Wailea Vacation Rentals

Wailea is a luxurious resort community located in the base of Mt. Haleakala on the south shore of the island. Here you will find several great white-sand beaches, including Wailea Beach, which was named “America’s Best Beach” by “Dr. Beach” in 1999. Wailea is also one of the world’s best golf destinations featuring three championship golf courses with breathtaking ocean views from every hole. So if you like to play golf, you will find Wailea a true paradise. There is a large selection of vacation rentals in Wailea, everything from condos to upscale villas. So start planning your Maui vacation today and find your perfect Wailea vacation rental below.

  • Specials From $79/nt! Maui Banyan Upscale Remodeled Studio Steps To Beach, Shops

    $79/NT August 15- October 15, 2017 *Specific arrival/departure date requirements may apply. ***Please do NOT use the "REQUEST TO BOOK" button without first inquiring via phone or email for availability/rate quote for your specific arrival and dep...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    79 USD - 149 USD

    nightly

    553 USD - 1,043 USD

    weekly

  • Totally Remodeled Maui Banyan - Gorgeous 1 or 2BR with High Ceilings and Extras!

    September Special: $99/nt 1-bedroom September 1- October 15, 2017 *We have 2 similar units at the Maui Banyan, our other unit, Q407, is VRBO #903526, the last 6 photos below are of the Q407 unit ***Please do NOT use the "REQUEST TO BOOK" button ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    99 USD - 199 USD

    nightly

    693 USD - 1,393 USD

    weekly

  • EASTER SPECIAL - $115/night + tax & cleaning - see details below

    This condo is located in a complex noted for its quiet, off-street, central location in beautiful Wailea. EASTER/APRIL/EARLY MAY AVAILABILITY: Arrive April 12th, depart any time in April!! $115/night plus tax (13.416%) and $70 cleaning. Extend...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    99 USD - 125 USD

    nightly

    805 USD - 805 USD

    weekly

  • Maui Banyan Remodeled Top Floor Unit Steps To Beach, Shops

    Low season specials for stays of 14 nights or more, or stays that completely fill gaps of 10 nights or more between existing bookings ***Please do NOT use the "REQUEST TO BOOK" button without first inquiring via phone or email for availability/ra...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    109 USD - 225 USD

    nightly

    763 USD - 1,323 USD

    weekly

  • Kam III Beach Condo - Kam Sands 1-204 -Views - Inner Court

    *************************************************** == - $110 NIGHT SPECIAL ** $110 per night June 15 - Sept 30th **************************************** Your second floor condo in building 1, unit #1-204 in Kamaole Sands resort is on the INN...

    1 Bedrooms, 2 Bathrooms, Sleeps 3

    HI>Kihei

    110 USD - 180 USD

    nightly

    910 USD - 910 USD

    weekly

  • Maui Ocean View Cottage in Tropical Surroundings

    Watch the sun set over the island of Lanai from your Maui lanai (porch). Whales, waves, and palm trees are also part of your view. Cottage has open-beam ceiling, tile floors throughout, and French doors making this cottage unique and charming. Fu...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    120 USD - 120 USD

    nightly

    770 USD - 770 USD

    weekly

  • Kamaole Sands 6-107 - Comfortable Ground Floor Condo, Inner Courtyard Near Swimming Pool

    Located in the #6 building, this inner courtyard ground floor condo affords guests quick and convenient access to the beautifully manicured gardens and popular swimming pool at the Kamaole Sands resort. Fully-stocked with all of the necessary coo...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Maui

    994 USD - 3,171 USD

    weekly

    120 USD - 396 USD

    nightly

  • GREAT RATES IN SOUTH KIHEI, Kamaole Beach, Newly redecorated and new furniture

    The Maui Banyan is one of the newest condominium complexes in Kihei. Our condo is located across the street from Kamaole Beach Park II, which has been awarded one of Maui's best white sand beaches. We take great pride in our home away from hom...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>kihei

    125 USD - 160 USD

    nightly

    875 USD - 1,120 USD

    weekly

    3,750 USD - 4,800 USD

    monthly

  • Haleakala Shores B-407 - 4th Floor Ocean View

    This Haleakala Shores 2-Bedroom condo is perfect for small families or two couples. The floor plan is open and spacious, and wall-to-wall windows give this condo bright light and gorgeous views. This condo has recently had all new hard-surface co...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Maui

    1,099 USD - 3,481 USD

    weekly

    130 USD - 432 USD

    nightly

  • Maui Banyan H-502 - Remodeled 1B/2Ba Condo with an Ocean View, Pool, and Nearby Beach

    This corner unit in the H building is sure to impress with it's extended balcony and outstanding view. Major renovations throughout the home, including beautiful stone tile flooring, crown molding, a brand new stunning kitchen, and updated and com...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    1,062 USD - 3,443 USD

    weekly

    130 USD - 432 USD

    nightly

  • Lovely Appointed Studio With Ocean & Mountain Views - Location, Best In Kihei

    Our lovely appointed and fully stocked studio boasts one of the best locations at The Banyan and in Kihei. It has ocean and mountain views from the lanai and is just a 3 minute walk to the famous Kamaoli Beach Park II. The small kitchenette ha...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kihei

    135 USD - 180 USD

    nightly

    950 USD - 950 USD

    weekly

  • Gorgeous Remodeled Kamaole Sands Ground Floor Unit

    Aloha! Welcome to our Kamaole Sands condo just across the street from Kamaole Beach Park III! Our condo is a very quiet, private, and newly remodeled ground floor unit with an extra large lanai that promises to make your Maui vacation one to rem...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    135 USD - 185 USD

    nightly

    1,295 USD - 1,295 USD

    weekly

  • First Class Renovation, Ocean View, Private Large Lanai on Maui. Kamaole Sands.

    Congratulations! You've discovered Kamaole Sands, the best holiday complex in Maui. Now you have found one of the best units in the complex! Top 10 Reasons Why this Unit Is For You: 1. Large Lanai-Far fewer than half the units in Kam Sands have...

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Kihei

    135 USD - 225 USD

    nightly

    1,575 USD - 1,575 USD

    weekly

  • Maui Beach Gem for 2! Inner Courtyard! 100 Yards from Kamaole 3 Beach, Kihei!

    “Boone 5 Condo” (Unit 6-202) is a superior 1-bedroom, 2-bath condo located in the Kamaole Sands complex at 2695 S. Kihei Rd, Kihei, Maui. Kamaole 3 Beach, one of the top rated beaches in Maui and all of Hawaii, is about 100 yards from the complex....

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Kihei

    139 USD - 219 USD

    nightly

    973 USD - 1,323 USD

    weekly

  • Maui Retreat,Completely Remodeled, 50 Ft Window Views Ocean/Mountain!!

    OCEAN/MOUNTAIN VIEWS - FULLY REMODELED Relax in comfort & enjoy all of Maui's activities using this remodeled bright & open floor plan 2 bedroom/2 bath, spacious condominium as your Maui retreat. Enjoy the expansive 50 ft window views which incl...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    140 USD - 240 USD

    nightly

    945 USD - 1,680 USD

    weekly

    3,900 USD - 5,400 USD

    monthly

  • Freshly Remodeled 1 BR/2 Bath Garden View Condo - Private And "beach Close"

    If you are looking for a condo rental that is high density and busy with many come-and-go travelers, then this complex might not be for you! Maui Kamaole is one of the newest complexes in South Kihei. Private and luxurious, this 23 acre property ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    145 USD - 265 USD

    nightly

    870 USD - 1,800 USD

    weekly

    3,850 USD - 3,850 USD

    monthly

  • Incredible Ocean View, Most Sought After Unit in Complex.

    This condo is in one of the most desirable locations in the complex. A full ocean view is available from almost anywhere inside the condo with a great lanai to sit and watch the whales jump. The upper pool and BBQ area are only steps from your g...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    145 USD - 235 USD

    nightly

    1,015 USD - 1,505 USD

    weekly

  • Kamaole Sands 5-211-Garden Area Pool and Sunset Views-Quiet Location

    Kamaole Sands Resort in South Maui, (A/C in BR and LR, Non-Smoking, Free WiFi Internet), Preferred Quiet Inner Courtyard not Outer Building, Large 818 sq. ft. plus outside lanai/patio on 2nd Floor with views of the Gardens, Pool and some Ocean/Sun...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    149 USD - 229 USD

    nightly

    1,603 USD - 1,603 USD

    weekly

  • Maui Kamaole A-110 - Outstanding Lanai Ocean View

    This 1-bedroom condo features a panoramic ocean view from the spacious lanai. Lovely furnishings and new updates and renovations make this one-bedroom condo the perfect spot for your Maui vacation. New carpet, entryway tile, and bedroom furniture...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Maui

    1,214 USD - 3,936 USD

    weekly

    150 USD - 495 USD

    nightly

  • Peaceful, Garden Walkout!!!

    Our bright and airy garden unit awaits you! This large, well-maintained 1 bedroom, 2 bathroom unit is fully furnished to meet all your needs and ensure your comfort. The kitchen is well-equipped including many nonstandard items such as, a rice c...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    155 USD - 250 USD

    nightly

    1,050 USD - 1,750 USD

    weekly

  • Popular Kamole Sands Quite One bedroom Avail 3/5-3/11 & 3/29-4/05 -Discounted

    One bedroom two bath remodeled kitchen and bathrooms. Nice Hawaiian/Island Décor. Lanai looks out to the beautiful tropical grounds. Close to pool, spa and exercise room. The ideal property with complete amenities makes Kamaole Sands the ideal pro...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 229 USD

    nightly

    1,323 USD - 1,603 USD

    weekly

  • Wailea Luxury - Quiet Privacy In Paradise - Best Resort - Walk to the Beach

    Hawaii Tax ID: W68471345-01 QUIET PRIVACY IN PARADISE The Palms #901 is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations on the property. Often the only sound you wil...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 379 USD

    nightly

    1,883 USD - 1,883 USD

    weekly

  • 2 BR /1 BR/STUDIO- T110 - PRIVATE, QUIET GROUND FLOOR END UNIT

    Aloha! **SPECIAL LOWER THAN OFF SEASON RATES FOR OCTOBER AND NOVEMBER** The Maui Banyan is sandwiched between Kamaole Beach I and II in sunny South Kihei. The island of Maui is best known for its beautiful selection of beaches and diversity. ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    159 USD - 319 USD

    nightly

    1,400 USD - 1,750 USD

    weekly

  • Complelely Remodeled Condo - Amazing Golf Course/Ocean Views - Wailea Luxury

    Hawaii Tax ID: W68471345-01 COMPLETELY REMODELED - GOLF COURSE & OCEAN VIEWS Grand Champions #168 is a impeccably kept one-bedroom two-bath luxury villa with amazing golf course and limited ocean views. The unit is located on the 7th fairway of...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 369 USD

    nightly

    1,743 USD - 1,743 USD

    weekly

  • Maui Kamaole 1B/2B, Great South Kihei Location, Sleeps 4

    Sleeps 4! Brand New furnishings! Kamaole Beach Park III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppe...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    1,113 USD - 2,990 USD

    weekly

    159 USD - 427 USD

    nightly

    4,770 USD - 7,470 USD

    monthly

  • Gorgeous , Great Ocean View, super clean, Summer specail $1050 + tax + ck in

    Aloha from Kihei. We would like to welcome you to a 'home-away-from-home' in our beautifully decorated condominium, unit 4-407 ( building 4, fourth floor) at Kamaole Sands. This is a 2 bedroom, 2 bath, 1188 sq. ft. condo with 30 foot high ceilin...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    160 USD - 250 USD

    nightly

    1,120 USD - 1,750 USD

    weekly

    4,000 USD - 5,700 USD

    monthly

  • Recent Remodel, Great Calif King Bed, Ocean/Mountain/Garden/ Views

    ALOHA! WELCOME TO OUR BEAUTIFUL, FULLY RENOVATED VACATION CONDO. SCROLL DOWN FOR ADDITIONAL PICTURES. Ekahi is ideally located in beautiful Wailea, with some of Maui’s best beaches, situated between affordable shopping and dining in Kihei, and w...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    162 USD - 355 USD

    nightly

    1,134 USD - 2,485 USD

    weekly

    7,050 USD - 7,050 USD

    monthly

  • BRAND NEW, OCEAN VIEW, LARGE LANAI, 120 yards to Beach

    ***SEND EMAIL FOR DETAILED QUOTE - USE THE BLUE BUTTON "Send email" *** *BRAND NEW LUXURIOUS 1040 SqFt 1bedroom 'Coral Suite' bld. 3, Unit 302 *PREMIUM LARGE LANAI *FULLY EQUIPPED *KING SIZE BED (Egyptian Cotton 650/t), (Bedroom is super quiet) ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    165 USD - 305 USD

    nightly

    1,155 USD - 1,995 USD

    weekly

  • Pride of Ownership 1 Bdrm, Upscale Furnishings, Ground Floor

    Relax, enjoy the gentle breeze, birds, tropical flowers and scents of Maui that surround you. Welcome to our newly renovated ground floor condo with a tropical garden view. We strive to create an ambiance that is welcoming and relaxing. Our Tommy...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kihei

    165 USD - 230 USD

    nightly

    1,610 USD - 1,610 USD

    weekly

  • Beautifully Landscaped Grounds with 2 Pools, Internet,Air Conditioning

    Surrounded by beautifully landscaped grounds, Hale Kamaole Resort is a great option for your Maui vacation. Walk to Kihei's Kamaole Beach Park III across the street and return to the condo complex for a dip in one of the two pools followed by a ho...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    168 USD - 247 USD

    nightly

  • Beautifully renovated condo #405, stunning ocean view. Locally owned/managed

    Hawaii tax ID GE/TA-064-787-608-01 Our elegant fourth-floor condo affords you all the conveniences of home, with all the sun and fun of Hawaii right outside your door! Book easy, breathe easy: Unlike most owners at Kihei Surfside, our family liv...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    169 USD - 349 USD

    nightly

    1,183 USD - 2,303 USD

    weekly

    9,870 USD - 9,870 USD

    monthly

  • Maui Banyan B-204 - Renovated Two-Bedroom Condo Near Front of Property.

    Step into this beautifully renovated two-bedroom condo, and let our home be your home. In the front "B" building on property, this Maui Banyan condo is popular for small families looking to be in the heart of South Kihei, nearby grocery,...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Maui

    1,372 USD - 4,978 USD

    weekly

    170 USD - 630 USD

    nightly

  • May dates available! Top floor corner unit w/beach toys & partial ocean views!

    Do you or your family need a vacation? Looking for paradise? Why not spend your vacation in our clean and comfortable 2-bedroom, 2-bath, partial ocean-view condo at the Maui Banyan condos in Kihei!?! This 2-bedroom floor plan is spacious with abou...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    171 USD - 322 USD

    nightly

    1,195 USD - 2,255 USD

    weekly

  • SPECIAL RATES! - On The Wailea Blue Golf Course! Fairway And Pool View!

    Grand Champion Villas sit on the Wailea Blue golf course. Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive W...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    179 USD - 215 USD

    nightly

    1,250 USD - 1,250 USD

    weekly

  • Spring/Summer $199 Fabulous Ocean View, Fully Remodeled, Private And Quiet

    Wailea Ekahi Unit 30C is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui! Ekahi #30C has a lovely ocean view and an beautiful and private lanai to view it from. Like our other units, #39...

    1 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Wailea

    180 USD - 375 USD

    nightly

    2,625 USD - 2,625 USD

    weekly

1