Koloa Vacation Rentals – Historic Charm Meets Island Luxury
Koloa vacation rentals blend historic charm with modern comfort on Kauai's sunny South Shore. Stay in restored plantation homes or luxury villas, just minutes from Poipu's beaches, golf, and shopping.
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 retreat 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 perfect 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.
Elegant Poolside Penthouse with Private Elevator
Summary:F300 | TA-018-220-0320-02Experience elegance in our Poipu Penthouse Villa, boasting luxury designer furnishings and gourmet kitchens. Stay cool with central A/C and enjoy elevator access directly into F300. Relax amidst tropical views and exceptional luxury in...
Ohana Retreat - Private Pool, Sleeps 29
OHANA RETREAT AT KOLOA KAI VACATION RENTALSYour Ultimate Group Getaway in PoipuWelcome to Ohana Retreat, a one-of-a-kind vacation rental in Poipu that can accommodate up to 28 guests, making it the perfect haven for large family reunions, retreats, or multi-family...
Elegant Pili Mai 14-J: Spacious 3BR Villa with Pools, A/C, and Beach Proximity
The Resort:Pili Mai was built in 2019 and features plantation-style design, cobblestone drives, tropical gardens, a large swimming pool, a children's pool, spa, and an air-conditioned fitness room. It is nestled between Kiahuna Golf Club and the beautiful Poipu beaches:...
Penthouse with Panoramic Ocean Views From Private Lanais
Welcome to your dream getaway on the Garden Isle! This top-floor penthouse in the heart of world famous Poipu Beach offers the perfect blend of luxury, comfort, and island charm. With soaring vaulted ceilings, four spacious bedrooms, and 3.5 baths, this retreat is...
Hale Keaka: Luxury Modern Estate w/ Pool, Outdoor Showers, Hot Tub & Ocean Views
This newly built 6-bedroom luxury retreat invites guests to experience Kaua‘i’s south shore in modern, ocean-view elegance. Set within the prestigious Kukui‘ula community in Koloa, Hale Keaka at Kukui‘ula blends architectural sophistication with relaxed island...
NEW! Luxury Plantation Home on Kiahuna Golf Course
About this spaceThis gorgeous Hawaiian Plantation Style home designed by a local architect, resides on the 8th fairway of Kiahuna Golf Course with views of Haupu Mountain.Spectacular Gourmet Kitchen , chefs will enjoy !Poipu features many beaches to indulge in surfing ,...
Poipu Sands 116 - Ground-Floor Condo with Pool & Hot Tub Access, Steps from Stunning Beaches
POIPU SANDS 116 AT KOLOA KAI VACATION RENTALSA Tropical Retreat with Stunning Ocean ViewsWelcome to Poipu Sands 116, a spacious 1,353-square-foot ground-floor condo nestled on the sunny south shore of Kauai. Featuring breathtaking ocean views, easy access to Shipwreck...
Poipu Kai Hale - Oceanfront Elegance at Makahuena Point
Welcome Poipu's Hidden Gem! This amazing home offers 3 bedrooms and 3 bathrooms on the ocean with incredible views of Poipu! Imagine your vacation experience in this gorgeous location with unparalleled and unobstructed 200°+ views. This spacious home consists of a...
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
We have just added a private pool & Spa and a 5 th bedroom suite(3/12/25),We have not updated the video yet but have added a few photos. AC in all rooms of home. 5 master suites with private bathrooms, each with a private lanai. Gourmet Kitchen, Large lanai deck for BBQ...
Luxury 4BR Penthouse at the Villas at Poipu Kai
Welcome to The Villas at Poipu Kai, one of the nicest luxury condominium resorts on the South side of Kauai in Poipu. These spacious and upscale villas are part of the Poipu Kai Resort that offers access to additional recreational amenities to all in the Poipu Kai...
Kuhio Shores 415 Top Floor Oceanfront Condo with new central a/c
Mini split Air Conditioning system just installed to make your Kuhio Shores 415 cooling experience perfect. Open windows, trade winds, fans to hear the soothing sounds of the ocean. And now if none of the above works you have use of a quiet, efficient air conditioning...
Maluhia Makai - Luxe Kukui'ula island retreat in Poʻipu; AC, private heated pool
This luxury home is 2200 ft.² of air-conditioned space that opens up to 1000 ft.² of an outdoor living lanai. The design of this home seamlessly marries the indoors & outdoors together to make a grand tropical outdoor experience. Pass through its custom entry wood...
New Listing! Exquisite Golf Course Sanctuary
Exquisite Golf Course Villa: A Private Island Sanctuary with access to Poipu Beach Athletic Club!Welcome to Wainani Villas, where refined elegance meets the serene beauty and beach living of Poipu Beach. Nestled alongside the prestigious Kiahuna Golf Course, this...
Kauai Vacation Rental - Kuhio Shores 319–Oceanfront, Sunset Views, A/C!
Enjoy spectacular ocean views in one of Koloa’s most sought-after oceanfront condominiums. This south and west facing 2-bedroom, 2-bath corner condo has a unique view of Kauai's unsurpassed sunsets. Floor to ceiling windows, an elevated position on the third floor and...
Beautifully renovated studio, shared pool and bbq, walk to beach
Prince Kuhio # 234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your luxurious island retreat in the heart of Poipu, Kauai! This beautifully renovated studio condo...
Honu Lani - Oceanfront Home with Pool and Amazing Views!
Youtube Video Presentation - https://youtu.be/cXeJePt8tlIRelax from your back yard while enjoying sunrise to sunset views from the pool, lanai, and master bedroom of this open and spacious 3 bedroom, 2.5 bath getaway vacation dwelling. The superb design offers high open...
Perfect family home with A/C! Amazing location, a short walk to Poipu beaches!
This private ranch-style home is located in the Lanai Villas section of Poipu Kai Resort. What makes this house special is the enclosed tropical backyard with a gate that leads out to a secluded greenbelt path for a short walk to Grand Hyatt, Shipwreck Beach and the...
Hale Moana - Ocean Front
HALE MOANA AT KOLOA KAI VACATION RENTALSOceanfront Elegance with Panoramic Views on Kauai’s South ShorePerched above the shimmering waters of Kukuiula Bay, Hale Moana is a luxurious oceanfront retreat that blends timeless charm, sophisticated design, and breathtaking...
Kiahuna Plantation Oceanfront Renovated Ground floor Steps to ocean W/D in unit
Guest to pay onsite management Castle Resorts direct at check in/out for required cleaning. Full check out cleaning for 1 bedroom units for 2025 is $268.00 plus 18.712% tax effective 1-1-26 Any stays over 10 nights also require a full mid stay cleaning at a cost of $110...
Hale Honu - 5 Star Oceanfront Home Overlooking Turtle Cove!
Perched above historic Koloa Landing, also known as Hanaka’ape Bay, Hale Honu boasts dominant bay and ocean views. Just off your private lanai is some of the best snorkeling and scuba diving the island has to offer. Giant sea turtles can be seen below swimming and...
FULL OCEAN VIEWS Poipu Beach House, LOVELY lanai and A/C
Aloha & welcome to our home - Hale Kika @ Poipu Kai resort. Hale Kika is an open concept beach house with great views from the main living area, 3 bedrooms and 2 1/2 bathrooms. Views from the house span from the Haupu Mountain to full ocean views. Our 2-storey home...
Halana Maile - Ocean Views, A/C, Beautifully Furnished Halana Maile Sleeps 8, 3200 sq. ft
HALANA MAILE AT KOLOA KAI VACATION RENTALSOcean-View Luxury Nestled on Kauai’s Crater RidgeWelcome to Halana Maile, a serene and luxurious retreat perched on the side of an ancient crater, offering breathtaking ocean views and easy access to Shipwreck’s Beach near...
2 Bedroom Poipu Condo with Pool, Hot Tub walk to Beaches
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 families and walking distance to the beach. This stunning condo has been upgraded throughout and is one of the few air-conditioned...
Luxe retreat with hot tub and pool access, private W/D, grill, AC, & gas range
Hale HaupuOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to your tranquil Hawaiian getaway! This newly-constructed upscale home is nestled in a quiet neighborhood away...
SPECTACULAR OCEANFRONT PENTHOUSE - Air Conditioned 3 Bedroom/3 Bathroom
Poipu Makai B3 is located on a bluff a couple of yards from the water with stunning, full uninhibited views of the ocean. Enhance your senses – the visual beauty of the waves crashing against the shoreline and the gentle sound of the living and breathing sea. Spend...
Now Booking! Enjoy your next vacation in our newly remodeled condo! Pool, A/C!
New listing and availability just opened for this brand newly remodeled, stunning studio condo! Our condo is perfect for a honeymoon stay or romantic getaway with a gorgeous garden view and air conditioning! The condo features a king bed, small dining table and chairs...
Breathtaking Ocean View Condo w/ new furnishings - Poipu Kapili #30
Amidst the luxurious oceanfront Poipu Kapili Resort, is an exquisite 1 bedroom, 2 bath remodeled single level, second floor holiday home endeared as Poipu Kapili 30. Perfectly manicured lawns, immense palm trees along with fragrant and vibrant blossoms promise a...
Maikalani at Poipu Kai By Parrish Kauai - quaint cottage for 4 with AC & private
Tucked into the Lanai Villas section of the tropical Poipu Kai Resort, Maikalani is a Kauai vacation rental home exquisitely decorated and outfitted with all the necessities of home, including zoned air conditioning. Located on the lush green belt with easy access to...
Stunning Oceanfront Property! Spectacular Ocean Views!
This exceptional oceanfront Penthouse is located on the sunny, south shore of Hawaii's Garden Island in Poipu. This beautifully remodeled, luxurious condo is just 30 feet from the ocean's edge. It offers 180-degree ocean, coastline and mountain views from the lanai,...
Beautiful Kukui'ula Home With Great Lanai Space
New pool just added! This home has it all, private hot-tub, brand new pool, fire pit, 2,000 sqftlanai, and enough room for the whole family with over 3,000 sqft of insideliving space! - 5,000 soft totalThis home is special with it's open indoor/outdoor main living area...
Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
Visit our remodeled ocean front get-away. The unit has been remodeled from top to bottom, from ceiling to floor. The master bedroom features a California King bed, night stands with reading lights, built-in cabinets for clothing storage, granite countertop, ceiling fan,...
Pali Nui – Gorgeous New Kukui'ula Villa
Jaw-dropping, breathtaking, spectacular: sometimes even the highest superlatives can seem like low-key understatement. Pali Nui—this uniquely gorgeous new Kukui'ula villa—is distinctively designed and stylishly curated, with artful décor, tropical allure, and...
Fabulous Location near Shipwreck Beach and Grand Hyatt Resort
We purchased this lovely ground floor garden view condo in April, 2013. This condominium has a large master bedroom with A/C. The master bedroom has an an en-suite master bath with a walk in shower. Our home also has a half bath for your convenience. Our spacious lanai...
Oceanfront Corner Villa w/ Air Conditioning
Unparalleled oceanfront views make Unit 1, a highly sought after corner unit, at Poipu Kapili the ideal vacation rental for your dream Kauai vacation. Poipu Kapili is a boutique luxury complex in the heart of Poipu, just minutes from many popular beaches for snorkeling,...
Hale Anuenue By Parrish Kauai - AC & walk to Poipu Beach!
Perched on the rim of Poipu Crater overlooking Poipu Beach to the west and Mount Haupu to the east, Hale Anuenue ("house of rainbows") offers the perfect spot to see rainbows when the skies offer liquid sunshine. Positioned for views of the morning sunrise glow over the...
Remodeled Kiahuna Ocean View Condo with A/C, Close to the Beach! No cleaning fee
Kiahuna Plantation Beach House #179 – Our Hawaiian HeavenWe welcome you to our Kiahuna Plantation Beach House. Unit #179 is our home away from home, and we look forward to sharing it with you. Our unit was completely remodeled with an open concept kitchen with quartz...
4 BDR, 3 BR, A/C, walk to beaches, restaurants and The Grand Hyatt
Nani O'Hana is a 4 bedroom, 3 bathroom luxury home located in the quiet neighborhood of Poipu Kai. The house is located in the Lanai Villas subdivision of Poipu Kai community where you can easily walk to beaches, tennis courts, pool, Grand Hyatt, Spa, restaurants and...
PoipuBeach-3rdFl-Partial Ocean- AC-Pool-Garden-313
Private top-floor corner unit in a peaceful building with AC and upgrades—tons of privacy! Enjoy access to the pool, stroll through lush Moir Gardens to reach Kiahuna Beach, and skip the resort fees. Beach gear is included for your convenience. This serene retreat is...
Kauai Bay House, Ocean Front, AC
KAUAI BAY HOUSE AT KOLOA KAI VACATION RENTALSOceanfront Luxury Overlooking Kukuiula BayWelcome to Kauai Bay House, a stunning two-bedroom, two-bathroom retreat perched above Kukuiula Bay on Kauai’s sunny South Shore. Offering breathtaking ocean and mountain views from...
14 Beds / 9 Bath / Central AC / Luxuriously Spacious / Accommodates 28!
NEW LISTING! 3 Separate Condos in the same building - On the 2nd & 3rd floor of a 3 story building. 1-5 Bedroom (3 Kings, 3 Queens) 3 Bath Sleeps 12 Adults2-4 King Bedrooms 3 Bath each sleep 8 Adults. BEST VILLAS AT THE REGENCY! A cut above the rest. Finest furnishings...
The ‘IMI OLA at Kiahuna Beach - Great Location on Kauai's South Shore -A/C
Aloha! E komo mai to our little slice of paradise. Located in the community of Kiahuna Plantation Resort in Poipu, Kauai in Unit 127. Our first-story walk out unit sits on a 35-acre beachfront resort with large rolling lawns, well maintained gardens, and a path that...
Charming 3br Cottage w AC, Ocean Views
New Listing! Welcome to Kukuiula Vacation Home #2, a charming ocean view beach cottage located in the heart of Poipu's desirable Kukuiula neighborhood. This single-story plantation-style home beautifully combines vintage Hawaiian charm with modern luxury, offering a...
Hale Nani: New Poipu Villa - Pool / Spa + Ocean Views
Breathtaking, sensational, divine. It’s impossible to overstate the appeal of this exceptional villa, with its spacious, elegantly appointed rooms and gorgeous grounds set against a dazzling backdrop of palm-fringed golf course, dramatic mountains, glittering ocean,...
Kuhio Shores 217 Superior Air Conditioned Condo at Kuhio Shores
Mini split Air Conditioning system just installed to make your Kuhio Shores 217 cooling experience perfect. Open windows, trade winds, fans to hear the soothing sounds of the ocean. And now if none of the above works you have use of a quiet, efficient air conditioning...
Hale o ka Nene: Luxury 6BR Estate with Pool, Spa & Golf Views
Welcome to Hale o ka Nene by Gather, a luxurious six-bedroom, six-and-a-half-bathroom estate on the sunny South Shore of Kaua'i. Perfect for families or group getaways, this private retreat accommodates up to 15 guests and features panoramic golf course views, a private...
Lei Hali'a - Steps Away from Poipu Beach with A/C!
Located just steps away from the world famous Poipu Beach and Brennecke’s Beach on Kauai’s sunny South Shore, Lei Hali’a is ready to help you create lasting vacation memories from this island paradise. From the spacious and comfortable outdoor living space...
Hale Pohaku Kai: Poipu Seaside Stunner
Hale Pohaku Kai is a paradise of paradoxes: elegantly furnished, yet casually comfortable; spacious & airy yet cozy, too; wonderfully private, but with Poipu’s world-class sandy beaches, parks, restaurants, shopping & lively local events only a few minutes away. The...
Wainani "Heated Pool, Hot Tub, Game Room & A/C"
5 night minimum stay required.Beautiful Wainani home overlooking the 4th Fairway of the Kiahuna Golf Course. Located in a cul-de-sac in the Wainani neighborhood in sunny Poipu. Close to shopping, dining and several beaches (Poipu Beach Park, Shipwrecks, Brennecke's to...
Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
TMK: 4-2-8-018-005-0001-000This custom designed Hawaiian plantation style cottage is located just off the Brennecke's beach side of Poipu Beach Park, 100 steps to the beach!This spacious house was designed and built in 2013 to be the perfect vacation retreat - its...
Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home
Coco Cottage at Poipu Beach is a classic, sugar plantation-style home located on the sunny south shore of Kauai. Completely rebuilt, it offers beautiful furnishings, a fully equipped kitchen, full-size washer and dryer, two air-conditioned bedrooms, each with a...