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.

  • 2 Bedroom 2 Bath Condo Close to Beach and Pool with Spa

    Recently remodeled condo in sunny south Maui. Located across the street from a glorious white sand beach at Kam III, Ideally located back from Kihei road to provide you a quiet retreat. Shopping and restaurants are just a block and a half away....

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    83 USD - 300 USD

    nightly

    1,700 USD - 1,700 USD

    weekly

    2,500 USD - 2,500 USD

    monthly

  • *SEPT SPECIAL $99/NT.* Beautiful Condo, Large Lanai! Paradise is waiting!

    Enjoy your Maui vacation in this recently updated, beautiful condo! Well-equipped kitchen has lovely new cabinets and granite counters. There is a queen sofa sleeper. King size bed in master bedroom. Quiet, state-of-the-art air-conditioner, only n...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    99 USD - 180 USD

    nightly

    870 USD - 1,100 USD

    weekly

    3,300 USD - 3,900 USD

    monthly

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

    ***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 departure dates. *Even if your dates show as available on our calendar, we are unable to accept ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    99 USD - 199 USD

    nightly

    693 USD - 1,323 USD

    weekly

  • Kamaole Sands Remodeled Ground Floor 1 Bedroom/2 Bath

    This unit (7-106) is a one-bedroom, two-bathroom condo on the ground floor of the Kamaole Sands complex in Kihei, Maui. At 818 feet, it is very spacious, easily accomodating four people. It has a private lanai which opens into a beautiful tropical...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    105 USD - 240 USD

    nightly

    1,680 USD - 1,680 USD

    weekly

    2,600 USD - 4,800 USD

    monthly

  • Beautiful Quiet Unit Steps From Maui's Finest Beaches

    Aloha from the beautiful valley isle! We are proud to share our little slice of paradise with you and your ohana. This unit is located directly across the street from Kamaole Beach park II. There are restaurants, shopping and endless activities wi...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    110 USD - 170 USD

    nightly

    700 USD - 1,100 USD

    weekly

    2,600 USD - 4,000 USD

    monthly

  • From $110 nt - Kam Sands / Inner Court / 3 min to Kamaole III Beach

    **************************************** == - $110 NIGHT SPECIAL ** $110 per night Aug 4 - Sept 30th **************************************** Our second floor condo #1-204 in Kamaole Sands resort is on the INNER COURTYARD with beautiful views....

    1 Bedrooms, 2 Bathrooms, Sleeps 3

    HI>Kihei

    110 USD - 170 USD

    nightly

    910 USD - 1,190 USD

    weekly

  • Super Kihei Location, Remodeled 1 BR 2 BA

    Well stocked kitchen with full size stainless appliances and quartz counters. New tile floors throughout. Body boards and beach chairs provided. Hair dryer, iron and ironing board, & safe. Tennis court. Two fully remodeled pool areas with, ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    119 USD - 289 USD

    nightly

    750 USD - 1,970 USD

    weekly

    2,900 USD - 7,500 USD

    monthly

  • From $119, Updated, A/C Throughout, King Bed, Large Lanai, Partial Ocean View

    Quiet, secure, third-floor unit number 305 in building 7 with a large lanai, newly and tastefully appointed throughout,centrally located within the resort complex with a marvelous view of the garden court yard and a peek-a-boo view of the ocean ma...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    119 USD - 199 USD

    nightly

    833 USD - 1,113 USD

    weekly

  • Memorable Maui Escape. Bright Sunny Condo Near Pool and Beach

    Our lovely condo will provide you with the perfect home away from home for your Maui vacation. As you sit on the lanai, amongst the swaying palm trees, you'll know you've picked the perfect vacation spot. This unit is on the second floor, at the b...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    125 USD - 205 USD

    nightly

    875 USD - 1,435 USD

    weekly

    3,000 USD - 3,000 USD

    monthly

  • Big Ocean View From Huge Lanai With An Affordable Price

    Located on the second floor with a great ocean view from the large lanai. The Master Bedroom has a king bed, television and has an attached 3/4 bath (shower). Second bedroom has 2 twin beds that can be made into a king bed. The hall bath has ...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    125 USD - 169 USD

    nightly

    1,043 USD - 1,183 USD

    weekly

  • $129 WAILEA SHORT OPENINGS: 1BD/1BA: SEP 19-21;OCT 4-6; OCT 27-31; NOV 10-15

    HI. TAX# W58284814-01 **LOVELY REMODELED KITCHEN - ELEGANT, TROPICAL-MODERN FURNISHINGS, NEW ISLAND DREAMS KING BED. $129/NT + $100 CLNG FEE + 13.42% TAX FOR ALL SHORT OPENINGS LISTED ABOVE. EVERYTHING ELSE IS BOOKED FOR THIS UNIT SEPT/OCT/NO...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    129 USD - 196 USD

    nightly

    1,295 USD - 1,295 USD

    weekly

  • Ocean View Studio With Breezy Gazebo!

    Surrounded by nature and delightful birds singing all day long, our studio is beautiful, clean and charming! The spacious lanai has a nice view of the ocean. Cool trade winds blow right through our little valley and the fantastic prayer/yoga gazeb...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    134 USD - 134 USD

    nightly

    908 USD - 908 USD

    weekly

    3,895 USD - 3,895 USD

    monthly

  • 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

  • ~BEAUTIFUL~ King Bed, large lanai, amazing sunsets! SPRING SPECIALS,Only til May

    You will not be disappointed by this 1 bedroom/1 bath condo. Providing a new King Bed in the bedroom with TV and A/C. The unit provides sofa sleeper in living area for extra sleeping arrangements, TV & A/C as well as a in unit washer/dryer. Ki...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    135 USD - 195 USD

    nightly

    805 USD - 1,225 USD

    weekly

    2,850 USD - 4,650 USD

    monthly

  • Wailea Beaches,Green Renovated Condo,Ocean/Lawn Views,A/c,also check out #509234

    We really accept most inquiries, but didn't book through VRBO. Now we must book through VRBO in order to get visibility on their site. To enjoy our GORGEOUS OCEAN VIEW, from our upscale, VERY GREEN, very sound proof, 2 Bedroom, 1 1/2 Bath Condo, ...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    139 USD - 275 USD

    nightly

    1,925 USD - 1,925 USD

    weekly

  • Building 3, ground floor, near pool.

    HI Tax # W12179586 Location, location, location. One bedroom, two bath, this condo is in the very desirable building three on the ground floor. No need to bother with elevators. The pool is a very short stroll from your lanai. Enjoy sipping your...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    139 USD - 239 USD

    nightly

    973 USD - 1,673 USD

    weekly

  • Wailea Beaches,Green Renovated Condo,Ocean/Lawn Views,A/c,also check out #402988

    BE one of the FIRST to enjoy our GORGEOUS OCEAN VIEW, from our NEWLY RENOVATED, NEWLY DECORATED, 2 Bedroom, 1 Bath Condo, just a 4 minute walk to the nicest Beach on Maui, Keawakapu! After renovating Honu Place VRBO Listing #402988, 2 years ago, w...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    139 USD - 275 USD

    nightly

    1,925 USD - 1,925 USD

    weekly

  • Maui Sunset. Oceanfront Condo ! from $110 Per Night..

    Nice updated 1 bedroom/2 bath ground floor units, which are air conditioned in both the living room and bedroom. Parking is very close by the unit. Swim in the beautiful pool and stroll around the grassy oceanfront grounds. Watch sunsets from th...

    1 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Kihei

    140 USD - 240 USD

    nightly

    980 USD - 1,680 USD

    weekly

    3,375 USD - 4,200 USD

    monthly

  • BRAND NEW Remodeled Beautiful 1 Bedroom Condo!

    *Take a look at our calendar for shorter openings in between reservations and contact us about special rates for them! Our freshly remodeled 3rd floor 1 bedroom, 1 bathroom unit is located in the T building, away from busy South Kihei Road and on...

    1 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kihei

    140 USD - 175 USD

    nightly

    1,225 USD - 1,225 USD

    weekly

  • TROPICAL MAUI!!! Visit this Summer and stay in Style...1b/2b Private Condo!!

    Maui Banyan complex and condo are located just a short walk to the Kamaole Beach Park II. This is one of South Maui's best Life Guarded Beaches. The unit is fully furnished with all the comforts of your own personal home. Also includes amenities...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    140 USD - 195 USD

    nightly

    840 USD - 1,225 USD

    weekly

    3,000 USD - 4,650 USD

    monthly

  • Very Large Ground Floor 1BR/2BA , Great Location Next to Wailea & Great Beaches

    Aloha! Your dream vacation starts with our beautiful new condo, located in Southwest Maui, in the town of Kihei. The Maui Kamaole complex borders on beautiful Wailea, known for excellent restaurants and world class shopping. The lush tropical gr...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    140 USD - 195 USD

    nightly

    1,155 USD - 1,365 USD

    weekly

    4,950 USD - 4,950 USD

    monthly

  • #1 Beautiful Kamaole Sands 1bedroom/2bath Condo

    Our one Bedroom, Two Bath, non-smoking condo has a great interior location in one of Kihei's best Resorts. Large pool, two Jacuzzis, right across from Kamaole III Beach Park, which has excellent swimming plus a large grassy picnicking area. The c...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    140 USD - 185 USD

    nightly

    910 USD - 1,155 USD

    weekly

    3,000 USD - 4,200 USD

    monthly

  • Fantastic And Unique Inner Court Location!!

    Since we live on Maui we supply lots of extras like beach chairs, umbrellas, coolers, beach toys and even some snorkel equipment. We also make sure that our condo is stocked with paper products, laundry soap, dishwasher detergent, condiments, spic...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    145 USD - 195 USD

    nightly

    1,365 USD - 1,365 USD

    weekly

  • 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 - 205 USD

    nightly

    1,015 USD - 1,330 USD

    weekly

  • 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

    150 USD - 245 USD

    nightly

    1,015 USD - 1,715 USD

    weekly

  • OCEAN VW 1B/1B Remodeled, KAMAOLE 3 BEACH CLOSE TO WAILEA

    Without a doubt this is one of the best locations in Hale Kamaole. This condo is new to the rental market and has undergone a remodel that will leave you wishing you could stay forever. The ground floor, walk out unit in the highly desirable buil...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    152 USD - 205 USD

    nightly

    1,435 USD - 1,435 USD

    weekly

  • Maui 'Toes In The Sand' Spectacular One Bedroom Oceanview Vacation Condo

    Aloha ! We would like to invite you to come and experience our special place in the sun. If youre looking for great ocean views to watch whales frolic in the ocean, or a beautiful beach to push your toes in the sand and enjoy the warm sunshine an...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    155 USD - 185 USD

    nightly

    1,295 USD - 1,295 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

  • Wailea Luxury - Walk To The Beach - Best Resort - Beautiful Garden/Ocean Views

    Hawaii Tax ID: W68471345-01 QUIET PRIVACY IN PARADISE - BEAUTIFUL GARDEN/OCEAN VIEWS The Palms #902 is a luxurious one-bedroom two-bath upstairs villa tucked away in a private and quiet corner in one of the nicest locations on the property. Th...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 379 USD

    nightly

    1,883 USD - 1,883 USD

    weekly

  • AIR CONDITIONED, GARDEN VIEW

    Our remodeled one bedroom two bathroom condo sits on the beautiful 15-acre Kamaole Sands Resort across from Kamaole Beach III. The condo has a master bedroom/bathroom, an additional full bathroom, a fully-equipped kitchen, a living room that conve...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 229 USD

    nightly

    1,323 USD - 1,603 USD

    weekly

  • Unbeatable Location On Kamaole Beach

    This third floor, perfectly located, inner courtyard condo in building 1 has a highly desirable single level floor plan. Situated at the end of the building, this unit offers increased privacy and views, with an extra window to watch the sunris...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    160 USD - 260 USD

    nightly

    1,020 USD - 1,720 USD

    weekly

    3,880 USD - 6,680 USD

    monthly

  • Beautiful Ocean/Golf Course View, Upgraded Mar/April Special

    BEAUTIFUL OCEAN VIEW , ON FAIRWAY. NEWLY UPGRADED & ELEGANTLY FURNISHED TOP FLOOR VILLA ! For those looking for a bit more luxury and elegance, this villa is for you. This is a beautifully furnished one bedroom, two bath unit with perhaps t...

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Wailea

    160 USD - 240 USD

    nightly

    1,120 USD - 1,680 USD

    weekly

  • Absolute Paradise! Enjoy Maui Kamaole at it's finest!

    We are the proud owners of a lovely condo in the M building, one of the newest and most private in the complex! This one bedroom, 2 full baths, air-conditioned, ground floor, garden view condo is in wonderful, like new condition, and of course,...

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Wailea-Makena

    160 USD - 260 USD

    nightly

    1,120 USD - 1,715 USD

    weekly

    4,500 USD - 7,285 USD

    monthly

  • Special Summer Rates! Golf Course Condo!

    NEW CARPET INSTALLED MAY 2016!!! REMODELED KITCHEN, MASTER BATHROOM AND GUEST BATHROOM HDTV's IN THE LIVING ROOM AND EACH BEDROOM. Aloha! Welcome to my beautiful 2 bedroom, 2 bath, condominium located in a serene setting overlooking the eig...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    165 USD - 285 USD

    nightly

    1,120 USD - 1,750 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • Haleakala Shores 2 bedroom, 2 bath condo - across the street from Kamaole Beach

    Haleakala Shores 2 bedroom, 2 bath condo - across the street from Kamaole Beach Park III . Features Queen size bed, 2 twin beds, a sofa sleeper in the living room, A/C and 3 TV's + complimentry High Speed Internet + wifi! Condo has just been remod...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    165 USD - 195 USD

    nightly

    1,365 USD - 1,365 USD

    weekly

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