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Wailea, HI Homes for Rent

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  • /20

    $21,183

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    155 Wailea Ike Place Unit SI ID1436437P, Wailea-Makena, HI 96753

    The advertised rate of $21,184/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    155 Wailea Ike Place Unit SI ID1436437P, Wailea-Makena, HI 96753
  • /20

    $6,711

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • 893 Sq Ft
    • Condo for Rent

    2695 S Kihei Rd Unit SI ID1295784P, Kihei, HI 96753

    The advertised rate of $6,711/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 20, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2695 S Kihei Rd Unit SI ID1295784P, Kihei, HI 96753
  • /20

    $7,732

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    155 Wailea Ike Place Unit SI ID1295779P, Wailea-Makena, HI 96753

    The advertised rate of $7,732/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 5, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    155 Wailea Ike Place Unit SI ID1295779P, Wailea-Makena, HI 96753
  • /20

    $7,161

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • 893 Sq Ft
    • Condo for Rent

    2695 S Kihei Rd Unit SI ID1295773P, Kihei, HI 96753

    The advertised rate of $7,161/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 10, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2695 S Kihei Rd Unit SI ID1295773P, Kihei, HI 96753
  • /20

    $11,352

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Condo for Rent

    2575 S Kihei Rd Unit SI ID1436434P, Kihei, HI 96753

    The advertised rate of $11,352/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 11, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    2575 S Kihei Rd Unit SI ID1436434P, Kihei, HI 96753
  • /20

    $5,236

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • Condo for Rent

    2575 S Kihei Rd Unit SI ID1237859P, Kihei, HI 96753

    The advertised rate of $5,237/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    2575 S Kihei Rd Unit SI ID1237859P, Kihei, HI 96753
  • /20

    $6,659

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft
    • Condo for Rent

    2575 S Kihei Rd Unit SI ID1436436P, Kihei, HI 96753

    The advertised rate of $6,659/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2575 S Kihei Rd Unit SI ID1436436P, Kihei, HI 96753
  • /20

    $8,439

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 968 Sq Ft
    • Condo for Rent

    2575 S Kihei Rd Unit SI ID1295752P, Kihei, HI 96753

    The advertised rate of $8,439/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 18, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    2575 S Kihei Rd Unit SI ID1295752P, Kihei, HI 96753
  • /13

    $3,000

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 750 Sq Ft
    • Condo for Rent

    160 Keonekai Rd Unit Keonekai Villages, Kihei, HI 96753

    Keonekai Villages / South Kihei / Furnished . This 2 bed, 1.5 bath second floor condo Features split A/C in the living room and both bedrooms, solid bamboo flooring, custom cabinetry, full size front-loader stackable washer and dryer, and a serene outdoor space on your own private covered lanai. In a great location situated near the entrance to the complex, parking could not be more convenient

    160 Keonekai Rd Unit Keonekai Villages, Kihei, HI 96753
  • /9

    $3,650 Per Month

    • 2 Beds
    • 2 Baths
    • 949 Sq Ft
    • Condo for Rent

    3950 Kalai Waa St, Kihei, HI 96753

    Wailea Fairway Villas - 2 bedroom 2 bath nicely furnished upstairs unit. This property is located on the Wailea Blue Golf Course and has a pool, jacuzzi, barbecue and gym. Close to beautiful beaches, great shopping and restaurants. Washer and dryer in unit, dishwasher, and split AC system. Two parking stalls - one assigned, one unassigned. Rent - $3,650/mo. plus GET $171.99. Tenant pays electric

    Jenny Meekhof AA Oceanfront Rentals & Sales

    3950 Kalai Waa St, Kihei, HI 96753
  • /31

    $7,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • Luxury Living with Ocean Views in Wailea at Kai Malu

    83 Kainehe Place, Kihei, HI 96753

    Experience the epitome of resort living in the heart of Wailea with this stunning, fully furnished Kai Malu home. This property boasts three spacious bedrooms and 2.5 well-appointed bathrooms, offering ample space for relaxation and comfort. The home is nestled within a secure, gated community, providing an added layer of peace of mind. The two-car garage offers plenty of room for vehicles or

    83 Kainehe Place, Kihei, HI 96753
  • /23

    $7,300 Per Month

    • 3 Beds
    • 3 Baths
    • 1,796 Sq Ft
    • Condo for Rent

    83 Kainehe Place Unit 9B, Kihei, HI 96753

    Experience the epitome of resort living in the heart of Wailea with this stunning, fully furnished Kai Malu home. This property boasts three spacious bedrooms and 2.5 well-appointed bathrooms, offering ample space for relaxation and comfort. The home is nestled within a secure, gated community, providing an added layer of peace of mind. The two-car garage offers plenty of room for vehicles or

    Dan Macdonell Hawaii Life (W)

    83 Kainehe Place Unit 9B, Kihei, HI 96753
  • /10

    $4,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    3311 Mapu Dr, Kihei, HI 96753

    3 Bedroom, 2 Bath upper level rental with 1,800 interior square feet and a 596 square foot ocean view lanai. New carpet, paint, appliances and split system A/C. Unfurnished, with no pets allowed. There is another rental on the lower level, as well as a detached ohana, making a total of three rentals on this property.

    3311 Mapu Dr, Kihei, HI 96753
  • /21

    $5,400 Per Month

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft
    • House for Rent

    2824 Ohina St, Kihei, HI 96753

    Your Maui Oasis awaits! We are seeking clean, reliable, and responsible tenants who will treat this property with care and respect. This meticulously remodeled two-story house offers a luxurious and tranquil living experience, ideal for enjoying the best of Maui. Completely updated 2 years ago, offering modern finishes and thoughtful details throughout. Spacious Gourmet Kitchen: Fully equipped

    Eduardo Gandolfo Maui Houses and Condos Realty

    2824 Ohina St, Kihei, HI 96753
  • /64

    $6,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,991 Sq Ft
    • House for Rent

    357 Kualono Place, Kihei, HI 96753

    Elegance Redefined: Ocean View Luxurious Home in Wailea PualaniPerched within the prestigious, gated enclave of Wailea Pualani Estates, this fully reimagined custom estate offers far more than ocean views; it delivers a rare, seamless integration of modern sophistication and untamed island beauty. Bordered by a lush, private greenbelt, the residence functions as your own exclusive

    357 Kualono Place, Kihei, HI 96753
  • /25

    $2,850 Per Month

    • 2 Beds
    • 2 Baths
    • 728 Sq Ft
    • Gorgeous, Clean & Modern Furnished 2/2 at Kihei Shores — Lowest Level Unit Near Kamaole III

    2747 S Kihei Rd, Kihei, HI 96753

    Welcome to this beautifully updated, furnished 2-bedroom, 2-bathroom ground-level unit at Kihei Shores, ideally located across the street from world-famous Kamaole Beach Park III. This cool, quiet, and newly renovated home offers the perfect blend of comfort, convenience, and island living.This fresh and airy unit comes fully furnished with all the basics you need, including cookware,

    2747 S Kihei Rd, Kihei, HI 96753
  • /37

    $2,800 Per Month

    • 1 Bed
    • 2 Baths
    • 818 Sq Ft
    • Fully Furnished, 1 Bed/2 Bath, Kamaole Sands

    2695 S Kihei Rd, Kihei, HI 96753

    This 1 Bed/2 Bath condo is located in one of the best properties in Kihei, Kamaole Sands, directly across the street from one of the best beaches in Kihei, Kamaole Beach III. Ground floor with tropical views, making it the perfect unit for your Maui home.As you enter, you'll be welcomed by the elegant and timeless furnishings. The living area features modern furnishings and a comfortable

    2695 S Kihei Rd, Kihei, HI 96753
  • /20

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 719 Sq Ft
    • Kihei Shores Condo Available on 8/1/26

    2747 S Kihei Rd Unit D201, Kihei, HI 96753

    Partially furnished 2 Bedroom, 2 bath condo. remodeled kitchen with granite counters and stainless steel appliances-stove, dishwasher, convection / microwave oven, & refrigerator. Modern, on-demand hot water heating system. Updated lighting fixtures, updated bathrooms, wood laminate and tile floors throughout. A/C , Ceiling fans, W/D, lanai. Kihei Shores is across from the beach and has a

    2747 S Kihei Rd Unit D201, Kihei, HI 96753
  • /16

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 750 Sq Ft
    • South Maui - Keonekai Villages - Ground Floor Furnished 2BR/1.5BA with 2 parking spaces

    160 Keonekai Rd Unit 1-103, Kihei, HI 96753

    Renovated and furnished 2 BR, 1.5 BA updated ground floor condo in Keonekai Villages. Building 1 is located in the beginning of the complex. Updated kitchen with cabinets, countertops, stainless steel fridge, range/oven, and dishwasher. Tiled floors throughout the unit and a washer/dryer in the unit for modern convenience. A/C in living room. Lighted ceiling fans. Updated bathrooms with nice

    160 Keonekai Rd Unit 1-103, Kihei, HI 96753
  • /22

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    2795 Kauhale St, Kihei, HI 96753

    Available Now - South Kihei – Dog Friendly, Brand New Renovated 3 Bed / 2 Bath with Ocean ViewsBe the first to enjoy this beautifully renovated, unfurnished upper-level unit of the main house with a separate entrance and two parking spaces. Everything is brand new and the home has not been lived in since the renovation.This very clean and modern 3-bedroom, 2-bathroom residence

    2795 Kauhale St, Kihei, HI 96753
  • /51

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft
    • Modern Elegancy at Makali'i in Wailea on the boarder of Makena - Finely Furnished 2 Bedrooms / 2 ...

    172 Holomoana Way Unit 102, Wailea, HI 96753

    Welcome to Makali‘i, Wailea’s premier private gated resort-style community. Nestled on nearly 9.5 acres, this exclusive enclave features just 68 luxury two- and three-bedroom townhome residences—each building has only four homes for ultimate privacy and tranquility.This finely furnished 2-bedroom, 2-bathroom residence blends mid-century modern design with refined Hawaiian cultural

    172 Holomoana Way Unit 102, Wailea, HI 96753
  • /31

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 750 Sq Ft
    • Fully Remodeled 2-Bedroom, 2-Bath Condo – Keonekai Villages #27-105

    160 Keonekai Rd, Kihei, HI 96753

    160 Keonekai Rd. #27-105, Kihei, HI 96753Be the first to enjoy this beautifully renovated 2-bedroom, 2-bathroom ground-floor condo after an extensive remodel that was just completed. With approx. 756 square feet of thoughtfully updated living space, nearly every aspect of this home has been refreshed to provide a clean, modern, and comfortable living environment.The functional

    160 Keonekai Rd, Kihei, HI 96753
  • /18

    $2,750 Per Month

    • 2 Beds
    • 2 Baths
    • 733 Sq Ft
    • Kihei Shores 2bd/2bth

    2747 S Kihei Rd Unit H208, Kihei, HI 96753

    Welcome to Kihei Shores!Experience the best of South Maui living in this stunning, top-floor residence at Kihei Shores. This Condo Offers offers a unique blend of modern luxury and island charm, located directly across the street from the golden sands of Kamaole Beach Park III.Condo is furnished, but can be unfurnished on request. Prime Location: As a top-level unit,

    2747 S Kihei Rd Unit H208, Kihei, HI 96753
  • /40

    $8,300 Per Month

    • 3 Beds
    • 3 Baths
    • 1,802 Sq Ft
    • Modern 3 Bedroom, 3 Bathroom Furnished Condo at Makalii in Wailea

    161 Holomoana Way, Kihei, HI 96753

    Perched in the hilltops of the Wailea sits this FULLY FURNISHED 3 bedroom, 3 bathroom condo with a 1 car garage.This modern condo, has approx. 2500sq ft of indoor and outdoor space, the interior boasts natural light with floor to ceiling windows and an open floor plan that intensifies the spacious open-air lifestyle desired on Maui. The kitchen is designed for entertaining and includes

    161 Holomoana Way, Kihei, HI 96753
  • /29

    $2,595 Per Month

    • 2 Beds
    • 1 Bath
    • South Maui 2 Bedroom / 1 Bathroom Unfurnished downstairs unit - Almost all Utiilities included! ...

    2709 Kauhale St, Kihei, HI 96753

    This unfurnished 2 bedroom/ 1 bathroom downstairs unit is located in S. Kihei very close to Wailea. This unit has a flexible floor plan with options on the layout-it could be a 2 bedroom with a small living/dining room or it could be a 1 bedroom using the primary/second room as a big living room/office opening up to the lanai etc. New dusk cherry luxury vinyl planking recently installed

    2709 Kauhale St, Kihei, HI 96753
  • /28

    $2,740 Per Month

    • 2 Beds
    • 1 Bath
    • 625 Sq Ft
    • 2 bed/1 bath Unfurnished condo in Pet Friendly Keonekai Villages

    160 Keonekai Rd, Kihei, HI 96753

    2 bedroom, 1 bathroom, 2nd floor, unfurnished & pet friendly condo at Keonekai Villages. This unit comes with 2 designated parking spots, newer luxury vinyl plank flooring and a fresh coat of paint throughout. Close proximity to beaches, dinning, shopping, schools and a dog park. There is no washer or dryer in the unit, although there is a washer/dryer in the building across from the

    160 Keonekai Rd, Kihei, HI 96753
  • /26

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 719 Sq Ft
    • Mostly furnished upstairs 2 bed., 2 full bathroom Kihei Shores condo

    2747 S Kihei Rd Unit H207, Kihei, HI 96753

    Two (2) full bathrooms in this mostly furnished unit.Granite counter tops in kitchenTwo barstool chairs at serving counter.Washer and Dryer in unit for your convenience.Air conditioner.Dining table w/4chairsCeiling fans with lighting.Tile and carpeted floors.Complex supplies pest control spraying quarterly both inside and out.One designated parking space and

    2747 S Kihei Rd Unit H207, Kihei, HI 96753
  • /23

    $3,650 Per Month

    • 2 Beds
    • 2 Baths
    • 949 Sq Ft
    • Wailea Fairway Villas 2 bedroom 2 bath furnished upstairs unit

    3950 Kalai Waa St, Wailea-Makena, HI 96753

    Wailea Fairway Villas - 2 bedroom 2 bath nicely furnished upstairs unit. This property is located on the Wailea Blue Golf Course and has a pool, Jacuzzi, barbecue and gym. Close to beautiful beaches, great shopping and restaurants. Washer and dryer in unit, dishwasher, split AC system.Two parking stalls - one assigned, one unassigned. Rent - $3,650/mo. plus GET

    3950 Kalai Waa St, Wailea-Makena, HI 96753
  • /16

    $2,750 Per Month

    • 2 Beds
    • 2 Baths
    • 728 Sq Ft
    • Townhouse for Rent

    2747 S Kihei Rd, Kihei, HI 96753

    Lovely fully furnished two-bedroom, two-bathroom ground-floor unit in Kihei Shores, set in a peaceful garden setting. This well-maintained condo is a joy to view and offers comfortable island living just across the street from the popular Kamaole III Beach Park. Kihei Shores also features a community pool and hot tub, making it an ideal place to relax and enjoy the Maui

    2747 S Kihei Rd, Kihei, HI 96753
  • /31

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 949 Sq Ft
    • Townhouse for Rent

    3950 Kalai Waa St, Wailea-Makena, HI 96753

    Ground floor golf course living at it's best at the Wailea Fairway Villas. This single level, no stairs 2 bedroom 2 bath is fully furnished and is perfectly located within walking distance to the Wailea Blue Golf Course and the Shops at Wailea.Enjoy the serenity and peace Maui has to offer in style. The unit includes an in unit washer/dryer and 2 large bedrooms with lots of storage

    3950 Kalai Waa St, Wailea-Makena, HI 96753
  • /29

    $5,950 Per Month

    • 3 Beds
    • 3 Baths
    • 1,568 Sq Ft
    • Wailea Fairway Villas Townhome With Ocean, Golf Course and Mountain Views

    3950 Kalai Waa St Unit V-101, Kihei, HI 96753

    Enjoy spectacular panoramic ocean, golf course, and Haleakala views from this Wailea Fairway Villas finely furnished 3-bedroom, 3-bathroom townhome in beautiful Wailea. This spacious end unit features a naturally bright and breezy open floor plan, vaulted ceilings and a well thought out kitchen design, with ample storage and high-end appliances. This 2-story unit is the complete package, with no

    3950 Kalai Waa St Unit V-101, Kihei, HI 96753
  • /33

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 750 Sq Ft
    • Keonekai Villages upstairs 2 bedroom, 1.5 bathroom unit, with 2 parking spaces

    160 Keonekai Rd Unit 25-202, Kihei, HI 96753

    Renovated and furnished 2BR, 1.5BA Unfurnished top floor unit with A/C, washer/dryer in unit, lighted ceiling fans, security screen door, granite counter tops, tile and wood floors and newer appliances. 2 Assigned tandem parking spaces, one covered and one uncovered. Very nice Haleakala views from your private top story lanai. Water, sewer, basic cable, internet & standard trash removal

    160 Keonekai Rd Unit 25-202, Kihei, HI 96753
  • /39

    $6,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft
    • Luxury Wailea Retreat in La’i Loa Villas

    36 Kai Malu Dr, Kihei, HI 96753

    Luxury resort-style living at La’i Loa Villas in Wailea. This brand-new, stunning 2-bedroom, 2-bathroom condo is located in a boutique building and offers 1,375 sq. ft. of beautifully designed interior space. A dramatic sliding glass door creates effortless indoor-outdoor living and opens to a generous 350 sq. ft. lanai with an outdoor wet bar and built-in BBQ, perfect for entertaining while

    36 Kai Malu Dr, Kihei, HI 96753
  • /44

    $4,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Single-family home with upstairs & downstairs rentals

    2641 Moolio Place Unit A, Kihei, HI 96753

    Single-family home with upstairs (unit A) & downstairs (unit B) rentalsUnit A. Fully Furnished 3BR/2BA Upstairs Home with Ocean & Mountain Views-Base rent: $4,800/month-Security deposit: $4,800Unit B. 1BR/1BA Ohana with Private Lanai and Backyard Views-Base rent: $2,500/month-Security deposit: $2,500

    2641 Moolio Place Unit A, Kihei, HI 96753
  • /24

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Keala O Wailea, Wailea Gateway

    71 Wailea Gateway Place, Kihei, HI 96753

    Welcome to Keala O Wailea, one of Wailea’s most desirable gated condominium communities, offering a refined blend of modern design, convenience, and island luxury. Completed in 2018, this beautifully maintained ground-floor residence features 2 bedrooms and 2 bathrooms, with approximately 1,200 square feet of interior living space plus an additional covered lanai of about 200 square

    71 Wailea Gateway Place, Kihei, HI 96753
  • /52

    $11,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,742 Sq Ft
    • Wailea's newest development, La'i Loa, 3 bedroom / 3 bathroom Furnished & Fabulous - Fall/Winter ...

    30 Kai Malu Dr Unit 101, Kihei, HI 96753

    Introducing a rare opportunity at Wailea's newest development, La'i Loa. A serene brand new 3 bedroom / 3 bathroom retreat embracing island elegance with modern grace. The expansive sliding window wall in the great room offers generous indoor outdoor living with mesmerizing views from the ocean-facing lanai. This conveniently located villa offers everything you need for a gratifying lifestyle at

    30 Kai Malu Dr Unit 101, Kihei, HI 96753
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