Private Estate Vacation Rentals in Hawaii – Perfect for Families, Groups & Celebrations

Hawaii private estate rentals offer unmatched privacy, luxury, and space - ideal for families, weddings, and group retreats. These expansive properties feature multiple bedrooms, pools, and scenic views, providing an unforgettable setting for celebrations or serene getaways across the islands.

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Private Estate, Ocean view, Pool & hot tub, desired elevation

Private Estate, Ocean view, Pool & hot tub, desired elevation

"Out of all our experiences with hosts on AirBnb, Kaili's was by far our most memorable. "
-Guest, Feb 2022

"The Lodge at Kaloko, Big Island Hawaii…what an amazing, unique place to experience. "
-Guest, July 2022

5/5
"Peaceful, Luxurious Getaway
The hosts were incredibly hospitable and very responsive.

5 bedroom
5 bathroom
Sleeps 16

from $2,123

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Luxury Oceanview Private Estate Pool & Hot Tub In Kaanapali-Rainbow Hale Maui

Luxury Oceanview Private Estate Pool & Hot Tub In Kaanapali-Rainbow Hale Maui

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.

4 bedroom
3 bathroom
Sleeps 8

from $1,626

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MauiJOY Villa -Heaven on Earth ~PRIVATE Estate OCEAN Views, Swimming 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 (place) and it's people as Ohana.

2 bedroom
2 bathroom
Sleeps 6

from $847

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3 bedroom Custom Home on lush 10 acre private estate with sweeping ocean views

3 bedroom Custom Home on lush 10 acre private estate with sweeping ocean views

Come stay and relax at this quartzite stone-sided custom built home on a 10 acre private estate located in historic Hawi on the Big Island of Hawaii. The house is built with loving care and attention to details by the owners. Our home is perfect for gatherings of family and friends.

3 bedroom
1 bathroom
Sleeps 8

from $570

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$6,500+sf Private Estate Hosted Bed & Breakfast w\/ 4 King suites$

6,500+sf Private Estate Hosted Bed & Breakfast w/ 4 King suites

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 minutes from downtown Kona and the beach. We also have hosts who live onsite to help you get acquainted with the house and the island.

5 bedroom
5 bathroom
Sleeps 12

from $1,286

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Family-Friendly Ocean View Cottage with Spa on 10 acre private estate

Family-Friendly Ocean View Cottage with Spa on 10 acre private estate

This custom-built, well appointed ocean view 1000 square foot cottage with outdoor spa is on a lush 10 acre private estate, botanical sanctuary and organic farm. Located in historic Hawi on the Big Island of Hawaii, this lovely space can sleep up to 4 people.

2 bedroom
1 bathroom
Sleeps 4

from $277

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Multi-Dwelling, Private Estate with Ocean Views and Two Hot Tubs TVNC#4284

Multi-Dwelling, Private Estate with Ocean Views and Two Hot Tubs TVNC#4284

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 east of the adorable town of Kilauea, this property is very close to the many incredible sights of the North Shore yet enjoys more sun and blue sky than most northern areas because it is not right at the base of the breathtaking mountains where most of the rain falls.

3 bedroom
1 bathroom
Sleeps 8

from $1,024

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Mauna Kea Villa 3003 - Exquisite Gated Private Estate

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 for eight+.

3 bedroom
2 bathroom
Sleeps 8

from $2,649

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