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.
Kiahuna Plantation partial oceanview,top floor,4 min walk to beach, pool,gym,+AC
Welcome to the famed Kiahuna Plantation Resort, located on the very desirable Poipu Beach. The Kiahuna sits on 35 acres of lush, tropical gardens, with orchids and lily ponds and boasts an expansive beachfront lawn surrounded by palm trees. The beach is a short stroll...
Waikomo 321 by Destination Kauai - A/C
E komo mai, welcome to Waikomo Stream Villas 321!This 1-bd/1-ba condo is on the second floor with landscaped views in the heart of sunny Poipu, minutes walk to nearby Kukui'ula Shopping Village. Explore the tranquil grounds to see the koi pond and greenery. Soak in the...
Crater 26 by Destination Kauai - Close to Poipu Beach
E Komo Mai – Welcome to Crater 26!Your peaceful retreat in sunny Poipu starts here.Enjoy garden views, open-concept living, and a private covered lanai — ideal for morning coffee or evening relaxation. The fully equipped kitchen features granite countertops and...
Milo Hae Hale welcomes you to Beautiful island of Kauai!
Beautiful Kiahuna Golf Village 3 Bedroom Home with Ocean Views *Fully Furnished* - Enjoy the serenity and privacy of the Milo Hae Hale. This beautiful 3 bed 3 bath home features privacy and comfort nestled within the exclusive Kiahuna Golf Village community on Kauai's...
Waikomo Stream Villas 332 - 2bed/2bath Air Conditioned, Club Membership
WAIKOMO STREAMS 332 AT KOLOA KAI VACATION RENTALSTropical Elegance with Distant Ocean ViewsWelcome to Waikomo Stream Villas 332, a beautifully designed two-bedroom, two-bath condo nestled in the heart of Poipu. With air conditioning in the downstairs bedroom and living...
Hale Ohana - Beachfront Premier Home with Privacy and Direct Beach Access!
Welcome to Hale Ohana, one of the historic Smith-Waterhouse Beach Homes, offering an idyllic beachfront retreat on a property passed down through the family since 1850. This serene home combines modern comforts with a rich family legacy, providing the perfect setting...
Hale Lani - Custom Built Ocean view Home on Golf Course with A/C
Located on the first fairway of the Kiahuna Golf Course, Hale Lani offers distant ocean views as well as the tranquility of Kauai mountain vistas. Custom built, this rich home features Honduran mahogany floors, floor to ceiling windows, cathedral ceilings, A/C in all of...
Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!
The Villas at Poipu Kai is the newest and most luxurious development within Poipu Kai Resort, located on the sunny south shore of Kauai! Unit C110 is a 3 bedroom 3 bathroom ground level luxury villa, boasting over 1,600 square feet of living space and a large lanai...
Hale Loke Cottage, 2 Masters, A/C, Use Of Resort Pool & Spa. Steps To Beaches
Hale Loke is a beautifully furnished and appointed single story detached cottage (no neighbors above or below). Hale Loke has two air-conditioned master bedroom suites and an a/c in the kitchen/living/dining area. The backyard has a BBQ grill, dining table, mountain...
OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C
Oceanfront 2bd/2ba Unit with Amazing Ocean Views & A/C. Oceanfront, 2 bedrooms, 2 bathrooms, Tile floors, tile showers, granite counters and bar, new comfy king bed and queen bed, wood cabinets and lovely island furniture. Equipped with all new linens beach and bath...
Kauai Love-Family Home 4B/2.5B, A/C, Greenbelt Access to 2 Beaches!
Welcome to Kauai Love—a bright, open-concept 4-bedroom, 2.5-bathroom home located on the scenic Poipu Kai Greenbelt. With room for up to 8 guests, this home is perfect for multi-generational families or groups of friends looking to relax, explore, and enjoy the best...
Prime Poipu Location Home - Air Conditioning, Well-Stocked Kitchen, near Hyatt
Our spacious garden view 4 bedroom 3 bath Poipu Garden Villa with its private tropical landscaped yard, is one of the exclusive Lanai Villa private homes of Poipu Kai. Our Villa guests have access to the Poipu Kai Swim and Tennis Club and you will find the key fob and...
Poipu Shores 207A Oceanfront Sanctuary, Corner Unit, w/AC
POIPU SHORES 207A AT KOLOA KAI VACATION RENTALSBreathtaking Oceanfront RetreatImmerse yourself in the beauty of Kauai’s southern coastline at Poipu Shores 207A, a stunning corner-unit condo offering unparalleled oceanfront views. Relax on the private lanai with your...
2br Oceanfront Poipu Cottage w/AC by Alekona Kauai - TVNC 1120
Updated with modern touches, the Lani Kai Cottage vacation rental in Poipu is just steps from the ocean and enjoys stunning ocean views from the primary bedroom, living area and kitchen. With two bedrooms and two bathrooms, this vacation rental can accommodate up to...
Expansive Oceanviews, AC, Walk to Poipu Beach
Our Big Kahuna is a 3650-square-foot, four-bathroom, five-bedroom residence that can accommodate up to fourteen guests using aero (inflatable) mattresses. This two-story residence merges our 3 bedroom, 2 bathroom unit upstairs unit and our 2 bedroom, 2 bathroom unit...
Deluxe OCEAN VIEW Ground Floor END UNIT....Heated PoolnWalk to the Grand Hyatt
EXCEPTIONAL IN EVERY WAY describes one of the best Poipu Sands condos available. Until you get there, you would not realize the advantages to this unit as compared to all the others. Unlike many of the others, this one is opposite the HEATED POOL area and close enough...
Beautiful Poipu 2 bdrm Ocean View Suite!
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...
Kiahuna Ocean View Ground Floor- in Unit Washer/dryer
Welcome to our beach bungalow on the sunny south shore of Kauai! Our ground-floor, one-bedroom, one-bath condo is located on the Kiahuna Plantation, the only white sand beachfront resort in Poipu. When you arrive at condo #28, you'll find that it is located on the...
Makahuena 5203 - Elima Building: Oceanfront 2BR Condo
Located on the southernmost point of Kauai, this unique oceanfront property is situated on the edge of a bluff providing spectacular views of the blue Pacific and the entire Poipu coastline from each unit. Incredible ocean views are the dominant feature of this resort...
Modern, Recently Updated, Walk to Beach, AC, Private Lanai + Pool, Sauna, Tennis
POIPU CRATER 16 AT KOLOA KAI VACATION RENTALSLuxury Living in a Tropical ParadiseWelcome to Poipu Crater 16, a newly renovated designer cottage that offers the perfect blend of luxury, comfort, and natural beauty. Nestled within a lush 7-acre dormant volcano crater,...
Beaches, Eats, Shops, Trees, Flowers, Frogs, Birds: Go Native!
Waikomo Stream Villas is a lovely SMALL RESORT property in the heart of POIPU'S BEST SHOPPING, DINING, AND BEACHES. A mature TROPICAL GARDEN with many flowering plants is the centerpiece of this 3.9 acre resort of several surrounding three-story wood buildings, a POOL...
Makanui 522 - Mountain Views, FREE membership to the Poipu Beach Athletic Club
MAKANUI 522 AT KOLOA KAI VACATION RENTALSMountain-View Condo with Pool Access and Close to Iconic BeachesWelcome to Makanui 522, a stunning 2-bedroom, 2-bathroom, 2-level condo offering breathtaking mountain views, modern comforts, and easy access to Poipu’s...
One-Bedroom Condo with A/C and Fantastic Ocean Views
Our Prince Kuhio 206 condominium is a charming one-bedroom unit that has been recently updated. This vacation retreat features slab granite counters, new kitchen and bath tile, new carpet, new appliances and cookware, and a generous king bed. It is close to everything...
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
Welcome to Kipuka Hale, a beautiful designed, newly renovated home. Located in a quiet, stunning neighborhood just two minutes to the world famous Poipu Beach. Our guests have full access to Poipu Beach Athletic Club, which includes a pool, hot tub, basketball/tennis...
Kolepa Kai: Beautiful 3 bed/3/5 bath Home
KOLEPA KAI AT KOLOA KAI VACATION RENTALSTropical Paradise on Kiahuna Golf Course in PoipuWelcome to Kolepa Kai, your ultimate Kauai getaway located on the stunning South Shore in the desirable Wainani neighborhood of Poipu. This beautifully appointed 3-bedroom, 3.5-bath...
SANDY BEACH RESORT New remodel with air conditioning. Beach 2min walk!
Paradise. This spacious beach home has a 2 LEVEL OPEN FLOOR PLAN with 2 bedrooms/2 bathrooms and A/C. We are building #37, Unit 243.BEACH: The Travel Channel named our Poipu Beach “America’s Best Beach” and we can see why. This beach is pristine with soft, clean...
Second-Floor Condo with Gorgeous View, Bikes, Lanai & On-Site Pool/Hot Tub/Gym
Pili Mai 2KOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your own private paradise at Pili Mai in Poipu, where you'll wake up each morning to gorgeous views of Kauai's...
Amazing Views in this 2 Bedrooms/2.5 Baths Condo
Imagine yourself living in this gorgeous location with amazing views of the deep blue ocean and lush tropical mountains. This spacious 2 bedroom/2.5-bathroom condo consists of a 2-story layout with high ceilings. It is the best location in the complex, situated on the...
POIPU OCEAN-FRONT CONDO, CAR avail, SUN, SURF, FISH, SNORKEL, COLD A/C!
Free Parking - 2 Elevators - No Resort Fees - Free Wifi Rental car available, at an extra charge, for guest use!Along with great location, you also enjoy a full East view of the Ocean from your own private lanai! You can get a glimpse of whales, turtles and other ocean...
Fall special for months of October & November. See calendar
Aloha! Come bring your ohana (family) and friends to sit on our beautiful wrap around patio at our beautiful Pu'uhonua (place of refuge) with breathtaking tropical views. The great room and kitchen are the heart of Pu'uhonua located on the 2nd floor featuring wrap...
Ground-Floor Beachside 1BR Retreat with Private Patio, Lawn, Pool & Health Club
Escape to our newly remodeled 1-bedroom, 1-bath condo, perfect for couples or small families seeking a beachside getaway. Located on the ground floor with no stairs, this condo offers a private patio opening onto an expansive grass lawn, ideal for kids to play or for...
Malia Makai - F - Honu - A/C, Ocean Views
MALIA MAKAI - F AT KOLOA KAI VACATION RENTALSHonuYour Modern Island Escape in PoipuWelcome to Malia Makai F – Honu, a newly renovated 2-bedroom, 1-bathroom cottage designed for relaxation and adventure in Poipu. From its vibrant island-inspired interiors to its prime...
Beautiful Private Cottage w/ AC in Sunny Poipu Beach Estates 5 Minutes to Beach!
This new, air-conditioned suite is in an exclusive neighborhood of Poipu, offering you the most rare and impressive accommodation the sunny South Shore has to offer. The rolling golf course greens that surround this property provide an open and airy feel. Enjoy the...
4 br Luxury Home in Kukuiula w Pool
Spectacular golf course views are just some of the highlights of the Pa'ina Makai vacation rental in the luxury Poipu community of Kukuiula. Pa'ina, meaning “to gather” in the Hawaiian language, is the perfect name for this home, which has many open living areas for...
Beautiful ground floor unit at Kiahuna plantation with A/C.
Aloha and welcome to paradise at Kiahuna Plantation Unit 86, a stunningly remodeled one-bedroom, one-bath condo on Kauai’s sunny south shore in Poipu Beach. Nestled in the northeastern corner of this 35-acre resort, this ground-floor retreat boasts zero-step...
Ground-Floor Gem Near the Beach with Lanai, WiFi, AC & On-Site Pool/Hot Tub
Pili Mai 2MOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Lush and manicured grounds, swaying palms, and views of the Kiahuna Golf Course and the neighboring mountains await at Pili...
Ocean-view condo with balcony, AC, washer/dryer & pool - walk to the beach
Prince Kuhio 319Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a relaxing Hawaiian escape at the Prince Kuhio condos of Kauai. Named in honor of the revered statesman and...
Hale Moana - Best Value Beachfront Home Steps from Beach!
Poipu Kauai’s perfect beachfront vacation home with the perfect price! Every room opens onto the huge covered lanai and has stunning ocean and sunset views. Spacious grounds at the waters edge. Queen and 2 Twin beds. A/C in bedrooms and living room as of May 2023!“A...
Makahuena 4205 by Destination Kauai - Partial Ocean View End Unit
E Komo Mai, Welcome to The Makahuena 4205!“The Makahuena” is located on the southernmost point of Kauai. This unique oceanside resort is situated on the edge of a bluff providing spectacular coastal views. This 2-bd/2-ba is a single-level condo on the second story...
Stone House - Beachfront Home with 180 Degree Coastline Views!
YouTube Video Presentation - https://youtu.be/0hYizfnECb8The Stone House is built on a point of land that has a 180 degree white water ocean view like no other! The home sleeps up to eight people and includes three bedrooms, two bathrooms and is adjacent to a white sand...
Poipu Koloa - 2 br unit Ocean/Garden view in Kauai
We can book Ocean Front/OV/Garden view unit if they are available.Price from the system is for Garden View unit. If you like OV, please request it.This is timeshare resort, per policy, unit number floating. Don't know exact unit be assigned until check in, but the view...
Palm-lined condo with easy beach access, pools, hot tubs, & tennis courts
Tropical Oasis at Poipu Kai 514Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say aloha to your next favorite vacation when you book a stay at this newly remodeled first-floor Poipu...
BEAUTIFUL BREATH-TAKING Ocean and Sunset Views w/ AC, Upscale Furnishing, & Art.
Enjoy Breath-Taking Beautiful Ocean views w/ AC, Upscale Furnishing, & Art.Our spacious split level condo offers incredible and unobstructed ocean views. The private lanai is the perfect spot for true relaxation, listening to the sounds of the waves crashing against...
koolkondo Kapili 52 Oceanfront Condo
Welcome to Koolkondo.com where you will experience luxury vacation rentals at its finest. Our stylish boutique hotel style condos and homes have it all. You will absolutely enjoy your home away from home with VIP concierge style services in modern island luxury! Our...
Kuhio Shores #211 - Best Value Oceanfront Condo in Poipu!
This air conditioned two bedroom two bath oceanfront unit is on the second floor of Kuhio Shores condominium located in sunny Poipu, Kauai. Fronting a sandy bay this complex has as an elevator and offers some of the best surfing, body-boarding, swimming and snorkeling...
nNew open concept Garden Delux Kiahuna, Partial Ocean View Retreat!
Celebrate Aloha and the tradition of Hawaii with a stay at our slice of paradise. You'll take a step back in time to a simple more relaxing period when you arrive at Kiahuna Plantation on the sunny south shore of the beautiful island of Kauai, 'The Garden Island'....
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Two bedrooms plus loft, 1 king bed, 1 queen, plus 2 twins in the loft, 2 full bathrooms, nice upgrades, washer and dryer in unit, lanai space, incredible views, great complex amenities.This brand new 2 Bedroom plus loft, 2 Baths condo is ready for your next vacation...
Poipu Oceanfront Penthouse AC, high WIFI, Well Stocked Kitchen, Beach Chairs
The stunning oceanfront Toyabrown Penthouse is located on Lawai Road, forty feet from the water and features a spacious oceanfront lanai (deck) overlooking four renowned Poipu surf spots, and is the perfect honeymoon accommodation. Note: A Top Floor Oceanfront Location,...
New! Poipu Paradise - Golf, AC, Pool
Imagine a perfect vacation rental in Poipu, Kauai, where you can relax in comfort and enjoy the best of island living. This 2-bedroom plus loft condo offers everything you need for a memorable stay.Poipu Paradise features two spacious bedrooms, each with comfortable...
Enchanting home with pool, hot tub, lanai, balcony, golf nearby, & washer/dryer
Makena-An Island ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha, and welcome to this relaxing and homey Hawaiian retreat on the island of Kauai. This vacation rental...