Vacation rentals in Kailua

4.87 out of 5 average rating, 465 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!

4.97 out of 5 average rating, 124 reviews

Place to stay in Kailua

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

4.8 out of 5 average rating, 196 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, 317 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.

A spacious studio unit features a kitchenette with modern appliances and a dining table. A large window offers a sweeping view of the ocean, bringing natural light into the room. The bed is neatly made with a light blue blanket, fostering a serene atmosphere.

4.85 out of 5 average rating, 236 reviews

Free Parking/Ocean View/Steps to Beach & Mall 33F

Fully newly remodeled in April this year! Everything is brand NEW! Amazing sweeping ocean view! Located on 33rd floor of Waikiki city, just a few minutes’ walk to the famous Waikiki Kahanamoku Beach & Lagoon, Ala Moana Beach Park, Ala Moana Shopping Mall, many restaurants , Cafes and Bars - everything is within walking distance. FREE PARKING is a Big Plus with a designated parking spot in the garage. You’ll have a great time in this brand new home with a queen bed and a sofa to stay!

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, 205 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.

The open-concept living area is highlighted by a modern kitchen with sleek white cabinetry and a stainless-steel appliances, including a refrigerator and dishwasher. A spacious living room features a dark sectional couch and a dining table, with large windows offering ocean views.

5 out of 5 average rating, 219 reviews

Ocean/Fireworks View Waikiki Walk to beach! 1BR

Renovated 1 bedroom/1 bathroom top floor apt in Waikiki. Beautiful 180 unobstructed panoramic ocean views from the Juliet balcony. See the Friday night fireworks and the sunset from the top! Queen size bed in bedroom. Bathroom has double sink, glass walk-in shower. Fully stocked kitchen. 24/7 security on site. Central A/C, Cable, WiFi included. Garage parking available for $33 a day. Five minute walk to Waikiki beach, Hilton hotel, Duke lagoon, and Ala Moana mall

Condo in Downtown Honolulu

4.98 out of 5 average rating, 249 reviews

Modern 1 Bedroom Condo in Downtown Honolulu

Aloha and welcome! Newly remodeled, clean and cozy 1 bedroom, 1 bathroom condo is in the heart of downtown Honolulu. Enjoy the views of the harbor and the city. We are a quick 10 min drive to beautiful Waikiki. Come explore all Oahu has to offer - surfing, swimming, snorkeling, relaxing on the beach, hiking, shopping, fine dining and more! Then unwind and relax in the comfort of the condo. We welcome you and hope you enjoy paradise at an affordable price.

4.93 out of 5 average rating, 220 reviews

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

♥ 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.

4.87 out of 5 average rating, 151 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

4.87 out of 5 average rating, 430 reviews

A spacious sleeping area is highlighted by a king-size bed dressed in a white coverlet. A futon is positioned alongside, complemented by decorative pillows. Soft natural light enters through multiple windows, while indoor plants add a touch of greenery to the peaceful ambiance.

Guesthouse in Kailua

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.

4.79 out of 5 average rating, 168 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

Beachfront

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Stay near Kailua's top sights

Lanikai Beach

460 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

260 locals recommend

Kailua beach vacation rentals

4.98 out of 5 average rating, 103 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

The beachfront setting showcases a stretch of light sandy beach adjacent to a modern condominium building. Clear blue waters reflect the sky, while gentle waves lap at the shore. Palm trees provide a tropical ambiance, with beachgoers enjoying the sunny day.

4.82 out of 5 average rating, 152 reviews

Waikiki Shore - Beachfront

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, 258 reviews

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

4.84 out of 5 average rating, 215 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

4.81 out of 5 average rating, 119 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!*

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.

4.95 out of 5 average rating, 218 reviews

Spectacular Views - Spacious 2BR Waikiki Penthouse

4.98 out of 5 average rating, 107 reviews

Ocean/Fireworks View Waikiki Walk to beach 1BR

Kailua home rentals

4.98 out of 5 average rating, 93 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, 129 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

4.94 out of 5 average rating, 137 reviews

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

Large family home 5 min from beach- with pool

4.78 out of 5 average rating, 166 reviews

Home in Kahuku

Spacious 1 Bedroom Condo in Turtle Bay

4.75 out of 5 average rating, 88 reviews

Home in Kailua

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

4.78 out of 5 average rating, 107 reviews

Home in North Shore

North shore Studio with sauna! - Walk to beach!

4.9 out of 5 average rating, 135 reviews

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

Slice of Paradise-3BR- Sleeps10-Max 8 Adults

4.94 out of 5 average rating, 144 reviews

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.

Home in Makaha Valley

Beautiful 4-BR Home| Near Beach| Mountain View

Beach home rentals in Kailua

5 out of 5 average rating, 19 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 Hauula

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

4.7 out of 5 average rating, 10 reviews

Home in Hauula

Orchid Paradise- AC, Close to beach

Home in Kahuku

Sweetheart Sale! Turtle Bay’s Kuilima West #104