Family-friendly holiday rentals in Poipu

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.

4.83 out of 5 average rating, 209 reviews

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

In the heart of Poipu lies a cozy 1-bedroom villa, centrally located to everything in Poipu Beach. Step into your home-away-from-home and be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, BBQ grill(in the common areas), and all the appliances you need to whip up delicious meals. Enjoy dining al fresco on the lanai, surrounded by lush greenery and the soothing sounds of nature. Air conditioning in the bedroom as of Jan 2025. *Jeep Grand Cherokee available for fee

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.

An aerial view captures the expansive Kiahuna Plantation Resort and surrounding landscape, featuring lush greenery and the coastline. A distinguishing arrow points to Building 23, highlighting its proximity to the sandy beach and clear blue waters. The backdrop includes mountains and distant shores.

4.98 out of 5 average rating, 318 reviews

Slice of Kiahuna Paradise-A/C-BEACHFRONT-POOL

NOTE: Pool & spa will be CLOSED for resurfacing 9/9/26-10/15/26. Remodeled bright & breezy top floor, corner unit in exclusive Bld 23. Steps away from Poipu Beach. Privacy. Whole home A/C (dual split in living & portable in bdrm). Fast Wifi. King bed,queen sleeper sofa & twin in the living room comfortably sleeps up to 4 people. New furniture & appliances.65” Smart tv. Loads of extra amenities, beach gear, fully equipped kitchen, suggested experiences & babysitters, offering a priceless 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

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.

4.8 out of 5 average rating, 101 reviews

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.

Home in Poipu

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!

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, 157 reviews

Little Rainbow Kauai | Beachfront, AC, Ocean View

This bright and airy updated condo is the ideal place to stay in sunny Poʻipū for couples, honeymooners + small families. The open living space is clean and welcoming with a coastal boho vibe, and you'll enjoy beautiful ocean + garden views from the huge upper-level lanai. Location is the absolute best - from the beachfront property, you can walk to several of the best beaches on the south shore, local coffee, restaurants, shops, and the incredible pool within minutes.

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.

4.94 out of 5 average rating, 287 reviews

Serene Location, AC, sleeps 4, pool access

Kiahuna Planation Resort #404. Located in building #40. Enjoy relaxing on the lanai listening to the birds sing. This peaceful and centrally-located condo of perfect for couples and families. Enjoy air conditioning located in the living room on those hot summer nights. The bedroom has a king bed and pocket doors to close for privacy. A queen bed folds out from the sofa to sleep 1 or 2 more people. Po’ipū Beach Athletic Club comes as a amenity with the condo.

Superhost

A heart-shaped floral arrangement is positioned on dark rocks at the edge of the water. The clear blue ocean stretches into the distance, with gentle waves lapping at the stones. A bright sky with scattered clouds complements the serene coastal scene.

4.87 out of 5 average rating, 214 reviews

Peaceful Poipu Condo

In the heart of Poipu this lovely property is located on the beautiful grounds of Poipu Kai just a short scenic stroll to the surf and sand at Poipu Beach. BBQ, pools and tennis courts on site and restaurants and shops close by make this an ideal location for a get away. This one bedroom oasis is just under 1,000 square feet and is complete with full kitchen, two TVs, WiFi and outdoor patio space.

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, 253 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.

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.