Family-friendly holiday rentals in Kailua

4.87 out of 5 average rating, 493 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!

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.

4.97 out of 5 average rating, 267 reviews

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, 382 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.

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.

4.97 out of 5 average rating, 107 reviews

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, 334 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.

4.97 out of 5 average rating, 114 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.

4.98 out of 5 average rating, 105 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) .

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.

4.94 out of 5 average rating, 278 reviews

SEArider TWO at Turtle Bay

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, This unit has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. This unit sits directly below our other property, SEArider ONE(search on airbnb).

4.98 out of 5 average rating, 131 reviews

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the gas grill for a tasty BBQ. We've got you covered with all the beach amenities you'll need to enjoy the crystal-clear waters and white sandy beaches. Whether you're looking for a romantic escape or a fun-filled family vacation, our property has everything you need to create unforgettable memories.

4.88 out of 5 average rating, 118 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.

Condo 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.

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.

4.76 out of 5 average rating, 124 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!

Popular amenities for Kailua family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 170 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~

Condo in Downtown Honolulu

A spacious bedroom showcases a large bed with white bedding against a turquoise wall. Floor-to-ceiling windows offer expansive views of the cityscape. A minimalist desk is positioned nearby, and a full-length mirror reflects the warm wooden floor.

4.95 out of 5 average rating, 107 reviews

Spacious 1BR Ocean/Sunset View w/Parking

Condo in Downtown Honolulu

A spacious living area contains a comfortable sofa, accent chairs, and a coffee table, all arranged on light-colored flooring. Two pieces of wall art adorn the walls, while large glass doors lead to a balcony offering views of the surrounding area.

4.96 out of 5 average rating, 177 reviews

Luxury Condo with Ocean Views & FREE Parking!

4.84 out of 5 average rating, 231 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

4.97 out of 5 average rating, 219 reviews

An ocean view from a balcony captures the landscape of palm trees gracefully swaying beside a sandy beach. The calm blue ocean stretches toward the horizon, blending seamlessly with the sky. Amenities such as pools and lush greenery are visible in the foreground.

Villa in Ko Olina

Ko Olina Oceanfront | Disney | Next Avail 07/24

4.94 out of 5 average rating, 190 reviews

An aerial view captures the sandy beach stretching along the coastline, bordered by lush green hills. Crystal-clear turquoise waters gently lap the shore, with a few beachgoers enjoying the day. Colorful umbrellas are dotted along the beach, creating a vibrant contrast against the natural surroundings.

Guest suite in Waianae

Slice of Paradise-Studio-Sleeps 4-Same$ for 4 as 2

Condo 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, 323 reviews

Elegant, Spacious Downtown Hideaway w/Parking

4.8 out of 5 average rating, 382 reviews

A serene pool area is surrounded by lush tropical foliage. The water is clear, reflecting the natural surroundings, with a thatched-roof cabana visible in the background offering shaded seating. The name 'Bamboo' is subtly integrated into the pool's design.

Condo in Waikiki

Large Corner Unit at Bamboo with Full Kitchen

Family- and pet-friendly home rentals

4.83 out of 5 average rating, 161 reviews

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.

Condo in Waikiki

Newly Renovated * Waikiki Beachside Retreat

4.92 out of 5 average rating, 24 reviews

Home in Kailua

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

4.84 out of 5 average rating, 327 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

A bright living room features modern furniture with a dark gray couch and two vibrant purple chairs. Natural light fills the space from large windows, framed by sheer curtains, and a piece of scenic artwork is displayed on the wall. A small coffee table holds decorative items.

4.95 out of 5 average rating, 139 reviews

Oahu Ocean View • Sleeps 14, Pool, Hot Tub, Beach!

4.87 out of 5 average rating, 69 reviews

Condo in North Shore

🏝 North Shore Island Bungalow, Steps to Beach

4.98 out of 5 average rating, 54 reviews

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

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.

4.9 out of 5 average rating, 98 reviews

Spectacular Oceanview Cottage

4.85 out of 5 average rating, 116 reviews

Apartment in Waikiki

Waikiki studio with balcony block from the beach

Family-friendly home rentals with a pool

A tranquil sleeping area features a spacious bed adorned with decorative pillows in shades of blue. Flanking the bed are two nightstands with minimalist designs. A nature-inspired wall art piece brings a calming ocean view to the room, softly illuminated by modern sconces.

4.92 out of 5 average rating, 170 reviews

The Seascape at Turtle Bay

4.73 out of 5 average rating, 93 reviews

Home in Kailua

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

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, 511 reviews

RusticLuxe — Go Fully Custom at Turtle Bay

4.73 out of 5 average rating, 15 reviews

Home in Hawaii Kai

Hawaii Kai 7-Bedroom Pool Home with Views!

4.91 out of 5 average rating, 294 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

4.91 out of 5 average rating, 171 reviews

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.

Condo in Waikiki

Ocean View w/ 2 private balconies; Steps to Beach

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, 239 reviews

♥ North Shore Paradise at Turtle Bay ♥

A modern living space is arranged with a comfortable sofa and a sleek coffee table. A large wall-mounted TV displays a marine scene. The kitchen area features white cabinetry and bar stools, while light wood flooring complements the decor. Natural light highlights the room's openness.