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10 Day Octob Ho'olei Stay -- Advice & Questions for Families

Santa Monica...
Level Contributor
19 posts
18 reviews
10 Day Octob Ho'olei Stay -- Advice & Questions for Families

My friends & I have just booked a 10 day stay at the Hoolei 3 bedroom! We're pretty excited as while we've visited the island 3 or 4 times, we always ended up staying at Honua Kai. Nothing wrong with it this time, but we thought it would be nice to experience another part of the island & with a toddler in the group, the pools of the GW were attractive. (It turned out hilton.com had pretty good rates, so we booked direct.)

A few random questions:

- Any advice on the "best" units? We're the "ocean view" level (not garden view or deluxe ocean view)

- Is it worth bringing any beach gear with us? When we visit the beach in LA, we typically have chairs + umbrellas + sand toys for the youngster.

- I know they offer a shuttle to from Ho'olei to the GW. The moms of the group are a bit worried about transporting the babies w/o car seats in the shuttle. How do other parents get their young ones back & forth? Just walk? Carry them on the shuttle? Use a car seat?

- How difficult is it to walk back & forth from Ho'olei to GW?

- What are the best pools for young kids at Ho'olei or GW?

- Likewise, any advice on good attractions/parks/beaches for a toddler in the area?

- I didn't want the toddler to miss out on Halloween (he liked it last year), so I was going bring his costume & take him to the kids parade in Lahaina. Good idea or bad idea? Any other advice to still give him a bit of the Halloween experience?

Group details:

5 adults (early 30s to early 40s), a toddler who will be just shy of 3, and two babies who will be 6 months & 10 months old.

Nanaimo, Canada
Level Contributor
28,042 posts
109 reviews
1. Re: 10 Day Octob Ho'olei Stay -- Advice & Questions for Families

I wouldn't bring the beach gear with you. Much easier to rent. Also, you can pick up sand toys at some of the thrift stores, of at ABC for cheap. Do be careful with the umbrella though! If the wind picks up, they can be considered a weapon!

I would absolutely head up to Lahaina for Hallowe'en! Just go early, and make it a West Maui day, if you can. The traffic will be heavy, for sure.

Check out Ulua Beach for an option. Also, just north, is the Kamaole Beach III. A lifeguard, as well as a grassy area, and trees that supply shade.

Schaumburg, Illinois
Level Contributor
81 posts
22 reviews
2. Re: 10 Day Octob Ho'olei Stay -- Advice & Questions for Families

You can also rent beach gear and toys from various places. We are going to try Ohana Sport and Beach Rentals, as they give free delivery if you order $50 or more. We also rented beach chairs from Snorkel Bob's in the past, although they did not rent umbrellas. Prices for weekly rentals were very reasonable at both places.


Level Contributor
71,034 posts
18 reviews
3. Re: 10 Day Octob Ho'olei Stay -- Advice & Questions for Families

Re Halloween, I would not go to Lahaina. You will find some fun there in the Wailea area and it would be much easier. They've started doing some parties and kid oriented things down south finally, just in the last couple of years.

San Diego...
Level Contributor
48 posts
193 reviews
4. Re: 10 Day Octob Ho'olei Stay -- Advice & Questions for Families

We have stayed at Ho'olei several times with our young girls, so here's my advice:

Since you booked with GW, you will have full access to their pools and beach club (towels, beach chairs, umbrellas, etc) and you can buy inexpensive beach toys at the ABC or Whaler's Store in the Shops at Wailea - much better than buying at the GW shops.

You can call the shuttle and they will pick you up at your villa and take you to either the GW side entrance or main entrance, or the Shops at Wailea. We always take our booster seats for the rental car, but I never put them in the shuttle. But this is a personal decision. The ride is literally across the street, but it is a busy street. You might want to call before you arrive and ask if they offer any car seats or booster seats in the shuttle mini-van. They are so nice and super accommodating, especially with families, that I can see them putting a couple in the van if they have them. And if they don't - that would be a great idea.

The walk to and from the GW is a bit of a trek if you have little ones (not only for them but all the STUFF). Definitely need a stroller because coming back up the hill to Ho'olei can be trying after a long day swimming. We stay on the very top row of villas so it is the furthest, but we still enjoy the walk to the GW (downhill) and then call for the shuttle to pick us up if needed. At the end of October, it will not be busy so the shuttles are fast and plenty.

Both the Ho'olei and GW have "baby beach" pools with zero entry and sand for them to play and sit. My girls spent many hours here happily occupied - which is so nice for us parents to sit and relax, take turns watching them, etc. A couple times they were not budging from the GW baby beach pool so we just ordered drinks and lunch on the chairs right there and ate while they played. (Ho'olei does not offer any food or drink service, bring your own).

As for activities with the little ones: Maui Ocean Center, Maui Tropical Plantation, Shops at Wailea (ice cream), and check if the Kula Country Farms Pumpkin Patch will still be open when you are there. We take the kids (the drive upcountry is fun in itself) and they love it! Very big pumpkin patch with corn maze, etc. This year we will go on one of our first days so they can pick a pumpkin and take back to the villa to enjoy during our stay.

Some tips for GW/Ho'olei that we have found useful: bring lots of $1 or $5s for tipping shuttle drivers (we save part of our recycling money during the year and bring this for all our tipping needs during the trip), the pool at Ho'olei is awesome and stays open late for a night swimming and jacuzzi (fun for the adults to have some time alone - take turns watching the kids), the poolside cabana massages at Ho'olei are beyond relaxing and easy to sign up for, the kids will be able to eat free with each paying adult at the GW, and there is no better meal than one on your lanai watching the incredible sunset (they come with BBQs).

Have fun!

5. Re: 10 Day Octob Ho'olei Stay -- Advice & Questions for Families

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