Family-friendly vacation rentals in Kailua

4.98 out of 5 average rating, 147 reviews

A spacious outdoor seating area is presented, featuring a large sectional couch adorned with blue cushions. A round coffee table occupies the center, set against a backdrop of mountains under a colorful twilight sky.

Home in Makaha Valley

Ocean View Haven, Hot Tub + 5 mins to Makaha Beach

💕 Spacious & Well-Equipped Home featuring tropical boho decor, a fully stocked kitchen, cozy and comfortable beds 😃 Unwind on our expansive lanai complete with a hot tub, dining table, and a plush sectional couch perfect for soaking in the surroundings. 💖 Amenities such as snorkeling gear, boogie boards, games 😍 Breathtaking views of mountains and ocean 😎 5-minute drive to beautiful Makaha Beach Park 😉1-hour drive to Honolulu, Waikiki, and the airport 👍Safe & quiet gated community

4.9 out of 5 average rating, 359 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 modern open-concept living space features a comfortable sofa and a decorative coffee table. The dining area includes a sleek kitchen island with bar stools. Natural light brightens the room through a large decorative mirror, while stylish accents and greenery enhance the coastal aesthetic.

4.97 out of 5 average rating, 204 reviews

Honu Hideout at Turtle Bay

Come escape to Honu Hideout on the exclusive North Shore of Oahu, and enjoy this newly renovated ground floor unit situated just a short walk away from the iconic Turtle Bay Resort and the most breathtaking and secluded beaches on Oahu. Far away from the hustle and bustle of Honolulu, this unit offers the peacefulness of the country and the proximity to infamous attractions for the vacation of your dreams. Relax and restore or adventure and explore, you choose, all within minutes of your door.

4.91 out of 5 average rating, 385 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, 109 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, 337 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.

4.88 out of 5 average rating, 156 reviews

The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.

Cottage in North Shore

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

4.97 out of 5 average rating, 116 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, 178 reviews

A private hot tub is positioned in the foreground, surrounded by lush tropical landscaping. The two-story home stands in the background, framed by picturesque mountain views. The outdoor space offers a well-maintained lawn and a patio area, inviting relaxation in a tranquil setting.

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!

4.93 out of 5 average rating, 137 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.

Guesthouse 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 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

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, 240 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.

4.93 out of 5 average rating, 112 reviews

Home in Kawela Bay

Condo near Turtle Bay w/pool, beach & BBQ

Experience laid‑back island living on Oahu’s North Shore, just steps from Turtle Bay and the beach. Relax on the patio with sunrise coffee or unwind after surf sessions. - Sleeps 4 | 1 bd + loft | 3 beds | 2 baths - Year‑round pool, tennis & pickleball courts - Beach access, beach essentials & kayak - Private patio/balcony w/ BBQ grill - Kitchen, Wi‑Fi, workspace & in‑unit washer/dryer - Family‑friendly: Pack ’n play, toys & board games

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, 398 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.

Condo in Makaha

Million $ View on Gorgeous Secluded Beach!

4.88 out of 5 average rating, 229 reviews

Aerial view captures the resort complex positioned along the shoreline, featuring three distinct buildings surrounded by lush landscaping. The calm lagoon reflects the pastel colors of the sunset, with a sandy beach and rocky outcrops enhancing the coastal scenery.

Villa in Kapolei

Studio Suite Ko Olina and MARRIOTT Beach Club

4.95 out of 5 average rating, 150 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

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!

4.96 out of 5 average rating, 169 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

Renovated Waikiki Studio • Walk to Beach

4.97 out of 5 average rating, 220 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 09/28

4.94 out of 5 average rating, 191 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, 324 reviews

Elegant, Spacious Downtown Hideaway w/Parking

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 163 reviews

A view from the lanai showcases a parking area with several vehicles, including a red SUV and a white Jeep. In the background, two-story buildings are visible, surrounded by lush greenery and palm trees. The ocean can be seen in the distance under a clear blue sky.

Condo in Waianae

Paradise Found Makaha Valley Comfy Condo

4.82 out of 5 average rating, 162 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, 26 reviews

Home in Kailua

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

4.84 out of 5 average rating, 328 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

4.95 out of 5 average rating, 141 reviews

Home in Waianae

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

4.91 out of 5 average rating, 78 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, 58 reviews

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

4.86 out of 5 average rating, 118 reviews

Apartment in Waikiki

Waikiki studio with balcony block from the beach

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 119 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!

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, 171 reviews

The Seascape at Turtle Bay

4.95 out of 5 average rating, 113 reviews

A balcony view features a small round table set for breakfast, with fresh fruit and pastries arranged on plates. The ocean can be seen in the distance, along with tall buildings of the Honolulu skyline. Natural light brightens the space.

Apartment in Waikiki

Oceanvw, walk 2 beach, $0 cleaning & park, kitchen

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, 160 reviews

Hale Soleil

4.91 out of 5 average rating, 195 reviews

Magical Skies Hale at Turtle Bay

4.89 out of 5 average rating, 265 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.

Apartment in Kawela Bay

Turtle Bay Corner Condo With A Fairway View!

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, 281 reviews

SEArider TWO at Turtle Bay

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.