Villa Rentals in Maha'ulepu Heritage Trail, HI: Compare 10+ Sites & Save

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  6.  Maha'ulepu Heritage Trail

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62 Best Villa Rentals in Maha'ulepu Heritage Trail (Starting from $679)

D211 Second Floor 3-bedroom Poolside Lanai
D211 Second Floor 3-bedroom Poolside Lanai
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

4 reviews

$795
Average price / night
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Kai Lani Ocean Villa Poipu • 5Bd • Pool&AC • Sleeps 20+
Kai Lani Ocean Villa Poipu • 5Bd • Pool&AC • Sleeps 20+
Villa
Koloa, HI, 96756, United States
0.6k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms25 Guests
10.0

Exceptional

3 reviews

$2098
Average price / night
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Poolside Villa With Private Lanai 3 Minute Walk To Poipu Beach
Poolside Villa With Private Lanai 3 Minute Walk To Poipu Beach
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$799
Average price / night
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3BR I Poolside Lanai Villa l Parking, Sunset View
3BR I Poolside Lanai Villa l Parking, Sunset View
Villa
Koloa, HI, 96756, United States
1.0k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$942
Average price / night
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Beautiful Poolside Villa Open Layout With Pool Fitness and Beach Access
Beautiful Poolside Villa Open Layout With Pool Fitness and Beach Access
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$809
Average price / night
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4BR I Elegant Poolside Penthouse l Private Elevator
4BR I Elegant Poolside Penthouse l Private Elevator
Villa
Koloa, HI, 96756, United States
1.0k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1648
Average price / night
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Incredible Luxury Villa in Paradise Near Shopping Golf and 3 Beaches
Incredible Luxury Villa in Paradise Near Shopping Golf and 3 Beaches
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$797
Average price / night
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4BR I Ground Floor Luxury Penthouse at The Villas | F100
4BR I Ground Floor Luxury Penthouse at The Villas | F100
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$1528
Average price / night
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Fabulous Villa Sleeps 6 Short Walk To Poipu Brennecke and Shipwreck Beach
Fabulous Villa Sleeps 6 Short Walk To Poipu Brennecke and Shipwreck Beach
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$799
Average price / night
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3BD/3BR Luxury Villa, AC, Pool, Walk to Beaches
3BD/3BR Luxury Villa, AC, Pool, Walk to Beaches
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$830
Average price / night
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C300 Custom 4 bedroom Ocean View Penthouse
C300 Custom 4 bedroom Ocean View Penthouse
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1199
Average price / night
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LUXURY VILLA - 3BR/3BA with Pool & A/C - Short Walk to Beaches
LUXURY VILLA - 3BR/3BA with Pool & A/C - Short Walk to Beaches
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

122 reviews

$1263
Average price / night
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D210 Second Floor 3-bedroom Poolside Lanai
D210 Second Floor 3-bedroom Poolside Lanai
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$679
Average price / night
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Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!
Villas at Poipu Kai 3 bed/3 bath luxury villa with central air conditioning!
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

201 reviews

$1145
Average price / night
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Ground Floor Poolside Villa Short Walk From Top Beach in Kauai With Great Pool
Ground Floor Poolside Villa Short Walk From Top Beach in Kauai With Great Pool
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$799
Average price / night
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3BR I Luxury Villa l Designer Furnishings, Central A/C
3BR I Luxury Villa l Designer Furnishings, Central A/C
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$1013
Average price / night
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E111 Ground Floor Poolside Patio
E111 Ground Floor Poolside Patio
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.7

Exceptional

3 reviews

$805
Average price / night
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3BR I Luxury Poolside Villa | Stunning Ocean View, Lanai
3BR I Luxury Poolside Villa | Stunning Ocean View, Lanai
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$964
Average price / night
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F211 Second Floor 3-bedroom Poolside Lanai
F211 Second Floor 3-bedroom Poolside Lanai
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$794
Average price / night
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3BR I Fabulous Villa | Walk to Poipu Beach, A/C
3BR I Fabulous Villa | Walk to Poipu Beach, A/C
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$887
Average price / night
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Ground Floor Luxury Penthouse in Poipu Kai
Ground Floor Luxury Penthouse in Poipu Kai
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1266
Average price / night
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3BR I Luxury in Paradise l Beaches, Golf, Shopping
3BR I Luxury in Paradise l Beaches, Golf, Shopping
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$892
Average price / night
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Elegant Poolside Penthouse w Private Elevator
Elegant Poolside Penthouse w Private Elevator
Villa
Koloa, HI, USA
1.1k from Maha'ulepu Heritage Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$930
Average price / night
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3BR I Poolside Ground-Floor Villa |Walk to Beach|Hot Tub
3BR I Poolside Ground-Floor Villa |Walk to Beach|Hot Tub
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$977
Average price / night
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3BR I Spacious Poolside Villa | Gourmet Kitchen, Lanai
3BR I Spacious Poolside Villa | Gourmet Kitchen, Lanai
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$1082
Average price / night
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4BR I Exclusive Ocean View Penthouse l Grand Lanai, A/C
4BR I Exclusive Ocean View Penthouse l Grand Lanai, A/C
Villa
Koloa, HI, 96756, United States
1.1k from Maha'ulepu Heritage Trail center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
9.8

Exceptional

8 reviews

$1900
Average price / night
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Wonderful 5 br 12 Poipu ocean view!  Oceanfront complex!
Wonderful 5 br 12 Poipu ocean view! Oceanfront complex!
Villa
Koloa, HI, 96756, United States
1.2k from Maha'ulepu Heritage Trail center

Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms12 Guests
4.0

Review score

1 reviews

$1891
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Maha'ulepu Heritage Trail.

Where to stay in Maha'ulepu Heritage Trail? Best neighborhoods & areas

Maha'ulepu Heritage Trail Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 62 verified villa rentals in Maha'ulepu Heritage Trail. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Maha'ulepu Heritage Trail vary depending on the season, location, and amenities. Rates typically start from around $679 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Maha'ulepu Heritage Trail are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Maha'ulepu Heritage Trail.

Yes, Maha'ulepu Heritage Trail offers a wide range of villas ideal for group stays. Many properties include 4 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Maha'ulepu Heritage Trail villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Maha'ulepu Heritage Trail often include highly sought-after amenities such as View, Wellness Facilities, and Fireplace/Heating. These features enhance comfort and convenience, making them especially popular among travelers visiting Maha'ulepu Heritage Trail.

To discover top-rated villas in Maha'ulepu Heritage Trail, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.