Family-friendly holiday rentals in Princeville

An open grassy area extends towards the ocean, revealing a clear blue sky dotted with fluffy clouds. Several lounge chairs are arranged on the lawn, facing the ocean views, providing a serene setting for relaxation.

4.97 out of 5 average rating, 185 reviews

Princeville Paradise By The Sea

Beautiful, newly refurbished, condo with the best ocean views in Princeville! Located in The Cliffs resort, this unit is nearest the ocean with a wonderful lanai to sit and watch the sunset. Be careful when cooking, as you may find yourself staring out the windows and losing track of what you were doing. Nearby Princeville Center and Hanalei town provide excellent dining and shopping experiences. The resort also has a pool area and sporting courts. See more at cliffsatprinceville "dot" com.

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4.99 out of 5 average rating, 168 reviews

LUX/MOD perfect base for island adventures - w A/C

This beautiful home in Princeville stands out with high-end finishes and modern interior design that creates a serene and luxurious atmosphere. Split A/C added throughout home in May 2025. Located a short stroll away from the Princeville Center shops, restaurants, & services. The property backs up to Princeville Golf Course w open space & views! The luxury 1 Hotel at Hanalei Bay is down the road. Enjoy Princeville’s easy access to Anini beach, Hideaway, Hanalei Bay, and community Farmer’s Market

Indoor spacesFamilyHospitality

An inviting lanai features a woven hanging chair beside a small round table. A steaming cup is placed on the table, accompanied by a book. The background reveals lush greenery and panoramic ocean views under a soft sunset glow.

4.99 out of 5 average rating, 363 reviews

~The Surfshack~ with breathtaking ocean views!!

A modern surf oasis nestled on an overlook with panoramic ocean views, stunning sunsets, and the famous Bali Hai. We were featured in the June issue Sunset Magazine. You'll never want to leave this modern Hawaiian styled 2 bedroom, 2 bath condo. We have everything you’ll need and want for the most relaxing stay of your island vacation and only steps away from food, drinks, the pool and the beach. Whale watch from the lana'i in the winter, or snorkel our beautiful Hideaways beach in the summer.

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A dramatic sunset paints the sky in shades of orange and pink over the ocean. Lush greenery lines the foreground, leading to a silhouette of mountains in the distance. A towering palm tree stands prominently, adding to the serene coastal scene.

4.96 out of 5 average rating, 113 reviews

Hale Luya-Ocean View Condo, Private Beach

Peace & Tranquility, this upper level end unit has amazing ocean & mountain views and a private beach! Condo is fastidiously clean, everything you will need for a perfectly tranquil stay. Walk to the 1Hotel Hanalei for a variety of world class restaurants. 2 min. to the Robert Trent Jones Makai golf course. 2 bedrooms w/ensuite bathrooms w/ king beds. Steps from the pool and Hideaways Pizza. Kitchen has all new appliances. Whale watching from the Lana'i w/ 4 comfy chairs. Convenient parking.

KitchenIndoor spacesParking

An aerial view reveals a serene landscape of lush green hills and distant mountains, with the blue Pacific Ocean visible in the background. A winding road leads through a residential area, showcasing homes with canopy-covered roofs and surrounded by tropical foliage.

4.91 out of 5 average rating, 105 reviews

The Palm Treehouse

The Palm Treehouse (#30) at Hanalei Bay Villas is uniquely situated between Kauai's North Shore mountains and ocean, allowing you to admire both at the same time. Elevated above the canopy of Makai Golf Course, the South side opens to a verdant valley and jagged mountain face. The front faces North, boasting brilliant views of the Pacific and sunsets. Excellent for bird and whale watching! Within walking distance are two beaches, restaurants, trails, and the world-renowned 1 Hotel Hanalei Bay.

Indoor spacesFamilyBathroom

A vibrant ocean scene is captured, showcasing various shades of blue and green in the water. Gentle waves can be seen lapping at a rocky shoreline, with lush greenery accentuating the coastline. The horizon is dotted with distant boats against a clear sky.

4.93 out of 5 average rating, 193 reviews

Remodeled Oceanfront Penthouse w/ Gorgeous Views!

Escape to paradise with this stunning ocean front 2 bedroom, 2 bathroom penthouse condo in beautiful Princeville! This updated condo boasts breathtaking views of the ocean from every room and is the perfect place to relax and unwind. The condo offers a fully stocked and updated kitchen. Plus, 2 well-appointed bedrooms, including a large master suite with an en suite bathroom. The additional bedroom is perfect for families, guests, or a remote office. Enjoy the lanai overlooking the ocean.

Indoor spacesFamilyAccuracy

The spacious living area is adorned with large windows offering ocean views and abundant natural light. A modern sectional sofa and a coffee table are complemented by tropical decor, while a spiral staircase adds architectural interest. The space features a light and airy atmosphere.

4.93 out of 5 average rating, 144 reviews

Executive 2 bdrm - Panoramic Ocean Views

Paradise awaits! This stunning two-bedroom executive condo has recently been remodeled and is the perfect home base for enjoying all the north shore has to offer. With ocean views from every room, immerse yourself in the serenity of the Pacific. The Cliff's is located in the exclusive resort community of Princeville and features a long list of amenities. Enjoy onsite concierge, pool, hot tub, tennis courts, covered BBQ area as well as a number of food trucks that visit throughout the week.

FamilyKitchenGetting around

An airy dining area features a wooden dining table accompanied by a long bench and white chairs. Large windows invite natural light, framing the lush outdoor greenery. Decorative plates adorn the wall, complementing the open layout and modern kitchen visible in the background.

4.99 out of 5 average rating, 120 reviews

New Deluxe A/C Home, Spectacular Mountains Views

Completely renovated luxurious home with A/C and breathtaking mountain views! The remodeled kitchen features all the essentials for your culinary endeavors. Enjoy the unrivaled beaches of Kauai, relax by the pool and hot tub, and sip your favorite beverage at the lanai bar. Explore the charming towns of Princeville and Hanalei or a round of golf at the Makai Golf Club. Our two office nooks, with awe-inspiring views, are perfect for remote work. Let the island aloha restore and refresh you.

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A spacious living area features large windows offering unobstructed ocean views and ample natural light. A round dining table is set for four, complemented by coastal-themed decor. Relaxing seating options, including a daybed, are arranged to take advantage of the captivating seaside scenery.

4.98 out of 5 average rating, 329 reviews

Sea and Sky Kauai, an Oceanfront Penthouse dream

This modern and newly renovated honeymoon beach retreat has breathtaking panoramic ocean and coastline views. Lounge in the daybed while gazing at the sweeping vista from Anini reef to Kilauea Lighthouse. Some have said "it feels like being on a ship at sea" as they witness whales breaching in the ocean and waves peeling on the reef from this magical location. A rare penthouse unit with high ceilings, views from every room, even the famous Bali Hai from the deck. Truly a couple's dream!

Indoor spacesFamilyOutdoor spaces

A spacious screened-in lanai is presented, featuring a wooden dining table set with plates and glasses. Soft seating options in the background provide a cozy atmosphere, while string lights create a warm glow. Lush greenery is visible through the surrounding windows.

4.98 out of 5 average rating, 136 reviews

Hibiscus House~tropical oasis Kauai

Escape to this private Hawaiian paradise, tucked away in a family friendly neighborhood minutes from Hanalei. Walking paths to shops, beaches, outdoor markets, cafes and grocery store are out the front door. Mornings on the lanai promise bird songs and tranquility as you sip your coffee or maybe you'll catch a few waves at Hanalei Bay before breakfast. Evenings dazzle here as you unwind and relax under twinkling cafe lights. You'll come for the beach but you'll stay for the rainbows.

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The modern retreat is nestled within lush greenery, showcasing a spacious yard surrounded by tropical trees. The house's exterior features a light-colored facade and a welcoming covered porch. Scenic mountain views are visible in the background, creating a serene environment.

4.98 out of 5 average rating, 172 reviews

Princeville at Hanalei North Shore Modern Escape

Hale Laniakea ~Princeville at Hanalei 4 Bedroom Modern Retreat Our home, Hale Laniakea (Immeasurable Heaven) is located in a private cul-de-sac in the best part of the beautiful Princeville at Hanalei resort. You will love being able to walk to Queen's Bath, Hideaways Beach & snorkel spot, the Makai Golf Course & Tennis Club & Pu'u Poa Beach on Hanalei Bay. Walk to 1 Hanalei Hotel where you can dine & see live music with a spectacular view. Hanalei is five minutes down the road.

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 401 reviews

An aerial view showcases a charming cottage surrounded by lush tropical foliage. A private hot tub is nestled on a deck, complemented by a cozy lounging area. Vibrant flowers and greenery create a serene outdoor space, enhancing the sense of seclusion and tranquility.

Cottage in Hanalei

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a secluded romantic haven nestled on an acre of lush gardens in Kauai’s breathtaking Wainiha River Valley. Perched on a bluff with panoramic valley views, this retreat offers tranquility and luxury. Unwind by your private pool and spa, surrounded by vibrant tropical flora, where nature creates an atmosphere of enchantment. Just a short drive away, explore some of the world’s most stunning beaches. Let this serene paradise immerse you in romance and blissful relaxation

FamilyIndoor spacesSolo travel

Popular amenities for Princeville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 113 reviews

Spectacular View A/C Condo in Heart of Princeville

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A private balcony features a wooden table set with dishes and cups amid colorful floral-patterned chairs. Lush greenery is visible in the background, accompanied by distant mountain views and a clear blue sky with fluffy clouds.

4.88 out of 5 average rating, 209 reviews

Spectacular Hanalei Bay Resort Newly Remodeled

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A large swimming pool is surrounded by tropical landscaping, featuring palm trees and vibrant flowers. A gentle waterfall cascades over rocks into the pool. Comfortable lounge chairs are positioned nearby, with a covered pavilion visible in the background.

4.96 out of 5 average rating, 103 reviews

Modern 2BR + Den Condo | Near Hanalei Bay & Beach

Indoor spacesFamilyCondition

A private lanai is featured with two wooden chairs and a round table, offering a serene view of the ocean and surrounding mountains. The setting sun casts a warm glow, enhancing the natural beauty of Hanalei Bay's landscape.

4.95 out of 5 average rating, 132 reviews

Breathtaking Unobstructed Hanalei Bay Views

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Superhost

A modern kitchen is equipped with stainless steel appliances, including an oven, microwave, and coffee maker. The cabinets feature a dark finish, complemented by a light countertop. Natural light floods in from large windows, offering a view of lush greenery outside.

4.84 out of 5 average rating, 594 reviews

Contemporary Family Condo (Princeville)

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An aerial view showcases a spacious home surrounded by lush greenery, with a large sand volleyball court prominently situated in the foreground. Scenic mountains and palm trees frame the landscape, providing a tranquil atmosphere. The home's multiple levels offer expansive outdoor spaces for relaxation.

4.92 out of 5 average rating, 123 reviews

Sunset Waterfall House In Kauai

KitchenFamilyShared spaces

4.96 out of 5 average rating, 146 reviews

Kauai Oasis | NEW Design • Luxe, AC, Pool, Beaches

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A serene outdoor view from the condo features lush green gardens and a vibrant array of tropical plants. In the background, the majestic mountains rise under a partly cloudy blue sky, creating a tranquil setting accessible from the slidng glass door.

4.92 out of 5 average rating, 308 reviews

Amazing Views above Beautiful Hanalei Bay

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Family- and pet-friendly home rentals

4.85 out of 5 average rating, 280 reviews

Mountain/Ocean views by Hanalei + Nāpali + Hot Tub

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4.85 out of 5 average rating, 288 reviews

Jewel of the Pacific. Seaside condo at Sealodge

KitchenFamilyLong stay

A scenic coastal view features rolling waves meeting the shore, framed by lush greenery and rugged cliffs. Gentle grasses sway in the foreground, while a clear blue sky stretches above, providing a serene backdrop to the vibrant ocean below.

4.84 out of 5 average rating, 105 reviews

Aloha Zen Oasis~Hawaii lifestyle~ Pool ~ No stairs

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A contemporary living space features a comfortable seating area with two gray armchairs and a sleek coffee table made of wood. Large windows showcase ocean views and provide natural light, while a cozy bed is located in the corner of the room.

4.89 out of 5 average rating, 151 reviews

Modern Ocean Views ~Lovebirds Paradise With AC

Indoor spacesFamilyCondition

Guest suite in Princeville

A spacious guest suite features a comfortable king bed adorned with decorative pillows and a flower accent. The room includes a seating area with a sofa, wood console table, and vibrant tropical decor, complemented by soft lighting from bedside lamps.

4.93 out of 5 average rating, 269 reviews

Tropical Escape | King Suite & Gear, North Shore

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Guest suite in Princeville

An airy living space is presented with large glass windows that offer views of the lush garden. A dining table made of wood is accompanied by green chairs, while a light-colored sofa and two woven chairs are arranged around a circular coffee table on a textured rug.

4.91 out of 5 average rating, 437 reviews

Modern Tropical Residence w Indoor/Outdoor Living

Indoor spacesKitchenCleanliness

A well-lit studio space features a California King bed with light bedding, complemented by two stylish seating areas. Natural wood beams accent the ceiling, while a round coffee table sits atop a woven rug. Sliding glass doors provide access to a lanai, inviting soft natural light.

4.88 out of 5 average rating, 464 reviews

Cool Studio- Minutes to Hanalei w/ AC

FamilyKitchenWalkability

4.93 out of 5 average rating, 107 reviews

Townhouse in Princeville

Spacious 3-bdr Pool, Hot Tub and free A/C

FamilyIndoor spacesPool

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 366 reviews

An open living space is presented with high ceilings and a large, modern kitchen area. A wooden dining table with seating for four sits in the center, complemented by stylish wicker chairs. A comfortable sofa and a decorative surfboard enhance the coastal aesthetic.

Townhouse in Princeville

North Shore Bungalow - w/ AC, bikes, beach gear

Indoor spacesFamilyLaundry

4.98 out of 5 average rating, 117 reviews

An open-concept living area features a wooden dining table set with neutral dishware, surrounded by stylish chairs. The modern kitchen, equipped with stainless steel appliances, is visible in the background. Bright light floods the space, complemented by ceiling fans and decorative touches.

Townhouse in Princeville

Quiet, Airy Condo with Lofted King Suite-2BR, 2BA

Indoor spacesFamilyLaundry

A dining area features a round glass table surrounded by four padded chairs. A potted orchid centerpiece adds a touch of color. Large windows frame the stunning ocean view, allowing natural light to brighten the space.

4.96 out of 5 average rating, 118 reviews

Pali Ke Kua Condo 207 w/Peloton, Shared Pool/Spa

Indoor spacesKitchenCheck-in

An expansive view of the ocean meets the horizon, showcasing varying shades of blue and turquoise waters. Waves break gently against the rocky shoreline. Lush greenery, including tropical plants, frames the scene, enhancing the coastal landscape under a bright blue sky with scattered clouds.

4.95 out of 5 average rating, 389 reviews

OCEAN FRONT 2b/2ba Princeville Kauai

FamilyIndoor spacesOutdoor spaces

The living area features a spacious white sofa complemented by tropical-themed cushions. Two woven chairs with green accents are positioned nearby. A wooden coffee table sits atop a round jute rug, enhancing the natural aesthetic. A potted plant adds a touch of greenery to the space.

5.0 out of 5 average rating, 56 reviews

Hanalei Bay Resort 9305 (Hanalei Bay Hideaway) AC!

FamilyIndoor spacesValue

5.0 out of 5 average rating, 55 reviews

NEW Hanalei Happiness - Modern Family Retreat

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A tranquil resort pool area features a curved hot tub integrated with natural rock. Lush landscaping surrounds the space, adding vibrant greenery. The main building is visible in the background, showcasing a modern design with multiple terraces.

5.0 out of 5 average rating, 17 reviews

Bali Hai Villas Resort *POOLS* ~ Now with AC!

KitchenFamilyPool

An open living area features large sliding glass doors that provide a view of the ocean and mountains. A comfortable sofa with colorful cushions is positioned beside a wooden table. The kitchen area is equipped with modern appliances, and a ceiling fan adds to the airy atmosphere.