Elegant private lanai off of the spacious living room

Enjoy a BBQ on your private lanai with your O'hana (family).

BBQ area on the lanai off of the living room to enjoy

Enjoy the beautiful tropical view from the large private lanai.

Open Gallery

Elegant private lanai off of the spacious living room
Enjoy a BBQ on your private lanai with your O'hana (family).
Seating for 8 on the spacious lanai
BBQ area on the lanai off of the living room to enjoy
Enjoy the beautiful tropical view from the large private lanai.
Seamless outdoor/indoor living while enjoying your Maui vacation
Relax in comfort
Incredible view from the living room
Luxury living while on your Maui vacation!
The chef in the family is sure to enjoy this beautiful kitchen
Seating for four at the island
Spectacular view while cooking with a gas stove top!
Plenty of beautiful counter space to create Maui meals!
Upstairs half bath off living room!
Entry way stairs!
Downstairs bedroom with access to lanai!
Downstairs bedroom features a comfortable king bed
Downstairs lanai off bedroom
Spacious lanai off the downstairs bedroom
Beautiful primary bathroom upstairs
Spacious primary bathroom
Tiled walk in shower in primary bathroom
Enjoy relaxing on the private lanai
Private lanai off the downstairs bedrooms
Downstairs primary Bedroom!
Downstairs primary bedroom with access to lanai!
Downstairs primary bedroom features a king canopy bed!
Primary bath with soaking tub!
Relax after a fun filled day of Maui!
Plenty of space to get ready for Maui adventures!
Tropical decor in the guest bedroom!
Guest bedroom features two queen beds.
Two queen beds in the guest bedroom
Downstairs second bathroom!
Tropical paradise awaits!
Welcome!
Community area to gather with family and meet new friends!
Fitness center at the Ho'olei
Fitness center
Cool off under the falls in the pool
Lounge poolside and soak up the Maui sunshine!
Cool off in the pool after lounging in the Maui sun!
Come on in!
Relax in the shade and enjoy the Maui breeze
Plenty of space for friends and family
Maui awaits!
Tropical Paradise awaits
Imagine cooling off under that waterfall
Lounge around the pool and enjoy your vacation!
Paradise awaits!
Relax in the shade
Enjoy swimming while watching the palms sway in the breeze
WELCOME!
Aloha!
Take in all that Maui has to offer!
Birds eye view!

Gallery View

Ho'olei 55-2

Wailea

3 Bedrooms 3.5 Bathrooms 8 Sleeps 2619 sq. ft.

Description
Rooms
Amenities
Reviews
Calendar
Location

This property is hotel zoned, and not being affected by the recent proposed legislation.

Relax and enjoy your Maui vacation in this spacious and gorgeous villa located at Ho'olei. The top floor includes a beautifully designed living room, featuring a 70 HD TV with surround sound, premium channels to enjoy, and complimentary wifi throughout the unit. The open floor plan flows into the gourmet kitchen, featuring a gas stove top of the line appliances, a large refrigerator with multiple freezer drawers, and is fully stocked with cookware, plateware, and glassware. Easily transport your groceries and luggage upstairs with your own personal elevator located in your unit!

The living room seamlessly flows outdoors onto the spacious covered lanai through stackable sliding glass doors. Enjoy outdoor seating, a large outdoor gas grill, and a mini fridge.

The primary Bedroom is located on the lower level and features a King Bed, large ensuite bathroom with soaking tub, walk-in shower, dual vanity sinks, and a walk-in closet! Enjoy your own private ground floor outdoor lanai with lounge chairs. The second primary Bedroom is also located downstairs with a King Bed and a full ensuite bathroom. The top floor features a guest bedroom with 2 full beds and a private ensuite bathroom. The main living area also has a half bath to use as well.

Additional amenities in the unit include full central AC, a private elevator within the villa, a full-sized washer and dryer, a private garage, covered carport across the driveway for a second vehicle, beach chairs, and beach towels to use at the beach or at the property pool!

Ho'olei property features a stunning pool with a waterfall, sandy beach area for children, and 2 Jacuzzis to enjoy. Feel free to take the beach towels provided in your unit down to the pool to use! There is also a fitness center to use next to the pool area, and a covered kitchen pavilion. Poolside massages are also available! This is a gated community with 24-hour security available.

Beach access is located directly across the street through the adjacent resort. You are able to dine at any of the resort's restaurants, as well as set up spa appointments at nearby properties, but please note that pool access at the adjacent resorts is not included with your reservation at this Ho'olei villa.

While we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve.

Hawaii Tax ID #: 130-596-9664-01

Rooms

Primary Bedroom

1 King

Guest Bedroom

1 King

Guest Bedroom

2 Queen

Amenities

Essentials

Air Conditioning
Dryer
Garage
Living Room
Parking
Iron & Ironing Board
Kitchen
Private Entrance
Shampoo
Washer
Linens
Washer & Dryer
Bed Linens
Hair Dryer
Wifi
Towels
Hot Water
Wireless Internet
Free wifi
Cable
Wifi speed 100mbps

Kitchen

Cooking Basics
Dishes & Silverware
Dishwasher
Microwave
Oven
Refrigerator
Toaster
Stove
Blender
Cookware
Garbage Disposal
Utensils
Ice Maker
Coffee Maker
Kitchen Island
Dining table
Rice Cooker
Tea Kettle

Facility

Free Parking
Gym/Fitness Room
Jacuzzi
Pool

Outdoor

Patio or Balcony
Balcony
Gas Grill
BBQ Area
Deck Patio Uncovered
Grill
Lanai Gazebo Covered
Tennis
Golf
Tennis
Fenced Pool
Fenced Yard
Outdoor
Deck
Outdoor Grill

Pool

Communal Pool
Hot Tub

Accomodations

Ceiling Fan
Dining Area
Dining Room
Tub/shower combination
Luxury
Cleaning: Optional
Other: Massage
Pets Not Allowed

Location

Wailea
Near Ocean
Beach

Car

Recommended

Special

Beach Chair
Beach Towels

Family

Bathtub
Children Welcome

Entertainment

DVD Player
Satellite or Cable
Television
Smart TV

Accessibility

Elevator

Reviews

5.0

(55 Reviews)

Write A Review

January 1, 2025

Highly recommend!

by Colm H

Great location, very close to the pool complex and front entrance, and 3 minute walk to beach. Unit was very clean, modern, spacious, stocked well with everything you need, and check-in and out was very smooth. Would highly recommend for a family or group.

September 4, 2024

Perfect Accommodation

by Carrie B.

Great location, perfect accommodation for my family of 5. Will be back!

September 4, 2024

Lovely and relaxing

by Beth H.

This home was so lovely and relaxing. The perfect place to stay to decompress and enjoy Maui.

July 29, 2024

Great place to be

by Yamila N.

Is a great place to be in Maui! The house has everything that you need to feel at home Thank you !

July 29, 2024

Terrific stay

by Seth F.

Great stay!!! We were given clear instructions for finding the place and getting in. Monique met us at check-in to show us around. The place was immaculate and very clean. We are a family of six, and it was quite comfortable ... plenty of space, i.e. no sofa sleepers required. Plenty of beds and bathrooms for all. Also, you get your own garage, which is great for the car. Almost beside this condo, there is a wonderful pool with waterfall and sand pool for kids, along with an great fitness center. The condo was well-stocked with towels, sheets, pillows, paper towels, kleenex, toilet paper, etc. We were given some shower amenities as well. The kitchen came with all the appliances you should need, but our favorite was a high-end Keurig, stocked with coffee. Oh, and a nice gift basket as well! The location is excellent, just across the street from the Grand Wailea. We really enjoyed the Wailea Beach Walk. In short, it was a terrific stay!

June 5, 2024

The home was perfect!

by Pam B.

We came to Hawaii to visit our son and grandchildren who live in Maui. This home was perfect for our needs, well stocked, and the pool area was fantastic.

May 14, 2024

Views are beautiful!

by Sandra W.

This was my first time using VRBO and I picked the best property. Views are beautiful, rooms are beautiful, location is great, everyone is friendly, pool is nice and my family was very happy. Thank you for the experience. I will be sure to return.

May 14, 2024

Very happy!

by Victor L.

We couldn't be happier with the accommodations. Everything was as listed and expected. CB Island was great - they met us for check-in and showed us around. We would definitely return to this property and/or other CB Island properties.

May 14, 2024

We had a great stay!

by Steven T.

We had a great stay with our family at the house. Exactly as described and spotless. Monique met us to show us around and was available the entire time with recommendations and answer any questions. Great spot for kids as it is close to the pool and the beach is very nice and kid friendly. The kitchen, grill, and lanai were great for meals at home. Would love to stay again!

April 1, 2024

Perfect Rental Spot

by Mark Wood

First time to Maui and first time staying at Ho'Olei. We will definitely be back and will stay at this property again. Everything was top notch and better than expected. The location is perfect for couples or families. A+++

February 5, 2024

Fourth time -every time - is a charm.

by Debbie LaCour

A lovely stay at Ho Olei. The villa is beautifully and comfortably decorated. Feels like vacation. The minute you enter!! This was our 4th stay at Ho Olei, and second through Coldwell. We were very happy with the service. Any questions we had were answered immediately. Thank you for a great week!!

October 17, 2023

FABULOUS SPOT

by Carmen R.

This property is super well maintained, the pool was fun and just a short walk. The condo was clean and well stocked with basics. The master shower was to die for!! My family and I highly enjoyed our time in this condo and would love to come back!

We are thrilled you enjoyed the luxury of Ho'olei, that master bathroom is truly something else! We are so pleased you loved your time here and would love to have you back anytime. Ho'olei 55-2 will be here waiting for you! Mahahlo!

October 5, 2023

Family trip

Our family enjoyed our stay here, but it was a bit topsy-turvy. The oven did not work in the unit and then we were asked to move units due to a "water leak". We never saw one and then never saw any workers there. It was very inconvenient to move 10 people during the middle of our vacation, but they did compensate us well for these difficulties. They made other promises along the way that they did not deliver on. This is an area for improvement. The units themselves and the location is beautiful.

August 7, 2023

Maui Family Vacation

by Christine J.

This is a great property in a beautiful area! The villa was very clean and had every amenity we needed. The closest beach is a short walk and so beautiful. Being able to walk to the Shops at Wailea was also a big plus. There are so many shops and restaurants within a 5-10 minute walk. I would definitely recommend this property and I would stay here again. Also the promptness with replies to any questions or concerns was exceptional!

July 17, 2023

Great Stay, entire family LOVED it

by Christopher C.

Our family of 8 had a great time at this residence. Everything was very clean and nice. Towels and beach chairs provided which was amazing. Washer and dryer was SUPER convenient to have. Easy access to Wailea as well as the pool in the community which the kids loved. Highly recommend!

May 11, 2023

Can not say enough great things!

by Sarah B.

This vacation rental was wonderful! The villa was beautifully appointed and offered great space - we loved it! It was a quick walk to Wailea Beach and the Ho'olei pool, which was wonderful & bigger than anticipated. The CBIP staff was great and the welcome basket was a nice touch. Shopping & restaraunts nearby. Would recommend the Luau at Wailea Beach Resort (was better than Grand Wailea and still walkable). This villa also had an elevator, which ended up being really convenient for transporting luggage upstairs.

Aloha Sarah, Thank you for your positive feedback! We're delighted to hear that you enjoyed your stay at our vacation rental. We take pride in our well-appointed villa, convenient location, attentive staff, and thoughtful amenities. We appreciate your recommendation and hope to welcome you back in the future!

May 7, 2023

Maui Family Fun

by Keith S.

Flawless experience from booking to checkout. The villa was exactly as advertised and just what we were looking for! Felicity was exceptional and was able to accommodate our request for an early check-in (we’re staying across the street at the Grand Wailea). She met us at check-in to walk us thru the property and answer any questions which was appreciated. The unit was so close to the pool and a short walk to the beach which we did each day. Will definitely look to stay here again when we plan our return visit to Maui!

Aloha Keith, Thank you for booking with CB Island Vacations and sharing your flawless experience! We're delighted to hear that Felicity provided exceptional service and the villa met your expectations. We appreciate your kind words and look forward to hosting you again on your next Maui visit!

April 11, 2023

Beautiful Home!

Everything was perfect. The house had everything you could think of for a great Maui Experience. We especially appreciated the beach chairs, towels and beach umbrella's. Made going to the Beach very easy.

Thank you for taking the time to review your stay at our condo. We're delighted to hear that you had a great Maui experience and that our condo had everything you needed for a comfortable stay. We understand the importance of having beach essentials readily available and we're glad to hear that you found our beach chairs, towels, and umbrellas to be useful. We hope to welcome you back soon for another wonderful stay!

March 18, 2023

Nice place to stay in Wailea

Comfortable, nice amenities, good proximity to hotels/restaurants. Secure and spacious for 7 of us.

Aloha Nicholas, Mahalo for staying with us at CB Island Vacations. We are delighted to hear you enjoyed your visit and hope to host you again soon.

February 22, 2023

Amazing Stay

by Ryan T.

We had an amazing time here. Check in and out was easy and smooth. The room was immaculate, clean, well stocked, and very high end. We could not ask for a better place to stay!”

February 11, 2023

Maui

by Estephan A.

It was great!

July 14, 2022

Well appointed and great place to stay with family!

We stayed as a family of 8, including two small children. We found that this villa was spacious, clean and a great layout for our family. One of the things I love staying at a hotel is for the concierge services. I did not miss that while staying at this villa. I was able to rent baby gear, get extra blankets and arrange for massages (autumn was amazing!) easily and conveniently via text. This location is perfect because you have easy access to the pool and the beach access and mall are in walking distance. We also walked to the Akamai coffee shop, which has fantastic coffee and lilikoi morning buns - important for those early morning jetlag induced wake ups!

June 6, 2022

Wailea family vacation

by Linda P.

Beautiful spot. Customer assistance was fantastic. House is beautiful and easy to maintain. Kitchen was great. Property very clean and very comfortable.

Aloha! So happy to hear you enjoyed the condo and that the customer assistance was fantastic. We strive to provide excellent service and receiving this feedback is great to hear. We hope to welcome you back to Maui soon!CB Island Vacations

April 18, 2022

A wonderful experience!

by Charles R.

We are so happy that we chose 55–2 Ho’ole. It was a beautiful villa with everything that we could ever ask for. A great location, a beautiful swimming pool for our young grandchildren, and a perfect layout for two grandparents and their young family. The two master bedrooms downstairs were comfortable and quiet, leaving an upstairs bedroom for the three children with their own TV. The beach is a reasonable walk away. The quality of the villa and the furnishings were excellent and we were very proud to stay there. we thought that it was reasonably priced for the quality we received. Coldwell Banker‘s was great to work with prior to the trip and during the trip. we would not hesitate to recommend this beautiful home.

April 12, 2022

Wonderful experience

by Joshua M.

We were very happy with our experience at Ho'olei! We had one issue with the toilet and someone came right away to fix it. We also had some miscommunication in terms of getting in but the management was right on top of it and this got resolved very quickly. Otherwise, the place was great, clean and all was in good order. The property description was accurate in all regards. We loved the proximity to the pool and to exit the property. The pool was great and the proximity to other hotel properties and retail centers was great. Also walking distance to a nice stretch of beach was really wonderful. The actual property was a beautiful space indoor and outdoor and they had everything that you could want in the kitchen and elsewhere. We would highly recommend this property for other families and would definitely come back for a future vacation.

March 21, 2022

Ho'oeli 55-2

by Suzanne K.

it was great! we really enjoyed it. only suggestion would be to provide more towels (regular towels not beach towels) so we don't have to launder every day.
other than that, all good

Aloha Suzanne,Thank you for staying with us, we love to hear how much you enjoyed your stay! Thank you for bringing the bath towel quantity to our attention, we will do an inventory check and add more! We look forward to having you back, mahalo.

January 31, 2022

Perfect Location in the Heart of Wailea

by John N.

The unit was great. It was exactly as advertised. The location was ideal to the pool and the walk to the beach. It provided many items such as beach towels and chairs which were utilized repeatedly. Ideal for families of 6-8 people. The property is well cared for.

Aloha and thank you for the great review. What a delight to read the notes from your recent stay! We make every effort to keep the unit well stocked and have everything you need at your fingertips for an enjoyable stay. We are happy that Maui has provided you with amazing views in such a great location. We look forward to welcoming you back for your next Maui vacation. Mahalo!

October 29, 2021

Great Stay

by John M.

Spacious and well appointed place! Good location. Quiet. Highly recommend!

August 19, 2021

Beautiful vacation with an ocean view

Great location and amenities. Quick walk to the beach. Convenient personal garage and car port parking for a second car. Responsive host who helped to fix the kitchen faucet with great response time.

March 10, 2021

Fantasy Island

by Nova L.

If I were to be a character on fantasy island this would be the home in which I would live out my most audacious dreams. Falling asleep on a mattress made of clouds to the gentle sound of ocean waves and awaking to a short stroll through tropical gardens to the beach could made anyone dream come true.

Aloha Nova,We love to hear such great feedback! We agree, this is where we would call home too! We look forward to having you back again in the future, mahalo.

January 11, 2021

Sweet Maui Retreat!

by Rita B.

Ho’olei 55-2 is a wonderful and spacious condominium. The kitchen is well stocked, the furnishings are lovely, and the towels and linens plentiful. This condo is a short walk across the street to the beach and is immediately next to the gym and condo pool. Maui is simply spectacular!!

Aloha, We are so happy that your experience far reached your expectations during your stay here on Maui. This property is so welcoming to our guest and we are so happy that you felt so relaxed and enjoyed the furnishings and thought the towels and linens were plentiful. While we try to make your experience here a special one, we also want to make sure that the kitchens are updated and are stocked so that you have everything you might need at your fingertips. We look forward to booking your next vacation here with us in the very near future!Mahalo!

December 30, 2019

Very nice property

by Carl W.

Wonderful location super relaxing. Walking distance to beach plus restaurants. Did a family meet up with my family from and had a great time.

December 18, 2019

Great find, perfect for a family or larger group.

Wonderful location, beautiful condo, had everything inside that we needed to enjoy our vacation. Stayed there with a large group of friends and everyone was able to have their space. I would stay there again.

October 21, 2019

Hawai’i vacation

by Randy N.

Experience was great, location was excellent. Villa was well maintained, clean, updated.

September 11, 2019

Ho’olei 55-2

by Margaret G.

Great location. Really enjoyed the pool

Aloha Margaret,Thank you for staying with us at Ho'olei 55-2 and we hope to be able to accommodate you again on your next visit to Hawaii.CB Island Vacations

July 26, 2019

July 18 - 24th

The unit was just as described. There were 7 of us and we all enjoyed the home. Plenty of appliances, spices, cookware. Location is perfect for a nice mooring stroll. Beach is not far away. We enjoyed our time and I will definitely use this unit again on our next trip to Hawaii.

April 17, 2019

Perfect stay

by Nick S.

The team welcomed us upon our arrival and gave us a tour of the house.
We loved staying in this house, location is perfect and the entire resort is clean and in a high standard. Pool is great and very close to the house.
Our kids loved it too.
We'll definitely stay here again next time.

March 12, 2019

Great place!

by Kathleen E.

Very nice location near pool and main gate. Very comfortable unit. Loved our stay here.

January 20, 2019

10 out of 10

by Adam S.

The pictures do it justice.

We just stayed here with a group of 6 and we were not disappointed. Spend as a little or as much time at the villa or head out on out and explore Wailea. Little Beach, Big Beach, and Lava Fields are all a short drive away.

The resort pool complete with hot tubs is dream-like.

January 14, 2019

Excellent property!

Perfect location, beautiful property. The home is well maintained and just like the pictures. Short walk to the beach.

December 5, 2018

Tudor Maui Vacation

by Michael T.

Unit 55-2 at Ho'olei was absolutely perfect for our family. There was more than enough space, it was very nice and in a beautiful setting, and very conveniently located next to the pool, gym and Grand Wailea. We simply loved it!

October 29, 2018

1st timer in Maui

by Greg E.

Our stay at this property was everything we wanted! The proximity to beaches and restaurants as well as the excursions we wanted was perfect. The property was very clean and provided ample space for the three couples we had staying there. The staff was wonderful and quick to respond to any questions that we had. We would love stay there again on our next visit!

October 11, 2018

AAA+ accommodation, beach and pool

by Samira M.

Ho'olei is located in Wailea, Maui at the beautiful Wailea beach. Peaceful and not over crowded though it helped that we went in October. The pool was very clean and quiet and the beach was a 5 min stroll away. The house was very clean, spacious and we enjoyed having the space when there are 6 of you in the family. Lovely place, highly recommended.

September 8, 2018

Great Maui Trip!

The house is perfect and had everything we needed. We had the best trip and the house was a big part of it!

August 24, 2018

Fantastic Villa

by Connie P.

Wonderful property. Rooms were nicely appointed. Perfect for two families. Kitchen well stocked. Sunset views were amazing. Easy walk to beach and nice pool. Clean and extremely comfortable. We loved every minute and hope to return.

August 19, 2018

Fantastic home and vacations!

by Jehyeong A.

Ho'olei 55-2 was exactly the same as photos. We stayed 4 days at Ho'olei 55-2. We were happy during our stay.
The accommodation was well located and in excellent condition.
Everything was great but, there was a slight inconvenience.
The bathroom pressure on the upper floor was a little low, and the sink in the lower small room was not drained well.
But, It'S not worth a ****.
I highly recommend Ho'olei 55-2 for family tourists.

August 12, 2018

August 2018

The condo was fabulous - luxurious, clean, comfortable!!! Great pool facilities and not too crowded. Close to shops and restaurants. Perfect choice for my family.

August 5, 2018

Review of Ho'olei 55-2

by Dave S.

Absolutely the best accommodations we've ever had. We've stay at Four Seasons, Kea Lani , Grand Wailea, Polo Beach and Makena Surf. Latest is Honua Lei i Kaanapali, which is very nice as well. But this was the BEAST by far. I took Sons family and 2 grandsons Room set up was ideal. Cant say enough good things

June 25, 2018

Delightful Stay

by Neil B.

The property is ideally located, just across from the beaches at Grand Wailea. Well stocked and with the absolutely necessary air conditioning. The property management company were really great. Prompt responses and help when needed. Thanks Josh.

June 16, 2018

Amazing!!!

by Robert D.

This is the best place we’ve have stayed in Hawaii. Great layout, great pool, great location! We couldn’t have asked for anything more.

May 25, 2018

A lovely place for family

by Diane P.

The condo was well equipped, clean and very well located. The management company was helpful if needed anything.

March 6, 2018

Maui How's O'Reilly vacation

by Wendy K.

This was our 2nd year staying in this condo. We love it!

March 2, 2018

Great family vacation

by Tina F.

The condo was just as nice as it’s pictures. There was lots of room for everyone to gather in the kitchen or lanai. The access to the beach was a easy short walk as stated. Would definitely recommend to anyone.

January 2, 2018

55-2 review for week of 12/24/17

Great location and property. Close to the pool and workout facility and 10 minute walk to the beach with access to chairs and umbrellas.

October 26, 2017

My 70th Birthday celebration

by Lamont & Margot M.

This was a special and important birthday celebration and vacation. My stay in Ho'olei 55-2 was exceptional. All of our expectations and accommodation were realized. All of our guest were throughout impressed with the condo and the amenities. Additionally, the weather, golf, and food was outstanding!
Thank you CBIP and Matt for your attention to the details, and follow up to ensure that our stay was was exceptional. Mahalo

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