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.

  • 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 - 1,890 USD

    weekly

    2,970 USD - 4,920 USD

    monthly

    99 USD - 270 USD

    nightly

  • Quiet, top Floor Fully loaded studio w/view across from beach ***DISCOUNTS AVAIL

    * Ask about special rates to fill calendar gaps. * tax includes 13.42% HI tax and 3.5% processing fee (3.5% processing fee can be avoided by by making the 2nd payment via check or money order in USD. Please ask prior to booking for more details) *...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kihei

    109 USD - 139 USD

    nightly

    973 USD - 973 USD

    weekly

  • Walk To The Beach, Across Kamaole III Beach Park, some ocean View from lanai

    The location of condo is super nice. Be at kamaole III beach in less than 5 minute walk and watch the sunset. It doesn't get super hot during the day and it cools off at night. You will wake up to the chirping of the birds in the morning and...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    119 USD - 199 USD

    nightly

    735 USD - 896 USD

    weekly

    2,850 USD - 3,450 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

  • 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

  • Up to 20% OFF this awesome 1 BR Ground Floor Condo at Hale Kamaole!!

    A warm aloha awaits you at Hale Kamaole. These spacious condominiums, set in beautifully landscaped grounds, are an ideal setting for a relaxing sun-soaked vacation. You can walk across the street to Kamaole Beach Park III, which is one of the mos...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    134 USD - 259 USD

    nightly

    1,813 USD - 1,813 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

  • 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

  • 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

  • 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

    145 USD - 220 USD

    nightly

    1,085 USD - 1,540 USD

    weekly

  • Spacious 1BR/2BA Condo Right Across From Kamaole Beach!

    Beautiful 1BR/2BA Condo at the Kamaole Sands in S. Kihei, just steps away from Kamaole Beach.. The condo is close to nightlife, shopping, dinning, public transport, the city center and beaches. You’ll love this condo because of the outdoors space,...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    145 USD - 250 USD

    nightly

    1,750 USD - 1,750 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

  • 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 - 245 USD

    nightly

    1,050 USD - 1,645 USD

    weekly

  • JUNE 2017 SPECIAL - BOOK 8 NTS GET 1 FREE NIGHT.... RATE APPLIES TO 2B/2B or 1B

    This 2B/2B can also be rented with optional selections: 1B/1B OR Hotel Style Room. CALL FOR RATES -- NEW FLOORING in kitchen, baths and bedrooms , plus upgraded Baths. The Unit is at the upper part of the complex in a quiet, garden setting. ...

    2 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Kihei

    159 USD - 269 USD

    nightly

    1,113 USD - 1,673 USD

    weekly

    4,000 USD - 7,000 USD

    monthly

  • Wailea Luxury - Front-Row Unit with Amazing Ocean & Golf Views

    Hawaii Tax ID: W68471345-01 FRONT-ROW UNIT - STUNNING OCEAN & GOLF COURSE VIEWS Wailea Ekolu #304 is a luxurious condominium situated at the front row of Ekolu on the 15th hole of the Wailea Blue Course with panaromic views of Molokini and Kah...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 379 USD

    nightly

    1,883 USD - 1,883 USD

    weekly

  • Remodeled,Ground Level,~A~C Throughout,King Bed,Everything Needed for Kids/Beach

    This beautifully remodeled ground level 1 bedroom 2 full bathroom condo features all new stainless steel appliances, air condition throughout, king size memory foam bed, 60 inch and 55 inch 4K flat screen TVs with Bluetooth Sound Bar/Subwoofer, qu...

    1 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Kihei

    159 USD - 259 USD

    nightly

    1,813 USD - 1,813 USD

    weekly

  • Location Location! Updated! Ground-Floor Inner Courtyard!

    You'll love our air-conditioned ground floor 1BR/2BA condo, centrally located in the inner circle of Kamaole Sands in Building 7, just steps away from the swimming pool and the beach. The lanai opens out to a beautiful tropical garden with large ...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    159 USD - 229 USD

    nightly

    1,113 USD - 1,113 USD

    weekly

  • Spectacular Haleakaala and ocean Views. $1150 per week special

    SPECIAL LOW SEASON RATE OF $1150 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

    165 USD - 300 USD

    nightly

    1,155 USD - 1,680 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

    165 USD - 200 USD

    nightly

    1,295 USD - 1,400 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

  • Feb 26 to Mar 7 available, 25% off! Top floor corner unit w/beach toys & 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

  • Wailea Ekolu 1407 Live the Highlife on the Best Island in the World

    Come take your next Hawaiian escape in our tropical getaway . It will be your home away from home . Located at the top of Wailea . Surrounded by three world class golf courses , five star hotel's , endless shopping at the shop's at Wailea right d...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Wailea-Makena

    175 USD - 360 USD

    nightly

    2,520 USD - 2,520 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

    179 USD - 270 USD

    nightly

    1,250 USD - 1,715 USD

    weekly

    5,250 USD - 7,285 USD

    monthly

  • 1BR Deluxe Condo in South Coast Maui; pools, BBQ area, kitchen, tennis courts.

    ***BOOK ONLINE NOW FOR INSTANT CONFIRMATION*** Need help from a real person? Please call our vacation specialists if you have any questions. We are the official partner for Aqua Hotels & Resorts for rentals at vacation resorts. Only rent from  o...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    183 USD - 363 USD

    nightly

  • Paradise Found!-Upstairs, Monster View, from $166.50/night

    Wailea Ekolu is a quiet low density condominium complex located in South Maui. Our unit offers gorgeous ocean views and all the comforts of home. Located away from street and pool noise, on the 16th Tee of the 'Old Wailea Blue' golf course. Clo...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    185 USD - 250 USD

    nightly

    1,225 USD - 1,659 USD

    weekly

    4,980 USD - 6,750 USD

    monthly

  • Tight on Budget? as low $162 per night in Wailea

    ALOHA & Welcome to the Wailea Ekolu Signature Suite #1403 Our management Team is close by if you ever need some assistance. Our guests rave about this spacious beauty - Perfect for Rest, Relaxation & Romance. Approx. 866 square feet of luxur...

    1 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>`Wailea

    185 USD - 185 USD

    nightly

    1,295 USD - 1,295 USD

    weekly

    4,725 USD - 4,725 USD

    monthly

  • A Room With A Beach View--Ground Floor Unit

    We have just (May 2015) taken full ownership of this unit that has been in our family for more than 30 years. It is directly across the street from Kam III beach...with the lanai facing the beautiful Kamaole Sands Gardens...and a great view of th...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kihei

    185 USD - 245 USD

    nightly

    4,400 USD - 5,600 USD

    monthly

  • Gorgeous Oceanfront remodelled unit with great view! Avail Apr 17-28!

    This fifth floor oceanfront condo at the Kihei Surfside Resort is located on the more private, quieter side of the building, and has a lovely direct ocean view from the kitchen, living room, dining area and lanai. It is one of the larger, 1 bedroo...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    185 USD - 315 USD

    nightly

    1,225 USD - 2,135 USD

    weekly

    4,350 USD - 4,950 USD

    monthly

  • Luxury Loft, Very Private Lanai Overlooks Lush Tropical Pool! K-205

    I have a beautiful 2 bedroom, 2 bathroom, 1280 sq. ft. loft unit which is AAA+ rated and offers 2 bedrooms, each with your own private lanai looking out on Haleakala and lush tropical vegetation and flowers. The unit has 2 full bathrooms, A/ C, f...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kihei

    185 USD - 360 USD

    nightly

    1,295 USD - 2,520 USD

    weekly

  • 'Best Vacation Ever' Say Our Guests! Luxurious & Affordable!

    You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit is immaculate and impeccably maintained. This unit offers wide open living space ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Wailea

    185 USD - 295 USD

    nightly

    4,650 USD - 4,650 USD

    monthly

  • Palms at Wailea #1005 Panoramic Ocean Views 1Bd 2Ba Sleeps 6 Great Rates!

    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>Wailea

    1,323 USD - 2,790 USD

    weekly

    5,670 USD - 8,070 USD

    monthly

    189 USD - 399 USD

    nightly

  • 1BR Condo w/ partial ocean view in Southern Maui; pools, BBQ area, kitchen.

    ***BOOK ONLINE NOW FOR INSTANT CONFIRMATION*** Need help from a real person? Please call our vacation specialists if you have any questions. We are the official partner for Aqua Hotels & Resorts for rentals at vacation resorts. Only rent from  o...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    193 USD - 373 USD

    nightly

  • Kihei Surfside #603 - The Ocean Awaits You!

    Experience the serenity of beautiful Maui at Kihei Surfside unit 603. All new floor to ceiling windows and glass railings show off the incredible 180-degree ocean views! Our unit had been upgraded with all new plush carpeting, beautiful roller sha...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kihei

    195 USD - 325 USD

    nightly

    1,435 USD - 2,135 USD

    weekly

  • High End Oceanfront Awesome View Cancellation Special Feb 24-Mar 1 Save $100/nt!

    This unit is a fifth floor, luxuriously appointed one bedroom, 1.5 bath condominium at the Kihei (Key-Hay) Surfside Resort, Maui, has a 180 degree absolute direct oceanfront view and the islands of Lanai, Kaho'olawe and Molokini are clearly visibl...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kihei

    195 USD - 325 USD

    nightly

    1,295 USD - 2,205 USD

    weekly

    4,650 USD - 5,250 USD

    monthly

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