Pililani means "close to heaven", which is an appropriate expression for this property. The magic of this land clearly speaks for itself, let alone the fabulous house and the many wonderful amenities. This is a heartful, warm and cozy place which is also cheery, vibrant and fun. Pililani is the ultimate gathering place for two or ten, for friends or families. When walking through the beautifully landscaped grounds, whether picking tropical flowers or sampling the fruit from the orchards, you can

5 Full Baths

5 Bed

10 Sleeps

Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the side of the volcano. The guest cottage is nestled into a private setting, with no close neighbors, plenty of privacy and an ocean view to the east, and Healeakala view to the side. The main house sits at the top of the hill, but does not interfere with the privacy of the cottage. We aspired not to a tai

1 Full Baths

2 Bed

4 Sleeps

Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the side of the volcano. The main villa sits at the top of the hill, with the privacy protected by an entry gate. We aspired not to live in a tailored gated community but rather to a feeling of informality in a serene, natural more rural setting. It was also important to us to be free as possible from the n

4 Full Baths

3 Bed

4 Sleeps

Welcome to Seaview! This is a unique family style vacation home, offers space for up to 10 family members or friends to vacation together, with considerable privacy. Nestled against a large gulch, the views sweep across the ravine, over the fields, to a panoramic view of the entire coastline from Hookipa down to Kahului. There is also a gorgeous view of the West Maui Mountains.. It is truly a setting that will restore peace and tranquility to your life. A vacation in Upcountry Maui is a

4 Full Baths

5 Bed

10 Sleeps

Within the gates of Sugar Cove, is a very special ocean front and beach front group of townhomes. This small, intimate property offers only three vacation homes for short term rental (the other 15 homes remain empty until the owners are on island). It's the perfect north shore environment for couples or families that want nicer lodging in an ocean front setting. Be sure to reserve early to claim your space. This spacious 2300 sf townhome has such fabulous views that it feels like indoor/

3 Full Baths

3 Bed

6 Sleeps

This charming cottage is located at the end of Anini Road across the street from the beach. It's a small dirt road so there's not much traffic to bother you. Anini is one of the calmest beaches on the North Shore as it's protected by the largest reef in the State. Not only is this beach great for little ones, it's usually good snorkeling too! This cottage is set back from the road and has a large yard for evening BBQ's. Clean and fresh best describe this choice home in secluded Anini Beach. E

1 Full Baths

2 Bed

4 Sleeps

This great 2 bedroom plus loft is at the end of Anini Road. A quick stroll across the dirt road and you're toes are on the sand! Anini is the largest reef in the State allowing calm ocean and snorkeling out your door pretty much all year round. One set of the twin beds can convert to a King bed, if preferred. A great location for a great vacation! Now offering free long-distance calls too! Pricing is based on occupancy of 1-4 guests. ***As required by Interpretive Administrative Zoning Rul

3 Full Baths

2 Bed

6 Sleeps

This unit is brand new to the Vacation Rental market. A quaint 2 bedroom, 2 bath cottage is perfect for a small family. Enclosed property with front yard space for playing on the grass. A beach access is just 1 house over, so in about 1 minute walk you will be on the sand at a portion of beautiful Kailua Beach. Downstairs has a split system AC which cools the living area, kitchen and master bedroom. Extra person Fee of $25 per night per person after the 4th guest. This property is a le

2 Full Baths

2 Bed

4 Sleeps

Aloha and welcome to Ocean Dreams Premier Grand Residence Villa 2203 at The Resort at Kapalua Bay, a 3.5 bedroom and 3.5 bathroom direct oceanfront and panoramic ocean view private residential vacation rental villa with combined total of 3,532 square feet of living space that comfortably accommodates up to 8 guests, set within the iconic Kapalua Bay Resort and Spa in the prestigious building 2 location. As of March 2026, the former Montage Kapalua Bay on Maui has transitioned to The Resort at K

3 Full Baths

3 Bed

8 Sleeps

This is a legally established property, please read below for more info... Hawaiiana home just steps from the world famous Kailua Beach. This Hawaiiana house second of two homes of the beachfront property. It is the perfect place to relax and enjoy paradise. The tropical large living room opens onto a spacious private lawn leading out directly via a secure gate beteen the two homes to a sandy walkway, steps to breathtaking Kailua beach. A rear private courtyard lanai with 15ft x 32ft

4 Full Baths

5 Bed

8 Sleeps