Vacation rentals in Kailua

4.87 out of 5 average rating, 473 reviews

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

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!

4.92 out of 5 average rating, 368 reviews

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

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.

4.8 out of 5 average rating, 198 reviews

A tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.

Guesthouse in Kailua

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

4.97 out of 5 average rating, 320 reviews

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 Makaha

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.

4.98 out of 5 average rating, 145 reviews

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

Escape to paradise in this brand new vacation rental located in the secluded Makaha Valley. Just a short drive away from some of the world's most beautiful beaches, enjoy endless opportunities for hiking, golfing, and soaking up the sun. Surrounded by lush mountains and pristine nature, this rental offers the perfect retreat from the hustle and bustle of everyday life. Take in the breathtaking ocean and mountain views and create unforgettable memories in this ultimate tropical getaway.

4.96 out of 5 average rating, 109 reviews

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

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.

4.96 out of 5 average rating, 98 reviews

A spacious bedroom is illuminated by natural light, showcasing a beautifully designed king-size bed with crisp white linens and a soft headboard. A large flat-screen TV is mounted on a wooden accent wall. The room features a cozy seating area and direct access to the patio.

Apartment in Waikiki

32F-Penthouse Pacific Monarch Studio-Ocean View

Experience the epitome of luxury with this stunning, spacious ocean view studio situated on the 32nd Penthouse floor right in the heart of Waikiki. Boasting breathtaking views of the ocean and Diamond Head, this upscale studio goes above and beyond to exceed all expectations. Indulge in the ultimate comfort and elegance while enjoying the convenience of being in the center of Waikiki, surrounded by the vibrant energy and beauty of this renowned beach destination.

A modern dining area features a large wooden table surrounded by eight upholstered chairs. Natural light fills the space through expansive sliding glass doors, which provide scenic ocean views. A decorative plant adds a touch of greenery, while an artwork piece complements the contemporary decor.

4.97 out of 5 average rating, 190 reviews

Penthouse, 2-Minute Walk to Beach/Free Parking

1700+ SQ. FT., FREE GARAGE PARKING AND WIFI. TWO-MINUTE WALK TO THE BEACH. Located in the hotel zone and in compliance with short-term rental laws, this gorgeous, remodeled Penthouse with Diamond Head and Ocean Views, located just 1.5 blocks from Waikiki Beach and the Honolulu Zoo, this 1,700+ s.f. (153.93 square meters) condo offers the style and comfort of a luxury hotel with a huge luxurious lanai, a large chef's kitchen, and a full-size washer and dryer.

4.79 out of 5 average rating, 169 reviews

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

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.

A balcony offers a view of the beach and ocean, framed by palm trees swaying in the breeze. The distant mountains create a serene backdrop. A round table and a chair are positioned on the balcony, providing a space to relax and enjoy the scenery.

4.92 out of 5 average rating, 229 reviews

Ocean View Beach Condo with private lanai

The only on-the-beach oceanfront condominium building in Waikiki! This spacious studio features a private lanai with stunning ocean and mountains view. Ocean breeze and breathtaking sunsets are guaranteed! King size bed, split AC, fully equipped kitchen, beach gear, and unbeatable walking distance to top Waikiki attractions, shops, and restaurants. Your perfect beachfront getaway awaits! STR#294

4.92 out of 5 average rating, 102 reviews

Turtle Bay Condo with Pool Access

Experience Turtle Bay without resort pricing! - 1-bedroom + loft, 2-bath condo with king bed - Clean, family-friendly atmosphere - Amenities include AC, free WiFi, and beach gear - Near beach - Access to 3 pools, tennis courts, and BBQ facilities - Explore local attractions like Shark's Cove and Polynesian Cultural Center - Gated community with 24/7 security for peace of mind

4.95 out of 5 average rating, 156 reviews

A modern living area is illuminated by natural light from large glass doors leading to a balcony. The space features a curved gray sofa and a wall-mounted TV, with a backdrop of a serene ocean view visible through the doors.

Apartment in Waikiki

High FL-Upscale Ocean View w/ Easy Beach Access~

Situated in one of the most vibrant neighborhoods in all of Waikiki, you'll be within steps away from many local restaurants, and shopping plazas. Most importantly, a quick 2 min walk to Waikiki beach, surrounded by cultural activities such as surf lessons and rentals. This stunning apartment is truly one of a kind, and it's the perfect choice for couples & memorable occasions.

Popular amenities for Kailua vacation rentals

Self check-in

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Stay near Kailua's top sights

Lanikai Beach

465 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

263 locals recommend

Kailua beachfront vacation rentals

4.96 out of 5 average rating, 105 reviews

A panoramic view captures the marina bustling with boats, with clear blue waters reflecting the sky. Lush palm trees line the area, and a sandy beach is visible in the distance, framed by the vibrant horizon and scattered clouds.

Apartment in Waikiki

*Remodeled Oceanfront in Waikiki - Ilikai Marina

A spacious balcony is accessed from the suite, featuring a table and chairs with a view of the Waikiki Marina. The scene includes boats in the water and distant ocean views against a backdrop of blue skies and scattered clouds.

4.98 out of 5 average rating, 212 reviews

★Panoramic OCEAN VIEW Studio Suite + FREE Parking

A panoramic view shows the ocean and Diamond Head from the sliding doors, framed by the open patio. The scene highlights lush greenery and the skyline of Waikiki against a bright blue sky with fluffy white clouds.

4.96 out of 5 average rating, 262 reviews

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

4.84 out of 5 average rating, 221 reviews

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 Makaha

Beach Beauty and Comfort in remote Oahu Paradise

4.91 out of 5 average rating, 291 reviews

The beachfront property is surrounded by lush greenery and palm trees, displaying multiple levels of residential units. The sandy beach extends to the clear blue waters, with mountain views in the background under a partly cloudy sky.

Condo in Punaluu

Secluded White Sandy beach just 30 steps away

4.81 out of 5 average rating, 123 reviews

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 Maili

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

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.

4.9 out of 5 average rating, 210 reviews

Amazing Waikiki Beach Views!!

4.92 out of 5 average rating, 259 reviews

A sweeping view of Turtle Beach is captured, showcasing soft golden sands meeting gentle waves. The ocean displays shades of blue under a cloudy sky, while a verdant mountain is visible in the background, adding a tranquil aspect to the coastal scenery.

Condo in Makaha

Let's make a dream

Kailua home rentals

4.98 out of 5 average rating, 95 reviews

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

Haleiwa Waterfront House

4.98 out of 5 average rating, 133 reviews

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

Waikiki Gem, Stunning Ocean View, Parking Included

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.

4.94 out of 5 average rating, 141 reviews

Large family home 5 min from beach- with pool

4.76 out of 5 average rating, 116 reviews

Home in North Shore

North shore Studio with sauna! - Walk to beach!

4.95 out of 5 average rating, 130 reviews

Family Ocean Oasis, Hot Tub, 5 min drive to beach

A scenic view of a paved road lined with tall palm trees swaying gently in the breeze. Lush greenery and colorful tropical flowers frame the roadway, enhancing the natural beauty of the surroundings. Soft sunlight filters through the clouds, casting a warm glow over the landscape.

4.94 out of 5 average rating, 151 reviews

Beautiful 4-BR Home| Near Beach| Mountain View

The exterior of a modern home is framed by lush green mountains. The structure features a combination of light and dark siding, a spacious driveway, and a garage. A stone wall planter is visible, decorated with tropical plants.

4.93 out of 5 average rating, 113 reviews

3BR New Construction w/Mt views, Close to Beach

4.95 out of 5 average rating, 20 reviews

Sunny Heaven 1 Bd Plus Loft

Beachfront home rentals in Kailua

5 out of 5 average rating, 20 reviews

The image captures a serene beach scene with soft, golden sand and gentle waves lapping at the shore. Lush green mountains rise in the background, creating a striking contrast with the clear blue ocean. Fluffy white clouds drift overhead, adding to the tranquil atmosphere.

Home in Punaluu

Ocean Views, Steps from Beach - 3 Bedroom/2 Bath

Home in Hauula

Orchid Paradise- AC, Close to beach

4.76 out of 5 average rating, 17 reviews

Spring Break Sale! Turtle Bay’s Kuilima West #104

5 out of 5 average rating, 13 reviews

Kaia Villa at Turtle Bay/North Shore Oahu

Home in Waikiki

4.67 out of 5 average rating, 9 reviews

Waikiki Close To Ala Moana, Pool and Parking!

4.89 out of 5 average rating, 9 reviews

Home in Waikiki

Honolulu Oasis for your Hawaiian retreat

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, 147 reviews

Serenity Beachfront Cottage- NUC No 90/TVU-0326

A beautifully landscaped yard features vibrant tropical plants illuminated by soft lighting. A spacious wooden deck provides a relaxing outdoor space, while the stunning sunset casts warm hues over the ocean and mountains in the background.