27

Wailea, HI Homes for Rent

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  • /20

    $3,500 Per Month

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

    2747 S Kihei Rd Unit A308, Kihei, HI 96753

    Property Id: 1844939 Beautifully remodeled and fully furnished 2BR/2BA condo in the heart of Kihei, Maui — perfect for traveling medical professionals. This spacious unit includes A/C, in-unit laundry, a fully stocked kitchen, and all utilities included. Relax on your private lanai with stunning ocean and sunset views. Just 1 block from Kamaole Beach Park III and walking distance to

    2747 S Kihei Rd Unit A308, Kihei, HI 96753
  • /9

    $3,650 Per Month

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

    3950 Kalai Waa St Unit 409951, 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 Unit 409951, Kihei, HI 96753
  • /45

    $6,961

    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 $6,962/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 16, 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
  • /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
  • /49

    $17,229

    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 $17,230/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 17, 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
  • /21

    $4,950 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
  • /37

    $7,108

    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 $7,109/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 7, 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
  • /11

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    3200 Wailea Alanui Dr, Kihei, HI 96753

    BY OWNER/AGENT: PALMS AT WAILEA #608 Beautifully upgraded and furnished B floor plan with laminate wood floors, granite countertops, brand new full size washer/dryer,, new dishwasher, full size refrigerator, new oven/microwave, resort style furnishings, new split AC system, large well furnished lanai, just steps to the very large pool and jacuzzi, BBQ's available to guests, free assigned parking

    Bruce Travis eXp Realty

    3200 Wailea Alanui Dr, Kihei, HI 96753
  • /31

    $11,524

    Total Monthly Price

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

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

    The advertised rate of $11,525/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 14, 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 ID1295779P, Wailea-Makena, HI 96753
  • /41

    $8,171

    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 $8,172/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 23, 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
  • /44

    $4,795

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • Condo for Rent

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

    The advertised rate of $4,796/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 10, 2027.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

    2575 S Kihei Rd Unit SI ID1237859P, Kihei, HI 96753
  • /33

    $9,625

    Total Monthly Price

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

    2575 S Kihei Rd Unit SI ID1295749P, Kihei, HI 96753

    The advertised rate of $9,626/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 22, 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 ID1295749P, Kihei, HI 96753
  • /49

    $12,496

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,076 Sq Ft
    • Condo for Rent

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

    The advertised rate of $12,497/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
  • /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
  • /37

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 949 Sq Ft
    • Furnished 2/2 Wailea Fair Villas Condo on the 11th Hole of the Wailea Blue Course

    3950 Kalai Waa St, Wailea-Makena, HI 96753

    Welcome to Wailea Fairway Villas unit Y102, 2-bedroom, 2-bathroom tastefully furnished condo remodeled (2022) with new carpet, new paint throughout, new furniture, new ceiling fans and newly polished and sealed travertine tiles and granite countertops. This complex sits on 12 acres of beautifully landscaped grounds, has a recreational area with a pool, jacuzzi, fitness room, kitchen and

    3950 Kalai Waa St, Wailea-Makena, HI 96753
  • /21

    $4,450 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Tropical oasis

    16 Hoohale St, Kihei, HI 96753

    Welcome to this charming 2 bedroom, 1 bathroom home located in the highly-desirable Kilohana Ridge neighborhood in Kihei, HI, with a world-class beach just steps away. This home can come partly furnished or unfurnished, your choice. This spacious downstairs area of the home features a large living room with hardwood and tile floors, perfect for relaxing in after a day at the beach. The private

    16 Hoohale St, Kihei, HI 96753
  • /44

    $4,800 Per Month

    • 2 Beds
    • 1 Bath
    • Newly Renovated Furnished 3BR/1BA Downstairs Unit with Pool Access in South Kihei

    2624 Moolio Place, Kihei, HI 96753

    Offered at $4,800/month + tax, this beautifully renovated and fully furnished downstairs 3-bedroom, 1-bath unit offers comfortable single-level living in highly desirable South Kihei, just minutes from beaches, shopping, and dining.The home features a brand-new modern kitchen with quartz countertops and an extended breakfast bar designed for casual seating and entertaining. All new

    2624 Moolio Place, 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
  • /14

    $3,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    825 Kumulani Dr, Kihei, HI 96753

    $3,950 / 2br - 1200ft2 - Maui Meadows 2nd floor 2 bed / 2 bath unit, w/ deck, view, & utilities825 kumulani, Kihei, HI 96753Gorgeous second floor 1200 square foot 2-bedroom, 2-bath unit with a large 340 square foot covered redwood deck, high ceilings, five closets, and an ocean view. The beautiful building is a pole house designed by the renowned Maui architect Frank Stiller.We

    825 Kumulani Dr, 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
  • /43

    $2,495 Per Month

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • 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

    $2,500 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

    Available now for 6mo. or 1 yr. lease. 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.

    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
  • /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
  • /80

    $8,200 Per Month

    • 2 Beds
    • 3 Baths
    • 2,032 Sq Ft
    • Beautiful Furnished, 2 Bed, 3 Bath, Gated Wailea Kai Home with Saltwater Pool and OceanView

    3150 Waiea Place, Kihei, HI 96753

    Discover the Epitome of Island Luxury in this Single-Level Home within a Secluded Gated Community in Wailea Kai.Welcome to 3150 Waiea Place a private home in highly desirable Wailea Kai neighborhood with spacious salt water lap pool. This single level home boasts many unique qualities rarely found in Wailea neighborhoods such as a gated driveway setback from the cul de sac for ultimate

    3150 Waiea Place, Kihei, HI 96753
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