrounded by lush landscaping. The calm lagoon reflects the pastel colors of the sunset, with a sandy beach and rocky outcrops enhancing the coastal scenery.
Villa in Kapolei
4.89 out of 5 average rating, 210 reviews

Studio Suite Ko Olina and MARRIOTT Beach Club

Guest favorite
A serene pool area is surrounded by lush tropical landscaping, featuring palm trees and colorful flowers. Lounge chairs are placed around the pool, which is framed by natural stone accents. A calm, inviting atmosphere is created by the clear blue water and sunny skies.
Condo in Kapolei
4.85 out of 5 average rating, 106 reviews

Ko Olina Beach Villas ★Ocean View★Free Parking★

Top guest favorite
A spacious living area features a comfortable seating arrangement with a textured sofa and a wooden coffee table. Large windows provide sweeping ocean views, while decorative plants and a wall-mounted TV add to the ambiance. A dining area with chairs is visible in the background.
Condo in Waikiki
4.98 out of 5 average rating, 104 reviews

ZEN Oceanfront Suite

Guest favorite
A sweeping view of the ocean is enhanced by a vibrant rainbow arching across the sky. Waves gently lap the shore, while a distant mountain creates a picturesque backdrop. The sandy beach is bordered by lush greenery, embodying a serene coastal landscape.
Apartment in Mākaha
4.84 out of 5 average rating, 213 reviews

Beach Beauty and Comfort in remote Oahu Paradise

Guest favorite
A private lanai offers sweeping ocean views, furnished with two comfortable chairs and a small table. The bright blue waters and greenery below are visible, enhancing the outdoor space's appeal. Sliding glass doors lead into a spacious living area, allowing for easy access.
Condo in Waikiki
4.88 out of 5 average rating, 121 reviews

Beachfront! Upgraded modern w Oceanview (WS1116)

Top guest favorite
The spacious living area features large windows that provide an unobstructed view of the ocean. A queen-sized bed, a twin bed, and a sleeper sofa are arranged in a light-filled room with hardwood-style floors. Decorative elements include a unique ceiling design and coastal-themed accents.
Condo in Waikiki
4.98 out of 5 average rating, 169 reviews

Beautiful Oceanfront Paradise Condo

Superhost
A private balcony is showcased with two light blue chairs positioned around a small table. The view highlights ocean waves and lush palm trees, creating a serene backdrop. The indoor-outdoor space invites relaxation with clear skies and gentle breezes.
Condo in Waianae
4.8 out of 5 average rating, 117 reviews

*Serendipity on the Moana! - Legal & Beachfront!*

Guest favorite
Two individuals float in calm, clear ocean water, each using a brightly colored inflatable inner tube. The water appears inviting and tranquil, and the sandy bottom is visible beneath the surface.
Condo in Hauula
4.77 out of 5 average rating, 260 reviews

Dreamy Beachfront Cottage with Breathtaking Views

Kailua home rentals

Guest favorite
Aerial view of a coastal property lined with homes along a sandy beach. Lush greenery and palm trees are visible, leading to a backdrop of mountains under a partly cloudy sky. Gentle waves lap against the shore, creating a serene beach environment.
Home in North Shore
4.98 out of 5 average rating, 88 reviews

Haleiwa Waterfront House

Guest favorite
A serene bedroom features a spacious bed with crisp white linens, complemented by soft, natural textures. Large windows showcase ocean views, while two woven light fixtures add warmth. A dresser provides additional storage, and a neutral rug enhances the calming atmosphere.
Home in Waikiki
4.98 out of 5 average rating, 123 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

Top guest favorite
A modern living area is furnished with a sectional sofa, accent chairs, and a coffee table. A spacious dining table is surrounded by white chairs. A ceiling fan and artwork decorate the room, while natural light streams in through the windows.
Home in Makaha Valley
4.94 out of 5 average rating, 132 reviews

Large family home 5 min from beach- with pool

Superhost
Home in Kailua
4.79 out of 5 average rating, 84 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Guest favorite
Home in North Shore
4.79 out of 5 average rating, 102 reviews

North shore Studio with sauna! - Walk to beach!

Guest favorite
Home in Makaha Valley
4.96 out of 5 average rating, 117 reviews

Family Oceanview Oasis, Hot Tub, 5min to beach

Superhost
Home in Kailua
4.71 out of 5 average rating, 7 reviews

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Superhost
An aerial view captures a sandy beach stretching along the coast, bordered by clear turquoise waters. Colorful umbrellas dot the beach, while small boats can be seen in the water. Lush green hills rise in the background, complementing the scenic landscape.
Home in Makaha Valley
4.89 out of 5 average rating, 129 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

Beach home rentals in Kailua

Home in Hauula
New place to stay

Orchid Paradise- AC, Close to beach

Home in Kahuku
5 out of 5 average rating, 3 reviews

Holiday Sale! Turtle Bay Kuilima Estates West #104

Home in Kahuku
5 out of 5 average rating, 3 reviews

Kaia Villa at Turtle Bay/North Shore Oahu

Home in Kaaawa
New place to stay

Oceanfront Escape Your Hawaii Home Away from Home

Guest favorite
Home in Hauula
4.93 out of 5 average rating, 54 reviews

"Hina Hideaway", Views, AC, Walkable to Beach

An aerial view showcases the lush greenery of Oahu's mountainous terrain in the background, while the gentle waves lap against the sandy shoreline in the foreground. The tranquil beach is bordered by a small collection of homes, reflecting the serene atmosphere of the area.
Home in Laie
4.63 out of 5 average rating, 116 reviews

"HALE HONU" North Shore Beach House

Home in Hauula
New place to stay

Tropical Tranquility | 2bd Beachfront

An outdoor area features a wooden picnic table situated on green grass, surrounded by a wooden fence and tropical plants. The bright blue sky and palm trees are visible in the background, creating a serene and inviting setting.
Home in Kailua
4.82 out of 5 average rating, 143 reviews

Serenity Beachfront Cottage- NUC No 90/TVU-0326

When is the best time to visit Kailua?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,255 ZARR4,272 ZARR3,845 ZARR3,845 ZARR4,050 ZARR4,050 ZARR4,050 ZARR3,930 ZARR3,657 ZARR3,913 ZARR3,828 ZARR3,947 ZAR
Avg. temp22°C22°C23°C24°C24°C26°C26°C27°C26°C26°C24°C23°C

Frequently Asked Questions

  • How is the weather in Kailua?

    Kailua's weather remains warm throughout the year with an average temperature ranging from 70°F (21°C) to 85°F (29°C). It sees the most rain from November to March, while the driest months are June to September.

  • What are some of the best things to do in Kailua?

    Popular activities in Kailua include swimming, kayaking, or windsurfing at Kailua Beach, hiking the scenic trails such as the Olomana Trail, and exploring local markets like the Kailua Farmers Market. Visitors also enjoy sampling local cuisine at the many eateries in town.

  • What is the best time of year to visit Kailua?

    Kailua is mostly visited during the summer months, particularly from May to September. Around this time, visitors can enjoy events such as the Kailua Independence Day Parade in July. The period between December and April is also popular, especially for those looking to escape colder weather.

  • What are the best places to stay in Kailua?

    Visitors to Kailua often prefer staying in places close to its natural beauty. Lanikai, known for its beach, and Enchanted Lake, a residential area with a shopping center, are popular choices. Notably, Maunawili, with its proximity to hiking trails, also attracts nature lovers.

  • What are the best places to visit in Kailua?

    In Kailua, Lanikai Beach and Kailua Beach Park are frequented by sun-seekers and water sports enthusiasts. Nature lovers often explore the Maunawili Falls Trail and the Kawainui Marsh. The Kailua Farmers Market is a favorite among food enthusiasts for its local produce.

  • What are some hiking trails in Kailua?

    Kailua has several hiking trails for nature enthusiasts. The Olomana Trail, offering three peaks of varying difficulty, and the Maunawili Falls Trail, leading to a waterfall, are popular choices. The relatively easy Pillbox Hike offers great views of the town and ocean.

  • What are some family activities to do in Kailua?

    Families in Kailua can enjoy a day at the beach, try stand-up paddleboarding, or visit Kalapawai Market for a picnic lunch. They can also explore Pillbox Hike for a fun family adventure or visit the Thursday Night Farmers Market for a taste of local food and culture.

  • What are some of the best day trip ideas in Kailua?

    From Kailua, day trips can include exploring the marine life at Hanauma Bay, hiking the Ko'olau Mountain Range, or visiting the Byodo-In Temple in the Valley of the Temples. Trips to the bustling city of Honolulu, just 19 km away, are also enjoyed by many.

  • Are there vacation rentals with a dedicated workspace in Kailua?

    Yes! Work meets play with ease at over 160 vacation rentals in Kailua featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Kailua?

    Four-legged friends are welcome in Kailua. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there Kailua vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 90 vacation homes with pools in Kailua, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Kailua?

    Experience the best of Kailua with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Kailua have self check-in?

    Absolutely! We offer over 40 house rentals with self check-in in Kailua. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Kailua have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Kailua. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Kailua have a bbq area?

    Absolutely! We offer over 70 house rentals with a bbq area in Kailua. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Kailua?

    Kailua has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

All about Kailua

With stretches of powdery white sand beaches, two reef-protected lagoons, and temperatures kept on the comfortable side of cool by ever-present trade winds, it’s no surprise Kailua is no longer the secret destination guarded by seasoned island vacationers that it once was. Located on the windward side of Oahu on a peninsula overlooking the crescent-shaped Kailua Bay and the Koolau Mountain range, Kailua is beloved for its small beach town vibe — a mellow yin to Honolulu’s metropolitan yang, with only a 25-minute drive separating the destinations.

There’s also an increasing possibility of rubbing well-tanned shoulders with vacationing celebrities drawn to the same soft sand beaches and tranquil aquamarine waters delivering on the promise of paradise. In Kailua you can revel in a variety of water sports. Hikers have a range of challenging trails to choose from, some leading to breathtaking mountaintop views, others to such secluded mountain-fed pools as Maunawili Falls, along with a network of leisurely footpaths awaiting within the 830 acres of Kawainui Marsh.

What are the top things to do in Kailua?

Lanikai Beach

Lanikai Beach is often described as one of the world’s greatest beaches, and it’s easy to see why, with its breathtaking stretches of sand and ocean overlooking two nearby islets, the Na Mokulua. The waters here are typically calm, with a protected coastline buffered from windpowered waves thanks to a sizable reef offshore, making it one of the more swimmable spots on Oahu. These placid coastal waters are hard to beat — especially for kayaking and paddleboarding — tempting the more adventurous to paddle around those two offshore islands colloquially referred to as the Mokes.

Kawainui Marsh

Binoculars and a camera are a must while visiting Kawainui Marsh, the state’s largest protected wetlands, a sanctuary where many of Oʻahu’s endemic, endangered, and migratory birds, fish, and other aquatic life can be observed in their natural habitat. Travel by foot or by bike along a paved three-mile round path in a watershed that fed ancient Hawaiians with its abundance.

BookEnds

If you identify as a bibliophile and/or a lover of Hawaiian history, you might lose yourself once entering the door of this small neighborhood bookstore. BookEnds is filled with an extensive collection of Hawaiiana reflecting the islands’ history through photography, arts and crafts, architecture, and music.

Quick stats about vacation rentals in Kailua

  • Total vacation rentals

    Explore 340 vacation rentals in Kailua

  • Nightly prices starting at

    Kailua vacation rentals start at R684 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 10,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    200 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    340 of Kailua vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Pool across Kailua rentals

  • 4.8 Average rating

    Kailua stays are highly rated by guests—averaging 4.8 out of 5!

More from Airbnb

Airbnb experiences

Experience something new

Airbnb services

Make your stay more special

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Kailua