Family-friendly holiday rentals in Kailua

4.9 out of 5 average rating, 355 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!

4.92 out of 5 average rating, 133 reviews

A serene beach scene captures the sun setting between two islands, casting a warm glow over the water. Gentle waves lap against the shore, while smooth rocks are visible in the foreground, providing a natural frame to the tranquil view.

Guest house in Kailua

Lanikai Oasis, Cozy Cottage 5 Min to Lanikai Beach

Lanikai Oasis, A Peaceful Island Retreat Tucked away in one of the most private and peaceful neighborhoods on Oʻahu, Lanikai Oasis is a serene cottage retreat just 5 minutes from Lanikai Beach, consistently ranked among the most beautiful beaches in the world. Perfect for a clean, calm, and relaxing vacation, this newly remodeled ohana unit offers modern comfort in a lush island setting. ideal for couples or quiet travelers seeking paradise. Hawaii Tax IDs GE-159-110-0416-01, TA-159-110-0416-01

4.97 out of 5 average rating, 104 reviews

The living area is characterized by high ceilings and natural light streaming through large windows. A comfortable gray sofa is accompanied by wooden chairs and tables, creating a welcoming gathering space. A neutral rug adds warmth, while tropical plants contribute to the serene atmosphere.

Home in Waianae

Makaha Hale - Serene 3 BR Home

Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

4.97 out of 5 average rating, 330 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.

Apartment 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.

4.97 out of 5 average rating, 110 reviews

The exterior of the cottage showcases a modern design with a welcoming front entrance and large windows. A two-car garage is visible on the right, while stunning mountain scenery frames the background. The sky is adorned with soft hues of pink and orange as the sun sets.

Cottage in Waianae

Cottage Nene - Luxury Home by Beaches & Mountains

Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.

4.96 out of 5 average rating, 171 reviews

Home in Makaha Valley

3BR, Near Beach, Game RM, Private Spa, Pool, Gym

Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

4.98 out of 5 average rating, 102 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

Location, location, location! This lovely DUPLEX home is perfectly situated on a beautiful white sandy beach and at the end of a quiet cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic Haleiwa Town rests in the heart of the north shore with Haleiwa being a 3 minute drive away and all the beautiful surf/swim beaches if not in front of the house then a mere 5 - 15 minute drive away (35 minute drive to the airport) .

4.88 out of 5 average rating, 115 reviews

A dining table is placed in front of large windows, offering a view of the ocean and a palm tree swaying gently. The clear blue sky contrasts with the water's gentle waves, creating a serene atmosphere.

Apartment in Punaluu

"Coconut Cottage by the Sea" Steps to the beach!

Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym & security.

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.

4.93 out of 5 average rating, 236 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.

4.96 out of 5 average rating, 129 reviews

A sea turtle glides gracefully in the clear, turquoise water, just beneath the surface. In the background, two small islands rise against a bright blue sky dotted with fluffy white clouds, creating a serene coastal atmosphere.

Place to stay in Kailua

Tropical Kailua Retreat | Walk to Beach + Gym

Walk to one of Hawaii’s most beautiful beaches, explore Kailua by kayak or bike, and relax in your own tropical retreat. The Honu (Turtle) Suite at La Bella’s Bed & Breakfast offers privacy, comfort, and island charm just minutes from the beach. Enjoy a queen bed with luxury linens, air conditioning, a full kitchen, private bathroom, private entrance, and outdoor seating area surrounded by tropical gardens on Oʻahu’s beautiful Windward Coast.

4.75 out of 5 average rating, 120 reviews

Home in North Shore

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm. Check my profile for other rentals!

4.87 out of 5 average rating, 452 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.

Guest house 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.

Popular amenities for Kailua family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.84 out of 5 average rating, 393 reviews

A private balcony features a round glass table surrounded by two wicker chairs, overlooking a vibrant blue ocean. Soft waves lap against a sandy beach, with palm fronds providing a tropical touch. A clear sky with scattered clouds complements the picturesque view.

Apartment in Makaha

Million $ View on Gorgeous Secluded Beach!

A spacious bedroom is furnished with a king-size bed and modern decor, featuring artwork above the bed. The living area offers a comfortable seating arrangement with large windows showcasing outdoor views. The serene beachfront scene includes high-rise buildings in the background, while the pool area is surrounded by lounge chairs and palm trees.

4.83 out of 5 average rating, 177 reviews

Steps to Waikiki Beach, Swimming Pool Free Parking

4.95 out of 5 average rating, 149 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 Waianae

Large family home 5 min from beach- with pool

4.85 out of 5 average rating, 117 reviews

A lush resort pool area is surrounded by palm trees and tropical foliage. Multiple pools are seen, including a spacious hot tub, with lounge chairs arranged around them. An outdoor seating area with tables and umbrellas is visible among the landscaped gardens, leading to distant ocean views.

Apartment in Kapolei

Ko Olina Beach Villa | Beach View | Resort Pool!

4.96 out of 5 average rating, 164 reviews

The spacious living area features two queen beds with plush memory foam mattresses. A soft blanket is draped across the bed. The walls are adorned with a tropical design, enhancing the modern aesthetic. Large windows allow natural light to fill the room.

Flat in Waikiki

Amazing Central Waikiki Wonder

Apartment in Downtown Honolulu

A spacious bedroom offers floor-to-ceiling windows with city views. The neutral-toned bedding is paired with a decorative pillow that includes the word 'love.' A stylish red lamp provides subtle lighting, and a decorative bench sits at the foot of the bed.

4.88 out of 5 average rating, 118 reviews

2BR High Floor Free Parking

4.84 out of 5 average rating, 229 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.

Flat in Makaha

Beach Beauty and Comfort in remote Oahu Paradise

Apartment in Downtown Honolulu

A modern high-rise building features a sleek glass exterior reflecting the vibrant surroundings. The ground level is marked by a wide entrance and large windows. Pedestrians are seen on the street, highlighting the bustling atmosphere of the area.

4.88 out of 5 average rating, 320 reviews

Elegant, Spacious Downtown Hideaway w/Parking

Family- and pet-friendly home rentals

The serene bedroom features a spacious bed with plush bedding and unique wall art. Ambient lighting and greenery create a soothing atmosphere. Direct access to the balcony enhances the natural light, while soft textiles add comfort to the space.

4.84 out of 5 average rating, 160 reviews

Newly Renovated * Waikiki Beachside Retreat

4.9 out of 5 average rating, 21 reviews

Home in Kailua

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

4.84 out of 5 average rating, 322 reviews

A panoramic view of Waikiki beach showcases golden sands and gentle waves lapping at the shore. High-rise buildings line the coast, with Diamond Head peak visible in the background against a clear blue sky.

Guest suite in Honolulu

DIAMOND ON DIAMOND HEAD

4.82 out of 5 average rating, 147 reviews

Waikiki Walkable Escape~Mins to Beach~Surf & Dine

4.92 out of 5 average rating, 74 reviews

A modern living room features a plush gray couch with decorative pillows, complemented by a round coffee table with a wireframe design. Natural light filters through sheer curtains, illuminating the space. A decorative vase and items on a wooden shelf add style to the inviting atmosphere.

Home in Pupukea

A/C Surfer family home 3 minutes walk to the beach

4.98 out of 5 average rating, 52 reviews

Aloha Surf Condo - Private Deck - Pool - E-Bikes

4.9 out of 5 average rating, 98 reviews

A landscaped yard is visible, featuring lush green grass and a variety of tropical plants. The sun sets in the background, casting warm light over the space. A paved walkway leads toward the house, which is partially seen on the right side.

Home in Waianae

Spectacular Oceanview Cottage

4.86 out of 5 average rating, 113 reviews

Flat in Waikiki

Waikiki studio with balcony block from the beach

Family-friendly home rentals with a pool

Sheer curtains gently frame an inviting entrance to a patio area, allowing natural light to filter through. A patterned rug lies on the floor, and wooden benches are positioned for seating. Lush greenery and a view of the golf course are visible beyond the glass doors.

4.92 out of 5 average rating, 509 reviews

RusticLuxe — Go Fully Custom at Turtle Bay

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.

4.91 out of 5 average rating, 141 reviews

Ocean View Penthouse, 32nd FL, 3 min walk to Beach

4.9 out of 5 average rating, 296 reviews

Nalu Blue - Turtle Bay

An open living space is presented with wooden cabinetry and granite countertops. A full kitchen is visible, featuring stainless steel appliances. Artwork depicting ocean waves adorns the wall. Natural light fills the area, illuminating a cozy seating arrangement and a wooden coffee table with decorative fruit.

4.96 out of 5 average rating, 139 reviews

Turtle Bay Condo. Delight in Paradise

4.73 out of 5 average rating, 15 reviews

Home in Hawaii Kai

Hawaii Kai 7-Bedroom Pool Home with Views!

4.9 out of 5 average rating, 258 reviews

A two-story building is framed by lush greenery and large windows. A white staircase leads to the upper level, while balconies are visible. The exterior showcases a light-colored facade that blends with the natural surroundings, creating a serene residential setting.

Flat in Kawela Bay

Turtle Bay Corner Condo With A Fairway View!

An aerial view captures the surrounding landscape near Turtle Bay, showcasing the proximity to the ocean. The layout includes green lawns, tennis courts, and the marked unit within a cluster of residences, all set against a backdrop of blue waters and a clear sky.

4.91 out of 5 average rating, 186 reviews

North Shore Getaway - Newly renovated!