Vacation rentals in Kailua

4.9 out of 5 average rating, 334 reviews

The beach features soft, golden sand stretching alongside clear turquoise waters. Lush greenery lines the shore, providing a natural backdrop. Gentle waves lap against the rocks near the water's edge, while distant mountains are visible under a partly cloudy sky.

Home in Kailua

Kailua Beach Park - 2 BR Cottage

Kailua Beach is 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 two minutes walk to step into the ocean at the beach. This a legal vacation rental, license1990/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 shower, sink and plumbing fixtures April 2022!

A spacious living area features large windows offering panoramic ocean views. Modern furnishings include a soft sofa adorned with decorative pillows, a stylish armchair, and a wooden dining table. Natural light brightens the room, enhancing the fresh coastal ambiance.

4.9 out of 5 average rating, 121 reviews

32nd Floor Penthouse. 3min walk to Waikiki Beach

Welcome to HaleHinano Penthouse, Waikiki Beach. Enjoy this rarely find 1BR Penthouse on the 32nd floor with panoramic ocean views of the crisp Hawaiian waters. This condo is fully renovated with modern furnishings and decor. Just a few steps away, you’ll be at beach fronts of Waikiki beach. You’ll be surrounded with local favorite fine dining, shopping plazas. -In unit washer and dryer. -Top roof Pool, Jacuzzi, BBQ -3 min walk to the Waikiki beach. -$35/day parking attached to the building.

A private lanai is shown, featuring a sleek outdoor dining table with two lanterns. The view captures the ocean with sailboats in the distance, alongside lush greenery and palm trees, creating a serene backdrop against the clear blue sky.

4.9 out of 5 average rating, 142 reviews

Ocean View w/ 2 private balconies; Steps to Beach

BEST LOCATION & OCEAN VIEWS! Steps to Waikiki Beach & all the action! No car needed Newly renovated condo 1/2 block to the beach on 9th floor of Waikiki Grand Hotel. Across from the Zoo in Kapiʻolani Park. Enjoy 2 private balconieswith Ocean/Diamond Head views. 1 Queen bed & 1 Queen Pull Out. Dividers provided to convert into 1 bedroom if needed. See photos of Full Kitchenette & beach gear included LEGAL VACATION RENTAL All taxes/fees included—your family or solo dream vacation starts here!

4.98 out of 5 average rating, 227 reviews

A spacious bed is centered against a vibrant mural featuring tropical leaves and abstract shapes. Soft lighting is provided by two pendant lights on either side, accentuating the warm wooden nightstands. Neutral tones create a serene atmosphere in this inviting bedroom.

Condo in Kahuku

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

4.92 out of 5 average rating, 353 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.

4.97 out of 5 average rating, 300 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 Waianae

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.

4.79 out of 5 average rating, 171 reviews

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

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

5 out of 5 average rating, 102 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.

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, 197 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.

An expansive balcony is visible, featuring a table and two chairs, overlooking a stunning ocean view. The azure waters and palm trees create a serene backdrop. Floor-to-ceiling glass doors provide natural light and seamless access to the outdoor space from the interior.

4.96 out of 5 average rating, 110 reviews

Waikiki Beachfront Home with Ocean and Beach View

* Aloha! Welcome to our happy place in the heart of Waikiki! * If you are looking for stunning ocean views directly from your bed, this is it! You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Our spacious bedroom, full kitchen, and freshly updated bathroom will make you feel just like home. Welcome to our little paradise!

4.87 out of 5 average rating, 149 reviews

Guest suite in Kailua

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

4.8 out of 5 average rating, 162 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.

Popular amenities for Kailua vacation rentals

Laptop-friendly workspace

Kailua beach vacation rentals

4.84 out of 5 average rating, 207 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 Mākaha

Beach Beauty and Comfort in remote Oahu Paradise

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.

4.88 out of 5 average rating, 118 reviews

Beachfront! Upgraded modern w Oceanview (WS1116)

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.

4.98 out of 5 average rating, 164 reviews

Beautiful Oceanfront Paradise Condo

4.8 out of 5 average rating, 116 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 Waianae

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

4.74 out of 5 average rating, 188 reviews

The image displays a waterfront view featuring a low-rise condominium surrounded by lush palm trees and mountains in the background. The water appears calm and reflective under a bright blue sky with scattered clouds, creating a serene coastal atmosphere.

Apartment in Hauula

30 Steps to the beach! Sleeps 4 TA154-814-0544-01

4.76 out of 5 average rating, 258 reviews

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

Dreamy Beachfront Cottage with Breathtaking Views

Superhost

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 Waianae

4.91 out of 5 average rating, 246 reviews

Let's make a dream

Aerial view of Waikiki Beach, showcasing the clear turquoise water and soft sandy shores. The natural jetty is visible, providing a calm swimming area, while beachgoers and sun loungers dot the coastline. Lush palm trees frame the scene, with buildings lining the shore in the background.

4.96 out of 5 average rating, 203 reviews

Spectacular Views - Spacious 2BR Waikiki Penthouse

Kailua house rentals

4.99 out of 5 average rating, 86 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

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, 130 reviews

Large family home 5 min from beach- with pool

Superhost

Home in Kailua

4.78 out of 5 average rating, 83 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Superhost

Home in Kailua

4.8 out of 5 average rating, 5 reviews

Kailua Vacation Home

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.

4.93 out of 5 average rating, 130 reviews

Beautiful 4-BR Home| Near Beach| Mountain View

4.87 out of 5 average rating, 304 reviews

A wide, sandy beach stretches along the shore, bordered by gentle waves and lush greenery. The sky above is filled with soft clouds, contrasting against the vibrant blue. The peaceful landscape invites relaxation and exploration along the coastline.

Home in Kahuku

Hawaiian Country Retreat - 30 day stays

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.

4.92 out of 5 average rating, 100 reviews

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

4.96 out of 5 average rating, 146 reviews

Kalo Homes - Makaha's Hidden Gem

Beach house rentals in Kailua

Home in Hauula

Orchid Paradise- AC, Close to beach

Home in Kahuku

Holiday Sale! Turtle Bay Kuilima Estates West #104

4.97 out of 5 average rating, 39 reviews

Home in Ewa Beach

Kamalani's Hale, beachfront- 30 day minimum stay

Home in Kahuku

Kaia Villa at Turtle Bay/North Shore Oahu

Home in Kaaawa

4.82 out of 5 average rating, 11 reviews

Oceanfront Escape Your Hawaii Home Away from Home

Home in Hauula

North Shore Beach House! Best Location