Ho'olei at Grand Wailea

We have gone to Ho Olei at Grand Wailea for many years, this is our annual spot and our happy place! We love the house we had, so much room and so comfortable. The grounds are kept so nice and the staff knows your name and they take care of every need. The kids, big and small will love the pools. Can't go wrong staying here.

We stayed in a 3 bedroom that was very spacious and clean. Plenty big for our family of 4 plus our niece fresh from college graduation who also stayed with us. The "uber" service via app was great and took us quickly to the main hotel and local restaurants/shops. Despite its vast size, the service at the pool and at the cabanas was wonderful. But unfortunately, my niece left her necklace on the dresser while tanning at the cabana and it disappeared after housekeeping came... On our last day, our niece (in her early 20s) left the 2 necklaces she'd worn the entire trip on her dresser to prevent tan lines at the cabana. She noticed the housekeepers entering as she left and almost hid them but figured it was a trust worthy hotel. Unfortunately, when we got home from the pool, her Tiffany necklace (a grad gift) was no longer there. After double checking everywhere in her room, I immediately called the Ho'olei desk hoping that if it was by accident, the housekeepers could check their rags before washing them. After an hour of not hearing back (and still seeing the housekeepers on property), my niece personally walked down to the office. They still wouldn't contact the housekeepers and said they had to send security. After waiting another half hour, I called again and a man (security?) finally arrived. While filling out a form, I asked him to contact housekeeping as we know it disappeared while they were there and was sure they'd be able to find it in their rags. He said he had no way of reaching housekeeping staff either. We finally left for our last dinner on the island and I texted the office asking them to let me know after they'd spoken to housekeeping, hoping I could give my niece some good news during dinner. They texted that they wouldn't be able to speak with housekeeping until later the following day (after check out). My niece called when she landed the following day and was told to wait for a call from their insurance to work on the claim. Management has yet to reach out to us. We spent tens of thousands on this vacation, reserved cabanas most days, ate a huge meal at Nobu...I really expected more from management. I don't understand why they couldn't address the situation in the moment and try to be more helpful instead of wasting our time on our last evening. My husband feels they're all "in on it" because there is no incentive not to steal when they just submit it to insurance and Grand Wailea doesn't care to follow up. Unfortunately, they lost our trust so we will never return.

When I was reading Nicole L.'s review below, I thought we must have had the same unit because I had almost the EXACT same experience. Then I looked through the photos and saw that it was actually a different unit that was just as poorly kept as the one my family stayed in! I thought that we just got a bad unit because they're all individually owned (even if booking through the resort, as we did), but apparently there are just very low standards for upkeep across the board. I'd avoid it if you have the option of staying elsewhere. To list our grievances.......... DISGUSTING carpets. There are black stains everywhere and it seems like they've never been cleaned. Stains and holes in the patio furniture cushions and pillows. Air conditioning didn't work for the first six days that we were there. Dishwasher didn't work (they couldn't replace it during our stay) and the dishes were all dirty in the cabinets when we got there. They said that they'd send someone to hand wash our dishes but didn't follow through. The pots and pans should have been thrown out ten years ago. Actually, they never should have been purchased. They had gross, cheap teflon pans and only metal cooking utensils...? So weird. The service from property management was fine. They took almost $900 off our nightly rate, but I still would have gladly paid more and stayed somewhere nicer. We were looking for five star accommodations, not a bargain. Overall, the resort was nice but also not five stars. I'd say four stars for the resort, with the Ho'olei side of things being more on par with a three star hotel. Food at the resort was okay but not amazing. Drinks were okay but not amazing. Service at the resort was inconsistent. Pools are fun for the kids, but the layout is challenging since you can't actually see where your kid is going. Skip it!