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.
New! Poipu Kapili, Sweeping Ocean & Fully Updated w/ Newly Installed Central AC
Just renovated! Enjoy ocean waves and sweeping views of the Pacific in this stunning Hawaiian style townhome in Poipu Beach, Kauai. Creature comforts: Newly Installed central air for a good nights sleep; do not lie awake to the sound of portable ACs that are at the...
Hale Lo'i Cottage: Luxury + Convenience in Poipu
This bright, spacious, brand-new 1-bedroom, 1-bath cottage has everything you could possibly need for a flawless vacation—and luxurious perks galore, including an outdoor lava-rock shower. Located in a quiet, upscale neighborhood, this charming tropical hideaway is...
Hale Makau – Luxury Poipu Vacation Home
Welcome to Hale Makau by Gather, a luxurious retreat set within an exclusive 10-lot gated community in Poipu. This stunning five-bedroom, five-and-a-half-bathroom home offers the perfect surroundings for your large group to experience a peaceful, secluded Kauai getaway....
Luxurious 4BR/4BA Presidential Suite AC Near Beach
Welcome to BlueTideVillas! Welcome to Poipu's newest luxury resort-style villas! This is a VERY spacious (2750+ total square feet), top floor villa featuring 4 bedrooms and 3 1/2 bathrooms, with three private lanai's to sit on and enjoy your favorite tropical drink....
Beachfront 1BR 1BA condo on beautiful Poipu Beach Kiahuna #2
New to VRBO!! Relax in your Kiahuna Plantation condo beachfront on the white sand at beautiful Poipu Beach. Building 1 consists of 3 units and is the only ground level building with no second floor, so no one above you. This fabulous property features vaulted ceilings...
Kauai Exclusive - Pane Makai Turtle Suite - Steps to the Beach!
With ample room and durable bamboo decor, this plantation-style beach suite is perfect for large groups, wedding parties and family reunions. Comfortably sleeping 7, look no further for the perfect gathering place for friends and loved ones! This 3000 square foot suite...
New Listing! Poipu Townhome with Resort Amenities
Poi'pu Townhome with Lanai, Pool and Gym Experience island living at this lovely Pili Mai townhome in Poipu, surrounded by Kiahuna Golf Course with breathtaking mountain and South Shore views. Elegant design meets tropical paradisePremium Location and Resort...
Hale Lo'i House: Luxury + comfort in sunny Poipu!
This bright, spacious, brand-new 4-bedroom, 3.5-bath house has everything you could possibly need for a flawless vacation—and luxurious perks galore. Located in a quiet, upscale neighborhood, this charming tropical hideaway is close to some of Kauai’s best beaches,...
Luxury condo with central A/C and golf and ocean views
Come and discover our beautiful new condo on the 9th fairway of the Kiahuna Golf course. Our brand new condo is set in the perfect location to see both distant ocean views and distant mountain views. We have a beautiful lanai where you can catch the sun setting and...
Breathtaking Part. Ocean View in Kauai!
The Point at Poipu is a dream vacation destination on the southernmost tip of Kauai. The resort overlooks the sands of Shipwreck Beach & is secluded among lush landscapes. After a day of exploring, return to the resort to relax in the spacious two-bedroom accommodations...
Condo in beautiful Poipu - 3Bd, 3Ba, pool, hot tub & AC
Polu (means blue in Hawaiian) Paradise is a Luxury condo located in sunny Poipu, Kauai at Pili Mai condo complex. One assigned parking space within close distance to main floor condo with A/C. Three bedrooms and 3 Bathrooms, sleeps up to 8 guests (2 California king...
Hale Lo'i + Cottage: 5BR home +pool in Sunny Poipu
This bright, spacious, brand-new 5-bedroom, 4.5-bath compound has everything you’ll need for a flawless vacation—and luxurious perks galore, including a swimming pool and an outdoor lava-rock shower. The five bedroom house, which sleeps 10, consists of a 4-bedroom,...
5 Star, Great for Families, 4BD w/AC, HTD Pool, Poipu Beach Athletic Club access
Hale O Ke Akamai is Hawaiian for "House of Art" which is evident when stepping inside. Be sure to view video located at the end of photos (slide #3). Private single-level 4 bedroom home with AC provides the Aloha spirit in the beautiful and tranquil setting of Kiahuna...
Gorgeous Kiahuna unit - fully remodeled Fall 2022!!
Open, airy and perfect location. You will feel like you're in the jungle with the floor to ceiling cathedral windows in the open living and dining room/kitchen. End unit with no one above or below you! Two floors with living and eating space upstairs and bedrooms on...
Kiahuna Plantation Resort 213 Ocean View 2 BD 2 BA
With breathtaking ocean views and a relaxed island feel, this two-bedroom condo offers plenty of space to unwind. Located near Kauai’s most beloved beach, it’s perfect for group getaways.- Two-level condo in building 34 with bedrooms & bathrooms downstairs and...
Alihi Lani 4: Full A/C - top floor Ocean Views! Upgraded throughout
ALIHI LANI. This small, six unit complex called a 'Real Gem' by the Ultimate Kauai Guidebook. Enjoy endless views from our oceanfront pool. The front landscaped area also has two gas grills and comfy lawn furniture. We are named 'Premier Hosts' by VRBO and won the Trip...
Hale Milo: Charming Garden Cottage in Sunny Poipu!
Country-cottage charm meets elevated-plantation panache in Hale Milo: this delightfully distinctive 2+BR/2.5BA home in Kukui'ula’s leafy Kaulu neighborhood. Lovely island-style details and pleasant surprises abound, from the expansive lanai overlooking a lush,...
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
New shortened cancellation policy! Book before it's gone! New ownership! New A/C in both Living and Bedroom! One of the only units in Kiahuna with Air Conditioning in both rooms!1bd/1b newly remodeled condo inside beautiful Kiahuna oceanfront resort. The perfect spot...
Poipu Paradise Beach Condo
Welcome to the South Shore of the Garden Island of Kauai and beach town of Poipu! Your stay at our well appointed modern beach inspired condo will be a wonderful place for your Hawaii vacation. Just a short 5 min walk on the greenway to Poipu's beaches for activities...
Hale Kai - Best Value Beachfront Home Steps from Beach
Youtube Video Presentation: https://youtu.be/-c1tR8mMI1gHale Kai in Hawaiian means “ocean house” as there are spectacular views of the coastline and a white sand beach from every room. This home sleeps four with two bedrooms, two bathrooms and laundry facilities. It...
New Remodel & Rare Find #35 w/ Oceanview, AC, and corner unit! Look no further!
It's all about the location, views, and our new remodeled unit! Located in building 7, one of the smaller buildings with only 6 condos, you are in the heart of this oceanfront resort and steps from the beach!Remodeled kitchen and bathroom, all new flooring throughout,...
Pili Mai by Gather: Stylish 3BR Condo w/ Pool, Lanai & Scenic Views
Welcome to Pili Mai by GatherDiscover your perfect island retreat at Pili Mai by Gather, a modern and stylish 3-bedroom, 3-bathroom condo located on the scenic Kiahuna Golf Course in sunny Poipu on Kauai’s south shore. With picturesque panoramic mountain and distant...
Poipu Kapili 22 - Ocean Views * Deluxe Furnishings * Central Air Conditioned
Oversized 1 bedroom / 2 full bathrooms; ocean views from premium 2nd floor location Spectacular views and deluxe furnishings will make Poipu Kapili #22 your home away from home. This spacious and comfortable home has an air conditioned master suite and living room....
Kiahuna Plantation Resort 203 Ocean View 2 BD 2 BA
- Two story condo with beds and baths downstairs and living areas upstairs looking out to the ocean- Walk-up, no elevators- Bright and airy with tropical accents- Wood floors upstairs, tile downstairs- Full kitchen with granite countertops and backsplash includes full...
Kiahuna Plant. Ground Floor #114,AC, Athletic Club, Tennis Courts and much more
Welcome to Sunny Poipu Beach! Enjoy this ground floor, newly decorated condo and relax on your private lanai while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips. Fast 200mgb Wifi, fully stocked kitchen, free parking, 24...
Kilohana At Poipu By Parrish Kauai - Private Pool with AC - Great for the Family
Kilohana at Poipu is a private tranquil vacation home nestled in the center of Kiahuna Golf Village and the Robert Trent Jones, Jr. golf course. This single-level home has a spacious indoor/outdoor living layout centered around a heated swimming pool and courtyard,...
Spectacular View Home for 20! Ocean, Mountain, golf views! 5min from Poipu beach
Brand new listing on VRBO; I'm a Super host for the past 3 years on Air B&BThis newly constructed luxury home sleeps 20+; it's perfection for multigenerational gatherings, vacationing with a few families or large groups. Partial ocean views sits backing the Kukui’ula...
Pili Mai 13B 4Bedroom AC POOL
Pili Mai 13B is your perfect Island home… With views of rolling greens and distant ocean views from the lanai and bedroom windows. While the entrancing Ha’upu Mountains greet you with Aloha. Pili Mai is an exclusive resort that provides a wonderful escape while...
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 offering 1,600 sq ft of thoughtfully designed indoor-outdoor living. Ideal for families or groups, this elegant space blends...
Pomaika'i : New Poipu Villa w/Pool+Spa Near Beach
This lovely, spacious South Shore home is the epitome of a laid-back vacation villa: located on the 18th fairway of the Kiahuna Golf Course, splashed with sunlight, canopied by blue skies, surrounded by tropical greenery. With its shimmering turquoise pool and whirlpool...
Kauai Exclusive - Pili Mai 7B - Four Bedroom Suite - AC, Pool & Fitness Center
Spacious 4-bedroom, 3.5-bathroom condo features two master bedrooms with En Suite bathrooms, upgraded amenities such as A/C, Marbau flooring, granite countertops and Bosch appliances, a washer, dryer and much more!The sparkling new Pili Mai Resort is an open-skied...
Poipu Prime Location near Hyatt - Well-Appointed Home with Hot Tub in Courtyard
Located in the Bayview Neighborhood of the upscale Poipu Kai Resort here on the sunny South Shore of Kauai, our guests have access to the Poipu Kai Resort pool and tennis courts. This 3,800 sqft two-story home is just a short stroll west along the tropical walkway to...
Hale Ohana Hau'oli - Charming Kukui'ula Villa with Geometric Pool + Spa!
From the striking stone-pillared entry to the enchanting backyard banyan tree, this delightful Kukui'ula villa radiates an irresistible island-style ambience. Indoors and out, Hale Ohana Hau'oli teems with beautifully curated details: tasteful contemporary furnishings...
3BR/3BA Villa: Central A/C! Short Walk To Beach!
Welcome to BlueTideVillas! This unit not only boasts among the BEST reviews in all of Kauai but is also newly upgraded to enhance your stay from April, 2024, onwards.Nestled in the heart of Poipu, this VERY spacious (1830+ square feet) villa is a newly remodeled and...
5 Bed 3 Bath Home in Poipu Kai
Hale Aouli is a beautiful newly renovated five-bedroom and three-bathroom custom home located in beautiful Lanai Villas in the Poipu Kai Resort. From the home, you will find walking paths to Poipu's finest beaches, restaurants, tennis courts, pool,...
Hale Makani Nui: Sea-View Hilltop Villa Near Beaches
This lovely hilltop villa, Hale Makani Nui, or House of Strong Wind, is delightfully elevated, in every sense of the word. Its picturesque placement at the crown of a gently sloping lot gives an enchanting estate-like feel to the entire property, while also providing...
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 setting that offers ultimate privacy and space to unwind in paradise.The Guest house features one king bed and one queen sofa...
Pili Mai Family Condo 5C, 3 Bedroom 3 Bath, Mountain View, Cool Lanai,
Pili Mai is the south shore's newest development and adjacent to Poipu's ocean view Kiahuna Champion Golf Course. Your dream vacation is waiting at this second story, 3 bedroom, 3 bath spacious condo. The lanai gives plenty of outdoor space to enjoy outdoor living for...
Hale Leimomi: Luxurious Comfort + Pool + Views!
In this sparkling new villa, laid-back comfort harmonizes—beautifully—with the ultimate in luxurious appointments & upscale amenities. Extraordinarily spacious, with 3,902 square feet under roof, Hale Leimomi combines the elegance of a 4-star resort hotel with the...
Beautiful Pili Mai Condo-2 Bdrm + sleeping den, sleeps 6, with A/C
Relax and enjoy modern living at Kauai’s newest townhome community, Pili Mai! This condo, also known as Nani Ka Hale, is located on the second and third floor of the building. It overlooks the lush greens of Kiahuna Golf Course and offers stunning distant ocean views...
Poipu Pili Mai 9B, Flexible Cancellation, 4 bdrm, AC, Sunset/ Golf Course View
This is a 3 story building with our 2 story unit located on second and third floors with entry to condo up a flight of stairs. We have four bedrooms, 2 on the second story (the condo's main floor) which are Master suites. While upstairs on the third floor there are two...
Sunny Side Waves-Beachfront Property-Ground Floor, Corner Unit-Sleeps 5-Remodel
Remodeled ground floor, corner unit in exclusive Bld 11. Steps from Poipu Beach! Only oceanfront condos in Poipu! One of only few air conditioned units (located in bedroom)! New cal-king bed in primary bedroom, queen sleeper sofa & twin in the living room. Expansive...
Newly remodeled with AC, gorgeous ground floor condo 87, 3 min walk to beach
Newest addition to our Kiahuna Plantation condos! We just purchased and started renting condo #87. For reviews, please look up our other units - VRBO 1300156, 1587209, and 2160974Dual AC in living room and bedroom.Fully remodeled 1bd/1b condo inside the stunning Kiahuna...
Ground-Floor Condo w/Shared Pool, Hot Tub, Free WiFi, and Central AC
Pili Mai 15AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in...
Hale Ho'ouluulu – Luxury Poipu Villa with Infinity Pool & Ocean View
Wherever you look, this stunning Kukui'ula villa inspires admiration, and sparks delight. First, there’s the expansive view: an enchanting parfait of rolling hills and verdant orchards in the foreground, the glittering sea beyond, and impossibly blue skies overhead....
Whispering Palms - Tranquility and Elegance
WHISPERING PALMS AT KOLOA KAI VACATION RENTALSTranquility and Elegance in Poipu’s Kiahuna Golf VillageWelcome to Whispering Palms, your luxurious Hawaiian retreat in the heart of sunny Poipu! Perfect for families, multi-generational groups, or friends traveling...
Lei Ohana - Private Pool, Separate Guest House
LEI OHANA AT KOLOA KAI VACATION RENTALSA Private Island Retreat in PoipuEscape to Lei Ohana, a luxurious ranch-style home offering over 3,000 square feet of spacious living on Kauai’s sunny south shore. Nestled in a tranquil residential neighborhood in Poipu, this...
Oceanview Condo w/Athletic Club Access, Shared Pool, Hot Tub, Free WiFi, & A/C
Pili Mai 13COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience Hawaii as a family? Feel right at home in 13C, even when miles away in the middle of the blue Pacific....
Sugar Mill Cottage at Poipu Kai By Parrish Kauai - short walk to beach & quiet l
Sugar Mill Cottage is located in the heart of the Poipu Kai Resort community. It is the perfect location for beach access to either Shipwrecks beach or Poipu Beach park. A short stroll in either direction will take you to sun and sand!Enjoy the air conditioned bedrooms...
Makanui Estate - AC, Sleeps 17
MAKANUI ESTATE AT KOLOA KAI VACATION RENTALSA Private Paradise for Your Kauai EscapeWelcome to Makanui Estate, a luxurious retreat in the heart of Poipu offering breathtaking ocean views, serene mountain backdrops, and spacious accommodations for your family or group....