Hawaii Private Estate Vacation Rentals
Hawaii private estate rentals are the ultimate choice for families, weddings, and group getaways seeking privacy, luxury, and space. From oceanfront villas on Maui to gated estates on the Big Island, these exclusive homes offer multiple bedrooms, private pools, chef kitchens, and lush tropical settings-ideal for celebrations or peaceful retreats.
Our curated collection of private estates in Hawaii spans all major islands - Maui, Big Island, Oahu, and Kauai - each offering secluded luxury with high-end amenities. Whether you need a 10-bedroom villa for a family reunion or a romantic estate for a destination wedding, you'll find the perfect base to experience paradise.
Many estates feature panoramic ocean views, outdoor kitchens, media rooms, tennis courts, and direct beach access. Guests enjoy resort-style living with the privacy of a home, often located near top beaches, scenic golf courses, and charming towns like Kailua-Kona or Kihei.
Key Features of Hawaii Private Estate Rentals
- Spacious multi-bedroom homes with 5-10+ bedrooms
- Private pools, hot tubs, and ocean-view lanais
- Chef kitchens, BBQ grills, and indoor/outdoor living areas
- Gated communities and secluded locations
- Event-friendly layouts for weddings and celebrations
- Concierge services, housekeeping, and optional chefs or massage therapists
- Proximity to beaches, golf, hiking, and island attractions
Looking for a smaller space with similar amenities? Browse our oceanfront rentals or luxury rentals.
Kilauea Ocean Bluff Estate – Luxury 2-Bedroom Home with Secluded Beach Access
Escape to this enchanting 12-acre estate with panoramic ocean, mountain, and river views. The main residence, guest bungalows, and bathhouse form a connected compound amid lush gardens. The great room with Teak sliding doors opens to the garden and ocean view. Custom...
MauiJOY Villa -Heaven on Earth ~PRIVATE Estate OCEAN Views, Swimming pool.
A PRIVATE ESTATE where you will experience Comfort, Ease, Quality, Carefree, Private, Relaxing, Heaven on Earth. Our permit number is BBKM 2014/0004.We believe in the Malama Hawaii program where visitors are respected as Ohana "family" and they in turn respect the aina...
Lovely, spacious private estate, 300 ft to Sunset Beach TA#083767910401
30 DAY RENTAL*****A beautiful, peaceful, private north shore estate, 300 ft from sunset beach. The main house has 4 bedrooms and 4 bathrooms and sleeps 8 in beds. You may rent the cottage for an additional 2 people-check availability-it's called the plantation cottage;...
Multi-Dwelling, Private Estate with Ocean Views and Two Hot Tubs TVNC#4284
Welcome to Kauai's magical North Shore!!! This 3 acre property with house and guest house offers pristine privacy and ocean views with a private path to a secluded beach. Kauai Vacation Hideaway also nurtures dozens of fruit trees that guests can pick from. Located just...
Diamond Head Luxe Private Estate with Pool | Sleeps 11
Diamond Head Luxe is a refined private estate in Honolulu’s coveted Diamond Head neighborhood, nestled at the end of a private road, and designed for effortless island living at scale. With generous interiors, seamless indoor-outdoor flow, and a resort-style pool...
Mauna Kea Villa 3003 - Exquisite Gated Private Estate
Wake each morning to the soothing sound of waves and end your days with fiery sunsets over the Pacific—this exceptional ocean view villa offers the perfect blend of privacy, luxury, and location. Nestled in an exclusive enclave just a short 7-minute stroll from the soft...