Family-friendly holiday rentals in Kailua

4.9 out of 5 average rating, 349 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!

Great stayGreat locationFriendly host

4.91 out of 5 average rating, 160 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

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!

Great locationGreat stayExcellent service

A modern kitchen and living area are depicted in the image. The kitchen features sleek white cabinets and a spacious island. A stainless steel refrigerator and stove are visible. Natural light fills the area through large sliding glass doors, overlooking a green landscape.

4.99 out of 5 average rating, 324 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

Quiet surroundingsGreat stayClean

4.97 out of 5 average rating, 325 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.

Excellent serviceSafeWell-equipped facilities

4.96 out of 5 average rating, 168 reviews

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!

Friendly hostGreat locationClean

4.96 out of 5 average rating, 112 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.

Near marketsWell-equipped facilitiesQuiet surroundings

4.92 out of 5 average rating, 104 reviews

Home in Kahuku

Cozy condo w/Turtle Bay, pool & beach access

Experience a relaxed North Shore retreat steps from Turtle Bay, with resort‑style perks and easy beach access. Enjoy self‑check‑in convenience and free parking as you settle in. - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Year‑round shared pool, tennis & pickleball courts - Beach access, beach essentials & kayak - Private patio or balcony w/ BBQ grill - Full kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly: Pack ’n play, toys & board games

Excellent serviceGreat stayGreat location

4.88 out of 5 average rating, 110 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 Hauula

"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 & FREE parking!

Well-equipped facilitiesCleanGreat stay

Condo in Downtown Honolulu

4.98 out of 5 average rating, 265 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.

Great locationExcellent serviceFriendly host

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, 229 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.

Excellent serviceCleanFriendly host

Guesthouse in Makaha Valley

A cozy studio space features a spacious bed with white linens and decorative accents. A kitchenette with wood cabinetry, appliances, and a dining area is visible. An armchair sits nearby, and large windows offer views of the outdoors, contributing to a bright and open atmosphere.

4.93 out of 5 average rating, 158 reviews

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

Friendly hostSafeStylish design

4.87 out of 5 average rating, 446 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.

Stylish designGreat stayClean

Popular amenities for Kailua family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 102 reviews

Spacious 1BR Ocean/Sunset View w/Parking

Stylish designQuiet surroundingsClean

4.85 out of 5 average rating, 115 reviews

A serene pool area is surrounded by lush tropical landscaping, featuring palm trees and colorful flowers. Lounge chairs are placed around the pool, which is framed by natural stone accents. A calm, inviting atmosphere is created by the clear blue water and sunny skies.

Condo in Kapolei

Ko Olina Beach Villa - Lagoon View - Free Parking

Great stayWell-equipped facilitiesQuiet surroundings

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, 175 reviews

Luxury Condo with Ocean Views & FREE Parking!

Friendly hostGreat locationStylish design

4.96 out of 5 average rating, 159 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.

Apartment in Waikiki

Amazing Central Waikiki Wonder

CleanNear marketsGreat stay

4.84 out of 5 average rating, 227 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

Friendly hostWell-equipped facilitiesGreat location

Guest suite in Makaha Valley

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.

4.94 out of 5 average rating, 183 reviews

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

Near marketsExcellent serviceGreat location

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, 133 reviews

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

Excellent serviceGreat stayGreat location

4.95 out of 5 average rating, 107 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

Great locationGreat stayWell-equipped facilities

Family- and pet-friendly home rentals

5 out of 5 average rating, 27 reviews

Top 1% Family-Friendly Home By Beach -Honu Hideout

5 out of 5 average rating, 16 reviews

Apartment in Honolulu

Newly Renovated Waikiki 1 Bedroom in Nice Location

4.85 out of 5 average rating, 157 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

Near marketsExcellent serviceWell-equipped facilities

4.83 out of 5 average rating, 313 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

Quiet surroundingsExcellent serviceNear markets

5 out of 5 average rating, 47 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, 92 reviews

Spectacular Oceanview Cottage

Great locationQuiet surroundingsGreat stay

Superhost

Apartment in Waikiki

4.86 out of 5 average rating, 110 reviews

Waikiki studio with balcony block from the beach

Great locationSafeStylish design

4.77 out of 5 average rating, 604 reviews

Condo in Waikiki

King Bed | Ocean View | Steps to Waikiki Beach

SafeGreat locationExcellent service

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, 163 reviews

The Seascape at Turtle Bay

SafeGreat locationStylish design

5 out of 5 average rating, 10 reviews

Apartment in Honolulu

Opihi Stunning View 1BR+Fun bunk/ Parking/Washer

4.9 out of 5 average rating, 293 reviews

Nalu Blue - Turtle Bay

Friendly hostStylish designSafe

A well-maintained octagonal pool is surrounded by a spacious patio, featuring a shaded seating area and lounge chairs. Lush greenery and palm trees enhance the tranquil environment. The pool's clear blue water is inviting under the sunlight, creating a refreshing space for relaxation.

4.96 out of 5 average rating, 149 reviews

Hale Soleil

Quiet surroundingsGreat locationFriendly host

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.

4.93 out of 5 average rating, 272 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

Great stayExcellent serviceQuiet surroundings

5 out of 5 average rating, 21 reviews

Home in Kahuku

Kaia Villa at Turtle Bay/North Shore Oahu

5 out of 5 average rating, 81 reviews

The living area features a comfortable sofa and an accent chair, with a flat-screen TV positioned on a rustic wooden unit. A dining area with four chairs is visible in the background. A colorful surfboard decorates the wall, complementing the light, airy space.

Townhouse in Kahuku

Beautiful Newly Renovated North Shore Condo !

Well-equipped facilitiesGreat staySafe

A spacious lounge area features a large sectional sofa, offering a comfortable gathering space. An inviting kitchen can be seen in the background, equipped with modern appliances. An outdoor pool is surrounded by lounge chairs, and a serene bedroom is highlighted, showcasing a neatly made bed.