Family-friendly vacation rentals in Koloa

4.96 out of 5 average rating, 118 reviews

Premier 3BR/3BA Ground Floor Poipu Condo with A/C

Welcome to Pili Mai 2J...one of Poipu's newest luxury projects. This premier ground floor, single level, three bedroom, three bathroom Moana unit, is generously laid out with maximum separation between the bedrooms for extra privacy. Newly built, this unit features a beautifully appointed kitchen, high end furniture and decor, a separate office area, laundry, and private lanai. Relax and unwind in style!! Steps away from the pool and fitness center and a short walk to Poipu Shopping Village.

FamilyIndoor spacesLong stay

4.98 out of 5 average rating, 100 reviews

Poipu Ocean View + AC | Pool & 3m Walk to Beach

Our spacious 1bed, 1 bath condo is the perfect place to unwind after a long day of adventuring around this beautiful island. Relax on the lanai with a tropical drink in your hand while watching the beautiful sunset. For more pictures follow us on IG @poipuparadise *3 min walk to swimmable beaches & restaurants *10 min walk to Shipwreck's Beach and The Hyatt *2 easily accessible pools *sweeping ocean views from the lanai Experience this Po'ipu Paradise... more details below in the listing

KitchenIndoor spacesPool

4.99 out of 5 average rating, 101 reviews

Beautiful 3 Bed Pili Mai condo, A/C

Aloha! Welcome to our 3-Bedroom, 2.5-Bath Condo on Kiahuna Golf Course This two-story, air-conditioned condo offers a peaceful retreat just 0.5 mi. from Kiahuna Beach and 1 mi. from Poipu Beach. Enjoy views of the golf course and mountains, away from road and pool noise. Ideal for families or groups, with 3 spacious bedrooms and 2.5 bathrooms. Key Features: Close to beautiful beaches, Air-conditioned & quiet, top-floor unit. *No Smoking or vaping thank you. Book your Kauai escape today.

FamilyKitchenHiking

An inviting pool area is illuminated by soft lighting as dusk approaches, featuring a large swimming pool with gentle fountains. A spacious clubhouse is visible in the background, surrounded by lush greenery and seating areas for relaxation.

4.95 out of 5 average rating, 125 reviews

NO STAIRS, CENTRAL AC, STEPS TO POOL, GYM, JACUZZI

Our home, PiliMai 2D is a first floor unit, no stairs and was upgraded to have travertine tile throughout the entire condo with no carpeting used in any space. We have furnished the condo with top notch furniture such as Palecek and installed beautiful Koa ceiling fans in all bedrooms, lanai, and living room. East facing large lanai allows beautiful views of sun rise over the Ha’upu Mountain range and rows of Royal Palm trees, and receives cooling easterly trade winds in the afternoons.

FamilyKitchenAccess

A bright and airy living space showcases a seating area with modern furnishings, including a large couch and two armchairs. A dining table is set with plates and decorative elements, while large windows offer views of the golf course and bring in natural light.

4.8 out of 5 average rating, 101 reviews

3bd/3b Retreat, Sleeps 10, AC, Family-Friendly

Escape to paradise in this relaxing 3 bed/3 bath retreat at the Pili Mai condos located on the Kiahuna golf course. This unit can sleep up to 10 guests, relax in its plush interiors, a cozy bunk room, and plenty of great living spaces to create lasting family memories. Walk to nearby shops, restaurants, and amazing beaches, or stay active in the gym, cool off in the pool, or book a tee time for golf. Book your stay today and start counting down till you vacation adventure beings!

KitchenIndoor spacesComfort

A bright living area is presented with a comfortable gray sofa adorned with orange cushions. A wooden coffee table sits center stage, surrounded by a textured area rug. Large windows with plantation shutters allow natural light to enter, complemented by greenery from a nearby potted plant.

4.98 out of 5 average rating, 251 reviews

Sunny Poipu, Mountain View, close to beach, A/C

When you step inside Pili Mai, you'll immediately experience a comfortable tropical ambiance, complete with air conditioning. This welcoming community boasts a pool and sports complex on-site, offering serene views of the mountains and gardens and golf course. It's a tranquil place to call home, just minutes away from the sunny Poipu area, with its restaurants, beaches, and shopping options.

KitchenFamilyBeach

An aerial view of a spacious outdoor pool area is displayed, featuring a large swimming pool alongside a hot tub. Lounge chairs are arranged around the pool, with umbrellas providing shade. Lush greenery and vibrant flowers surround the space, enhancing the tropical atmosphere.

4.99 out of 5 average rating, 123 reviews

Poipu Paradise Condo, 3Bd, 3Ba, pool, hot tub & AC

Paradise Villa located in sunny Poipu Beach. Main floor w/easy access and A/C. 3 Bedroom, 3 Bath, w/washer and dryer that sleeps 8. Surrounded by Kiahuna Golf course and amazing mountain views. Walk to dining, shopping, golf and Poipu beach. Two King Size master suites and a 3rd bedroom with 2 sets of bunk beds. Amenities: Pool, Childrens Pool, hot tub, exercise room, gas bbq.

FamilyKitchenBathroom

An outdoor lanai features comfortable seating with tropical-patterned cushions and a coffee table. A coastal view of the ocean is visible in the distance, complemented by lush green foliage surrounding the space. Ceiling fans provide cooling, enhancing the inviting atmosphere for relaxation.

4.9 out of 5 average rating, 119 reviews

Oceanview Cottage| Walk to PoipuBeach |Free Parkng

Welcome to Hale Nani Kai, your “House of the Beautiful Sea,” where every moment feels touched by the ocean. Stroll to Poipu Beach, relax on the shaded lanai, or watch waves roll in as turtles rest along the shore. Enjoy stunning views of Brenneke’s and Poipu Beaches, with winter whale sightings in the distance. It’s the perfect Poipu retreat for sun, surf, and complete relaxation.

KitchenFamilyView

4.96 out of 5 average rating, 194 reviews

Kiahuna Hale Kai II

Experience the beauty of Kauai from Kiahuna Hale Kai II, our 2-bedroom oceanview retreat located in the heart of the iconic Kiahuna Plantation Resort in Poipu. Located on Kauai’s sunny south shore, Poipu is known for having the island’s best weather year-round — making it the perfect setting for romantic getaways, family vacations, and unforgettable island adventures.

FamilyKitchenDecor

4.87 out of 5 average rating, 123 reviews

An aerial view captures the expansive beachfront property overlooking Kiahuna Beach, with lush green lawns and palm trees leading up to the sandy shore. Several sun loungers are visible on the grass, providing a relaxing spot near the water's edge.

Vacation home in Poipu

BEACH! 2min walk | BBQ | Gym | Pool | Snorkeling

Beach lover’s paradise! 2min walk to the Kiahuna Beach ☞ Beachfront w/ garden views ☞ Free resort access* ☞ Shared backyard + BBQ + dining ☞ Private balcony w/ sun loungers ☞ Fully equipped + stocked kitchen ☞ Bluetooth/AUX sound system ☞ 50" QLED Roku TV ☞ Beach essentials ☞ Parking → 1 car 5 mins walk →Poipu Athletic Center 6 mins drive → DT Koloa

FamilyKitchenPool

4.99 out of 5 average rating, 208 reviews

A modern two-story home features a white exterior with contrasting dark trim and large windows. The double garage is prominently displayed, with stylish doors that enhance the architectural design. A covered balcony extends from the upper level, inviting outdoor relaxation. Clear blue skies provide a vibrant backdrop.

Townhouse in Poipu

Poipu-Walk to the Beach-Sunny Kauai Retreat

Great location/price is right Beautiful and simple new home. This two bedroom two bath house in Poipu Beach Estates is walking distance from great restaurants, shops and epic snorkeling spots. Access to beach chairs, umbrellas, and sand toys provided. The property also comes with pool/gym access to Poipu Beach Athletic Club.

FamilyIndoor spacesAccess

A serene pool area is framed by lush greenery and palm trees, with comfortable loungers positioned around the pool. The ocean is visible in the background, alongside a clear blue sky, enhancing the tranquil atmosphere of the landscape.

4.92 out of 5 average rating, 154 reviews

Oceanfront Paradise! Poipu Sunsets, Pool & Views!

Indulge in the epitome of coastal luxury at our oceanfront condo. Dive into leisure with pool and tennis amenities, and experience ultimate comfort with air-conditioned bedrooms. * Please note: The Poipu Kapili Pool will be closed from Monday, September 14, 2026 until approximately Saturday, October 10, 2026.

KitchenIndoor spacesAir conditioning

Popular amenities for Koloa family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A living area features a comfortable blue-striped sofa and two rattan chairs. A coffee table sits in the center on a textured rug. Light streams in through sliding glass doors, leading to a verdant outdoor space, enhancing the open feel of the room.

4.95 out of 5 average rating, 284 reviews

Serene Location, AC, sleeps 4, pool access

Indoor spacesFamilyAmenities

A spacious living area is presented with large windows that allow natural light to fill the space. Seating is provided by a dark green sofa and patterned armchairs. A dining table is visible in the background, complemented by a fully equipped kitchen area. Decorative artwork adorns the walls.

4.98 out of 5 average rating, 173 reviews

Oceanview in Heart of Poipu

KitchenFamilyNearby

A light and airy kitchen area features a modern counter with white bar stools and a vintage mint green mixer. Decorative elements include a surfboard mounted on the wall and open shelving displaying glassware and plants, enhancing the coastal theme.

4.98 out of 5 average rating, 155 reviews

Little Rainbow Kauai | Beachfront, AC, Ocean View

FamilyKitchenSleep quality

The entrance to the Makahuena condo complex is showcased, marked by a sign displaying the name against a backdrop of lush tropical plants and palm trees. A paved pathway leads into the property, with a glimpse of the buildings visible in the background.

4.92 out of 5 average rating, 146 reviews

Poipu Waterfront Paradise Condo

Indoor spacesKitchenBathroom

4.85 out of 5 average rating, 109 reviews

Poipu tropical garden view w/AC. No stairs!

FamilyIndoor spacesAccuracy

A spacious living area features a comfortable sofa and decorative pillows, complemented by a wooden coffee table and side tables. Large windows offer views of the outdoors, and a ceiling fan provides airflow. Natural light brightens the room, enhancing the inviting ambiance.

4.98 out of 5 average rating, 153 reviews

BEAUTIFUL Pili Mai 6C Condo SUNNY POIPU!

KitchenIndoor spacesSleep quality

An aerial view captures a vibrant beach with clear turquoise waters gently meeting sandy shores. Lush green lawns are dotted with tall palm trees, and visitors can be seen enjoying various water activities, including paddleboarding. Umbrellas provide shade along the sandy coastline.

4.95 out of 5 average rating, 138 reviews

Upgraded, A/C, Ocean View, In Unit W/D, KP 248

FamilyIndoor spacesComfort

4.95 out of 5 average rating, 135 reviews

A view from a covered lanai captures lush green surroundings and glimpses of the ocean in the distance. Palm trees sway gently against a bright blue sky adorned with fluffy clouds. Outdoor dining furniture is positioned in the foreground, inviting relaxation and enjoyment of the scenery.

Apartment in Poipu

The Surf Shack | Ocean Views | A/C

FamilyIndoor spacesParking

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 354 reviews

A private lanai features a round table with two woven chairs, overlooking a scenic ocean view. Lush green grass and gentle waves are visible, framed by swaying trees under a clear blue sky.

Condo in Wailua

Beachfront oceanside condo paradise AC/pool/HT 247

Indoor spacesFamilyDecor

4.98 out of 5 average rating, 267 reviews

A tranquil outdoor space features a small table set with two coffee mugs. Lush greenery surrounds the area, complemented by flowering plants. In the distance, the ocean is visible beyond the well-maintained lawn and palm trees, creating a serene environment.

Condo in Wailua

Beachside Walk Out Condo/Pool/A/C Ocean Views 144

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 108 reviews

Townhouse in Princeville

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

FamilyIndoor spacesHospitality

4.95 out of 5 average rating, 404 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

Indoor spacesKitchenHot tub

4.9 out of 5 average rating, 112 reviews

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.

Home in Princeville

The Palm Treehouse

FamilyKitchenTV

4.81 out of 5 average rating, 108 reviews

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.

Condo in Princeville

Aloha Zen Oasis~FALL Special~New Pool ~ No stairs

FamilyIndoor spacesLocation

4.94 out of 5 average rating, 101 reviews

A single-story house is framed by tall palm trees, set on a lush green lawn. The sky is partly cloudy, with bright sunlight peeking through, illuminating the surrounding greenery and creating a serene outdoor atmosphere.

Home in Kilauea

Northshore 5 acres plantation style home TVNC 4273

KitchenIndoor spacesCondition

4.9 out of 5 average rating, 318 reviews

Condo in Kapaa

Stunning OceanViews, Kitchen, King bed, WiFi, 203

KitchenIndoor spacesLayout

Family-friendly home rentals with a pool

A serene outdoor pool is surrounded by lounge chairs and lush tropical greenery. A shaded cabana is visible in the background, featuring a blue umbrella. Tall palm trees sway gently in the breeze against a bright blue sky.

4.84 out of 5 average rating, 208 reviews

Ask about Jeep Grand Cherokee. A/C in bedroom!

KitchenIndoor spacesCheckout

4.85 out of 5 average rating, 126 reviews

A two-story villa is framed by tall palm trees and vibrant tropical foliage. The sky is bright and clear, highlighting the lush gardens that surround the home. Colorful flowers add to the serene atmosphere, creating a welcoming entryway.

Townhouse in Poipu

Beautiful tropical villa, private, walk to beach

KitchenIndoor spacesCheck-in

A spacious living room offers comfortable seating on a sectional sofa, complemented by natural light through large windows. A view of the landscaped yard extends towards the distant mountains, while decorative elements incorporate natural textures and colors.

4.98 out of 5 average rating, 101 reviews

Poipu Modern Island House with AC & Pool/Gym Access

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 105 reviews

Poipu Kapili:Ocean Views; New Split ACs/Windows

FamilyIndoor spacesBeach

Superhost

A large pool is surrounded by lush tropical landscaping, featuring vibrant pink and red flowering plants. Lounge chairs are positioned around the pool area. The clear water reflects the blue sky above, providing a refreshing retreat.

4.74 out of 5 average rating, 250 reviews

Cal King Bed/ Surf board included!

KitchenIndoor spacesTV

A table is set with two glasses of white wine beside a plate featuring slices of cheese and fresh fruit, including a pineapple and papaya. The setting sun casts a warm glow over the green lawn and surrounding tropical vegetation.

4.9 out of 5 average rating, 255 reviews

Ocean views/AC/free parking/walk to beaches in 10!

FamilyKitchenLayout

A dining area with a wooden table is surrounded by wicker chairs, set for a meal with plates and silverware. Large windows allow natural light to illuminate the space, showcasing views of the golf course and mountains beyond. A decorative plant adds a touch of greenery.

4.97 out of 5 average rating, 195 reviews

Ocean Views A/C Stunning Poipu 9iCondo Golfcourse

FamilyIndoor spacesLayout

A comfortable living area features a light blue sofa, a wooden coffee table, and a pair of lounge chairs. Large sliding glass doors open to a private lanai surrounded by greenery, allowing natural light to fill the space. Wall-mounted shelves display decor and books.