Family-friendly vacation rentals in Kailua

4.87 out of 5 average rating, 506 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!

KitchenIndoor spacesAir conditioning

4.99 out of 5 average rating, 132 reviews

Home in Makaha Valley

Beach 6 Min|BBQ|Community Pool+Gym|Peaceful+Gated

Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!

Indoor spacesKitchenHospitality

4.97 out of 5 average rating, 343 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.

Indoor spacesFamilyHospitality

4.88 out of 5 average rating, 272 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!

Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th with cool breezes, washer & dryer, and Split A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax and enjoy a true authentic Hawaiian experience!

Indoor spacesFamilyOutdoor spaces

An open layout features a kitchen with modern appliances and a dining area, complemented by bar seating. The loft area with a visible sleeping space is showcased above, while natural light floods through large windows, enhancing the airy atmosphere of the living space.

4.89 out of 5 average rating, 261 reviews

Legal STR: Aloha at Turtle Bay w/ Loft

TMK #570010270107 STR license # 51 Quiet upstairs unit with loft. Cooling trade breezes drift from the lanai through to the master bedroom. Walk to golf, restaurants and the beaches at the Ritz Carlton Oahu at Turtle Bay. 2 swimming pools, tennis and pickleball on site. Has beach toys and gear, tennis and pickleball rackets. WiFi, cable and Smart TV’s. Drive to North Shore beaches and local shopping. Gated, 24 hour security. One parking spot included. 2nd parking spot with permit.

KitchenIndoor spacesHiking

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.

4.91 out of 5 average rating, 357 reviews

NEWLY RENOVATED (2021) Turtle Bay Haven!

NEWLY RENOVATED condo (2021) at Turtle Bay on Oahu's world famous North Shore. Enjoy more than 5 miles of secluded beaches, 2 private swimming pools, 2 private tennis & pickle ball courts, 2 PGA golf courses, horseback riding & fine dining all less than a 5 minute walk from your front door! The condo was completely remodeled in 2021 (Kitchen, Bathrooms, Flooring, decor as well as AC throughout). This 1Bed, 2Bath unit is one of the few Legal and licensed vacation rentals on the North Shore!

Indoor spacesKitchenCheckout

4.88 out of 5 average rating, 164 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.

FamilyKitchenWalkability

4.98 out of 5 average rating, 121 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.

KitchenIndoor spacesComfort

4.97 out of 5 average rating, 120 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-Lic. B&B

La Bella’s B&B is a luxury island retreat on O‘ahu’s beautiful windward side, blending farmhouse charm with beach elegance. Two private suites are available, each with a private entrance, bathroom, kitchenette, AC, luxury bedding Wi‑Fi, and parking. The spacious Nai‘a Suite features a king bed and relaxing atmosphere perfect for couples or small families. Enjoy beautiful gardens, beach gear, nearby shops and eateries, and a short walk to the beach with warm onsite hosts.

KitchenFamilyBackyard

4.88 out of 5 average rating, 464 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.

Indoor spacesKitchenAccuracy

4.86 out of 5 average rating, 118 reviews

A vibrant pink hibiscus flower stands prominently in the foreground, with lush green foliage surrounding it. In the background, a corner of the apartment is visible, featuring a light green exterior and a covered area, enhancing the tropical atmosphere of the property.

Home in Kailua

Tropical Hideaway Near the Beach

We live in a quiet neighborhood which is close to the beach, bus stop or shopping. It’s a mile walking to Kailua beach. The apartment has a bedroom, living room/kitchenette and bathroom which are part of the house but has a separate entrance and private yard with a gate. We must rent on a monthly basis according to Hawaii vacation rentals. If you need a different amount of time please contact me. No pets allowed.

Indoor spacesFamilyLocation

4.81 out of 5 average rating, 335 reviews

A serene beach area features gentle waves lapping at the shore. A sailboat rests on the soft, sandy beach, surrounded by a calm aqua-blue ocean. Lush greenery and houses frame the sandy expanse under a clear blue sky with scattered clouds.

Home in North Shore

Haleiwa Dream Location

Newly renovated home, excellent location, just 650 feet walking distance to beach and 5-minute bike ride to Haleiwa Town. This is a great getaway for singles, couples, or families wishing to explore without needing to drive. 30-day minimum rental required. Note the beach in the top photo is directly across the street.

Indoor spacesKitchenView

Popular amenities for Kailua family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An open dining area is highlighted by a large wooden table with seating for six, complemented by natural light from sliding glass doors. The adjacent kitchen features modern appliances and a spacious island with bar seating, creating a welcoming atmosphere for gatherings.

4.96 out of 5 average rating, 138 reviews

Hawaiian Pakele (escape)

Indoor spacesKitchenAir conditioning

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, 114 reviews

Makaha Hale - Serene 3 BR Home

KitchenFamilyCheckout

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.

4.95 out of 5 average rating, 153 reviews

Large family home 5 min from beach- with pool

FamilyIndoor spacesShared spaces

4.95 out of 5 average rating, 122 reviews

A bright living area features large sliding glass doors offering unobstructed views of the ocean. Comfortable seating is arranged around a coffee table, with a TV mounted nearby. Tropical decor and tile flooring create a relaxing atmosphere, inviting guests to enjoy the coastal scenery.

Apartment in Makaha

9K Hawaiian Princess - Alii Hale Aina

FamilyKitchenLong stay

4.91 out of 5 average rating, 155 reviews

A spacious bedroom features a king-size bed with an elegant quilt and decorative pillows. Two nightstands with stylish lamps are positioned on either side. Floor-to-ceiling windows offer panoramic views of the ocean, filling the room with natural light.

Condo in Waikiki

#3103 2BR/2BA|Beachfront, Free Parking, Gym & Pool

KitchenIndoor spacesGetting around

4.9 out of 5 average rating, 130 reviews

An aerial view captures the resort buildings set against a pastel sunset, bordered by a calm lagoon. Palm trees and landscaped grounds are featured alongside the sandy beach, with rocky outcrops visible in the foreground, creating a serene coastal environment.

Condo in Kapolei

Studio Suite @ Ko Olina Marriott Vacation Club :D

KitchenIndoor spacesAmenities

4.92 out of 5 average rating, 102 reviews

A bright living area offers a panoramic view of the ocean through large windows. The space includes a cozy sectional sleeper sofa, a 75-inch 4K Smart TV mounted on the wall, and twin bunk beds with light bedding, set against neutral decor.

Apartment in Waikiki

40F-High-FL Ocean View-1 Bedroom-Waikiki Beach!

FamilyKitchenBeach

4.9 out of 5 average rating, 156 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-Same$ for 10 as 2

Indoor spacesFamilyDecor

Family- and pet-friendly home rentals

Superhost

Apartment in Waikiki

4.86 out of 5 average rating, 122 reviews

Waikiki studio with balcony block from the beach

KitchenIndoor spacesNearby

4.85 out of 5 average rating, 338 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

Indoor spacesFamilyWifi

4.94 out of 5 average rating, 154 reviews

Private SPA, Sleep 12, Beach 5 min

Indoor spacesKitchenHiking

4.87 out of 5 average rating, 127 reviews

A view of the shoreline featuring a mountainous landscape, partially covered by green vegetation. The calm water reflects the bright blue sky, with a few white clouds gently drifting overhead. The natural scenery suggests a peaceful coastal environment.

Condo in Waikiki

Peaceful cozy comfortable apartment

FamilyIndoor spacesDecor

4.95 out of 5 average rating, 148 reviews

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

Indoor spacesKitchenLocation

4.81 out of 5 average rating, 134 reviews

A spacious living area is visible, featuring a comfortable couch with decorative pillows. Two queen-size beds are arranged in the background, complemented by large windows offering mountain and canal views. A cozy armchair is positioned nearby, and soft natural light illuminates the space.

Apartment in Waikiki

Pool, Jacuzzi, Parking, AC, WiFi, Cozy Beds & View

KitchenFamilyComfort

Superhost

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

4.82 out of 5 average rating, 164 reviews

Newly Renovated * Waikiki Beachside Retreat

KitchenFamilyBeach

4.93 out of 5 average rating, 30 reviews

Home in Kailua

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

FamilyIndoor spacesHiking

Family-friendly home rentals with a pool

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, 290 reviews

SEArider TWO at Turtle Bay

Indoor spacesFamilyBeach

A private outdoor space features a cozy seating area with a white cushioned sofa and a wooden coffee table. A blue lounge chair is positioned beside the table, and a large umbrella provides shade. Soft string lights create a warm ambiance among surrounding plants.

4.95 out of 5 average rating, 349 reviews

Beautiful North Shore Turtle Bay Condo

Indoor spacesKitchenHospitality

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.

4.94 out of 5 average rating, 248 reviews

♥ North Shore Paradise at Turtle Bay ♥

Indoor spacesFamilyLayout

4.77 out of 5 average rating, 168 reviews

A private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.

Condo in Punaluu

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Indoor spacesKitchenAccess

Superhost

4.9 out of 5 average rating, 188 reviews

Turtle Bay Condo Lilinoe

FamilyKitchenAir conditioning

A granite countertop separates the kitchen from the open living area, which features a soft seating arrangement with a lamp providing ambient lighting. Large windows invite natural light, revealing a view of the surrounding greenery. Dining plates are set on a wooden table, enhancing the inviting space.

4.89 out of 5 average rating, 206 reviews

Turtle Bay Condo, 2 Bedroom, sleeps 6

KitchenIndoor spacesTV

4.93 out of 5 average rating, 116 reviews

Home in Kawela Bay

Condo near Turtle Bay w/pool, beach & BBQ

KitchenIndoor spacesAir conditioning

An open living space showcases a dining area with a circular table and metal chairs, surrounded by natural wood accents. A large wall art piece features a world map. A sliding glass door leads to a private lanai offering views of the golf course.