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 Resort 307 Royal Garden 1 BD
This airy second-floor condo provides plenty of space to unwind, with tranquil garden views and gentle island breezes – an ideal retreat for two.Unit 307 Garden View 1 Bedroom 1 Bathroom • Second floor end unit with private lanai• Fully equipped kitchen includes full...
Poipu Luxury Oceanfront Condo - Kuhio Shores 413
Welcome to a quietly luxurious two-bedroom, two-bath condo set directly above the Pacific in the heart of Poipu. Under new ownership, this beautifully refreshed retreat has been thoughtfully redesigned with comfort and refined island living in mind — natural textures,...
Tropical Comfort – 1BR Villa with Lanai at Sheraton Kaua‘i Resort
Set along Kaua‘i’s famous sunny South Shore, this 1-Bedroom Villa at Sheraton Kaua‘i Resort offers the perfect mix of island charm and modern comfort. With approximately 550–600 square feet of space, this villa is ideal for couples or small families looking to enjoy...
Koloa Kauai 2 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in the distance this condo is what Hawaiian living is all about. Stay close to home and play around at...
Luxury Ocean-View 2BR Condo | Walk to Poipu Beach | Sleeps 6
Kahala 321 at Poipu Kai Resort – Spacious Island Retreat Near Poipu BeachesRelax and recharge at Kahala 321, a beautifully appointed condo located within Kauai's sought-after Poipu Kai Resort. Set amid lush tropical landscaping, this inviting island retreat offers the...
Special Lawai Beach Resort- 2 bedroom
Welcome to your tropical sanctuary on Kauai’s sun-drenched South Shore! Located directly across from the world-famous Lawai Beach, our condo at the Lawai Beach Resort offers the perfect blend of island relaxation and unparalleled adventure. Whether you are here to swim...
Hale Laule'a at Kukui'ula by Gather: 5BR Luxury Estate w/ Pool & Views
Set within the prestigious Kukui'ula community in Koloa, Hale Laule'a at Kukui'ula is a contemporary island retreat offering five bedrooms, seven baths, and accommodations for up to 11 guests. Overlooking manicured golf fairways with mountain and ocean views beyond,...
Pili Mai at Poipu #13J By Parrish Kauai - Great family location
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 newest resort development and has a choice of two, three, and four bedroom luxury condominiums.This central Poipu location...
Garden-View 2BR at The Point – Bright Poipu Villa with Lanai & Island Comfort
Enjoy a relaxed island retreat in this spacious two-bedroom, two-bath garden-view villa at The Point at Poipu on Kauaʻi’s sunny south shore. Designed for families or groups who want comfort and space, the villa features a master bedroom with a king-size bed and en-suite...
Ho'ona Beach House - Oceanfront Living in the Heart of PoipuHo'ona Beach House offers a rare opportunity to stay directly on the ocean in one of Poipu's most desirable locations. Positioned just 30 feet from the water's edge, this single-level, three-bedroom, three-bath...
Luxury 2-bedroom condo with AC in charming Koloa
Escape to this delightful condo in picturesque Koloa. With two comfortable bedrooms, including a king bed and two twin beds, guests find plenty of space to relax. The two full bathrooms feature refreshing showers and are stocked with all you will need, including a...
Poipu Beach 2 BR/2BA Townhouse A/C ~Lanai w/BBQ
Breezy 2-bedroom, 2-bath Poipu townhouse with air conditioning and a private lanai with BBQ, just minutes from Poipu Beach, snorkeling, dining, and shopping. You will have access to the Poipu Beach Athletic Club. They are a full gym, with pickle ball courts, classes and...
Makahuena 1205 – Fully Renovated Ocean-View Condo with A.C. Throughout
Summary:Fully renovated ocean-view condo at Makahuena in Poipu with sweeping Pacific views from every room. Features split air conditioning throughout, modern interiors, resort pool and hot tub, and walkable access to Poipu Beach, Brennecke’s, Shipwreck’s Beach, and the...
Tropical 2BR Partial Ocean View Villa at The Point at Poipu
Discover the beauty of Kauai from this well-appointed two-bedroom partial ocean suite at Hilton Vacation Club The Point at Poipu. Spacious and inviting, it’s perfect for up to six guests seeking a mix of comfort, amenities, and island charm.Your suite includes two...
Point at Poipu with AC in bedrooms and various resort amenities
Welcome to this gorgeous timeshare in Koloa. This perfect two-bedroom retreat features a queen bed and a two twin bed, plus a cozy living room with a full bed pull out sofa for extra comfort. Guests enjoy two bathrooms, including one with a relaxing jetted bathtub. The...
Kauai Modern Luxury •Near Beach •A/C •Golf Views •WiFi •Huge Kitchen •Sleeps 12
• New Poipū luxury with central A/C• Sunrise/sunset golf views from relaxing lanai• Huge modern fully stocked kitchen + high-end appliances• High end furniture from Restoration hardware• Comfortable mattresses + extra linens if needed• Spacious dining + fast WiFi with...
Spacious Poipu Home with Guest House, Resort-Style Outdoor Living & Pool!
Welcome to an exceptional luxury retreat in the prestigious Poipu Beach Estates, tucked away on a quiet cul-de-sac just minutes from world-class beaches, shopping, and dining. Designed for both relaxation and entertaining, this stunning island retreat offers expansive...
New! Studio Suite with Pool by Beach with AC
Presenting Bird of Paradise Suite! Relax and replenish at this unique and tranquil getaway. Quiet studio retreat with king bed, AC, private lanai and delightful heated pool. Semi private backyard is shared only with identical sister suite.Conveniently steps from access...
Kahala 723 “Apana O Lani” – 2 Lanais, King Bed, Island Serenity
Kahala 723 – “Apana O Lani” (Piece of Heaven)Welcome to Kahala 723, affectionately named “Apana O Lani,” meaning “Piece of Heaven.” This beautiful 1,000 sq. ft. condo captures the true spirit of island living — open, airy, and perfectly designed for comfort and...
Kiahuna Plantation Resort 177 Ocean View 1 Bedroom
Relax and take in sweeping ocean and south shore views from this bright, comfortable second-floor end unit. Enjoy cool breezes and the comfort of air conditioning as you unwind after a day exploring Kaua‘i’s beaches and beauty.Unit 177 Ocean View 1 Bedroom 1 Bath•...
Special Lawai Beach Resort- 2 bedroom
Welcome to your tropical sanctuary on Kauai’s sun-drenched South Shore! Located directly across from the world-famous Lawai Beach, our condo at the Lawai Beach Resort offers the perfect blend of island relaxation and unparalleled adventure. Whether you are here to swim...
Kauai Makanui 712 – Spacious 2BR/2BA Island Retreat for Relaxation Now
Welcome to Kauai Makanui 712, a bright and spacious 2-bedroom, 2-bath retreat. Thoughtfully designed for comfort and island living, this home is the perfect base for your Kauai getaway whether you’re here to explore the South Shore or simply relax in paradise.The...
Kaua‘i 2BR Ocean-View Escape – Lanai Living, Full Kitchen & Poipu Beach Nearby
Discover the perfect blend of island comfort and spacious living in this two-bedroom, two-bath villa at The Point at Poipu on Kauaʻi’s sunny south shore. Ideal for families or friends traveling together, the residence includes a master bedroom with a king bed and...
Riverfront condo across from ocean. Sleeps 6
This memorable condo is the perfect home base for your trip to Poipu. Guests will find one comfortable bedroom with a king bed and two spacious living rooms featuring a sofa bed each, ideal for extra company. The bathroom includes a relaxing bathtub with shower and a...
Koloa Kauai 2 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab!Flowing waterfalls, a crystal clear Koi pond, and hundreds of tropical plants make This resort appear the stuff of dreams. Nestled in over twenty acres of lush tropical gardens overlooking...
Garden-View 2BR at The Point – Bright Poipu Villa with Lanai & Island Comfort
Enjoy a relaxed island retreat in this spacious two-bedroom, two-bath garden-view villa at The Point at Poipu on Kauaʻi’s sunny south shore. Designed for families or groups who want comfort and space, the villa features a master bedroom with a king-size bed and en-suite...
Hale O‘Kapeka – Spacious 3BR Poipu Home with Ocean Views & Hawaiian Soul
Welcome to Hale O‘Kapeka, a beautifully cared-for home that blends island soul with everyday comfort. Located in the heart of sunny Poipu, this spacious three-bedroom, two-bath retreat invites you to relax, unwind, and experience Kauaʻi with intention. With nearly 2,000...
New Listing 3 Bedroom on the Golf Course in sunny Poipu
Welcome to Pili Mai 7I, a stylish 3-bedroom condo in Kauai’s exclusive Pili Mai resort. Overlooking the lush landscape and Kiahuna Golf Course, this multi-level retreat is just minutes from Poipu Beach, shopping, and dining. Designed with classic plantation-style charm,...
Pili Mai 6I – Golf Course Views, Distant Ocean Views, Central A/C
Summary:Spacious 3-bedroom, 2.5-bath two-story condo at Pili Mai overlooking the Kiahuna Golf Course with distant ocean and sunset views. Features central A/C, a gourmet kitchen, two private lanais, and modern island design. Enjoy resort-style pools, fitness center, and...
Direct Oceanfront Poipu Palms 101, Pool, Sunsets
Welcome to Poipu Palms #101, a rare ground-floor oceanfront corner condo in one of Poipu’s most peaceful boutique complexes. With just 12 units, enjoy an intimate coastal retreat. Watch turtles and whales from the sundeck, relax on the oversized lanai at sunset, and...
Marriott's Waiohai Beach Club in perfect Koloa 2 bedroom Sleeps 6
Welcome to Hawaiʻi's Garden Isle, Kauaʻi. The unspoiled terrain invites you to explore rugged cliffs, towering waterfalls and lush foliage. Marriott's Waiohai Beach Club is a superb location on the golden sand crescent of Poʻipū Beach, widely considered one of America's...
Regency at Poipu Kai 123 By Parrish Kauai - Short walk to Beach
The Regency at Poipu Kai offers some of Kauai’s most refined condo accommodations on the South Shore. Fully air-conditioned and beautifully furnished, each villa features stylish interiors and modern amenities—delivering relaxed island living just minutes from Poipu...
Garden-View 2BR at The Point – Bright Poipu Villa with Lanai & Island Comfort
Enjoy a relaxed island retreat in this spacious two-bedroom, two-bath garden-view villa at The Point at Poipu on Kauaʻi’s sunny south shore. Designed for families or groups who want comfort and space, the villa features a master bedroom with a king-size bed and en-suite...
Poipu Beach• AC• Walk Out• 3-Min to Beach • Pool • Surf School• Snorkel• Turtle
Welcome to your peaceful Poipu Beach retreat The Palm House — a perfectly located, ground-floor walkout condo just a short 3-minute stroll through lush, tropical gardens to the shoreline. Set in one of the most walkable and convenient areas of Poipu, this home offers a...
Charming 3BR Koloa Shore Cottage with ocean views and AC, sleeps 6 in Poipu
Be one of the very first guests to stay in this brand-new-to-market vacation rental.Welcome to Koloa Shore Cottage — your peaceful escape at the historic Koloa Landing area in sunny Poipu, also known as Whalers Cove. Step outside and take in breathtaking views of the...
Kainani Vacation Home 10: 5 BR Ocean View Home with Pool
Welcome to Kainani Vacation Home 10- where trade winds, golden sunsets, and effortless island living come together in one stunning home. With ocean and golf course views, nearly 4,700 square feet of indoor-outdoor living, and a layout designed for gathering, relaxing,...
Discover Paradise at Marriott’s Waiohai Beach Club - 2 Bedroom Island View
Escape the ordinary and embrace the extraordinary at Marriott’s Waiohai Beach Club, where stunning natural beauty and endless fun await. Nestled on the golden shores of Kauai, this two-bedroom villa offers the perfect family getaway, combining all the comforts of home...
Hilton's Point at Poipu - Luxury 2 Bedroom Villa
Weeks are offered on a Friday, Saturday, and Sunday check-in & out in SEVEN NIGHT INCREMENTS.The REQUEST TO BOOK feature is a request for a reservation, not a confirmed stay. Please do not reserve your airfare until you have communicated with us and we have accepted the...
Spacious, family friendly Waikomo Streams condo with pool - walk to Baby Beach
Waikomo Stream Villas 131Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your tropical paradise in Poipu, HI! This charming condo is nestled amidst lush landscaping and...
Kahala 633 – Ocean-View 1BR Near the Beach
Summary:Top-floor 1-bedroom condo with ocean views overlooking Brennecke’s Beach and the Poipu Kai greenbelt. Features vaulted ceilings, private lanai, portable A/C in the bedroom, full kitchen, washer/dryer, beach gear, and access to Poipu Kai pools, tennis courts, and...
New listing! Poipu Condo with Pool, Jacuzzi, Gym
Welcome to your Kauai paradise at "Kauai Pili Mai 15F," a stunning 2-bedroom, 2-bathroom vacation rental nestled in the heart of Poi'pu. This beautifully designed property offers a perfect blend of comfort and luxury, ideal for families or groups of friends seeking a...
Tropical Comfort – 1BR Villa with Lanai at Sheraton Kaua‘i Resort
Set along Kaua‘i’s famous sunny South Shore, this 1-Bedroom Villa at Sheraton Kaua‘i Resort offers the perfect mix of island charm and modern comfort. With approximately 550–600 square feet of space, this villa is ideal for couples or small families looking to enjoy...
Marriott Waiohai Beach Club: 2 bedroom Villa oceanfront resort on Poipu Beach
Marriott's Waiohai Beach Club - 2 Bedroom, 2 Bath, Full Kitchen, sleeps 8. Full Resort Access.Units assigned upon check-in. Full access to the resort’s services and amenities are included with every reservation. Located on the beautiful Poipu beach on the island of...
2/2 BEACHFRONT RESORT w AC, Poipu Bch, Kiahuna Gardenview, Pool/Gym/Courts
AC throughout the condo. This is the only condo resort in Poipu on a sandy beach! Other condos are on a rocky shoreline or a long walk or drive to the beach. This beautiful and spacious 2-level garden view condo has a full sized kitchen with everything you need to feel...
HGVC Point At Poipu 2 Bed 2 Bath Unit
PLEASE DO NOT RELY ON CALENDAR FOR AVAILABILITY! THIS IS A TIMESHARE RESORT AND THEREFORE DATES COME AND GO EVERY DAY. PLEASE USE "ASK OWNER A QUESTION" BUTTON FIRST TO INQUIRE ABOUT AVAILABILITY. DO NOT SEND A BOOKING REQUEST BEFORE CONFIRMING YOUR DESIRED DATES ARE...
Family Retreat: 2BR Villa at Sheraton Kaua‘i Resort
Located on Kaua‘i’s sunny South Shore, the 2-Bedroom Villa at Sheraton Kaua‘i Resort is the perfect choice for families or groups seeking space, comfort, and direct access to Po‘ipū Beach. With approximately 1,100 square feet of living space, this villa comfortably...
Makahuena 2-105 Ocean View 2 Bedroom 2 Bath, Sleeps 6, Ground Floor
Beautiful new renovation to this charming two bedroom 2 bath, ground floor condo. The living and dining areas are spacious and breezy, just steps from the pool. Generous kitchen for cooking fabulous meals, and the lanai looks out over the ocean with a great view of...
Welcome to Wainani Sunset Estate – your island home away from home. This retreat features four suites with walk-in closets, en-suite baths, and split AC. Cook and gather in the open kitchen and dining area, then step outside to the lanai with BBQ, lounge, and fire-pit...
The three-bedroom cottages at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling spa...
Pili Mai 6M by Gather: Garden-View Condo w/ Lanai & Beach Access
Tucked along the Kiahuna Golf Course in sunny Poipu, Pili Mai 6M blends resort comfort with Kauai’s signature indoor-outdoor ease. This single-level, three-bedroom, three-bath condo offers 1,478 square feet of bright, air-conditioned living space framed by golf-course...