Owner Direct Vacation Rentals in Kihei

The Best Owner Direct Vacation Rentals in Kihei. Explore thousands of vacation home rentals, large cabins, and villas near Kihei

Wailea Grand Champions 183 From US $563
         

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New
House
  • Air Conditioner
  • Parking
  • Pool
Mana Kai #614 2 Bedroom Condo From US $538
         

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New
Condo
  • Pool
  • View
  • Wheelchair Accessible
Tropical Serenity - Charming Maui Banyan Studio From US $250
         

8.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool
Sugar Beach Resort From US $405
         

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8.0 (70 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • View
Kihei Retreat w/Kamaole Sands Resort Amenities! From US $790
         

Wailea Ekahi 38B From US $517
         

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New
House
  • Air Conditioner
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Beautiful Kihei Condo - Walk to the Beach! From US $305
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Kihei

Over 7730+ Luxury Places to Stay in or Near Kihei
Wailea Beach Villas WBV-PH 412 by KBM From US $9,660
         

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New
Apartment
  • Air Conditioner
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South Maui's Best Family Reunion Spot From US $8,919
         

9.8 (44 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $6,574
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Kihei

Over 6827+ Top-Rated Vacation Rentals with a Pool in or Near Kihei
Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $485
         

Stunning Views from only double lanai Penthouse unit. From US $348
         

10.0 (257 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Kihei

Over 55+ Pet-Friendly Vacation Rentals in or Near Kihei
Residence Inn by Marriott Maui Wailea From US $457
         

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8.0 (27 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Residences at Kamaole Sands Resort From US $766
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
AC Hotel by Marriott Maui Wailea From US $475
         

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8.2 (123 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ocean View Residence From US $1,018
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Four Seasons Resort Maui at Wailea From US $1,408
         

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9.0 (146 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
The Kalama Residence From US $691
         

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6.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Resort Retreat Studio-Walk to Beach, Shops, Dining with AC, WIFI From US $296
         

9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Kihei on PetFriendly.io

Large Vacation Homes & Villas in Kihei

Over 261+ Large Vacation Homes & Villas in or Near Kihei
Mana Kai Maui From US $391
         

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6.4 (18 Reviews)
Apartment
  • Pool
  • View
  • Wheelchair Accessible
Wailea Beach Villas M312: Your Hawaiian Paradise From US $1,987
         

10.0 (15 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Hale Kai O Kihei From US $314
         

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8.5 (144 Reviews)
Apartment
  • Pool
  • View
  • Wheelchair Accessible
Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

Exquisite Oceanfront Wailea Beach Villas B202 From US $4,010
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Kihei

Over 2756+ Wheelchair Accessible Vacation Homes in or Near Kihei
Fairmont Kea Lani, Maui From US $814
         

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9.0 (143 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Kauhale Makai by Coldwell Banker Island Vacations From US $779
         

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8.0 (1 Review)
Condo
  • Pool
  • View
  • Wheelchair Accessible
Newly updated- Ground floor 1 bedroom steps from the beach! From US $348
         

Island Surf 601A From US $189
         

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7.0 (6 Reviews)
House
  • Air Conditioner
  • Pool
  • View
Boutique Oceanfront Studio Vistas From US $383
         

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9.6 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Kauhale Makai 333 From US $444
         

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New
Apartment
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  • Pool
  • View
Endless & Elegant Vistas From US $409
         

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10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Grand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort From US $853
         

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8.2 (71 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Kihei Varoom and Airbnb Places to Stay Under $200

Over 208+ Kihei Varoom and Airbnb Places to Stay Under $200
Kihei Akahi Resort - Unit C603 From US $165
         

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6.0 (1 Review)
House
  • Parking
  • Pool
  • View
Kihei Akahi From US $179
         

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8.2 (596 Reviews)
Condo
  • Parking
  • Pool
  • TV
Deluxe style Camper with all features and ammenties From US $163
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Kihei Akahi Resort - Unit C313 From US $135
         

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7.7 (3 Reviews)
House
  • Parking
  • Pool
  • View
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Kihei Akahi Resort - Unit C618 From US $138
         

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9.0 (3 Reviews)
House
  • Parking
  • Pool
  • Accessibility
MBH109 Charming & Updated Maui Banyan 2 Bath From US $176
         

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9.8 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Kamaole Sands 7-207 From US $199
         

9.0 (2 Reviews)
House
  • Parking
  • Pool
  • View

Instantly Bookable Vacation Homes in Kihei

Over 5113+ Instantly Bookable Vacation Homes in or Near Kihei
Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
PAW 1706 Remodeled Wailea 1BD w Pool AC Near Beach From US $413
         

9.8 (9 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Elegant Oceanfront Vistas From US $298
         

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New
House
  • Air Conditioner
  • Parking
  • Pool
2 Bedroom Overlooking Beach and Ocean From US $1,126
         

Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais! From US $790
         

About Kihei Vacation Rentals

With more than 7739 Kihei vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kihei.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Kihei, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kihei. Places to stay near Kihei are 772.62 ft² on average, with prices averaging $608 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Kihei with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kihei

Type Count
Holiday Apartments 1131
Vacation Homes 883
Villas 135
Resorts 115
Hotels with Suites 64
Cottages 17
B&B 8
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Kihei

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kihei.

Weather in Kihei

View the weather forecast for Kihei before booking your Kihei Vacation Rentals to confirm your best time to go.

December - February
High 27°C       Low 17°C
March - May
High 30°C       Low 18°C
June - August
High 32°C       Low 21°C
September - November
High 32°C       Low 18°C