Ho'olei Resort S2, Wailea, Maui

This spacious professionally-decorated townhome has all the comforts you expect from a five star experience. The world renowned Grand Wailea resort located across the street offers a world class spa, shopping and beach.

Whether your group has many children, adults or seniors, this home is recommended for all age groups. The private elevator accommodates anyone who might not be comfortable with the stairs and we a pack and play stroller and high chair.

We are proud to be part of the L'Occitane family by providing these beauty essentials start-up kits during your stay. For over 30 years L'Occitane has best drawn inspiration from Mediterranean and traditional provincial techniques to create a natural beauty product dedicated to your well-being.



Driving Directions

Vacation Rental Features

Accomodation  :  Private Home, 3 Bedrooms, 3.5 Baths (Sleeps 8-10)

Accomodation Amenities Notes  :  * Air Conditioning * Washer * Dryer: Private laundry room in the home. * Linens Provided * Garage: One car attached garage. * Covered Parking: One additional parking spot, if needed. * Elevator: Inside the unit - for handicap guest only. Please give advanced notice at the time of booking, if the elevator is needed.

  • Bedroom Name : Master bedroom
  • Bedroom Type : Bedroom King Beds : 1
  • Bedroom Name : Bedroom 2
  • Bedroom Type : Bedroom Queen Beds : 2
  • Bedroom Name : Bedroom 3
  • Bedroom Type : Bedroom Queen Beds : 1
  • Amenities
    • accept credit card
    • air-conditioning
    • alarm clock
    • ceiling fans
    • central heating
    • cold water dispenser
    • filtered water
    • fitness room
    • hair dryer
    • jacuzzi
    • laundry soap
    • linens provided
    • local activities guide
    • paper towels
    • private chef
    • shampoo
    • soaps basic
    • telephone
    • toilet paper
    • towels provided
  • Local area information
    • near by airport:    Kahalui 18.5 - Miles
    • near by bar/pub:    Wailea 0.1 - Miles
    • near by beach:    Wailea 0.1 - Miles
    • near by golf:    Wailea Blue Golf Course 0.1 - Miles
    • near by highway intersection:    State Highway 31 0.1 - Miles
    • near by restaurant:    Wailea 0.1 - Miles
  • Entertainment
    • books
    • CD
    • DVD
    • games adults
    • satellite or cable
    • stereo system
    • videogame console
  • Kitchen
    • 4 ring stove
    • blender
    • clothes dryer
    • coffee grinder
    • coffee maker
    • cooking utensils
    • dish washer
    • freezer
    • grill
    • ice maker
    • iron & board
    • microwave
    • oven
    • refrigerator
    • toaster
    • washing machine
  • Swiming Pools
    • communal pool
    • heated pool
    • outdoor pool
  • Outdoor Features
    • deck wood
    • outdoor grill gas
    • patio stone/concrete
    • porch/lanai
    • beach chairs  -  2
    • bicycles  -  0
    • garage  -  1
    • garden chairs  -  2
    • parking  -  2
    • parking off street  -  1
  • View/Location
    • near the ocean
    • resort
  • Communications
    • broadband access
    • wireless broadband
  • Other Amenities
    • beach chairs
    • beach towels
    • cooler small
  • Attraction
    • eco tourism
    • forests
    • rain forests
    • reefs
    • restaurants
    • scenic drives
    • volcano
  • Suitability
    • children
    • ask
    • elderly or infirm
    • ask
    • wheelchairs
    • ask
    • pets
    • ask
    • long term renters welcome
    • non smoking only
  • Activities (on-site or nearby)
    • cycling
    • fishing
    • golf
    • mountain biking
    • paragliding
    • sailing
    • scuba diving or snorkeling
    • surfing
    • swimming
    • tennis
    • water skiing
    • wind-surfing
    • beachcombing
    • bird watching
    • deepsea fishing
    • hiking
    • luaus
    • sight seeing
    • snorkeling
    • sound/bay fishing
    • surf fishing
    • whale watching
  • Testimonials

      Hawaiian Paradise


      What a wonderful place to spend a vacation, even nicer than the pictures. Beautiful townhouse with many upscale amenities. Just sit back and enjoy! The pool area was very nice, even u-boat thousands of feet replica watches more inviting after sunset as the area is lit up with torches. You'll be just a short walk to the Wailea beach area. This is one of the most beautiful beaches I have ever seen. The townhouse had several beach chairs and towels that you could use as well. There are many places to shop and eat within a short walking distance. Would I recommend this as a vacation place, an easy "yes". Cheers!

      What a Nice Place


      Truly a spectacular home with wonderful amenities. I can't say enough about the property and surrounding area. Close to pool and workout room. First class. Very convenient to have a connected garage.

      Magnificient Home in Wailea, Maui


      Beautiful home in Ho'olei, Wailea Maui. Home is as advertised. Photos do not do this home enough justice. Home was in perfect condition upon arrival. Local staff is fantastic. All my pre-booking questions were answered to my satisfaction. I plan to rent from owners again! And, have already recommended owners and property to friends and co-workers. This is a great home in a great locale!

      Mahalo and Aloha



      We had a great time in Maui made all the better by your beautiful townhome and the service we received by your staff. We will surely recommend your home to any of our friends heading to Wailea.

      Mahalo and aloha,




      Hey Sara and Chirssy,

      Fabulous!!! We had the most wonderful time, and staying in your lovely place(s) was one of the main reasons that everything went so smoothy. The wedding was "almost perfect", and both bride and groom are still in a state of bliss - and that's the best thing.

      The units were both gorgeous, and so clean and well-appointed - we cooked several meals during our stay, and so enjoyed the easy access to everything in the kitchen. I want those cabinets!!!

      Our guests were amazed and delighted with their accomodations, and we all enjoyed the lanais, and especially so in S-6, where the sliding doors disappeared into the walls and brought the lanai right into the great room . . . so beautiful.

      The children involved (two babies, one four months and the other three months) were comfortable and happy, as were their parents. The pool was lovely, and both babies "swam" for the first time with their mothers. Everyone at the complex was polite and friendly, and the pool staff in particular was warm and helpful - each and every one.

      I didn't have the opportunity to meet anyone there on site except Eric, who was most hospitable and kind while showing us around on our arrival. I'd like you to know that after our long plane trip, and a few anxious moments when my wallet disappeared temporarily at the car rental agency in Kahalui, Eric's calm presence, friendly smile, and helpful service was much appreciated.

      Thank you again for all of your help, and for helping to make our "destination wedding" the best! We thoroughly enjoyed ourselves, and so did our guests.


      Kristie Yunker

      Stop searching, this is THE place!

      2016-04-22 This is an outstanding condo - it is very spacious and very clean we felt right at home -- our plans changed at the last minute and there were only 4 of us traveling, so the third bedroom went unused, but it did give us a few extra towels to use! We bbq'd a few nights on the wonderful lanai, but ate out most nights, Monkey Pod was our favourite and we went there a few times. The greeter/property manager was very helpful and answered all of our questions. The only downside to accommodations of this sort is you have to launder your own towels, but plenty of beach towels and bath towels are provided and it is really not a big deal to throw in a load every couple of days to have fresh towels for the next day.....a small price to pay for space and luxurious surroundings you find yourself in at the end of the day. The condo is well equipped with almost everything you need from two styles of wine openers, to a juicer to a Keurig and a regular coffee pot to aluminum foil and ziplock bags. Yes you have to realize you have no privileges at Grand Wailea hotel across the street (can't use their pool or sign to your room), but we did use the Spa and I highly recommend it! We walked through the GW everyday to the beach and it is a very nice walk through the immaculate grounds of the Grand Wailea -- plenty of others doing it so not a problem at all. There is a private elevator in the unit but we did not use it, but would be great for anyone with a physical disability. One thing not to miss is the sunrise and bike ride down Haleakala! Well worth the 3am pickup time and you only bike down from about 7000 feet and it wasn't as scary as I thought.



      You know, you are very lucky to have someone like Daisy helping with all the repetitive details involved in taking care of all your visitors!  I am impressed with her attitude and cheerful outlook!  Take good care of her; she is a rare treasure!

      Thanks Again,


      LOVED unit 12-2


      Hi Chrissy, we LOVED unit 12-2 so close to the pool and gate. It was so gorgeously furnished and so comfortable. We are SO sad to leave, thank you and we'll be in touch.

      Pam Stone



      Hi Chrissy,

      I just wanted to drop you a quick e-mail to let you know we had a wonderful time staying at your place in Wailea.  It was perfect in every way for our family – and we will come back... perhaps as early as next year (and stay longer!).  Seriously, we couldn’t imagine any improvements to our accommodation, location, etc.  Thanks so much!

      Hope you don’t mind if we contact you again when it’s time to return – you’re at the top of our list!!!

      Sincerely, Ian and Jen



      Hi Chrissy,

      I have been meaning to sit down and write this email since we got home last week. We had such a wonderful time at your family's condo at the Ho'olei. It is a beautiful home in a glorious location. Thank you so much for all your attention to detail -- from supplying the high chairs (better than the ones we have at home!) to the playpens to gettting a baby gate on a moment's notice and, of course, to the early check-in which was so wonderful since the GW reservations failed to get us in before 4:00pm!

      Most of all, though, I want to thank you for the generosity and care that you showed our family on the day of the tsunami alert. You don't even know us and yet welcomed and encouraged us to enjoy your beautiful home (mansion!) in the mountains, far away from any potential danger. It was a wonderful day and a special memory from our vacation. We are so grateful and feel so blessed to have connected with your family. You are truly special people, the likes of which it is easy to begin to believe do not exist in today's hustle and bustle world where even neighbors remain strangers. Your act of kindness to our family, and the others you rescued that day, is a treasured gift that we will never forget.

      Thank you again so much. I will be recommending you all to all my friends as the "go-to" people for a rental on Maui!



      Very room, nicely appointed

      2014-05-06 We chose his complex and the unit in general primarily because of the pool for our then 2 yr 4 month old daughter. The pool is great - well designed so even if it is busy it doesn't feel like you're at a las vegas pool. It is about a 2 minute walk We had my five adults and one toddler and there was plenty of room. The unit is well appointed. In the words of my mother-in-law, if you haven't found what you're looking for, you just haven't looked long enough. The owner and her reps were helpful, prompt and acted very professionally. Beach via the Grand Wailea is about a ten minute walk with a toddler and her paraphernalia in tow. The Lanai is very large and well shaded so you could use it all day long. Just because you can't have every thing, please note that you can see the ocean in the distance when you're standing on the lanai, but not when you're sitting down and enjoying you Mai Tai. (I knew this when I booked the unit.) Skip the food Grand Waliea, which is lifeless and they genuinely seemed displeased to see us. I recommend a nice night out at the lobby bar at the Four Seasons. Nothing cheap about it, but nice drinks, good pupus (spelling) and their is some quality live music including traditional Hawaiian music and dance. Great atmosphere. Monkey Pod is good. Great happy hour. Halimale General Store is my favorite restaurant on the Island. I've had my last three birthday lunches there. I recommend going for lunch and then going to Makawao (spelling) and Paia. Also during the day, you can see the pineapple fields. Aloha.

      Villa is outstanding!

      2014-09-11 Our family thoroughly enjoyed the Ho'olei Villas! We had stayed at the Grand Wailea 3 times in the past when our daughters were younger. Renting the Villa was a totally different experience and since we like to cook, having a beautiful and fully stocked kitchen was perfect! We enjoyed several dinners/grill-outs using the Wolf gas grill out on the massive Lanai! The Villa is stocked with every possible thing you'd need, from beach items to cooking utensils. The bedrooms are tastefully decorated and the furniture is exceptional, with incredibly comfortable beds and beautiful bedding. Large HD tv's in each bedroom. Our Villa was in the closet grouping of Villas to the Grand Wailea, making the walk an easy 5-10 minutes across the street. It was the best of both worlds, having the privacy and convenience of being able to cook for ourselves, yet take advantage of all the GW resources. My daughters got hooked on the Spa Grande Terme hydrotherapy circuit! The Ho'olei pool was not crowded and there was no problem finding a lounge chair at any point during the day. Lastly, access to the Dolfun Scuba outfit at the Grand Wailea was first class and a great resort dive resource. We were able to complete 6 dive days! Their staff was awesome-big thanks to Charles, Eric & Vic! We rode underwater scooters out to a shipwreck and that was sensational! Best of luck with your vacation! You can't go wrong with the Villas at Ho'olei!

      Spacious, comfortable and luxurious. Great complex and location

      2014-04-18 We spent a week at the home and everything was perfect. Our party consisted of 2 families with children aged from 3 to 14. The home is furnished with style and has excellent accommodations and all ammenities necessary for a perfect stay. The lanai is very large and has a very nice barbecue and dining table as well as lounge chairs. All bedrooms are large and beds are very comfortable. The bathroom next to the master bedroom is very spacious and cozy. The back yard is very private - it felt as if it was only for us to use. The garage has all the beach gear we neeeded - niche chairs and umprella as well as many other toys. The Ho'olei complex itself is very nice with the pool being much better than many resort pools on Maui. There are at least 5 amazing beaches located within a 5 minute drive from the home with convenient loading/unloading zones and plenty of parking. We would defintely recommend this home to anyone and would certainly loved to come back in the future.

      Absolutely Beautiful Villa!

      2014-05-13 Hi Chrissy, Just wanted to say what a great time we had in Maui! The villa is absolutely beautiful! It had everything we needed and more. It was great to have the pool to use and to have a very short walk to the beach. The kids were very happy to have their own beds and it was great for my daughter to have her own space. I would definitely recommend your unit to our friends and family. Hoping we can come back soon. Thanks again. Kathy


      2013-04-23 We loved our week at Hoolei in Maui. It was perfect in every way for me, my wife, our two 4-year old twin girls, and my mother-in-law. The whole family under one roof with plenty of room for all. First, the condo is located across the street from the Grand Wailea, the Four Seasons Wailea, and public access to the beautiful and serene Wailea Beach. We dined at both hotels, we did the luau at the Grand Wailea, and the condo is in walking distance to the Wailea Shopping Center and other fabulous restaurants. Second, the condo is immaculate, furnished nicely, and so relaxing it was hard to leave. But when we did leave, the pool at Hoolei was perfect to lounge at and the kids loved the waterfall and secret cave at the pool. Everyday it was Waliea Beach in the morning and the Hoolei pool in the afternoon. I miss it already. We BBQ'd several times on the large lanai, and the nearby street was not an issue at all as far as noise or safety. Actually it was convenient to be so close to the pool and the resorts across the street, which were very welcoming destinations. I can't write anything negative about the condo, Hoolei, or the location since it was better than described, and the owner is very attentive and professional. I would not hesitate to book here again, and we are already planning another trip in the near future to Maui and Hoolei!


      2012-12-04 I just wanted to say thank you for providing this lovely home for us to enjoy. Everything was in perfect order. We were thankful for the beach chairs, cooler, boogie boards and sand toys which were used daily. There is no doubt we will be back again! We had a wonderful time!

      Great Home

      2013-02-20 Thank you for letting us rent your home for the week. We had more than enough space to feel at home and only wish we could have stayed longer. Our three kids (ages 9, 13, 15) enjoyed having their own space and loved that the pool was only a short walk away. (If you have younger children, the home has a nice lawn in the backyard for them to expend energy.) It was also nice to be within walking distance to The Shops at Wailea--especially Lappert's! We were happy to find a nice and quiet gated complex. (The road noise was only noticeable when we were eating on the lanai but it didn't bother us.) The owners and their employees are very kind and helpful. Their genuine care for our family's experience was evident from the pre-booking plans of our vacation to the end of our stay. Thank you Chrissy, Daisy, Eric and Lolita!

      Thanksgiving in Paradise

      2012-12-07 Thank you so much for a wonderful vacation! LOVED the condo, it was amazing for our family and had everything we needed and then some. From the kids to my mother, everyone was thrilled at how comfortalbe, clean, and convienent the place was. We will be back!!

      A family retirement celebration!

      2012-12-04 We were so excited to travel with our family to Maui. When we arrived we were overwhelmed with your beautiful home! Loved the grill, the super nice kitchen and the layout of the home. There were 7 of us which included 2 grandsons ages 6 and 4 and the house was perfect for us! It didn't take us long to find the beautiful beaches around. We would enjoy the beaches in the morning and then end at the pool after lunch, which the kids loved. It was so nice to have the option to eat at the house or try the many restaurants in the neighborhood. Your home is in a perfect location to the beach, shopping and restaurants. Thank you for all the extras you provided such as beach towels, beach chairs and helpful information! I am looking forward to the next time we visit Maui and hope to stay at your home! Thank you!


      2016-09-25 First class accommodation and services for our party of six adults. Crissy and Eric were always helpful and a pleasure to work with. On time, rapid response to questions and very friendly. Eric was especially helpful briefing us on the unit and area.. The unit is located across the street from the Grand Wailea without the crowds and noise. Convenient beach access and outstanding pool area. Did I mention that it was quiet? We found everything needed for a relaxing and stress free vacation. Groceries and shops were 5 minutes by car. We enjoyed walking for miles along the beach path and looking for turtles. Sunbathing, snorkeling and paddle boarding were some of the activities we enjoyed as well as many car trips around the island. We were so impressed with the entire experience that we will do this again.

      Great Place

      2016-08-25 Pictures don't do justice to this condo! The place is located in a private community accross the street from the Grand Wailea. The swimming pool area is beautiful and quiet. You walk through the hotel to get access to the beach, and you can rent their chairs / umbrellas. The Wailea shops are only a few blocks away. The unit itself was impeccably maintained and it had all the items we would have otherwise had to pack for a beach vacation - beach towels, chairs, umbrellas, toys, cooler, etc. The condo has two levels. There are 2 large bedrooms downstairs with their own bathrooms and a third bedroom with its own bathroom upstairs. The kitchen has great appliances and had all the utensils we needed to make some home-cooked meals. The grill was top notch. There was plenty of room for the six of us to spread out and relax. The central air was a plus! They also provided a lengthy guide of all the places they recommend as well as contact info for babysitting and house cleaning help and car rental and airfare discounts. We will definitely come back!

      What a Place

      2016-04-17 This is a beautiful home that was darn near perfect for our stay in Wailea. It has the most completely equipped kitchen imaginable and the furnishings and appointments throughout the home are lovely. The folks I dealt with regarding all phases of this rental were very helpful and accommodating. I misread the location map and was disappointed to find that we didn't have an ocean view as some of the other homes did. One couple in our group was unhappy about the TV situation in their room but overall there's not much to complain about here!!

      More than we could have ever expected -- OUTSTANDING!

      2015-12-30 Besides the unit being amazing - the community and location were truly fantastic ! We holiday in Hawaii twice a year and this was the first time we didn't stay at a resort only because we were traveling with an extended family of 6. Never going to a resort again !! Even if it's just the two of us !!! A beautiful condo community pool , minutes to the beach, miles of running paths , a short walk to restaurants, luxury shopping, basic grocery needs - and a team who was responsive and available to answer any questions. Thank you to the Ho'olei Homes Team ! The experience was fantastic! We will definitely be back.

      The Perfect Vacation!

      2015-06-18 True to it's description in every way! My family and parents/in-laws just spent 7 wonderful days in beautiful Maui and T-2 was lovely! We love to cook and the kitchen amenities were bountiful. The bedrooms were spacious and comfortable. The bathrooms were beautiful with plenty of towels. I loved the fact that the house supplied plenty of beach towels, beach chairs, large cooler, umbrellas for us to use at the beach. When at the house, we spent most of our time on the lanai either drinking morning coffee or enjoying house-made pina coladas in the evening. The nights were quiet and peaceful. We would walk down to the Grand Wailea and see the beautiful tiki torches flickering in the night, the blue pool lit up and hear the soft sounds of luau music. Kihei was less than a 10 minute drive away where we could shop and also grab a bite to eat if we didn't feel like cooking. We spent every day at the Ho'olei pool which was even prettier in person. We made sure we fit snorkling in every morning and Makena Beach as well as Ahihi Bay were very close to our accommodations (great snorkling locations!). Working with Chrissy and Daisy was so easy and communication was effortless. Thank you for such a great week! Next time we come to Maui, we will definitely stay at Ho'olei again!

      Lovely Condo

      2014-05-15 This condo was perfect for our family of 6 (me and my husband, our two kids (ages 2 and 10 months), and my parents). It is very comfortable and child friendly while being beautifully decorated. It is clean and updated with a fabulous well-appointed kitchen. It is open and airy and has a huge lanai with a gas grill. The condo is located near the Ho'olei pool and also close to the Grand Wailea Resort and the beach access. There is not an ocean view from this condo, but we spent a lot of time at the beach so we did not miss having a view. We shopped around quite a bit and found this to be the very best rate for a luxury condo in Weilea. A pack and play, a high chair and a stroller were provided so we did not have to pack or rent any baby equipment. Beach chairs, umbrellas and towels were also provided. We really enjoyed spending time at the smaller beach in Makenna, just down the road. The Ho'olei pool is wonderful with a waterfall and a hot tub. it was perfect for our kids and we loved that it was not as crazy and noisy as some of the big resort pools. We really enjoyed eating at Cafe Au Lei in Kihei. The food was excellent and the price was very reasonable. It is popular with locals. Booking this condo and working with Ho'olei Homes was really easy. Chrissy and Daisy were really nice and helpful. We will stay here again and I certainly recommend it.

      My Maui Homeaway from Home

      2016-10-07 I cannot say enough great things about this home and our experience with Chrissy, Daisy, Eric and the entire team at Ho'olei Homes. First off the home is beautiful, the pictures really don't do it justice. We brought our moms here as a thank you for all they've done for us and they were so impressed, felt like they were spoiled, honestly lived up to the vacation I had envisioned for them. I wish my real home looked like this one, plenty of space, impeccably decorated, no detail was forgotten, including beach chairs, boogie boards, umbrellas, etc. The pool and hot tub area on the grounds were amazing as well, honestly I thought it was far better than the Grand Wailea, very peaceful and relaxing. Chrissy and her team somehow managed to offer every accomodation far exceeding the best hotels and at the same time giving us personal attention (I felt like she was a good friend). Advice on where to visit, what restaurants have the best crepes, sushi, view of the sunset, etc., even going above and beyond offering to arrange transportation when our flight was delayed 11 hours and past the car rental closing hours. We didn't end up needing to use that but I appreciated the fact that we could have. I am so grateful that I chose this home, this is the first time I have used VRBO and honestly I was a bit hesitant, worried that we wouldn't get what we had been promised. We ended up getting far more than I had expected and had a lovely trip. Thank you, Kathy Jo

      Clean, well-kept, with excellent amenities

      2016-08-07 A very well-maintained luxury condominium in a complex right across the street from the Grand Wailea resort. The listing was accurate - everything was found to be as described. Everything was clean, everything worked properly. Tastefully decorated but still with a contemporary modern theme. Kids enjoyed the HDTV flatscreens in almost every room, each with DVD players. The washer and dryer were very useful. The pool for the condominium was in excellent condition, and had its own waterfall and grotto. It was never crowded. The Grand Wailea resort was just across the street, and the beach was only a ten minute walk from the front door of the condo. Very close to many shopping and dining opportunities. Highly recommend the Monkeypod kitchen.

      Fantastic property

      2016-06-21 Team was great. Property fantastic. Will definitely come back.

      B-E-A-U-T-I-F-U-L Home

      2016-04-15 This was my first time in Hawaii and this place is beautiful. The maintenance guy at the place was so helpful, even helped us pack all our stuff in the house. Being right across the street from the Grand Wailea was pretty cool too. Not too far from shopping, eating and just laxing in the sun. Would differently stay here again. The place was stocked with all that is needed to have a great week.

      Enjoying Our Stay

      2016-12-17 We are really enjoying our time at Ho'olei Villas. This unit is beautiful, well appointed, close to pool, with peekaboo ocean views. Chrissy and her team are very easy to work with. This is our second time staying at the Ho'olei Villas at the same time of year. We love coming to week before Christmas, due to no crowds, beautiful decorations at the resorts, beautiful weather (not too hot). We have a 15 month old with us this time and the baby amenities at this condo, are perfect (stroller, highchair, pack n play) We have visited Maui over 20 times and The Ho'olei Villas is our favorite place.