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Compare 55 Villas in Kaupakulua with updated reviews, rates, and availability.

Gated 2-story beach house with big yard
Exterior

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (40)
"We had a great time in Kihei and the place was perfect for my family. The yard was amazing and we could walk to the beach!"
Gated 2-story beach house with big yard
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-
Spacious open floor plan with stackable patio doors

Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-

9.6 out of 10, Exceptional, (66)
"Everything was fabulous from our contact with Monica to get us checked in and deliver packages shipped from home to the beautiful accommodation to the pool to the location. We will be back with our family of 8 very soon."
Special Promotions! Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-
Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance
Fabulous heated~ private~ plunge pool to enjoy!

Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance

10.0 out of 10, Exceptional, (2)
"This villa was beautifully decorated, super clean and very convenient yet private and quiet. CB Island vacations was so attentive, and knowing it was my birthday, rewally surprised us at our welcome . Everything was perfect...really. Barbara"
Stunning 3BD/4BA Andaz Villa! Huge Private Yard with Pool! Modern Beach Elegance
Experience Ho'olei 24-2! Gorgeous 3 Bedroom Garden View Villa at Ho'olei!
Oversized lanai surrounded by lush tropical foliage

Experience Ho'olei 24-2! Gorgeous 3 Bedroom Garden View Villa at Ho'olei!

9.6 out of 10, Exceptional, (40)
"This was the perfect unit for our family of four. From the three bedrooms, to the spacious lanai, to the short walk to the pool, it fit all of our needs. The short walk to the beaches and shops and close proximity to golf courses were a bonus, as well. While we were out enjoying Maui during the day, we looked forward to coming back to our beautiful condo in the evenings. The kitchen was very well equipped and the washer and dryer gave us a mid vacation wardrobe boost. The communication was spot...
Experience Ho'olei 24-2! Gorgeous 3 Bedroom Garden View Villa at Ho'olei!
Aloha Villas Resort | 12 Bed, 12.5 Bath
view from villa 1 lanai

Aloha Villas Resort | 12 Bed, 12.5 Bath

9.8 out of 10, Exceptional, (43)
"No detail, communication or service was less than spectacular. From the fully equipped villas to games and lush greenery, we enjoyed our home in paradise for two weeks. Thank you to Jude and Mary for promptly responding to our needs throughout our stay."
Aloha Villas Resort | 12 Bed, 12.5 Bath
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Ocean view from upper lanai

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

10.0 out of 10, Exceptional, (51)
"Communication prior to going was easy and thorough. Condo was lovely and clean and well equipped. Property grounds were beautiful and very well maintained, with a gorgeous pool and gym. If issues came up response was quickly handled...there are many battery operated blinds in the home that need charging prior to guests' arrival. One of the blinds didnt work and it was fixed that evening. The view is spectacular from the upper sitting area! Property itself is up a hill, across from the...
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Book 5 Nights, Get 6th Free + Late Check-Out!
Sit back and relax on the large private lanai

Book 5 Nights, Get 6th Free + Late Check-Out!

10.0 out of 10, Exceptional, (8)
"This was the best location, easy to get to beach and mall"
Book 5 Nights, Get 6th Free + Late Check-Out!
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
Direct oceanfront views!

New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202

10.0 out of 10, Exceptional, (1)
"Lovely residence. Beautiful views of water and beach."
New Listing! RARE, DIRECT OCEANFRONT Wailea Beach Villa B202
Free Night! Free Late Check Out! Free Future Stay!
Floor to ceiling pocket doors with ocean views from sofa

Free Night! Free Late Check Out! Free Future Stay!

10.0 out of 10, Exceptional, (72)
"We have stayed in Wailea many times and at this property(not this unit) before as well. It was almost perfect with the exception that my wife would like to see bathrobes . Whatever . It was perfect. "
Free Night! Free Late Check Out! Free Future Stay!
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
Enjoy your indoor/outdoor living space with amazing ocean views!

Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

10.0 out of 10, Exceptional, (60)
"A beautiful property with all the amenities you could ever need. "
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY
Living area

I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (1)
"Loved the location! right next to shopping dining loved adult pool with another pool for children property”feels” smaller beautiful patios with waterfalls running nearby the property landscaping is lush and beautiful"
I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY
Oceanview Penthouse, sleeps up to 16 guests!
Lele Penthouse Living Area

Oceanview Penthouse, sleeps up to 16 guests!

9.6 out of 10, Exceptional, (13)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Ocean view from upper lanai

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

10.0 out of 10, Exceptional, (51)
"Wrong entry code for property gate. Snuck in with a car who went around us. Never received a “personal code” to actually enter the unit. Waited in garage for a return call that thankfully granted us access Everything was great after that except that only one card worked for the unit out stay. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Breathtaking view from the adults only Makai pool

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

10.0 out of 10, Exceptional, (65)
"We were there for our 50th anniversary with family- 4 adults and 2 children! Great location, beautiful condo "
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

9.6 out of 10, Exceptional, (47)
"The property was very nice. Great location. Very clean. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Living room with modern decor

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.4 out of 10, Exceptional, (62)
"This was our second time staying in this unit, and it was just as great as the first. Perfect location, well-priced, and comes as advertised. Will continue to recommend for anyone staying on Maui!"
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Living area

I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (23)
"We love the house. It was perfect for the family. The only downside was the master bedroom is very warm compared to the rest of the house. Also, there is mold in the master bathroom shower but overall it was a great place to stay. The pool is very nice And the location can’t be beat. "
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Full ocean view~ with direct views of the neighboring islands

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (24)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Free Night! AMAZING LOCATION in the HEART of WAILEA!! WBV H102!
Open~ Airy and Bright Floor Plan!

Free Night! AMAZING LOCATION in the HEART of WAILEA!! WBV H102!

9.8 out of 10, Exceptional, (60)
"We were there for a conference next door at the Marriott but staying in this unit (for the second year in a row) gave us a perfect retreat from the day-to-day commotion of the venue. Always impeccably maintained and supplied!"
Free Night! AMAZING LOCATION in the HEART of WAILEA!! WBV H102!
Ho'olei 55-3 gorgeous upscale living!
Gorgeous Private lanai!

Ho'olei 55-3 gorgeous upscale living!

9.8 out of 10, Exceptional, (51)
"Clean, beautiful area and property. Highly recommended. Easy access to public beach."
Ho'olei 55-3 gorgeous upscale living!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kaupakulua

Aston Maui Hill
Aerial view

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (752)
"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...
Aston Maui Hill
Maui Beach Vacation Club
Aerial view

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (699)
"Great!"
Maui Beach Vacation Club
Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (494)
"It is a nice rental property in a nice location overall. It has multiple buildings and units with b ACH direct access. There are several swimming pools, many people have fun playing in swimming poor. Also it is one of best sunsets from the main swimming poor and from the central lawn field. I am really enjoyed. The unit we stayed is large one bed room equipped with a full kitchen set, if someone like cook inside. There are many high ended restaurants and a shopping mall in a short during...
Wailea Ekahi - CoralTree Residence Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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