Hawaii Private Estates for Rent

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 ...

4 bedroom
4 bathroom
Sleeps 8

from $1,654

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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. Not only is this house an amazing home for large families or groups to enjoy, but it's so centrally located to most top beaches, grocery and shopping on the...

5 bedroom
5 bathroom
Sleeps 16

from $2,123

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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 ...

2 bedroom
2 bathroom
Sleeps 6

from $845

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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...

4 bedroom
3 bathroom
Sleeps 8

from $570

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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...

3 bedroom
2 bathroom
Sleeps 4

from $255

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

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 ...

5 bedroom
6 bathroom
Sleeps 12

from $1,256

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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 ...

3 bedroom
5 bathroom
Sleeps 8

from $1,085

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Mauna Kea Villa 3003 - Exquisite Gated Private Estate

This exquisite, singlelevel, gated, oceanview private estate offers a sunken great room with sliding glass pocket doors for indooroutdoor island living, a magnificent kitchen with topoftheline appliances, custom cabinetry, and woodwork, as well ...

3 bedroom
3 bathroom
Sleeps 8

from $2,414

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