SUNNY POIPU, 2 beds rooms-2 bathrooms, air conditioningFrom $482/night · Sleeps 4
Old Koloa and Poipu Rentals
Koloa Vacation Rentals
Koloa Vacation Rentals – Historic Charm Meets Island Luxury
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 stay 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 right 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.
Rental Listings
Koloa Vacation Rentals Listings
Map View · Page 28
Koloa Vacation Rentals Map
SUNNY POIPU, 2 beds rooms-2 bathrooms, air conditioningFrom $482/night · Sleeps 4
Stunning Oceanfront Escape| 2BR w/ Balcony & ViewFrom $483/night · Sleeps 6
Kiahuna Plantation Resort 217 Ocean View 1 BedroomFrom $492/night · Sleeps 4
Kiahuna Plantation Resort 185 Ocean View 1 BedroomFrom $495/night · Sleeps 4
Serene Ocean-View, Vaulted Ceilings, Private Lanai & Resort Access -Unit 27From $495/night · Sleeps 4
Pili Mai Family Condo 15I, 3 Bedroom 2.5 Bath, Sleeps 8From $499/night · Sleeps 8
Walk To The Beach! Family Friendly 2 Bedroom Condo in Kauai - Sleeps 6!From $508/night · Sleeps 6
Aston Poipu Kai Kauai 211 | Tropical Garden Views – Pool & Hot TubFrom $509/night · Sleeps 6
Poipu Kapili Condo 4 by Alekona Kauai - 2BR OceanfrontFrom $509/night · Sleeps 5
Aston Poipu Kai | Steps to Beach | Private Lanai | Pool Access | Great LocationFrom $514/night · Sleeps 4
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
HGVC Point At Poipu 2 Bed 2 Bath UnitFrom $534/night · Sleeps 6
NEW LISTING! Spacious Condo with Resort AmenitiesFrom $535/night · Sleeps 8
Kiahuna Plantation Resort Partial Ocean 2 BedroomFrom $536/night · Sleeps 6
Kiahuna Plantation Resort 150 Royal Garden 1 BDFrom $538/night · Sleeps 2
Walk to Poipu Beaches - Spacious 3BR Retreat!From $549/night · Sleeps 8
Spacious, updated 2BD/2BA condo close to beaches!From $553/night · Sleeps 6
Hilton's Point at Poipu - Luxury 2 Bedroom VillaFrom $557/night · Sleeps 6
Aston Poipu Kai | Walk to Beach | Pools | Garden ViewsFrom $566/night · Sleeps 4
Aston at Poipu Kai • Walk to Beach • 2 Pools • Tennis • Resort LivingFrom $577/night · Sleeps 4
Aston Poipu Kai Kauai 921 | Tropical Garden Views – Pool & Hot TubFrom $580/night · Sleeps 4
Ground-Floor Ocean-View, Private Lanai & Lawn, Resort Pool & Tennis -Unit 8From $585/night · Sleeps 4
Beachside King Suite, Open Lanai & Beach Lawn, Resort Pool & Tennis -Unit 12From $585/night · Sleeps 4
Kiahuna Plantation Resort 116 Partial Ocean 2BD 2BFrom $587/night · Sleeps 6
Kiahuna Plantation Resort 33 Ocean View 1 BedroomFrom $600/night · Sleeps 4
Spend Thanksgiving 2026 in Paradise! 2BR/2BA condo at The Point at PoipuFrom $601/night · Sleeps 6
Oceanfront End Unit, Lanai Steps from the Sand, Pool & Pickleball -Unit 3From $608/night · Sleeps 3
Kiahuna Hale Kai IFrom $614/night · Sleeps 4
Makahuena 5202 by Alekona Kauai: 2BR Pure Oceanfront Condo w ACFrom $636/night · Sleeps 6
From $482/night
SUNNY POIPU, 2 beds rooms-2 bathrooms, air conditioning
Breezy 2-bedroom, 2-bath Poipu townhouse with air conditioning and a private lanai with BBQ, just minutes from Poipu Beach, snorkeling, dining, and...
From $483/night
Stunning Oceanfront Escape| 2BR w/ Balcony & View
Relax on your private balcony with garden or ocean views, prepare meals in the fully equipped kitchen, and enjoy peaceful days surrounded by tropical...
From $492/night
Kiahuna Plantation Resort 217 Ocean View 1 Bedroom
Oceanfront living at its finest—this one-bedroom condo on the 3rd floor offers stunning views, direct beach access, and cozy cottage charm. A perfect...
From $495/night
Kiahuna Plantation Resort 185 Ocean View 1 Bedroom
Enjoy stunning ocean views from this inviting 2nd floor condo, just moments from the shoreline. With a laid-back island vibe and all the comforts of...
From $495/night
Serene Ocean-View, Vaulted Ceilings, Private Lanai & Resort Access -Unit 27
Elevated on the second floor, Unit #27 offers something special: a wide, elevated perspective over the entire beachscape, with sweeping, unobstructed...
From $499/night
Pili Mai Family Condo 15I, 3 Bedroom 2.5 Bath, Sleeps 8
NEW TO OUR PORTFOLIO!PROFESSIONAL PHOTOS COMING SOON!Pili Mai is one of Poipu's newest complexes with a great location, close to beaches, golf,...
From $508/night
Walk To The Beach! Family Friendly 2 Bedroom Condo in Kauai - Sleeps 6!
The Point at Poipu, located on Kauai’s picturesque south shore, offers a serene oceanfront escape. Nestled between lush gardens and the sparkling...
From $509/night
Aston Poipu Kai Kauai 211 | Tropical Garden Views – Pool & Hot Tub
Pool Enhancement Project NoticeTo enhance our amenities, the Regency Association of Apartment Owners will be conducting a pool resurfacing project...
From $509/night
Poipu Kapili Condo 4 by Alekona Kauai - 2BR Oceanfront
Poipu Kapili Condo 4 is a two-bedroom oceanfront retreat that pairs sweeping ocean views with spacious, comfortable island living. On the entry...
From $514/night
Aston Poipu Kai | Steps to Beach | Private Lanai | Pool Access | Great Location
Welcome to Manualoha 803, a charming and comfortable one-bedroom garden view condo located within the highly desirable Poipu Kai Resort. Surrounded...
From $534/night
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...
From $534/night
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...
From $534/night
HGVC Point At Poipu 2 Bed 2 Bath Unit
Hello!PLEASE DO NOT RELY ON CALENDAR FOR AVAILABILITY. THIS IS A TIMESHARERESORT AND THEREFORE DATES COME AND GO EVERY DAY.PLEASE USE "ASK OWNER A...
From $534/night
HGVC Point At Poipu 2 Bed 2 Bath Unit
Beautiful 2BR/2BA Oceanfront Villa at The Point at Poipu – Weekly StaysAloha and welcome! Please read before booking:This is a timeshare resort, and...
From $534/night
HGVC Point At Poipu 2 Bed 2 Bath Unit
Beautiful 2BR/2BA Villa at The Point at Poipu – Weekly StaysAloha and welcome! Please read before booking:This is a timeshare resort, and...
From $534/night
HGVC Point At Poipu 2 Bed 2 Bath Unit
Beautiful 2BR/2BA Oceanfront Villa at The Point at Poipu – Weekly StaysAloha and welcome! Please read before booking:This is a timeshare resort, and...
From $535/night
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...
From $536/night
Kiahuna Plantation Resort Partial Ocean 2 Bedroom
Enjoy partial ocean views and tropical breezes from this spacious split-level two-bedroom condo on Kauai’s most famous beach. Ideal for families or...
From $538/night
Kiahuna Plantation Resort 150 Royal Garden 1 BD
Beautifully appointed and newly renovated, this ground-floor one-bedroom condo offers peaceful surroundings on Kauai's famous Poipu Beach. A cozy,...
From $549/night
Walk to Poipu Beaches - Spacious 3BR Retreat!
Welcome to Poipu Lani, a fully updated, poolside retreat in the Regency at Poipu Kai Resort, one of Kauai’s most desirable vacation destinations.This...
From $553/night
Spacious, updated 2BD/2BA condo close to beaches!
Spacious accommodations for the whole family and friends on Kauai’s sunny south shore! A two-story end unit that sleeps 6 guests, with lots of...
From $557/night
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...
From $566/night
Aston Poipu Kai | Walk to Beach | Pools | Garden Views
Welcome to Kahala 611, a comfortable and conveniently located ground-level condo within Poipu Kai Resort on Kauai's sunny south shore. Offering easy...
From $577/night
Aston at Poipu Kai • Walk to Beach • 2 Pools • Tennis • Resort Living
Pool Enhancement Project NoticeTo enhance our amenities, the Regency Association of Apartment Owners will be conducting a pool resurfacing project...
From $580/night
Aston Poipu Kai Kauai 921 | Tropical Garden Views – Pool & Hot Tub
Welcome to Kahala 921, a comfortable and inviting condo located within the popular Poipu Kai Resort on Kauai's sunny south shore. Perfectly...
From $585/night
Ground-Floor Ocean-View, Private Lanai & Lawn, Resort Pool & Tennis -Unit 8
Step off your private lanai and onto the front lawn, the Kiahuna Beach is right there, less than a minute walk away, perfect for morning strolls or...
From $585/night
Beachside King Suite, Open Lanai & Beach Lawn, Resort Pool & Tennis -Unit 12
From your private lanai, the view opens up: wide beach lawn and open ocean views stretching to the horizon. As an end unit, you'll enjoy extra...
From $587/night
Kiahuna Plantation Resort 116 Partial Ocean 2BD 2B
- Nicely appointed, newly furnished, two-story condo with beds and baths downstairs and living areas upstairs looking across the grounds to the ocean...
From $600/night
Kiahuna Plantation Resort 33 Ocean View 1 Bedroom
Wake up to panoramic ocean views in this charming 2nd floor condo, just steps from the sands of Kauai’s iconic beach. A peaceful, fully equipped...
From $601/night
Spend Thanksgiving 2026 in Paradise! 2BR/2BA condo at The Point at Poipu
Treat your family to an unforgettable Thanksgiving getaway on Kauai's beautiful South Shore! This highly sought-after Thanksgiving Week reservation...
From $608/night
Oceanfront End Unit, Lanai Steps from the Sand, Pool & Pickleball -Unit 3
There's beachfront, and then there's this. Unit #3 sits on the ground floor of Kiahuna's Building One, one of the most coveted positions in the...
From $614/night
Kiahuna Hale Kai I
*JUST LISTED! FULL RENOVATION COMPLETE JULY 2026!*Experience the beauty of Kauai from Kiahuna Hale Kai I, our fully remodeled top-floor oceanview...
From $636/night
Makahuena 5202 by Alekona Kauai: 2BR Pure Oceanfront Condo w AC
These are the ocean views you came to Kauai for - expansive, unobstructed, and entirely your own.Perched above the dramatic Poipu coastline at...