Cozy studio condo with AC and WiFi in charming Koloa/ PoipuFrom $147/night · Sleeps 2
Old Koloa and Poipu Rentals
Koloa Vacation Rentals
Koloa Vacation Rentals – Historic Charm Meets Island Luxury
Koloa, located on Kauai's sun-drenched South Shore, blends plantation-era charm with upscale vacation comfort. As the site of Hawaii's first sugar plantation, this historic town retains its cultural heritage through preserved architecture, small-town streets, and local artisan shops.
About Koloa Vacation Rentals
Vacation rentals in Koloa include beautifully restored plantation cottages, spacious homes, and luxury villas equipped with modern comforts like private lanais, chef-style kitchens, and resort-style amenities. Whether you're planning a romantic stay or a multigenerational stay, Koloa accommodations cater to all types of travelers.
Key Features of Koloa Rentals
- Charming plantation homes and modern villas with private lanais
- Access to shopping, restaurants, and heritage walking trails
- Short drive to Poipu Beach, hiking trails, and golf courses
- Family-friendly and couple-ready options with local flair
- Close proximity to Kauai's sunny coastal attractions
Nearby Attractions & Local Highlights
- Stroll the Koloa Heritage Trail and learn about the town's plantation history
- Explore the beaches, dining, and snorkeling opportunities in Poipu
- Play a round at the nearby Kukuiolono or Poipu Bay Golf Course
- Visit the Spouting Horn blowhole and the National Tropical Botanical Garden
Why Stay in Koloa?
Staying in Koloa offers the right balance between cultural immersion and resort-style relaxation. It's a convenient home base for discovering Kauai's South Shore, with easy access to both natural and historical treasures. For travelers wanting proximity to beaches but a quieter, more historic setting than Poipu, Koloa is an ideal fit.
Browse and book your Koloa vacation rental below to enjoy the best of Kauai's heritage and hospitality on the South Shore.
Rental Listings
Koloa Vacation Rentals Listings
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Koloa Vacation Rentals Map
Cozy studio condo with AC and WiFi in charming Koloa/ PoipuFrom $147/night · Sleeps 2
Summer Deal Poipu 2BR Retreat with Resort Pool and Beach AccessFrom $230/night · Sleeps 6
Wainani Sunset EstateFrom $842/night · Sleeps 8
Spacious Poipu Home with Guest House, Resort-Style Outdoor Living & Pool!From $1,055/night · Sleeps 11
Summer Deal Ground Floor 3BR Poipu Condo with Pool Beach AccessFrom $266/night · Sleeps 6
Poipu Sands at Poipu Kai #213 By Parrish Kauai - ocean view & walk to the beachFrom $311/night · Sleeps 4
Regency at Poipu Kai 123 By Parrish Kauai - Short walk to BeachFrom $433/night · Sleeps 8
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & ACFrom $994/night · Sleeps 8
Kick back at Lay Back Larry's on Brennecke's Beach, Poipu, Kauai Island!From $999/night · Sleeps 6
koolkondo 2597 Halalu Main homeFrom $1,240/night · Sleeps 12
Luxury 2BR Villa at Marriott Waiohai • Pools, Beach & Resort AmenitiesFrom $1,300/night · Sleeps 8
New Listing! Poolside Poi'pu Condo - 2BR KahalaFrom $204/night · Sleeps 4
VERY SPECIAL Renovated 1 Bdrm Condo - A/C - Oceanview, Athletic Club AccessFrom $280/night · Sleeps 2
Walk to 3 Poipu Beaches • Spacious 2BR/2BA Condo with A/C, Resort Pools & TennisFrom $332/night · Sleeps 4
New Listing 3 Bedroom on the Golf Course in sunny PoipuFrom $392/night · Sleeps 6
Pili Mai 6J by Gather: Golf View Poipu Condo w/ Lanai, Pool, A/C, Hot Tub & GymFrom $465/night · Sleeps 6
Hale O‘Kapeka – Spacious 3BR Poipu Home with Ocean Views & Hawaiian SoulFrom $470/night · Sleeps 6
Nihi Kai 201 Ocean ComfortFrom $476/night · Sleeps 4
Makahuena 1205 – Ocean Views, Full A.C. + P.B.A.C. AccessFrom $499/night · Sleeps 6
Hale Hoʻomalie – Private Pool & Golf ViewsFrom $516/night · Sleeps 8
koolkondo 2597 Halalu CompoundFrom $1,181/night · Sleeps 16
Hale Hanohano by Gather: Luxury Poipu Estate w/ Pool, Spa, Lanais & Ocean ViewsFrom $2,127/night · Sleeps 16
New Listing! Treetop Getaway with Athletic ClubFrom $151/night · Sleeps 2
August Sale!! Walk to Baby Beach From a Family-Friendly Condo with PoolFrom $184/night · Sleeps 6
Restful, beautiful one-bedroom ocean view condo in Sunny PoipuFrom $213/night · Sleeps 4
Kahala 723 “Apana O Lani” – 2 Lanais, King Bed, Island SerenityFrom $217/night · Sleeps 4
Aloha Escape-Oceanview-Newly UpdatedFrom $238/night · Sleeps 5
Walk to Poipu Beach | Garden Condo | AC, Pools, Hot Tub & TennisFrom $295/night · Sleeps 5
New listing! Lovely Poipu Condo with Gym and PoolFrom $301/night · Sleeps 8
Riverfront condo across from ocean. Sleeps 6From $314/night · Sleeps 8
Ocean and Sunset Views - Poipu - A/C - Pool - W/D -Walk to beaches -Fun in SunFrom $314/night · Sleeps 4
Kahala 633 – Ocean-View 1BR Near the BeachFrom $349/night · Sleeps 4
Regency 620 - Beautiful 3 Bedroom Overlooking Regency PoolFrom $428/night · Sleeps 6
From $147/night
Cozy studio condo with AC and WiFi in charming Koloa/ Poipu
Koloa, Hawaii
★★★★★ 5 reviews
Nestled in Koloa, this delightful condo is a tranquil oasis for guests seeking a serene getaway. With a cozy bedroom and a well-equipped bathroom...
From $230/night
Summer Deal Poipu 2BR Retreat with Resort Pool and Beach Access
Koloa, Hawaii
★★★★★ 5 reviews
Welcome to Kauai Makanui 712, a bright and spacious 2-bedroom, 2-bath retreat. Thoughtfully designed for comfort and island living, this home is the...
From $842/night
Wainani Sunset Estate
Koloa, Hawaii
★★★★★ 5 reviews
Welcome to Wainani Sunset Estate – your island home away from home. This retreat features four suites with walk-in closets, en-suite baths, and split...
From $1,055/night
Spacious Poipu Home with Guest House, Resort-Style Outdoor Living & Pool!
Koloa, Hawaii
★★★★★ 5 reviews
Welcome to an exceptional luxury retreat in the prestigious Poipu Beach Estates, tucked away on a quiet cul-de-sac just minutes from world-class...
From $266/night
Summer Deal Ground Floor 3BR Poipu Condo with Pool Beach Access
Koloa, Hawaii
★★★★★ 4 reviews
Sleeps 6 | Ground-Floor 3BR/3BA | Central AC | Walk to Beach and GolfWelcome to Pili Mai 2M, a spacious 1,580-square-foot, ground-floor retreat in...
From $311/night
Poipu Sands at Poipu Kai #213 By Parrish Kauai - ocean view & walk to the beach
Koloa, Hawaii
★★★★★ 4 reviews
Our luxurious Kauai vacation rentals at Poipu Sands offer spacious layouts, large covered lanais, a private heated resort swimming pool, community...
From $433/night
Regency at Poipu Kai 123 By Parrish Kauai - Short walk to Beach
Koloa, Hawaii
★★★★★ 4 reviews
The Regency at Poipu Kai offers some of Kauai’s most refined condo accommodations on the South Shore. Fully air-conditioned and beautifully...
From $994/night
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
Koloa, Hawaii
★★★★★ 4 reviews
Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to...
From $999/night
Kick back at Lay Back Larry's on Brennecke's Beach, Poipu, Kauai Island!
Koloa, Hawaii
★★★★★ 4 reviews
Kick back at Lay Back Larry's our Brennecke's Beach bungalow which we remodeled in 2025 for optimum style and comfort. Walk to the beach then come...
From $1,240/night
koolkondo 2597 Halalu Main home
Koloa, Hawaii
★★★★★ 4 reviews
Welcome to your dream escape in Poipu Beach Estates! This beautifully upgraded, two-story luxury vacation home is the perfect blend of island...
From $1,300/night
Luxury 2BR Villa at Marriott Waiohai • Pools, Beach & Resort Amenities
Koloa, Hawaii
★★★★★ 4 reviews
Book with Chairman owners! This marvelous beach resort in Koloa is perfect for your escape. Access to Resort Amenities is included for our guests....
From $204/night
New Listing! Poolside Poi'pu Condo - 2BR Kahala
KOLOA, Hawaii
★★★★★ 3 reviews
Poolside Poi'pu Condo - 2BR Kahala at Poipu KaiDr. Beach, one of the worldʻs foremost beach experts, ranked Poipu Beach as the #1 beach for 2026....
From $280/night
VERY SPECIAL Renovated 1 Bdrm Condo - A/C - Oceanview, Athletic Club Access
Koloa, Hawaii
★★★★★ 3 reviews
This stunning, TOTALLY RENOVATED UPSCALE 1 bedroom condo is a step above all other 1 bedroom condos in this resort due to its unique GROUND FLOOR...
From $332/night
Walk to 3 Poipu Beaches • Spacious 2BR/2BA Condo with A/C, Resort Pools & Tennis
Koloa, Hawaii
★★★★★ 3 reviews
Enjoy a spacious 2 bedroom 2 bathroom condo in Poipu Kai, just a 7 to 11 minute stroll to Poipu Beach, Brennecke’s Beach, and Shipwreck Beach. With...
From $392/night
New Listing 3 Bedroom on the Golf Course in sunny Poipu
Koloa, Hawaii
★★★★★ 3 reviews
Welcome to Pili Mai 7I, a stylish 3-bedroom condo in Kauai’s exclusive Pili Mai resort. Overlooking the lush landscape and Kiahuna Golf Course, this...
From $465/night
Pili Mai 6J by Gather: Golf View Poipu Condo w/ Lanai, Pool, A/C, Hot Tub & Gym
Koloa, Hawaii
★★★★★ 3 reviews
Modern island living awaits at Pili Mai 6J, a bright and spacious condo overlooking the Kiahuna Golf Course in sunny Poipu. With fairway views, a...
From $470/night
Hale O‘Kapeka – Spacious 3BR Poipu Home with Ocean Views & Hawaiian Soul
Koloa, Hawaii
★★★★★ 3 reviews
Welcome to Hale O‘Kapeka, a beautifully cared-for home that blends island soul with everyday comfort. Located in the heart of sunny Poipu, this...
From $476/night
Nihi Kai 201 Ocean Comfort
Koloa, Hawaii
★★★★★ 3 reviews
Summary:Spacious two-level oceanview condo just steps from Brennecke’s Beach and Poipu Beach Park. Nihi Kai 201 features newly added split-system air...
From $499/night
Makahuena 1205 – Ocean Views, Full A.C. + P.B.A.C. Access
Koloa, Hawaii
★★★★★ 3 reviews
Summary:Fully renovated ocean-view condo at Makahuena in Poipu with sweeping Pacific views from every room, split air conditioning throughout, and...
From $516/night
Hale Hoʻomalie – Private Pool & Golf Views
Koloa, Hawaii
★★★★★ 3 reviews
Summary:Single-level Poipu retreat with private pool, jetted tub, golf course frontage, and mountain views. Located in the peaceful Kiahuna Golf...
From $1,181/night
koolkondo 2597 Halalu Compound
Koloa, Hawaii
★★★★★ 3 reviews
2597 Halalu CompoundWelcome to your dream escape in Poipu Beach Estates! This beautifully upgraded, two-story luxury vacation home is the perfect...
From $2,127/night
Hale Hanohano by Gather: Luxury Poipu Estate w/ Pool, Spa, Lanais & Ocean Views
Koloa, Hawaii
★★★★★ 3 reviews
A statement of island elegance in Koloa’s sun-drenched Poipu district, Hale Hanohano at Kukuiula is a 6-bedroom, 5.5-bath luxury estate designed for...
From $151/night
New Listing! Treetop Getaway with Athletic Club
Koloa, Hawaii
★★★★★ 2 reviews
Paradise Awaits with Exclusive Beach Club Access - Kiahuna PlantationWake up to tropical breezes and treetop living at this peaceful 3rd-floor...
From $184/night
August Sale!! Walk to Baby Beach From a Family-Friendly Condo with Pool
Koloa, Hawaii
★★★★★ 2 reviews
Summary:Walk the family to Baby Beach in the morning, cool off in the pool after lunch, and let dinner stretch out on the lanai among the gardens....
From $213/night
Restful, beautiful one-bedroom ocean view condo in Sunny Poipu
Koloa, Hawaii
★★★★★ 2 reviews
Welcome to your Kauai escape! This inviting one-bedroom is located just steps from the beach, offering an ideal home base for relaxation and...
From $217/night
Kahala 723 “Apana O Lani” – 2 Lanais, King Bed, Island Serenity
Koloa, Hawaii
★★★★★ 2 reviews
Kahala 723 – “Apana O Lani” (Piece of Heaven)Welcome to Kahala 723, affectionately named “Apana O Lani,” meaning “Piece of Heaven.” This beautiful...
From $238/night
Aloha Escape-Oceanview-Newly Updated
Koloa, Hawaii
★★★★★ 2 reviews
Unwind in Koloa at this delightful condo. This cozy space features 1 bedroom with a comfortable king bed, a living room with a sofa bed, pack n play,...
From $295/night
Walk to Poipu Beach | Garden Condo | AC, Pools, Hot Tub & Tennis
Koloa, Hawaii
★★★★★ 2 reviews
Spacious Garden Condo with Loft – Walk to Poipu & Brennecke's BeachEscape to the beauty of Poipu and enjoy a relaxing stay in this spacious...
From $301/night
New listing! Lovely Poipu Condo with Gym and Pool
Koloa, Hawaii
★★★★★ 2 reviews
Spacious South Shore Condo with Mountain Views and Resort AmenitiesDiscover this sophisticated 1,576 sq. ft. two-level retreat in Pili Mai, offering...
From $314/night
Riverfront condo across from ocean. Sleeps 6
Koloa, Hawaii
★★★★★ 2 reviews
This memorable condo is the perfect home base for your trip to Poipu. Guests will find one comfortable bedroom with a king bed and two spacious...
From $314/night
Ocean and Sunset Views - Poipu - A/C - Pool - W/D -Walk to beaches -Fun in Sun
Koloa, Hawaii
★★★★★ 2 reviews
Experience exceptional ocean views and sunsets from this extraordinary lanai. You can watch seasonal dolphins and whales, and the shifting colors of...
From $349/night
Kahala 633 – Ocean-View 1BR Near the Beach
Koloa, Hawaii
★★★★★ 2 reviews
Summary:Top-floor 1-bedroom condo with ocean views overlooking Brennecke’s Beach and the Poipu Kai greenbelt. Features vaulted ceilings, private...
From $428/night
Regency 620 - Beautiful 3 Bedroom Overlooking Regency Pool
Koloa, Hawaii
★★★★★ 2 reviews
Summary:Top-floor 3-bedroom, 3-bath home in Poipu Kai with central A/C, vaulted ceilings, two private balconies, and access to Regency pools and hot...