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

  • 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 - 1,575 USD

    weekly

  • Upgraded condo - Kamaole III Beach Condo - Views - Inner Court location

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

    1 Bedrooms, 2 Bathrooms, Sleeps 3

    HI>Kihei

    110 USD - 180 USD

    nightly

    910 USD - 1,260 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

    2,500 USD - 7,500 USD

    monthly

  • 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

  • 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

  • LUXE AND SPACIOUS WAILEA STUDIO: NEXT OPENINGS APRIL

    HI. TAX ID# W58284814-01 ALSO HAVE A HIGH SEASON OPENING IN OUR OTHER LISTING #58293. ONE BEDROOM/ONE BATH LUXURY APARTMENT IN HEART OF WAILEA. PLEASE SEE OUR LISTING #58293 FOR THIS LAST MINUTE AVAILABLE IS: FEB 03-11, 8 NTS AND MAR 10-24, ...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    125 USD - 154 USD

    nightly

    875 USD - 1,078 USD

    weekly

  • Ocean View, Beautifully Renovated, 1 Bedroom Condo Across From Kamaole 3 Beach

    'One of the best second floor views.' Comfy condo has just been remodeled with beech wood cabinets in kitchen and bath as well as new walk in shower. Artistically designed with colorful tiles. Wood flooring in entrance and kitchen. Carpet in bedro...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    129 USD - 189 USD

    nightly

    1,323 USD - 1,323 USD

    weekly

  • Hale Kamaole #135 South Shore, Great Location, Great Rates, Sleeps 4

    Kamaole Beach #3 is just across the street from Hale Kamaole. This beach is one of the best beaches in the world. Whale watch, snorkel, walk the beach and witness the most amazing sunsets imaginable. Hale Kamaole features two pool areas, gas gril...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    903 USD - 1,990 USD

    weekly

    3,870 USD - 5,970 USD

    monthly

    129 USD - 284 USD

    nightly

  • 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

  • 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

  • Kamaole Sands #10-208 Oceanview, Great Rates, Fantastic Location, Sleeps 4

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

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    973 USD - 2,600 USD

    weekly

    4,170 USD - 5,970 USD

    monthly

    139 USD - 371 USD

    nightly

  • Very Private and Beautifully Renovated! from $140

    Free high speed wireless internet and unlimited long distance phone calls to US Mainland and Canada. Rent directly from on-island private owner - not a management company. Come enjoy the Maui sun and stay in our lovely, fully remodeled one-bedro...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    140 USD - 195 USD

    nightly

    980 USD - 1,365 USD

    weekly

  • 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

  • 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

    149 USD - 249 USD

    nightly

    975 USD - 975 USD

    weekly

    3,900 USD - 3,900 USD

    monthly

  • LUXURY WAILEA 1 BD/1 BA: NEXT OPEN $185/NT: APR 7-11; APR 18-MAY 2

    HI. TAX# W58284814-01 **LOVELY REMODELED KITCHEN - ELEGANT, TROPICAL-MODERN FURNISHINGS, NEW ISLAND DREAMS KING BED. APR 7-11 $185/NT + $100 CLNG FEE + TAX APR 18-30 " " " " " " AFTER APRIL 30 $175/NT...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    150 USD - 205 USD

    nightly

    1,295 USD - 1,435 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 - 1,645 USD

    weekly

  • Full Ocean Views, 2 Pools 2 Spas, 2 Bath, Large Master , Specials going on Now

    ** Whale Watching right in front of you. ** Located in South Kihei-Wailea area, across the street from beautiful Kamaole III beach and Keawakapu Beach. Maui Kamaole is an upscale low-rise condo complex on 23 acres. Beautifully Decorated with Vi...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    150 USD - 235 USD

    nightly

    1,295 USD - 1,645 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

  • 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 - 1,400 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

  • 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

    4,770 USD - 7,470 USD

    monthly

    159 USD - 427 USD

    nightly

  • Popular Kamole Sands Quite One bedroom

    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

  • 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

  • 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

  • *Great Inner-Courtyard - Ground Floor Location*

    Welcome to our clean and bright 1-bedroom/2-bathroom condo in one of the best condominium resorts in South Kihei. The unit located on the ground floor, overlooks a tropical garden, with a partial ocean view. We are walking distance to ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    170 USD - 225 USD

    nightly

    1,575 USD - 1,575 USD

    weekly

  • 2 Bed, 2 bath stunning ocean view, air conditioned, upgraded Kamaole Sands

    Kamaole Sands is an award-winning condo complex situated just across from one of the best beaches on Maui. Kamaole Sands III beach, is recognized as one of the best beaches in Maui. Boogie board, surf, snorkel straight off the beach. We have seen...

    2 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kihei

    170 USD - 345 USD

    nightly

    2,415 USD - 2,415 USD

    weekly

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

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property, lush with tropical landscaping. There i...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    1,225 USD - 2,990 USD

    weekly

    5,250 USD - 8,070 USD

    monthly

    175 USD - 427 USD

    nightly

  • Beautiful Front Row, Full Ocean View Condo

    Our luxurious fully remodeled, non-smoking, front-row condominium is furnished and decorated to meet your highest expectations. It offers spectacular panoramic views of popular Kamaole III Beach and the ocean and neighboring islands beyond. Watch ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    175 USD - 295 USD

    nightly

    2,065 USD - 2,065 USD

    weekly

  • Spectacular Haleakaala and ocean Views. $1250 per week special

    SPECIAL LOW SEASON RATE OF $1250 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

    178 USD - 300 USD

    nightly

    1,246 USD - 1,680 USD

    weekly

  • ** Maui Kamaole 1 Bedroom Front Row Private Ocean View **

    Maui Kamaole is on the border of Kihei and Wailea, making it easy to walk and drive to popular beaches, restaurants, and attractions in both beach towns. The property is set on a hill overlooking the ocean and consist of 23 beautifully landscaped ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    179 USD - 250 USD

    nightly

    1,750 USD - 1,750 USD

    weekly

  • Serene & Lovely, 2BR/2BA, Ocean View -BIG SUMMER/FALL DISCOUNTS!

    This exquisite Wailea hideaway is in the peaceful, perfectly manicured Wailea Ekolu Villages. It is downstairs, 1100 sf (plus lanais), 2 Bedroom, 2 Bath, complete with an open lanai that fronts the lush golf course greenway and a private lanai o...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    180 USD - 230 USD

    nightly

    1,260 USD - 1,600 USD

    weekly

    4,500 USD - 6,000 USD

    monthly

  • Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach

    Our COMPLETELY REMODELED CONDO (new pictures are now online) at the Maui Banyan is uniquely situated on the top floor of the much sought after G building which boasts the best location at The Banyan. It is just a few minutes walk to Kamaole II Be...

    2 Bedrooms, 2 Bathrooms, Sleeps 7

    HI>Kihei

    180 USD - 368 USD

    nightly

    1,190 USD - 2,575 USD

    weekly

    4,900 USD - 8,650 USD

    monthly

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