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.

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North Shore Oahu Gated Private Estate on lush 1 acre near Sunset Beach

SPECIAL -10% OFF for any booking received through SEPTEMBER 2023Welcome 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,...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Haleiwa, Hawaii

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,...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 16
📍 Kailua-Kona, Hawaii

Rainbow Hale Estate Ka'anapali - Luxury Oceanview Estate with Pool & Hot Tub

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Lahaina, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

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;...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Haleiwa, Hawaii

Ohi'a Kona Estates: Hosted Bed & Breakfast with 5 Bedrooms

Celebrate your Hawaiian holiday with friends & family in your own Bed & Breakfast dedicated to you and your group!!Away from the hustle and bustle of tourists and traffic, Ohi'a Kona Estates is located in the hills above Kona with beautiful views of the Pacific and 15...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Kailua-Kona, Hawaii

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...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Haleiwa, Hawaii

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...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Kilauea, Hawaii

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kamuela, Hawaii

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