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.
North Shore Oahu Gated Private Estate on lush 1 acre near Sunset Beach
Welcome to the Green Pineapple, a gorgeous 3 bedroom estate on Oahu's North Shore. Take a walk down memory lane in style, as this gorgeous North Shore Oahu estate has all the charm of Hawaii's vintage era, in this two-story, luxury home. *400mb high speed internet &...
Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub
🌴 The Lodge at Kaloko – Luxury Estate in KonaPrivate 5BR villa | Pool | Hot tub | Ocean views | Near Kua BayWelcome to The Lodge at Kaloko, a luxury gated estate in the lush Kona Cloud Forest — just 15 minutes from Manini‘owali Beach (Kua Bay), downtown Kona,...
Rainbow Hale Estate Ka'anapali - Luxury Oceanview Estate with Pool & Hot Tub
Set on 5.13 acres within the gated Kaanapali Coffee Farms, this single-level estate offers sweeping ocean views, three king suites and a convertible den to accommodate up to 8 guests. The gourmet kitchen features a built-in espresso machine; the saltwater infinity pool,...
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;...
North Shore Private Estate
This lush private estate offers sweeping ocean and mountain views from a hilltop above the beach. Custom throughout and fully equipped, the main house has 3 bedrooms/2 baths; the included private suite has a queen bed, bath, kitchenette, and separate entry. Set on a...
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...
Mauna Kea Villa 3003 - Exquisite Gated Private Estate
This exquisite, single-level, gated, oceanview private estate offers a sunken great room with sliding glass pocket doors for indoor/outdoor island living, a magnificent kitchen with top-of-the-line appliances, custom cabinetry, and woodwork, as well as a dining table...