Poipu Kapili 22 by Alekona Kauai - 1BR Ocean view condoFrom $318/night · Sleeps 4
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
Loading rental map…
Map View · Page 26
Koloa Vacation Rentals Map
Poipu Kapili 22 by Alekona Kauai - 1BR Ocean view condoFrom $318/night · Sleeps 4
Kiahuna Hale Kai IIIFrom $318/night · Sleeps 4
Kiahuna Plantation Resort Royal Garden 1 BedroomFrom $323/night · Sleeps 4
Kauai South Shore Escape with Spacious 2BR at Poipu Resort RetreatFrom $325/night · Sleeps 6
Kiahuna Plantation Resort 47 Royal Garden 1 BDFrom $328/night · Sleeps 4
Garden View Suite w/ Patio & Full KitchenFrom $329/night · Sleeps 6
Garden View 2BR Retreat in KauaiFrom $329/night · Sleeps 6
Prince Kuhio 108 - Spacious, A/C, close to beachFrom $329/night · Sleeps 4
Kiahuna Plantation Resort Garden View 1 BedroomFrom $330/night · Sleeps 4
Tropical Comfort – 1BR Villa with Lanai at Sheraton Kaua‘i ResortFrom $333/night · Sleeps 4
Tropical Garden Retreat w/ Pool & KitchenFrom $333/night · Sleeps 6
Spacious 2BR w/ Kitchen, Pool & Family PerksFrom $333/night · Sleeps 6
Palm Breeze Paradise-AC | Gym | Ocean Views | PoolFrom $341/night · Sleeps 6
Pili Mai at Poipu #03F By Parrish Kauai - Central AC, steps to pool, spa & gym!From $341/night · Sleeps 6
Sheraton Kaua'i - StudioFrom $342/night · Sleeps 2
Kauai Oceanview Fall Break-AC,Pool,Sea ViewsFrom $342/night · Sleeps 6
Pili Mai 12K Spacious 3BR with Central ACFrom $344/night · Sleeps 6
Kiahuna Plantation Resort 84 Royal Garden 1 BDFrom $345/night · Sleeps 4
Double Studio Suites with Private Pool and AC, walk to BeachFrom $346/night · Sleeps 4
Tropical 2BR Partial Ocean View Villa at The Point at PoipuFrom $346/night · Sleeps 6
Steps from the Beach! Exclusive 3/2.5 home in Poipu. Utilities Included!From $349/night · Sleeps 6
Pili Mai 4G by Alekona Kauai- Fitness/Pool AccessFrom $350/night · Sleeps 7
Pili Mai 13C By ParrishFrom $351/night · Sleeps 6
Kiahuna Plantation Resort Partial Ocean 1 BedroomFrom $352/night · Sleeps 4
Manualoha 904 Spacious 3BR Near Poipu BeachFrom $353/night · Sleeps 8
Kiahuna Plantation Resort 58 Royal Garden 1 BDFrom $353/night · Sleeps 4
Kiahuna Plantation Resort 318 Partial Ocean 1 BDFrom $356/night · Sleeps 4
Poipu Sands 121 Ocean Views By Suite ParadiseFrom $358/night · Sleeps 6
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| ACFrom $364/night · Sleeps 8
Kiahuna Plantation Resort 232 Royal Garden View DeFrom $367/night · Sleeps 4
Kiahuna Plantation Resort 139 Partial Ocean 1 BDFrom $370/night · Sleeps 4
Pili Mai at Poipu #13G By Parrish Kauai - Great family locationFrom $371/night · Sleeps 6
Kiahuna Plantation Resort 161 Ocean View 1 BedroomFrom $372/night · Sleeps 4
From $318/night
Poipu Kapili 22 by Alekona Kauai - 1BR Ocean view condo
Koloa, Hawaii
The condos at Poipu Kapili are loved for plenty of reasons- the stunning oceanfront setting, easy access to Poipu's best shopping and dining, and...
From $318/night
Kiahuna Hale Kai III
Koloa, Hawaii
Experience the beauty of Kauai from Kiahuna Hale Kai III, our top-floor oceanview retreat located in the heart of the iconic Kiahuna Plantation...
From $323/night
Kiahuna Plantation Resort Royal Garden 1 Bedroom
Koloa, Hawaii
Nestled near Kauai’s most iconic shoreline, this cozy one-bedroom cottage-style condo offers serene garden views and all the comforts you need. A...
From $325/night
Kauai South Shore Escape with Spacious 2BR at Poipu Resort Retreat
Koloa, Hawaii
Hawaii Hurricane Update: - No storm alert or damage assessment has been published by this property.- Po'ipu and the South Shore were the hardest-hit...
From $328/night
Kiahuna Plantation Resort 47 Royal Garden 1 BD
Koloa, Hawaii
Ideally located near Kauai’s iconic shoreline, it’s a tranquil home base for your stay. Enjoy this cozy 2nd floor unit that blends cottage charm with...
From $329/night
Garden View Suite w/ Patio & Full Kitchen
Koloa, Hawaii
Discover the beauty of Kauai's South Shore, just minutes from Shipwreck Beach. This spacious 2-bedroom suite features a full kitchen, private lanai,...
From $329/night
Garden View 2BR Retreat in Kauai
Koloa, Hawaii
Escape to Kauai's beautiful south shore and enjoy a peaceful garden-view retreat surrounded by lush tropical landscapes. Located near Shipwreck...
From $329/night
Prince Kuhio 108 - Spacious, A/C, close to beach
Koloa, Hawaii
*Hurricane Lowell Update: Prince Kuhio is open and guest-ready, but hurricane recovery and repairs are still underway in the complex and surrounding...
From $330/night
Kiahuna Plantation Resort Garden View 1 Bedroom
Koloa, Hawaii
This charming one-bedroom, cottage-style condo offers peaceful garden views just steps from Kauai’s most famous beach. Ideal for couples or small...
From $333/night
Tropical Comfort – 1BR Villa with Lanai at Sheraton Kaua‘i Resort
Koloa, Hawaii
Due to damage sustained during the recent hurricane activity in Hawaii, this resort is currently closed while assessment and recovery efforts are...
From $333/night
Tropical Garden Retreat w/ Pool & Kitchen
Koloa, Hawaii
Tucked away in the natural beauty of Kauai’s southern tip, this vacation retreat offers a dream escape overlooking the stunning Shipwreck Beach....
From $333/night
Spacious 2BR w/ Kitchen, Pool & Family Perks
Koloa, Hawaii
Experience the beauty of Kauai’s southern coast with an unforgettable oceanfront retreat overlooking the stunning landscapes near Shipwreck Beach....
From $341/night
Palm Breeze Paradise-AC | Gym | Ocean Views | Pool
Koloa, Hawaii
Wake up to sweeping Pacific views at Palm Breeze Paradise, a beautifully updated, air-conditioned condo in the heart of Poipu. Enjoy cool comfort...
From $341/night
Pili Mai at Poipu #03F By Parrish Kauai - Central AC, steps to pool, spa & gym!
Koloa, Hawaii
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's...
From $342/night
Sheraton Kaua'i - Studio
Koloa, Hawaii
Escape to the beautiful island of Kauai and enjoy a relaxing villa stay surrounded by tropical gardens and breathtaking natural scenery. Located near...
From $342/night
Kauai Oceanview Fall Break-AC,Pool,Sea Views
Koloa, Hawaii
Wake up to sweeping Pacific views at Kauai Oceanview, a beautifully updated, air-conditioned condo in the heart of Poipu. Enjoy cool comfort indoors...
From $344/night
Pili Mai 12K Spacious 3BR with Central AC
Koloa, Hawaii
Summary:Pili Mai 12K is a spacious 3-bedroom, 3-bath condo in the heart of Poipu, located in one of Kauai’s newer resort communities. This...
From $345/night
Kiahuna Plantation Resort 84 Royal Garden 1 BD
Koloa, Hawaii
Experience island charm in this garden-view, one-bedroom condo just moments from Kauai’s most famous beach. With a welcoming cottage style and space...
From $346/night
Double Studio Suites with Private Pool and AC, walk to Beach
Koloa, Hawaii
Private Villa and exclusive use of 2 identical suites! The suites sit side-by-side in sunny Poipu, perfect blend of privacy and space for couples,...
From $346/night
Tropical 2BR Partial Ocean View Villa at The Point at Poipu
Koloa, Hawaii
This resort has been impacted by recent hurricane activity in Hawaii. Conditions and resort operations can change as recovery efforts continue. We...
From $349/night
Steps from the Beach! Exclusive 3/2.5 home in Poipu. Utilities Included!
Koloa, Hawaii
This spacious upstairs long term rental offers the perfect blend of comfort and island living just steps away from Baby Beach on Kauai's sunny south...
From $350/night
Pili Mai 4G by Alekona Kauai- Fitness/Pool Access
Koloa, Hawaii
Pili Mai 4G is a vacation rental condo located just a stone's throw from Poipu's best attractions, Pili Mai 4G is where your search for the perfect...
From $351/night
Pili Mai 13C By Parrish
Koloa, Hawaii
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's...
From $352/night
Kiahuna Plantation Resort Partial Ocean 1 Bedroom
Koloa, Hawaii
This one-bedroom, cottage-style condo offers a peaceful island retreat with a partial ocean view. Located on Kauai’s most famous beach, it’s perfect...
From $353/night
Manualoha 904 Spacious 3BR Near Poipu Beach
Koloa, Hawaii
Summary:Manualoha 904 is a spacious 3-bedroom, 3-bath condo located in the heart of Poipu Kai, just a short walk to Poipu Beach, Brennecke’s Beach,...
From $353/night
Kiahuna Plantation Resort 58 Royal Garden 1 BD
Koloa, Hawaii
Enjoy the beautiful garden views from this first floor one-bedroom condo with A/C – perfect for relaxing in a peaceful tropical setting.• First floor...
From $356/night
Kiahuna Plantation Resort 318 Partial Ocean 1 BD
Koloa, Hawaii
Catch a glimpse of the sparkling Pacific from this charming 3rd floor condo, featuring partial ocean views and a welcoming cottage-style feel—just...
From $358/night
Poipu Sands 121 Ocean Views By Suite Paradise
Koloa, Hawaii
Tropical Comfort and Ocean Breezes at Poipu Sands, KauaiWelcome to your island retreat at Poipu Sands, a spacious and beautifully styled two-bedroom...
From $364/night
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Koloa, Hawaii
Welcome to our luxury 3BR/3BA estate in Poipu Beach Estates, just ½ mile from the beach. Perfect for families or groups, the property offers a...
From $367/night
Kiahuna Plantation Resort 232 Royal Garden View De
Koloa, Hawaii
This charming one-bedroom condo features relaxing garden views and a warm, cottage-inspired feel. Ideally located near Kauai’s iconic shoreline, it’s...
From $370/night
Kiahuna Plantation Resort 139 Partial Ocean 1 BD
Koloa, Hawaii
Enjoy the gentle island breeze and partial ocean views from this cozy one-bedroom cottage-style condo. Just steps from Kauai’s most iconic beach,...
From $371/night
Pili Mai at Poipu #13G By Parrish Kauai - Great family location
Koloa, Hawaii
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's...
From $372/night
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
Koloa, Hawaii
Gaze out at the Pacific from this 2nd floor ocean view condo, just steps from Kauai’s most iconic beach. A perfect blend of comfort and scenery,...