Pili Mai by Gather: Stylish 3BR Condo w/ Pool, Lanai & Scenic ViewsFrom $345/night · Sleeps 6
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
Map View · Page 8
Koloa Vacation Rentals Map
Pili Mai by Gather: Stylish 3BR Condo w/ Pool, Lanai & Scenic ViewsFrom $345/night · Sleeps 6
Luxury 3BR Poipu Paradise: Pool, Hot Tub, Gym, AC, Golf CourseFrom $393/night · Sleeps 6
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & PickleballFrom $595/night · Sleeps 10
3BR I Poolside Ground-Floor Villa |Walk to Beach|Hot TubFrom $812/night · Sleeps 6
Hale Nani at Kukui'ula - Luxe Family Hideaway with Poolside Living in PoipuFrom $919/night · Sleeps 14
New! Luxury Split-Level Retreat at Pili Mai 15EFrom $331/night · Sleeps 9
An Endless Summer 132- Poipu Beach, KauaiFrom $363/night · Sleeps 4
OCEANFRONT RESORT in Koloa-Poipu with AMENITIES INCLUDING WIFI, walk to beachFrom $383/night · Sleeps 6
3BR I Luxury Poolside Villa | Stunning Ocean View, LanaiFrom $482/night · Sleeps 6
Malu Makani by Alekona Kauai: 2 BR Luxury Oceanview Kukuiula Condo w private pool, AC, large lanaiFrom $808/night · Sleeps 4
Hale Kohola by Alekona Kauai: Brand New 4BR Home w AC, close to beaches, shopping, diningFrom $976/night · Sleeps 10
Hale Makai - Oceanfront Honeymoon Haven with Pool and ACFrom $1,541/night · Sleeps 2
3 Bedroom Luxury Home w/Private PoolFrom $1,673/night · Sleeps 8
POIPU RESORT, 2BDRM, F/K, Washer/Dryer, POOL, WIFI, daily fresh towel exchangesFrom $424/night · Sleeps 6
Kauai Exclusive - Pili Mai 7E - Three Bedroom Suite - AC, Pool & Fitness CenterFrom $605/night · Sleeps 6
Elevated Island Elegance in Kukui'ula - A Refined Retreat in PoipuFrom $750/night · Sleeps 9
3BR I Poolside Lanai Villa l Parking, Sunset ViewFrom $829/night · Sleeps 6
Elegant Poolside Penthouse with Private ElevatorFrom $946/night · Sleeps 8
Hale Kahakai by Alekona Kauai: Luxury 4BR Bali-Inspired Home in Kukuiula w AC, private poolFrom $2,070/night · Sleeps 10
Kauai Oasis - Luxury 6 BR Kukui'ula Estate with Infinity PoolFrom $2,654/night · Sleeps 22
Oceanview 1 Bedroom at Lawai Beach Resort, modern and updated!From $317/night · Sleeps 4
2 Bedroom Poipu Condo with Pool, Hot Tub walk to BeachesFrom $338/night · Sleeps 6
Private Kōloa Retreat | Pool + Golf Course Views | Near Poʻipū BeachFrom $450/night · Sleeps 8
Kiahuna Plantation 029 By Parrish Kauai - On Poipu Beach!From $468/night · Sleeps 4
3BR I Spacious Poolside Villa | Gourmet Kitchen, LanaiFrom $540/night · Sleeps 6
Whispering Palms - Tranquility and EleganceFrom $875/night · Sleeps 8
Kukuiula Cottage #27 By Parrish KauaiFrom $1,016/night · Sleeps 6
Hale Naia By Parrish Kauai - oceanfront viewsFrom $1,190/night · Sleeps 6
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.From $1,799/night · Sleeps 12
Hale Ka Pua Ola – Private Luxury Retreat in Kukui'ulaFrom $1,827/night · Sleeps 12
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28From $1,844/night · Sleeps 28
Architectural Stunner in Kukui'ula - 4 BR Oceanview Villa with Infinity Pool & SpaFrom $2,010/night · Sleeps 9
koolkondo 2597 Halalu Guest houseFrom $239/night · Sleeps 4
From $345/night
Pili Mai by Gather: Stylish 3BR Condo w/ Pool, Lanai & Scenic Views
Welcome to Pili Mai 14K, a contemporary three-bedroom, three-bath condo located on the scenic Kiahuna Golf Course in Poipu on Kauai’s sunny south...
From $393/night
Luxury 3BR Poipu Paradise: Pool, Hot Tub, Gym, AC, Golf Course
Same listing as https://airbnb.com/h/pilimai5j. Welcome to your upscale island sanctuary! Nestled within Poipu's premier Pili Mai Resort, this...
From $595/night
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
This Poipu luxury farmhouse is a spacious 5-bedroom retreat just a half mile from Poipu Beach on Kauai's south shore. Ideal for large families or...
From $812/night
3BR I Poolside Ground-Floor Villa |Walk to Beach|Hot Tub
Summary:E110 | TA-120-625-1520-01Walk to the best beaches on Kauai! In a tranquil setting surrounded by lush tropical landscaping, unwind in the...
From $919/night
Hale Nani at Kukui'ula - Luxe Family Hideaway with Poolside Living in Poipu
Hale Nani is a modern 5-bedroom luxury retreat located in one of Kauai's most exclusive neighborhoods at Kukui'ula. Featuring a private heated pool,...
From $331/night
New! Luxury Split-Level Retreat at Pili Mai 15E
Luxury Split-Level Retreat at Pili Mai #15E | Poipu ParadiseProperty OverviewWelcome to this stunning split-level home at the prestigious Pili Mai...
From $363/night
An Endless Summer 132- Poipu Beach, Kauai
Located on the most popular beach in Kauai for a reason! Sandy beach and warm ocean water with a large grassy area for lounge chairs for the best...
From $383/night
OCEANFRONT RESORT in Koloa-Poipu with AMENITIES INCLUDING WIFI, walk to beach
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM,...
From $482/night
3BR I Luxury Poolside Villa | Stunning Ocean View, Lanai
Summary:D210 | TA-019-101-6960-01Enjoy tropical views and elevated comfort at Villa D210, part of the Poolside Villas at Poipu Kai. This spacious...
From $808/night
Malu Makani by Alekona Kauai: 2 BR Luxury Oceanview Kukuiula Condo w private pool, AC, large lanai
Kainani #1 is a 2-bedroom, 2-bathroom villa nestled in the heart of paradise, offering an unparalleled experience of comfort, convenience, and...
From $976/night
Hale Kohola by Alekona Kauai: Brand New 4BR Home w AC, close to beaches, shopping, dining
Be among the first to enjoy this brand-new luxury vacation home in the prestigious Poipu Beach Estates neighborhood. Ideally situated between The...
From $1,541/night
Hale Makai - Oceanfront Honeymoon Haven with Pool and AC
Hale Makai is a stunning 1-bedroom, 1.5-bath oceanfront retreat in Poipu on Kauai's sunny south shore, offering unparalleled luxury for couples...
From $1,673/night
3 Bedroom Luxury Home w/Private Pool
Settle into a blissful sense of calm at Hale Anuenue, which means ''House of the Rainbow'' in Hawaiian. This three-bedroom, three-and-a-half-bath...
From $424/night
POIPU RESORT, 2BDRM, F/K, Washer/Dryer, POOL, WIFI, daily fresh towel exchanges
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM,...
From $605/night
Kauai Exclusive - Pili Mai 7E - Three Bedroom Suite - AC, Pool & Fitness Center
Summary:Brand New spacious 3 bedroom, 2.5 bathroom condo features two master bedrooms, upgraded amenities such as A/C, Marbau flooring, granite...
From $750/night
Elevated Island Elegance in Kukui'ula - A Refined Retreat in Poipu
Graciously set within the exclusive enclave of Kukui'ula, this thoughtfully designed 3-bedroom, 3.5-bath residence offers an elevated South Shore...
From $829/night
3BR I Poolside Lanai Villa l Parking, Sunset View
Summary:F211 | TA-018-220-0320-02Walk to Kauai’s top beaches from Villa F211, surrounded by lush tropical landscaping in the heart of Poipu. Relax in...
From $946/night
Elegant Poolside Penthouse with Private Elevator
This Poipu Penthouse Villa is a 4-bedroom, 3.5-bath penthouse in the gated Villas at Poipu Kai, offering 2,000 square feet of upscale living with...
From $2,070/night
Hale Kahakai by Alekona Kauai: Luxury 4BR Bali-Inspired Home in Kukuiula w AC, private pool
Hale Kahakai is a stunning four-bedroom luxury vacation rental in the highly desirable Kukuiula neighborhood in Poipu. Inspired by the villas in...
From $2,654/night
Kauai Oasis - Luxury 6 BR Kukui'ula Estate with Infinity Pool
Kauai Oasis is a brand new luxury retreat in Kauai's prestigious Kukui'ula community, offering over 7,000 square feet of indoor-outdoor living. With...
From $317/night
Oceanview 1 Bedroom at Lawai Beach Resort, modern and updated!
Our newly updated ocean view condo on the 2nd floor of Lawai Beach Resort is ready for you!Recently updated with chevron flooring, new bathroom...
From $338/night
2 Bedroom Poipu Condo with Pool, Hot Tub walk to Beaches
Summary:Regency at Poipu Kai 911 is an air conditioned, ground floor suite located just steps to the pool. This 2-bedroom, 2-bath suite is great...
From $450/night
Private Kōloa Retreat | Pool + Golf Course Views | Near Poʻipū Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for...
From $468/night
Kiahuna Plantation 029 By Parrish Kauai - On Poipu Beach!
Kiahuna Plantation Resort is the only beachfront condominium resort in Poipu. The plantation style architecture is surrounded by over thirty acres of...
From $540/night
3BR I Spacious Poolside Villa | Gourmet Kitchen, Lanai
Summary:D211 | TA-018-220-0320-02Welcome to your tropical retreat in sunny Poipu! Villa D211 is a luxurious 3-bedroom, 3-bathroom poolside villa...
From $875/night
Whispering Palms - Tranquility and Elegance
Summary:Spacious 4-bedroom home in Poipu’s Kiahuna Golf Village with air conditioning, a furnished lanai, home office, and complimentary Poipu Beach...
From $1,016/night
Kukuiula Cottage #27 By Parrish Kauai
This handsomely designed and decorated Kauai cottage offers the details of early plantation days yet with the modern conveniences of central air...
From $1,190/night
Hale Naia By Parrish Kauai - oceanfront views
Enjoy the best of island life at one of Poipu’s finest Kauai oceanfront rentals. The 2 bedroom, 2 bathroom coastline gem is in a prime location for...
From $1,799/night
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.
***** Construction Disclaimer ***** A new home is currently being built next door, with construction taking place Monday through Friday, 8:00 a.m. –...
From $1,827/night
Hale Ka Pua Ola – Private Luxury Retreat in Kukui'ula
Hale Ka Pua Ola is a luxurious 4-bedroom vacation rental located in the prestigious Kukui'ula community on Kauai's south shore. Designed for seamless...
From $1,844/night
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28
Ohana Retreat is Poipu's ultimate group getaway, offering luxurious island living across two private homes and two guest houses that together...
From $2,010/night
Architectural Stunner in Kukui'ula - 4 BR Oceanview Villa with Infinity Pool & Spa
Hale Oma'oma'o is a breathtaking new villa in Kukui'ula, blending striking modern architecture with natural island beauty and luxurious comfort....
From $239/night
koolkondo 2597 Halalu Guest house
Welcome to your dream escape in Poipu Beach Estates! This beautifully upgraded one bedroom guest house is tucked away in a serene, palm-fringed...