Travel Some Twosome - Vacation Rentals in Kihei

Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
  • Air Conditioner
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  • Pool
Modern & Polished Oceanfront Vistas From US $524
         

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10.0 (20 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,138
         

10.0 (206 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Corner Unit With Views From Every Window-Awesome Reviews From US $347
         

10.0 (202 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Kihei

Over 7771+ Luxury Places to Stay in or Near Kihei
Polo Beach Club POL-109 by KBM From US $9,471
         

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8.0 (1 Review)
Condo
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  • Pool
Wailea Elua Village Resort by KBM From US $9,199
         

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New
Condo
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South Maui's Best Family Reunion Spot From US $7,431
         

9.8 (44 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $5,335
         

10.0 (7 Reviews)
House
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  • Pool

Top-Rated Vacation Rentals with a Pool in Kihei

Over 6738+ Top-Rated Vacation Rentals with a Pool in or Near Kihei
Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $483
         

Romantic, Luxury, Sensual Retreat - Couples Only From US $588
         

10.0 (207 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Kihei

Over 51+ Pet-Friendly Vacation Rentals in or Near Kihei
Gated 2-story beach house with big yard From US $1,011
         

10.0 (83 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Maui What a Wonderful World Bed & Breakfast From US $339
         

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9.3 (61 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ocean View Residence From US $507
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Maui Sunset Oasis- Top Unit w/AC, watch whales from from Lanai (Dec-Apr) From US $483
         

Condo w/Private Lanai, Ocean View & On-Site Pool! From US $306
         

9.6 (33 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Kihei on PetFriendly.io

Large Vacation Homes & Villas in Kihei

Over 278+ Large Vacation Homes & Villas in or Near Kihei
Villa Moana Maui From US $1,892
         

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New
Villa
  • Air Conditioner
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  • View
BEACHFRONT MAUI KIHEI HOUSE From US $1,440
         

9.8 (173 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,383
         

10.0 (62 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $480
         

Wheelchair Accessible Vacation Homes in Kihei

Over 2712+ Wheelchair Accessible Vacation Homes in or Near Kihei
LOW JUNE RATES NOW ! RESERVE SOON ! From US $532
         

10.0 (149 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hale Hui Kai #112 From US $420
         

10.0 (1 Review)
House
  • Pool
  • View
  • Wheelchair Accessible
Endless & Elegant Vistas From US $409
         

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10.0 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Direct Oceanfront/Beachfront Luxury! Recently Remodeled From US $823
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Kihei Vacation Rentals and Airbnb Places to Stay Under $200

Over 200+ Kihei Vacation Rentals and Airbnb Places to Stay Under $200
Maui Vista 1207 From US $197
         

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7.8 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Paradise Jays Maui Island Breeze From US $126
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Great Rates - Clean and Cozy Condo! From US $197
         

9.8 (170 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Cozy Maui 'Treehouse' with lovely views and amenities From US $181
         

9.8 (98 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Kihei

Over 5075+ Instantly Bookable Vacation Homes in or Near Kihei
Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $695
         

Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $545
         

10.0 (137 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront Condo B303 June 27-July 3rd still available . From US $1,112
         

10.0 (101 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
1BR/1BA BEACHFRONT PRIVATE GREAT LOCATION GREAT REVIEWS! From US $501
         

10.0 (75 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Maui Family Owned & Managed - Wailea Grand Champions Villa From US $463
         

2BR/1BA BEACHFRONT GREAT LOCATION EXCEPTIONAL REVIEWS From US $610
         

10.0 (54 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Kihei Vacation Rentals

With more than 7780 Kihei vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Travelsometwosome 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 Travelsometwosome 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 784.3 ft² on average, with prices averaging US $588 a night.

Travelsometwosome 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 1357
Vacation Homes 742
Resorts 137
Villas 125
Hotels 62
Cottages 14
B&B 8
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Kihei

Pro Tip: Travelsometwosome makes it easy to compare the best listings on Travelsometwosome homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Travelsometwosome 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 82°F       Low 63°F
March - May
High 86°F       Low 66°F
June - August
High 90°F       Low 71°F
September - November
High 90°F       Low 66°F

Kihei Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kihei?
How many vacation rentals are available in Kihei?

Currently, the total number of properties listed in 2026 is over 7780 in the Kihei area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kihei.