Maui Vacation Homes

MVP Iolani Guest Cottage - 2BR Home

• 2 Bed
• 1 Full Baths

From $975.00 / night

Romantic, unique, charming coral rock cottage perched on the edge of Maliko Gulch. Swing in the hammock, or play tennis on the clay court. This is a property for nature lovers, romantics, and anybody looking for a quiet escape from reality. Wake up surrounded by plants and trees, and an endless blue sky. With lodging like this, why would anybody consider staying in a condo with thousands of other tourists? The Iolani Guest cottage is fabulous for a Maui Honeymoon, quiet escape, or anybody th

MVP Pililani House - 5BR Home

Rating: 4.9

• 5 Bed
• 5 Full Baths

From $4200.00 / night

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

MVP Pinnacle Cottage - 2BR Home

Rating: 5

• 2 Bed
• 1 Full Baths

From $975.00 / night

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

MVP Pinnacle Main Home - 3BR Home

Rating: 5

• 3 Bed
• 4 Full Baths

From $2985.00 / night

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

MVP Seaview - 5BR Home

Rating: 5

• 5 Bed
• 4 Full Baths

From $4350.00 / night

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

Ocean Dreams Villa 2203 at Montage Kapalua Bay

Rating: 5

• 3 Bed
• 3 Full Baths

From $2199.00 / night — Total price: $6597.00

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

Rainbow Hale Estate - 3BR Home plus Den

Rating: 5

• 3 Bed
• 3 Full Baths

From $5025.00 / night

Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali a Family Retreat or Private Honeymoon Get -away. Surrounded by 5 acres of Maui tropical plantation, lies a spectacular estate like you've always dreamed of, with the lifestyle you've always dreamed of living. Secluded and in a private, gated community, it is convenient to all of West Maui's famous beaches, restaurants and activities. This property has 3 bedrooms, all with ensuite bathrooms, a bath, plus a 4th den/library, that is comp

Sea La Vie L510 at Wailea Beach Villas

• 2 Bed
• 2 Full Baths

From $1395.00 / night — Total price: $4185.00

Situated on the 5th TOP FLOOR of the penthouse/tower building of the Wailea Beach Villas Resort, Sea La Vie L510, a fully redecorated and remodeled 2.5 bedroom, 2 bath suite, offers expansive and superlative direct west-facing panoramic views of the Pacific Ocean, Wailea Beach and the Wailea Resort area. Only a few residences on the upper floors of the Wailea Beach Villas offer such exceptional views. This villa is well above the family pool where birdsong and the rustling of palm tree fronds pr

Sea Shells Beach House on Ka'anapali Beach

Rating: 5

• 3 Bed
• 3 Full Baths

From $2195.00 / night — Total price: $6585.00

Sea Shells is an updated and beautifully sprawling family-friendly beach-front vacation residence with a heated lagoon pool, jacuzzi, powerful air conditioning, 3 bedrooms and 3.5 bathrooms, all set directly west Maui's astoundingly beautiful Kaanapali Beach. NEW PHOTOS of new appliances, decor and furnishings are forthcoming eventually, as the current ones do not do this one-of-a-kind, all-around guest-favorite vacation residence justice. The west-facing home serves up glorious scarlet sunsets

SeaSpirit 811 at Andaz Maui at Wailea Resort

• 3 Bed
• 4 Full Baths

From $2495.00 / night — Total price: $7485.00

SeaSpirit Villa 811 at Andaz Maui at Wailea Resort is a contemporary styled, privately-owned and independently-managed luxury 3 bedroom, 4 bath ocean view second floor resort residence. SeaSpirit is set in a prime location within the resort just steps from Mokapu Beach and the resort's swimming pools and dining venues. Experience this tropical paradise on the beach where you can rest and relax within SeaSpirit Villa 811, “Your Own Private Paradise”, with spacious surroundings, exqui