Pili Mai 8K - Spacious Comfort with Ocean & Golf Views in PoipuFrom $508/night · Sleeps 6
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 24
Koloa Vacation Rentals Map
Pili Mai 8K - Spacious Comfort with Ocean & Golf Views in PoipuFrom $508/night · Sleeps 6
Aloha Kai | AC | Pool & Hot Tub | Beach AccessFrom $558/night · Sleeps 5
Beautiful Marriott's Waiohai Beach Resort + Resort Amenities includedFrom $665/night · Sleeps 8
The Lodge at Kukui‘ula - Bungalow 7From $1,578/night · Sleeps 4
Poipu Ground-Floor Gem | New A/C, Sleeps 6, Walk to Shopping & DiningFrom $193/night · Sleeps 6
Summer Deal Poipu Golf Villa with Pool Hot Tub and Beach AccessFrom $214/night · Sleeps 8
1 Bedroom Ground Floor Condo in Sunny Poipu with Tropical Gardens, AC and Pool!From $223/night · Sleeps 5
Luxury 2-bedroom condo with AC in charming KoloaFrom $278/night · Sleeps 4
Stunning Ocean View Condo on the beach w AC, Kiahuna Plantation, Poipu BeachFrom $300/night · Sleeps 4
Topical ocean front 2-bedroom condo with AC in charming KoloaFrom $303/night · Sleeps 5
Walk to Poipu Beach, Grand Hyatt & Brennecke's/Poipu Kai Charming CondoFrom $319/night · Sleeps 4
New! Studio Suite with Pool by Beach with ACFrom $323/night · Sleeps 2
*NEW* 180-Degree Pacific Views from Your Poipu LanaiFrom $362/night · Sleeps 4
Nihi Kai Villas 700 Ocean Views ACFrom $372/night · Sleeps 4
Kiahuna 183 AC, Ground Floor Ocean View PBACFrom $383/night · Sleeps 4
KP241 Ground & 2nd FL Lanai - Beach•Pool•GymFrom $384/night · Sleeps 6
Pili Mai 6I – Golf Course Views, Distant Ocean Views, Central A/CFrom $397/night · Sleeps 8
Ground Floor Garden Access moments from BeachFrom $420/night · Sleeps 4
Point at Poipu Kauai Oceanfront Condo 2 BR fully equipped in Oceanfront Resort.From $421/night · Sleeps 6
2/2 BEACHFRONT RESORT w AC, Poipu Bch, Kiahuna Gardenview, Pool/Gym/CourtsFrom $440/night · Sleeps 5
Kuhio Shores 416 — Spectacular Top-Floor Oceanfront, ACFrom $459/night · Sleeps 4
Makahuena 2305 By Parrish Kauai - Great family space with ACFrom $492/night · Sleeps 6
Kauai Escape at The Point at Poipu –Spacious Ocean View 2-Bedroom VillasFrom $519/night · Sleeps 6
Aston Poipu Kai Kauai 422 | Garden View Haven – Pool & Hot TubFrom $523/night · Sleeps 4
Kiahuna Plantation Resort 66 Partial Ocean 2BD 2BAFrom $575/night · Sleeps 6
Kiahuna Plantation Resort Ocean View 2 BedroomFrom $580/night · Sleeps 6
Poipu 3BR/3BA corner villa, poolside, A/CFrom $755/night · Sleeps 6
Marriott Waiohai Beach Club • Walk to Poipu Beach • Resort Access Included. 2BRFrom $800/night · Sleeps 8
Luxury Poipu Kai 3 Bedroom Villa with Pool and Tennis!From $850/night · Sleeps 8
2 Story Ocean-View 2BR, 2 Lanais, Vaulted Ceilings, Resort Pool -Unit 23From $945/night · Sleeps 6
Ho'ona Beach House by Alekona Kauai: 3BR Oceanfront Poipu ParadiseFrom $1,055/night · Sleeps 6
Kauai Modern Luxury •Near Beach •A/C •Golf Views •WiFi •Huge Kitchen •Sleeps 12From $1,141/night · Sleeps 12
Hā’upu HaleFrom $1,210/night · Sleeps 12
From $508/night
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...
From $558/night
Aloha Kai | AC | Pool & Hot Tub | Beach Access
Escape to a beautifully updated condo in Kiahuna Plantation, where tropical comfort meets resort-style living. Relax on your private lanai with ocean...
From $665/night
Beautiful Marriott's Waiohai Beach Resort + Resort Amenities included
Book with Chairman owners! This marvelous beach resort in Koloa is perfect for your escape. Access to Resort Amenities is included for our guests....
From $1,578/night
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,...
From $193/night
Poipu Ground-Floor Gem | New A/C, Sleeps 6, Walk to Shopping & Dining
Summary:Ground-floor comfort at Waikomo Stream Villas 502 in Poipu, Kauai. This spacious one-bedroom condo sleeps 6 with two sleeper sofas and...
From $214/night
Summer Deal Poipu Golf Villa with Pool Hot Tub and Beach Access
Pili Mai 13M - Golf Course Villa in PoipuThis beautiful, ground-floor villa in exclusive Pili Mai Resort combines modern luxury with all the...
From $223/night
1 Bedroom Ground Floor Condo in Sunny Poipu with Tropical Gardens, AC and Pool!
Summary:Welcome to your sunny South Shore escape at Waikomo Stream Villas 200—where modern comfort meets lush tropical beauty in the heart of Poipu....
From $278/night
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...
From $300/night
Stunning Ocean View Condo on the beach w AC, Kiahuna Plantation, Poipu Beach
Brand new upgraded 1-bedroom condo with AC, upper level for amazing views! The space features a beautiful king bed and a cozy sofa bed, perfect for...
From $303/night
Topical ocean front 2-bedroom condo with AC in charming Koloa
Get ready to relax in this luxury 2-bedroom condo in Koloa. The space features a king bed and a queen bed, perfect for a small group or family....
From $319/night
Walk to Poipu Beach, Grand Hyatt & Brennecke's/Poipu Kai Charming Condo
Experience Poipu like a local in this adorable 1-bedroom 1-bath condo. Relax in a comfortable Cariloha king bed with AC with additional sleeping...
From $323/night
New! Studio Suite with Pool by Beach with AC
Presenting Bird of Paradise Suite! Relax and replenish at this unique and tranquil getaway just steps from the Grand Hyatt. Quiet studio retreat with...
From $362/night
*NEW* 180-Degree Pacific Views from Your Poipu Lanai
Summary:Take breakfast onto the lanai and watch the Pacific fill the horizon from one end to the other. This second-floor Kuhio Shores condo sleeps...
From $372/night
Nihi Kai Villas 700 Ocean Views AC
Summary:Spacious ocean-view 2-bedroom, 2.5-bath condo at Nihi Kai Villas in sunny Poipu — just a short walk to Brennecke’s Beach and Poipu Beach...
From $383/night
Kiahuna 183 AC, Ground Floor Ocean View PBAC
Summary:Kiahuna Plantation 183 is a ground-floor, 1-bedroom ocean-view condo in Poipu’s only true beachfront condominium resort. Just steps from...
From $384/night
KP241 Ground & 2nd FL Lanai - Beach•Pool•Gym
Mahalo for checking out our unit with Kauai Island Homes!IMPORTANT: The pool and hot tub at Poipu Athletic Club will be renovated Sept 9-Oct 15....
From $397/night
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...
From $420/night
Ground Floor Garden Access moments from Beach
This room was just remodeled, new flooring, new kitchen, new furniture. Kiahuna Resort is the perfect ocean front complex, with a rolling green,...
From $421/night
Point at Poipu Kauai Oceanfront Condo 2 BR fully equipped in Oceanfront Resort.
This oceanfront Resort provides a magnificent view of the Pacific Ocean. The Point at Poipu Resort is located in the South Shore of Kauai, Hawaii....
From $440/night
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...
From $459/night
Kuhio Shores 416 — Spectacular Top-Floor Oceanfront, AC
Summary:Experience spectacular top-floor oceanfront living at Kuhio Shores 416. Enjoy panoramic Pacific views, split air conditioning, a private...
From $492/night
Makahuena 2305 By Parrish Kauai - Great family space with AC
Located on the southernmost point of Kauai, this unique oceanfront property is situated on the edge of a bluff providing spectacular views of the...
From $519/night
Kauai Escape at The Point at Poipu –Spacious Ocean View 2-Bedroom Villas
Luxury Kauai 2BR Ocean Villa w/ Lagoon Pool & SpaWeeks are offered on a Friday, Saturday, and Sunday check-in & out in SEVEN NIGHT INCREMENTS.The...
From $523/night
Aston Poipu Kai Kauai 422 | Garden View Haven – Pool & Hot Tub
Welcome to Makanui 422, a spacious and inviting condo located within the desirable Poipu Kai Resort on Kauai's sunny south shore. Surrounded by...
From $575/night
Kiahuna Plantation Resort 66 Partial Ocean 2BD 2BA
Enjoy soft ocean breezes and glimpses of the sea from this partial ocean view one-bedroom condo. Ideally located near the shore, it’s a cozy and...
From $580/night
Kiahuna Plantation Resort Ocean View 2 Bedroom
Enjoy sweeping ocean views from this spacious split-level two-bedroom condo on Kauai’s most iconic beach. Perfect for families or couples traveling...
From $755/night
Poipu 3BR/3BA corner villa, poolside, A/C
Welcome to our beautifully appointed corner villa at The Villas at Poipu Kai!This second-floor, 1,600 square foot three-bedroom, three-bath condo in...
From $800/night
Marriott Waiohai Beach Club • Walk to Poipu Beach • Resort Access Included. 2BR
Book with Chairman owners! This marvelous beach resort in Koloa is perfect for your escape. Access to Resort Amenities is included for our guests....
From $850/night
Luxury Poipu Kai 3 Bedroom Villa with Pool and Tennis!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Enjoy tropical foliage and pool views with an exceptional level...
From $945/night
2 Story Ocean-View 2BR, 2 Lanais, Vaulted Ceilings, Resort Pool -Unit 23
Unit #23 is special at Kiahuna. This two-story, two-bedroom end unit in Building Five is designed for guests who want more; more space, more privacy,...
From $1,055/night
Ho'ona Beach House by Alekona Kauai: 3BR Oceanfront Poipu Paradise
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...
From $1,141/night
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...
From $1,210/night
Hā’upu Hale
Welcome to Hā’upu Hale, your tropical retreat in sunny Poipu, Kauai! This spacious and luxurious 4-bedroom, 3-bathroom home is perfect for families...