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.
The Lodge at Kukui‘ula - Bungalow 10
Indulge in the opulent comfort of the two-bedroom bungalows at The Lodge at Kukui‘ula on Kaua'i, offering privileged access to the esteemed amenities of The Club at Kukui'ula. This exclusive enclave along Kaua'i's southern coast boasts an 18-hole Tom Weiskopf designed...
The Lodge at Kukui‘ula - Bungalow 9
Nestled in the exclusive Kukui'ula resort on Kaua'i's stunning south shore, this luxurious one-bedroom bungalow offers an unparalleled Hawaiian retreat. Bungalow 9 seamlessly blends indoor and outdoor living, capturing the essence of island life in a sophisticated...
The Lodge at Kukui‘ula - Bungalow 7
Bungalow 7 is a spacious ocean-view vacation home along Kaua'i's ideal southern coastline. It is the only two-story bungalow in our collection, offering commanding ocean views from the upstairs primary bedroom. This bungalow is conveniently within walking distance of...
The Lodge at Kukui‘ula - Bungalow 6
Welcome to Lodge at Kukui'ula Bungalow 6, a luxurious two-bedroom private retreat nestled on the pristine South Shore of Kauai. This idyllic bungalow offers the perfect blend of tranquility, modern comforts, and island charm. Designed with meticulous attention to...
The Lodge at Kukui‘ula - Bungalow 5
Experience the ultimate Hawaiian getaway at Lodge at Kukui'ula Bungalow 5, a luxurious one-bedroom retreat nestled within the stunning Kukui'ula community on Kaua'i's south shore. This beautifully designed bungalow offers an intimate escape, perfect for couples or solo...
This three-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i offers 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...
Situated on a private walk up cul-de-sac within walking distance from The Club at Kukui'ula, Bungalow 1B allows guests to experience golf-view one-bedroom tropical living. This 1,275 sq. ft. bungalow opens into a high-ceilinged kitchen and living area with couch and...
Kukui'ula Bungalow 1A is a beautiful one-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i. It offers 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...
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...
Hale Hanohano by Gather: Luxury Poipu Estate w/ Pool, Spa, Lanais & Ocean Views
A statement of island elegance in Koloa’s sun-drenched Poipu district, Hale Hanohano at Kukuiula is a 6-bedroom, 5.5-bath luxury estate designed for seamless indoor–outdoor living and panoramic ocean, mountain, and golf course views. With over 5,200 square feet of...
Koloa Kauai 3 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Settle in and immerse yourselves in the beauty and wonder of Kauai with those closest to you. Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in the...
Hale Hoʻomalie – Private Pool & Golf Views
Summary:Single-level Poipu retreat with private pool, jetted tub, golf course frontage, and mountain views. Located in the peaceful Kiahuna Golf Village, this spacious 3-bedroom home features open-concept living, a fully equipped kitchen, two lanais, and beach gear for...
Relax in Paradise – Studio at Sheraton Kauai Resort
Find your tropical getaway in this Studio Villa at Sheraton Kaua‘i Resort, ideally located on the sunny South Shore in Po‘ipū. Perfect for couples or solo travelers, this villa is thoughtfully designed comfort with easy access to resort amenities.Inside, you’ll find a...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢’𝐬 Gorgeous Waiohai Club Beachfront Resort + Amenities
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of Poʻipū Beach, Koloa’s most sought-after 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐖𝐚𝐢𝐨𝐡𝐚𝐢 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛 𝐑𝐞𝐬𝐨𝐫𝐭.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬...
Kauai 2 Bedroom Villa Sleeps 8
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.The resort is beautifully landscaped with waterfalls and lagoons, lush tropical plants, and the sandy shores of Poipu Beach just steps away. While the beach is perfect for children, the...
Poipu Luxury — 2BR 2BA A/C Condo with Resort Amenities, Walk to Beaches & Trails
*** HOT NEW LISTING ***Unwind and discover paradise at your private sanctuary in Poipu Kai. This spacious, elegantly updated 2-bedroom, 2-bath A/C condo blends comfort, privacy, and adventure—perfect for couples or families. Set amid lush gardens and featuring modern...
Regency 620 - Beautiful 3 Bedroom Overlooking Regency Pool
Summary:Top-floor 3-bedroom, 3-bath home in Poipu Kai with central A/C, vaulted ceilings, two private balconies, and access to Regency pools and hot tubs. Walk to Poipu Beach, Brennecke’s Beach, and coastal trails.The Space:REGENCY 620 AT KOLOA KAI VACATION...
Pili Mai 13M - Golf Course Villa in Poipu by Coldwell Banker
Pili Mai 13M - Golf Course Villa in PoipuThis beautiful, ground-floor villa in exclusive Pili Mai Resort combines modern luxury with all the conveniences of Poi'pu.Nestled within the exclusive Pili Mai Resort, this lovingly maintained 3-bedroom, 3-bathroom sanctuary...
Luxury 6BR Ocean View Estate Home in Kukuiula
Framed by panoramic ocean views and painted sunsets over Popiu, this single-story, 6 bedroom luxury vacation home captures the essence of sophisticated island living. The home's southwest-facing orientation welcomes golden light throughout the day, transitioning...
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...
Relax in Paradise – Studio at Sheraton Kauai Resort
Find your tropical getaway in this Studio Villa at Sheraton Kaua‘i Resort, ideally located on the sunny South Shore in Po‘ipū. Perfect for couples or solo travelers, this villa is thoughtfully designed comfort with easy access to resort amenities.Inside, you’ll find a...
2BR Ocean View Baby Beach Cottage
Why Guests Love Hale KoleaDesigned with couples, newlyweds, and anniversary getaways in mind, this intimate cottage provides the perfect setting to relax, reconnect, and savor island life. Wake to the sound of the ocean, linger over slow mornings at Baby Beach, and wade...
Poipu Modern Luxury Home - Lo'i Hale
Escape to Kaua’i’s sun-drenched South Shore and experience island living at its finest in this beautifully designed 3-bedroom, 3.5-bath retreat just minutes from world-famous Poipu Beach. Nestled on a quiet cul-de-sac and surrounded by lush tropical landscaping, this...
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...
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...
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
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 beautiful common area with 2 large outdoor Lanais. Enjoy AC in each of the bedrooms, premium kitchen with quartz, and modern...
NEW LISTING! Spacious Condo with Resort Amenities
Spacious Golf Course Condo with Resort Amenities - Poipu, KauaiThis 1,600 sq. ft. two-story villa offers views of Kiahuna Golf Course, surrounding mountains, and ocean glimpses from a private lanai. Located on Kauai's sunny South Shore, just minutes from Poipu Shopping...
Kukuiula Makai Cottage #22 By Parrish Kauai
A modern island retreat in Kukuiula. Sleek, serene, and effortlessly stylish, this 4-bedroom, 4.5-bath Kukuiula villa pairs refined minimalism with laid-back island charm. Designed with a modern aesthetic, the home features clean architectural lines, curated...
Summary:Enjoy oceanfront comfort just steps from Poipu Beach at Nihi Kai 201. This spacious two-level villa offers 1,507 sq. ft. of living space, beautiful ocean and pool views, multiple lanais, and easy access to Brennecke’s Beach. With resort amenities—including a...
New Listing! Treetop Getaway with Athletic Club
Paradise Awaits with Exclusive Beach Club Access - Kiahuna PlantationWake up to tropical breezes and treetop living at this peaceful 3rd-floor retreat, featuring a private lanai with lush garden views, all just a short stroll to Kiahuna Beach.Your Poipu Escape Includes:...
New listing! Lovely Poipu Condo with Gym and Pool
Spacious South Shore Condo with Mountain Views and Resort AmenitiesDiscover this sophisticated 1,576 sq. ft. two-level retreat in Pili Mai, offering spectacular mountain and tropical landscape views in desirable Poipu.Property Features: • Spacious, open floor plan with...
FANTASTIC! Ocean View Marriott Waiohai beach club 2 BDRM villa
, Full Resort AccessWelcome to Hawaii's Garden Isle, Kauai. 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 Poipu Beach, widely considered...
Escape to paradise at Pili Mai 2M
Ground-Floor Luxury Kauai Retreat Escape to paradise at Pili Mai 2M, a lovely 3-bedroom, 3-bathroom ground-floor haven that perfectly captures the essence of Kauai's South Shore. Accommodating up to 6 guests, this 1,580 square foot home offers garden and mountain...
Pili Mai 8K - Spacious Comfort with Ocean & Golf Views in Poipu
Summary:Spacious 3-bedroom, 3-bath condo at Pili Mai overlooking the Kiahuna Golf Course with distant ocean views. This single-level home features central A/C, a large furnished lanai, modern kitchen, and resort-style amenities including pools, fitness center, and BBQs....
koolkondo 2597 Halalu Compound
2597 Halalu CompoundWelcome to your dream escape in Poipu Beach Estates! This beautifully upgraded, two-story luxury vacation home is the perfect blend of island elegance and laid-back comfort. Complete with a one bedroom Guest house, it is tucked away in a serene,...
Scenic Kauai Stay Near Allerton Garden + Free Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, a full kitchen, a private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether...
Kukuiula Makai Cottage #12: Plantation-Style 2BR Retreat in Poipu
Kukuiula Makai Cottage #12 is a charming cottage nestled in the heart of Poipu’s highly sought-after Kukuiula neighborhood. This single-story plantation-style retreat blends vintage Hawaiian charm with upscale modern comforts. Featuring two bedroom suites, this cottage...
Kiahuna Plantation Resort 232 Royal Garden View De
This charming one-bedroom condo features relaxing garden views and a warm, cottage-inspired feel. Ideally located near Kauai’s iconic shoreline, it’s a great choice for a calm and comfortable getaway. Unit 232 Royal Garden View 1 Bedroom 1 Bath• End unit with walk out...
koolkondo 2597 Halalu Main home
Welcome to your dream escape in Poipu Beach Estates! This beautifully upgraded, two-story luxury vacation home is the perfect blend of island elegance and laid-back comfort. Tucked away in a serene, palm-fringed setting, the property offers ultimate privacy and...
New Listing! Poolside Poi'pu Condo - 2BR Kahala
Poolside Poi'pu Condo - 2BR Kahala at Poipu KaiExperience the best of Poipu in this perfectly positioned condo with the convenience of poolside living and easy beach access. This bright, modern 2-bedroom retreat features travertine floors, granite countertops, and...
Kiahuna Plantation Resort 84 Royal Garden 1 BD
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 for up to four guests, it's the perfect spot to unwind Unit 84 Garden View Deluxe 1 Bedroom 1 Bath• Walk out to the lawn...
Kiahuna Plantation Resort 112 Royal Garden Vw 1B
Relax in this ground floor garden-view condo, where cottage-style warmth meets island tranquility. Located near Kauai’s most beloved beach, it’s a welcoming space to unwind after a day of exploring. Unit 112 Royal Garden View 1 Bedroom 1 Bath• Fully equipped kitchen...
Regency Villas 212 Lush Garden By Suite Paradise
Regency Villas 212 – Your Spacious Kauai Getaway for Work, Play, and Family TimeWelcome to Regency Villas 212, a beautifully upgraded retreat designed to host up to six guests in style and comfort. Perfect for families, couples traveling together, or professionals in...
Hana Hou Hale: Poipu Oceanfront Villa and Guest House
Poipu Hana Hou Hale & Ohana is THE vacation home of your dreams. Situated in sunny Poipu, with first-class views of the sparkling Pacific, this picturesque home is equipped with everything you need for an unforgettable stay on Kauai. Enjoy uninterrupted sunrise and...
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to offer. With luxury and elegance from the moment you pull into the driveway, Hale Waipo’o is sure to be your luxury home away...
Oceanfront Elegance With Stunning Views - Double-Sized Lanai & Full AC
**A 10% discount off the rental rate will be automatically applied to stays of 7 days of longer!**Aloha and e komo mai to Poipu Shores 304A - the perfect setting for an unforgettable oceanfront experience on Kauai's south shore. From the double-sized lanai to the fully...
Aloha Escape-Oceanview-Newly Updated
Unwind in Koloa at this delightful condo. This cozy space features 1 bedroom with a comfortable king bed, a living room with a sofa bed, pack n play, and twin blow up mattress, and bathroom. Newly updated with a beautiful modern coastal design with an old surf touch....
Poipu Kai Regency 412 - Two-bedroom Garden View
Poipu Kai Regency 412 - Two-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath ensuite with shower/tub comboBedroom 2: 2 TwinsSecond bathroom: full bath with shower/tub comboSleeps: 4 peopleAC: NoneLaundry: in...
Poipu Kai Kahala 921 - One-bedroom Garden View
Poipu Kai Kahala 921 - One-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedBathroom: full bath ensuiteOccupancy: 2AC: noneLaundry: in condoCoffee maker: BrewTV: livingroom and bedroomThis highly sought-after property is located on the island...
Poipu Kai Kahala 114 - Two-bedroom Garden View
Poipu Kai Kahala 114 - Two-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath ensuite with tubBedroom 2: 2 TwinsSecond bathroom: full bath with shower tub comboLivingroom: Queen sofa bedAC: Portable AC in primary...