Hand-picked Hawaii vacation rentals & condosEvery view checked

Hoolei, Maui

Ho'olei is a gated community in Wailea, located across from the Grand Wailea and Four Seasons Resorts. Ho'olei was named the #1 resort in Hawaii by Conde Nast Traveler 2019 Readers' Choice Awards, and along with nearby Wailea Beach Villas is currently the highest rated resort in Hawaii based on guest reviews. Ho'olei also has the distinction of being the lowest density resort on Maui, averaging 4 units per acre.

Ho'olei offers a luxurious experience for vacationers. The resort features a stunning pool with a waterfall, grotto, sandy beach area for children, and two jacuzzis. Guests can also enjoy a state-of-the-art fitness facility, men's and women's saunas, locker rooms with showers, and a covered pavilion area with a refrigerator and microwave oven. With 24-hour onsite security and access to various amenities, Ho'olei provides a comfortable and enjoyable stay for vacationers. It's between a 5 and 10 minute walk to Wailea Beach, depending on unit location.

    Hoolei Quick Facts:


  • Address: 146 Hoolei Cir,Wailea, HI 96753
  • Property Size: ~30.1 acres (120 units)
  • Reviews: 4.93 / 5.0 (from 1417 reviews)
  • Average Price: $1585/night for 3 bedroom units
  • Rentals: Hoolei Vacation Rentals

The Top 8 Highest Rated Rentals at Hoolei

Hoolei Average Rates


As of November 2026, the average price of a 3 bedroom unit at Hoolei is $1585. These averages include Hawaii's 18% accommodation tax as well as the cleaning and booking fees rentals charge. Also note that prices vary depending on the specifc unit and season (holiday rates are usually higher). Visit the Hoolei Rentals page to see specific unit prices for your dates.

What Do Guests Think? An Analysis of 875 Guest Reviews


Reviewer Portrait

The following executive summary is based on a comprehensive and impartial AI analysis of guest reviews. Keep in mind that all units are individually owned, and review scores among units can vary considerably.

Ho’olei delivers a luxury home-away-from-home feel in Wailea: spacious multi-bedroom villas (often with en-suite baths), high-end kitchens, and sweeping lanais that open for true indoor–outdoor living. Guests repeatedly rave about panoramic ocean and sunset views (with winter whale sightings), quiet, beautifully kept grounds, and a resort-caliber pool complex with hot tubs, waterfalls, a shallow kid area, and a good fitness center. It’s a favorite for families and multigenerational groups thanks to the generous layouts, privacy, and easy gathering spaces.

Location is a standout. Most villas are a short walk or quick drive to Wailea Beach, the Shops at Wailea, restaurants, coffee, and golf. Many units come thoughtfully stocked with beach gear (chairs, umbrellas, coolers, wagons, boogie boards) plus plenty of towels and laundry facilities; kitchens are typically well equipped for cooking and lanai grilling. Check-in is usually smooth, hosts/managers are highly responsive, and welcome touches (snack baskets, early/late check-in when possible) are common.

Know before you go: independent Ho’olei rentals generally do not include access to Grand Wailea pools (the on-site Ho’olei pool complex is praised but bring your own towels). Some lower-row or road-adjacent villas report noticeable road noise on the lanai, and the uphill walk back from the beach can be tiring for some—many guests simply drive and park. As with any large community, occasional maintenance or cleanliness hiccups appear (AC or appliance issues, BBQs needing cleaning, tropical ants), but most were addressed quickly. Supplies and beach gear quality can vary by unit, so check listings. Overall, reviewer sentiment is overwhelmingly positive: luxe, roomy villas in a prime Wailea location with a serene pool scene and stellar views.

This summary is based on a comprehensive analysis of 875 reviews

Recent Hoolei Reviews


Gorgeous property and incredible home. Our trip could not have been better!
Jeff A.
August 2026

All was great- except the floors were dirty. Under our feet and socks were always dirty walking in the unit
Celeste F.
July 2026

Outstanding property - would recommend highly.
Davis J.
July 2026

This place was amazing and the host was extremely responsive as I was trying to decide what resort to stay at. Even though it is not ocean or pool views the views out the windows are beautiful with all the Hawaiian landscape/foliage that is so beautiful. When this place lists that it is the closest unit to the pool and beach it is a true statement. The pool is basically a few steps away from the unit and beach is across the street and through the Grand Wailea resort which is absolutely beautiful and a fun place to walk through. I would love to have been able to use the facilities there but you have to book through them to use them. I believe you can buy day passes which I would strongly consider if we came back because it is amazing. The pool here is beautiful too and offers perfect size and layout for both kids and adults and was never crowded at all, we never struggled to find lounge chairs. Again, the unit itself is stunning, the decor and detail is over the top. The outdoor kitchen was perfect and had everything we needed. We did a fishing trip through Green Island Charters and scored dinner for a couple nights and had everything we needed to grill and serve a great meal. They even had some of the basics like salt/pepper, wide variety of spices, plastic wrap, and plenty of paper products, dishwasher detergent, laundry detergent, nice, branded hand soap, shampoo and conditioner etc.... I would strongly recommend this place! Thank you, Derek Stattin!!!!!
Rita G.
July 2026

The villa is lovely. Starting to show its age in some ways. Good location, especially if you have a car. Walking to the beach is challenging.
Robert C.
July 2026

Fantastic experience! Everything as advertised and described!
Steven J.
July 2026

Great property and condo. Our family enjoyed all the amenities. Would definetly reccomend and stay again.
Wayne M.
July 2026

Excellent location that met all of our family’s needs. Vacation of a lifetime.
Steve S.
July 2026

An amazing property! The check-in process was flawless, communications were excellent, every amenity, including several, we didn’t think about, was provided and top notch! Highly recommended, could not be more pleased!
Wayne B.
July 2026

The unit is beautiful and was very comfortable for our family. The ocean view from the lanai was just perfect! The elevator in the unit was very helpful for my father who has a hard time with stairs. The property management company was very responsive when we needed something or when we had any issues as well. Our only complaint would be it would have been nice if sand toys and bodyboards were with the beach items instead of having to purchase them during our stay.
Gina B.
July 2026

Loved the place. Views of the sunset and ocean are spectacular from the Lanai. Perfect for a large family or group. Rooms nice and spacious. Beds comfortable. Kitchen was very well stocked with plates, dishes, cups, and all that we need. Would stay here again. Pool was very nice. It was like being at a fancy resort pool, without the crazy crowds. Easy walk to the beach. The unit was stocked with plenty of chairs, umbrellas, and other beach equipment.
Daniel W.
July 2026

Great unit, wonderful stay
Lisa K.
July 2026

The location, size, quality, and cleanliness of the villa were perfect for our needs. We enjoyed the large rooms, functional wifi, attached garage, laundry, the lanai, gym, and pool area. The Wailea shops and beach are a 10m walk away. The entire property and neighborhood were clean and quiet for our entire visit. The only (small) problem I had was finding where to take out the garbage, but a quick call to the office resolved that, as the tech stayed on the line and talked me through it as I walked there. We would definitely stay here again.
Tony D.
July 2026

Clean, well stocked home with breath taking views and close proximity to the beach and shops without being fully immersed in the chaos or heavy people trafficThis was the perfect vacation for this family of 6. Thank tou
Nick P.
July 2026

We stayed 3 weeks with 3 generations of our family. Beautiful property in a great location. A couple issues with A/C but nothing major and quick responses when we needed help.
Nicole W.
July 2026

We had such an amazing time! We have stayed at Ho’olei through Grand Wailea for many years, so we’re a little worried that this wouldn’t feel as special. We were very wrong - we felt very pampered from the moment we walked in! They had excellent amenities, and a wonderful welcome basket, complete with coffee - thank you, we needed that! Now that my kids are older, this was perfect. They loved the pool table especially. We hope we get the opportunity to come back again very soon.
Joanna T.
July 2026

We had a great stay at this beautiful property. It is well appointed and is close to everything we wanted to do! The views are great from the back balcony!
Gregory P.
July 2026

We wanted our entire family under one roof, and this home delivered perfectly. Every family member group had their own room, including the grandchildren, who were comfortably settled in the media room on the pullout sofas.The kitchen was impressively well-stocked — so much so that our own groceries could only find a home on the countertops. The lanai was a true highlight, offering lovely evenings outdoors with the convenience of pull-down shades whenever we needed them.The pool was a wonderful fit for our family, and the walk down the hill to reach it was a pleasant bonus. Driving and parking was also an option. Our host was very helpful and responsive questions.We enjoyed a wonderful family vacation!
Clare M.
July 2026

Clean, well appointed, well maintained property. Gorgeous lanai views. Easy access to pool and short trip to beach. Would absolutely book again!
Lori Joy G.
July 2026

Plenty of space for a lot of people to relax!
Melissa T.
July 2026

Great location near the Grand Wailea and beautiful home. Our family could not be happier. Thank you.
Steve S.
July 2026

Everything was even better than expected. We were impressed by the way the kitchen was stocked with every utensil needed and all the supplies provided. It was clean and very comfortable for our family of 8. One minor glitch was that I was notified the unit was ready for us to check in but when we arrived about 45 minutes later, we were met by someone from the office who said she had to do a "security check" before we were allowed to enter, so we had to wait about 30 minutes before we could go in. We did not mind enjoying the Maui sun for a half hour. The only comment was that there were no beaters found for the hand mixer in the kitchen. If that's the only "complaint" from a group of 8, I would say you're doing very well with your preparations! We thoroughly enjoyed the accommodations and would stay there again. Pricey but not excessive for what you get and besides, one must expect to pay for Paradise!
Patrick Y.
July 2026

We had a great week. Property is located within walking distance of many places which worked great for our family. Beautiful place and house had everything you needed - kitchen was well stocked as well as chairs and towels for the pool or beach. Great pool in the neighborhood, and a fairly easy walk to the beach. Would definitely stay here again.
Rosanne P.
July 2026

Perfect upscale accommodations for a family of seven which included three generations- parents, children and grandchildren. Every room was spotless upon arrival. Kitchen appliances and all supplies necessary were available for the eight nights we stayed.Many beach chairs and several coolers were provided in the garage for our day trips to the ocean. These were spotless as well which is saying a lot considering how much sand you bring back from every beach visit. Communication with the host was excellent. We had a fantastic time and highly recommend this Ho’olei condo. We hope to return soon.
Valanna A.
July 2026

Amazing property. Very clean. We will be back.
Todd B.
July 2026

From the moment we arrived, we were impressed with this incredible villa and excited for our stay! The accommodations are spectacular, beautiful, and immaculate! The large chef's kitchen was well-stocked with pots, pans, utensils, and enough supplies to get us through our vacation! The primary bedroom is a lovely sanctuary with its own private outdoor area. All of the bedrooms have comfortable beds and en-suite bathrooms. The lanai and outdoor kitchen were great places for family meals and relaxation. We have stayed in other luxury Vrbo properties, but no others met the attention to detail that Ho'olei 24-1 has. Allison and Dan at CB Island Vacations were professional, gracious, thoughtful, and outstanding! They were quick to answer any questions, and they made sure that our vacation was a fantastic experience!We truly appreciated the thoughtful and generous welcome food gift and the complete organic spice set that was available for our use. Even supplying laundry detergent, dishwasher pods, dish and hand soap, and large shampoo, conditioner, and body wash pumps in each of the bathrooms was much more than most properties provide.Our family of six, including three teenagers, loved this home! The location is amazing! The villa is a 2-minute walk to the beautiful pool and gym and a few more minutes to the beautiful beach and Grand Wailea across the street.We have fabulous family memories of an outstanding stay at Ho'olei 24-1! Mahalo!
Marilyn M.
July 2026

Communication was excellent!
Jerome R.
July 2026

The place is everything you could hope for we loved our stay and would definitely stay there again
Gary C.
July 2026

This condo was beautiful. It had a fantastic view for the sunset every night. The rooms were spacious and modern. One of my favorite places to stay. Will definitely book this condo again.
Bryan S.
June 2026

Place was spot on to the pics and description. Amenities and location are top notch. Will definitely be staying here again in the future.
Jason A.
June 2026

Amazing view from the balcony. Loved grilling out there for our family while watching the sunset. Very spacious unit for our family of 5. And an even closer walk to the beach than we had anticipated. Highly recommended!
Mike E.
June 2026

We just returned home after spending a week at this beautiful condo. This was the perfect home away from home for our family of four, plus Grandpa! Things we loved: the lanai for morning coffee and sunset dinners; the kitchen was perfectly sized; and I loved that cooking didn't feel like work with such a breathtaking view. The bedrooms with ensuite bathrooms were perfect for our setup - everyone had their own, which was really nice. Plus, a powder room on the main level! I learned that I loved memory foam mattresses (the master bed was so comfy!), and the huge shower in the master bedroom was heavenly. Honestly, everything about the home felt perfect! Thank you for supplying shampoos, body wash, detergent, dish soap, etc. That made it very easy to move right in and feel at home. My only disappointment was having the non-working elevator. I could have sworn it was marketed with an elevator when we booked 6 months earlier. It ended up working out, but I would have worried a lot less had we had one. I'm not sure if the elevator will eventually be repaired, but that is my only red flag for future renters. If you have someone with accessibility needs, please confirm before booking. Even with that, we'd give the property five stars. It was really beautiful, and the neighborhood's location was perfect!
Amy M.
June 2026

Very easy to work with our host. We had a couple of asks and they were very accommodating. We will definitely rent from them again. The Villa is an easy walk from the Grand Wailea and the ocean. Although we actually preferred hanging out at the Villa pool. It was less crowded and more refined. Thanks again for a great week.
neuhausr
June 2026

We enjoyed our week in Maui. The house was as pictured and close to restaurants at the resorts. The host answered our questions quickly. We enjoyed the pool close by down the hill. The beach was also down the hill and after the Grand Wailea resort. The lanai had a lovely view and the kitchen was well stocked.
Grace T.
June 2026

This was by far the best VRBO we’ve ever stayed at! The hosts were fantastic, the location was close to everything we wanted to do, and there was more than enough space for our entire family to relax and enjoy our vacation. The home was clean, comfortable, and had everything we needed for a great stay. We highly recommend staying here if you’re visiting Maui—you won’t be disappointed!
Aliyah G.
June 2026

Absolutely perfect home for our trip. Beautiful view, close to shops, restaurants and beach. The house we so comfortable and has everything you need. Kitchen was perfect for cooking meals there and we loved relaxing on back deck. Would absolutely come back to this home when we visit Maui.
Brooke H.
June 2026

Great week at Ho’olei. The kitchen and family room areas are awesome. The unit is a short walk to the beach, shops and restaurants. The property management was helpful and responsive.
Jeff K.
June 2026

Beautiful facility with all the amenities and incredible view.Only two recommendations going forward. The first would be to get a new dishwasher or at least the internal components and provide access to the grand Wailea facilities.
Robert W.
June 2026

Wonderful house and wonderful vacation
Sandy W.
June 2026

Beautiful accommodations with stunning views. Fully equipped, hosts thought of everything to make our stay easy and enjoyable. We loved it!
Shawn A.
June 2026

Great property, awesome patio. Only critique, bring an extra blanket for beds, aheets very thin.
ryan w.
June 2026

Great location and beautiful villa. We had 8 people stay on a family vacation and everyone loved it. The pool was nearby and an easy walk to the beach and great shopping area.
Matthew O.
June 2026

We spent 4 nights at the property and everything was great. The unit itself was clean, had everything needed for a comfortable stay and was very well appointed. The view was absolutely amazing, the property had great pools & amenities and the communication with the property management was excellent. We loved the unit and would book it again without hesitation. Highly recommend.
Jim D.
June 2026

We had a great stay! The location was excellent, and the amenities were fantastic. We had a group of nine people, and there was plenty of space for everyone to be comfortable. Everything was clean, well-maintained, and made for a relaxing and enjoyable experience. We would definitely stay here again and highly recommend it to larger groups visiting the area.
Kaitlyn R.
June 2026

We had a wonderful time. The condo was perfect. We had everything we needed. Matt was a gracious host and made us feel welcome. The location was prime. Just across the street from the beach in beautiful Wailea.
BARBARA JANE D.
June 2026

This is a beautiful property in an excellent location -- easy walking distance to the beach and just far enough away for a chill experience at the complex's pool or on the property's lanai. Beautiful ocean views.My husband and three adult kids enjoyed this property. There was plenty of room for everyone. The kitchen is well stocked for cooking and entertaining. All of the bedrooms and bathrooms were very nice and comfortable. The stocked beach items (chairs, umbrella and wagon) in the garage were very much appreciated. The unit is also beautifully decorated in a very tasteful Hawaiian theme. We would definitely stay here again.
John M.
June 2026

Our Wailea Villa was Amazing! Everything was perfect including location (near Grand Wailea, Four Seasons & The Shops @ Wailea), amenities, large kitchen (with every appliance or utensils) to the outdoor kitchen/sitting areas, the elevator AND the pool! We were in paradise! Mahalo
Teresa H.
June 2026

From the Moment we arrived to this 21-6 unit at Ho‘olei, it truly felt like a luxury retreat! The villa was so beautiful and modern, with upscale furnishings, thoughtful design, and a warm comfortable feel throughout. The whole home and especially kitchen are stocked with everything and anything you could need.The bedrooms and living spaces were open and comfortable, and every detail seemed carefully considered. I appreciated the extra nice bedding, and the primary bathroom was a highlight for me - especially the large soaking tub which was perfect for unwinding after a long day out and about. One of the things I loved most about Ho‘olei and this Unit in particular was how peaceful and secluded it felt. The setting is quiet and private with the layout and surrounding tropical landscaping, yet still close to everything Wailea has to offer. The four seasons is right across the street and it was so nice to be able to walk there for dinner and back :)We also ESPECIALLY enjoyed the beautiful and lush pool area, which was peaceful, open till 10 pm and never felt crowded. I would happily recommend it to anyone looking for a one-of-a kind Maui getaway. We left feeling refreshed and already looking forward to a return visit!
Lindsey S.
June 2026

It is a lovely condo. The highway noise was bad when sitting out on the lanai, but the garden view is so peaceful. Short walk to the pool, and our teens walked to the shops at Wailia every day for coffee and shopping.
Pam B.
June 2026

Enjoyed a 70th birthday for my husband . Couldn’t find many 4 bedrooms with Queen/King beds this is a plus when renting as a group. Had all the amenities you need for BBQ’s and big breakfasts!! Love the walks on the beach and swimming in the pool. Everything was perfect. Thanks
Colette a.
June 2026


Or feel free to contact us if you need help finding a place to stay. We are Hawaii's vacation rental experts.

Oceanfront Rentals

hawaii condo resort
Discover Maui's best oceanfront rentals, all with beautiful ocean views.
Oceanfront Rentals

Rental Search

hawaii condo
Use the rental search page to find the best rentals for your preferences.
Rental Search

Condo Guide

Hawaii condo guide
Research the options with the world's most comprehensive Maui condo guides.
Maui Condos