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.

  • Affordable Luxury, Great Location, Beach Across Street, *Free calls to Canada*

    Aloha! Welcome to our little piece of paradise. We are happy to share with you our beautiful, clean and well equipped condo with a modern kitchen, including stainless steel appliances, granite counter tops, back splash and honey maple cabinets....

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    95 USD - 170 USD

    nightly

    665 USD - 1,190 USD

    weekly

  • Kamaole Sands #5103 Private 1 Bd 2 Bath Condo Inner Court Sleeps 4

    Kamaole Sands is the premiere property in South Kihei. It is located across the street from Kamaole Beach III. Have a picnic, whale watch, swim, snorkel, stand-up paddle board, walk miles on the beach and watch the most amazing sunsets imaginable...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    693 USD - 1,323 USD

    weekly

    99 USD - 189 USD

    nightly

    2,970 USD - 4,920 USD

    monthly

  • Kamaole Sands #8102 Gorgeous private 1 Bd 2 Bath with great rates!

    Kamaole Sands is the premiere property in South Kihei. It is located across the street from Kamaole Beach III. Whale watch, swim and snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush tropic...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    693 USD - 1,323 USD

    weekly

    99 USD - 189 USD

    nightly

    2,970 USD - 4,920 USD

    monthly

  • Kamaole III Beach Condo - From $110 nt - Views - Inner Court location

    **************************************** == - $110 NIGHT SPECIAL ** $110 per night Aug 4 - Sept 30th **************************************** Your second floor condo in building 1, unit #1-204 in Kamaole Sands resort is on the INNER COURTYARD w...

    1 Bedrooms, 2 Bathrooms, Sleeps 3

    HI>Kihei

    110 USD - 170 USD

    nightly

    910 USD - 1,190 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

  • Delightful, Cheerful, Bright And Perfect Studio Surrounded By Tropical Birds!!

    The songs of Lovebirds, Doves, Java Sparrows and Finches will get your days on Maui off to a cheerful start as you awaken to the divine sunrise and the scent of fresh ocean air! We offer a gorgeous and newly renovated studio, with lots of windows...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    132 USD - 132 USD

    nightly

    924 USD - 924 USD

    weekly

    4,000 USD - 4,000 USD

    monthly

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

    DECEMBER SPECIAL: ONE WEEK LEFT, DEC. 3RD TO THE 11TH. CONTACT THE MANAGER FOR A DISCOUNTED RATE. 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 ...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kihei

    135 USD - 180 USD

    nightly

    950 USD - 950 USD

    weekly

  • #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

  • 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

  • BEST VALUE!! - DIRECT Ocean & Sunsets Views - Best Beach Access

    Haleakala Shores A102 PRIME LOCATION: clean, bright, comfortable and cozy!!.. "your second home on Maui"... spacious open floor plan.. perfect for couples, singles, family's, retirees and of course "world travelers".. with easy access and conveni...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI> Maui

    140 USD - 329 USD

    nightly

    1,323 USD - 2,303 USD

    weekly

    4,200 USD - 7,650 USD

    monthly

  • Romantic 1 BR Condo-MAJOR REMODEL, JULY, 2014, New living/dining area furniture

    Relax, enjoy the gentle breeze, take a deep breath and enjoy the birds, flowers and scents of Maui that surround you. Our quiet location is surrounded by the Wailea Old Blue Golf Course & adjacent to the Wailea Tennis Club & Wailea Town Center; m...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Wailea-Makena

    140 USD - 200 USD

    nightly

    1,400 USD - 1,400 USD

    weekly

  • Oceanview, Beach Across St, Newly Decorated, Favorite Bldg 10 - GREAT RATES!

    Your PERFECT MAUI GETAWAY is ACROSS THE STREET FROM ONE OF THE BEST BEACHES ON MAUI in the most requested Building #10 on the second floor, with the BEST VIEWS in Kamaole Sands. You can enjoy ROMANTIC MAUI SUNSETS from the PRIVACY of the EXTRA LAR...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    140 USD - 230 USD

    nightly

    980 USD - 1,610 USD

    weekly

    4,200 USD - 6,900 USD

    monthly

  • 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

  • Ocean View, Tropical Garden End Unit, NEW Air Conditioning Walk to Keawakapu Bch

    Attention: Beach Lovers! Our condo is in the best location in Sunny South Kihei, bordering Wailea and across the street from the most beautiful beach on Maui...Keawakapu Beach. This unpretentious Maui complex has a wonderful Hawaiian feel with lu...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    145 USD - 190 USD

    nightly

    950 USD - 950 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • $149/nt Low Season Specials- Stylish Designer Condo- Lots of Extras!

    ***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 ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    149 USD - 299 USD

    nightly

    1,183 USD - 2,093 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

  • Palms at Wailea #1803 Large Private Lanai, Spacious, Great Location, Sleeps 4

    Palms at Wailea #1803 is ground floor 1 bedroom, 2 bath garden view unit with a/c in the bedroom only, a fully-equipped kitchen, washer & dryer, 2 flat screen TVs, DVD player, telephone, and wireless Internet. The bedroom features a California kin...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    1,050 USD - 2,093 USD

    weekly

    150 USD - 299 USD

    nightly

    5,250 USD - 8,070 USD

    monthly

  • 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

  • Family-friendly 2-bedroom condo with a beautiful ocean view!

    This family-friendly condo is comfortable, clean, and in a fantastic location on property. The owners take great care to provide a welcoming home for guests throughout the year. Installations such as new ceiling fans, plantation shutters, HD tele...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    945 USD - 2,380 USD

    weekly

    155 USD - 340 USD

    nightly

    4,500 USD - 8,250 USD

    monthly

  • Family Friendly Ground Floor 2-Bedroom - No stairs required!

    Ideal for families, this is a rare two-bedroom condo that does not require stairs. With both bedrooms on the same level, this condo is convenient for guests of all ages. It's location on property is ideal, with nearby access to the pool area, as ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    945 USD - 2,415 USD

    weekly

    155 USD - 345 USD

    nightly

    4,800 USD - 8,250 USD

    monthly

  • 25% off unbooked '16 nights, 1BR, 2 full ba. Updated, Corner Unit, Peek of Ocean

    We're offering 25% an unbooked nights in 2016, 3 night min. W41284112-01 On island owners. Either we or our property manager are here ensuring this unit is in perfect condition to welcome you to Maui. The condo has been recently updated with de...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    155 USD - 235 USD

    nightly

    6,300 USD - 6,300 USD

    monthly

  • Spectacular Haleakaala and ocean Views. $1100 per week special

    SPECIAL LOW SEASON RATE OF $1100 per week. BEGINNING 4/15/2017 TILL 12/15/2017. ALOHA to Maui Kamaole ('mow-ee ka-ma-'ol-ay)... Just two blocks from Wailea in the quiet south end of Maui. The low-rise 'building cluster' concept of Maui Kamaole le...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    157 USD - 300 USD

    nightly

    1,099 USD - 1,680 USD

    weekly

  • 5 Star Wailea Luxury @ Kihei Prices, Maui Kamaole, 2br/2ba, Ocean View, Sleeps 7

    Maui Kamaole's Most Gorgeous Luxury Condo Maui Kamaole, located in South Kihei & next to Wailea, is a tranquil, low-rise residential complex situated on 23 beautifully landscaped acres. There are two large swimming pools, tennis courts, Jacuzzi's...

    2 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kihei

    159 USD - 399 USD

    nightly

  • 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

    159 USD - 275 USD

    nightly

    1,253 USD - 1,925 USD

    weekly

  • Beautifully Renovated! Ocean View! Ground Level! Building 10! 100yds to Beach!

    Welcome to ‘Hughes Maui Condo’ – ground floor unit #113 of building 10 at the Kamaole Sands Resort. This is a beautifully renovated 1 bedroom condo with 2 full bathrooms and very nice furnishings throughout. Our condo is located on the walk-out f...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 239 USD

    nightly

    1,113 USD - 1,673 USD

    weekly

  • Summer Value Season Dates Available

    Welcome to our Maui Getaway at Maui Kamaole. We are delighted to offer you accommodations at our home in paradise. Maui Kamaole is one of Maui’s premium condo locations in South Kihei. The complex is a 2 story complex located in a beautifully ma...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    160 USD - 235 USD

    nightly

    945 USD - 1,645 USD

    weekly

  • By top Maui sandy beaches your beautiful, well supplied, comfy 2/2 condo awaits

    Fantastic condo at best South Maui location with access to all the vacation amenities one can wish for! Pools, tennis courts, BBQ / picnic areas and walking distance to restaurants, stores and more. Steps away from the golden sandy beach of Kamaol...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    165 USD - 269 USD

    nightly

    1,813 USD - 1,813 USD

    weekly

  • Beautiful & Spacious 2BR Condo - Very Quiet

    The Maui Kamaole is a luxurious low-rise, townhouse-style complex on 23 tropical acres set on a hill overlooking the ocean. The property has two beautiful swimming pools. The pool closest to our unit is set in a tropical garden with a waterfall a...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    165 USD - 343 USD

    nightly

    1,100 USD - 2,400 USD

    weekly

    3,900 USD - 7,800 USD

    monthly

  • Upgraded 2 BR Single Level - and Kamaole Beach 3

    Single Level 2 bedroom - No loft (Rare find), - unit #9-105 Two Bedrooms - Two Bathrooms Owners Hawaii Tax ID W44615546-01 see owner Availability Calendar on the owners web site (link is below just above photos) See LINK to owners web site belo...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    170 USD - 279 USD

    nightly

    1,330 USD - 1,533 USD

    weekly

  • Private studio apartment overlooking the ocean and neighboring islands

    On the beach, most popular end unit on the ocean. Overlooks Lanai and West Maui Mountains. Mini frig, microwave, coffee maker, iron, hair dryer, flat screen TV with BluRay. Large picture window with no walkway for added privacy. Bistro style d...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    170 USD - 200 USD

    nightly

    1,190 USD - 1,400 USD

    weekly

    5,100 USD - 6,000 USD

    monthly

  • UP TO 20% OFF!! Beautiful 2-Bedroom Condo across from Kamaole Beach 3

    This condominium resort (Kamaole Sands) sits on 15 acres of beautifully manicured grass, tropical flowers, and ponds with fountains and waterfalls. There are two heated pools, hot tubs, a game room, workout room, and four tennis courts all spread ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    171 USD - 326 USD

    nightly

    2,054 USD - 2,054 USD

    weekly

  • Wailea serenity -1B - serene paradise near golf, beaches, & tennis

    This Grand Champions condo (#15 in building #2) is located in the heart of beautiful Wailea, a short walk to the beach, and in the middle of the renowned Old Blue Golf Course. South Maui, with the best weather in the world, is the ideal location ...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kihei

    175 USD - 275 USD

    nightly

    1,120 USD - 1,925 USD

    weekly

    4,500 USD - 6,900 USD

    monthly

  • Wailea Ekolu Oceanview 2B/2B Groundfloor - Relax on the Lanai

    ENJOY THE BEAUTIFUL MAUI SUNSET! Sharon's spacious, 1,300 square foot Wailea Ekolu condominium is a two bedroom, two bath, ocean view unit. Located on the ground floor, it is surrounded by grass and lush island foliage. The condo accommodates f...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Wailea

    175 USD - 255 USD

    nightly

    1,225 USD - 1,785 USD

    weekly

    4,725 USD - 6,885 USD

    monthly

  • 60' To The Water. Spectacular Oceanfront Condo At Keawakapu Beach

    Spectacular Oceanfront Condo Between Keawakapu & Kamaole Iii Beaches - Sleeps 4. Our Gorgeous Newly Remodeled 1br/1ba Kihei Surfside Resort condo is on the 3rd floor and has spectacular oceanfront views. It has a King bed in the bedroom and a Qu...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    179 USD - 329 USD

    nightly

  • CHRISTMAS WEEK 2016 SPECIAL! 7 NIGHTS FOR $1899 OCEANVIEW 1 BR/ 2 Ba

    * TERMS OF CHRISTMAS WEEK 2016 DEAL DEAL BELOW* My beautiful condominium is located in South Maui, on the Wailea/Kihei border. The area is populated with beautiful luxury resorts, shopping, restaurants, golf and beaches. My condominium is direct...

    1 Bedrooms, 2 Bathrooms, Sleeps 2

    HI>Kihei

    179 USD - 299 USD

    nightly

    1,813 USD - 1,899 USD

    weekly

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