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

Discover Hawaii’s most luxurious private estates, ideal for large families, groups of friends, or those planning a special event. These expansive vacation homes offer the ultimate in space, comfort, and seclusion-complete with multiple bedrooms, gourmet kitchens, lush gardens, and sweeping ocean or mountain views.

Perfect for family vacations, group getaways, or milestone celebrations, many estates also serve as stunning venues for weddings, retreats, and private parties. Enjoy features such as private pools, outdoor entertainment areas, and proximity to Hawaii’s top attractions - all while having the entire property to yourselves.

Start planning your unforgettable island escape. Browse the listings below to find the ideal estate rental that fits your vision for luxury, privacy, and celebration in paradise.

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Luxury Kaloko Estate on Big Island Hawaii
Luxury Kaloko Estate on Big Island Hawaii
Luxury Kaloko Estate on Big Island Hawaii

Luxury Kaloko Estate on Big Island Hawaii

Immerse yourself in the tropical paradise of The Lodge at Kaloko, a unique and spacious estate nestled on 3 acres at 2,200 feet elevation on the Big Island. This luxurious property offers a perfect retreat for large families, groups, or corporate gatherings, comfortably sleeping 15 guests across five beautifully appointed bedrooms, including four primary suites with private baths and memory foam mattresses.

  • 5 bedroom
  • 5 bathroom
  • Sleeps 16
Hawaii> Kailua-Kona
from $2,123 
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Luxury Rainbow Hale Estate in Kaanapali Maui
Luxury Rainbow Hale Estate in Kaanapali Maui
Luxury Rainbow Hale Estate in Kaanapali Maui

Luxury Rainbow Hale Estate in Kaanapali Maui

Welcome to Rainbow Hale Estate, Maui's premier vacation retreat nestled on over 5 acres of lush tropical plantation in Kaanapali. This spectacular estate offers the perfect blend of privacy, luxury, and breathtaking views, making it an ideal destination for family getaways or romantic honeymoons.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Lahaina
from $1,626 
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Private Ocean View Estate at MauiJOY Villa
Private Ocean View Estate at MauiJOY Villa
Private Ocean View Estate at MauiJOY Villa

Private Ocean View Estate at MauiJOY Villa

A private estate offering a serene Maui getaway where comfort, privacy, and natural beauty come together. Situated on half an acre adjacent to undeveloped land, MauiJOY Villa boasts breathtaking 180-degree ocean views of three islands and is nestled above the bustling resorts of Wailea, including The Four Seasons and The Grand Wailea.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kihei
from $847 
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Hawi Ocean View Estate with Private Gardens
Hawi Ocean View Estate with Private Gardens
Hawi Ocean View Estate with Private Gardens

Hawi Ocean View Estate with Private Gardens

Come stay and relax at this stunning quartzite stone-sided custom home nestled on a 10-acre private estate in historic Hawi on the Big Island of Hawaii. Built with love and attention to detail by the owners, this home is perfect for family gatherings and friends' reunions.

  • 3 bedroom
  • 1 bathroom
  • Sleeps 8
Hawaii> Hawi
from $570 
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Ohi'a Kona Estates Hawaiian Retreat with Ocean Views
Ohi'a Kona Estates Hawaiian Retreat with Ocean Views
Ohi'a Kona Estates Hawaiian Retreat with Ocean Views

Ohi'a Kona Estates Hawaiian Retreat with Ocean Views

Discover the perfect Hawaiian escape at Ohi'a Kona Estates, a serene retreat nestled in the hills above Kona. This estate offers four spacious one-bedroom suites, each featuring a king bed, private bath, living area, and modern amenities. Guests enjoy stunning views of the Pacific Ocean, cool breezes, and a temperate climate, making it ideal for relaxation and exploration.

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Kailua-Kona
from $1,286 
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Ocean View Cottage in Hawi, Big Island Hawaii
Ocean View Cottage in Hawi, Big Island Hawaii
Ocean View Cottage in Hawi, Big Island Hawaii

Ocean View Cottage in Hawi, Big Island Hawaii

This charming, custom-built cottage offers stunning ocean views and is nestled on a lush 10-acre private estate in Hawi, Big Island. Spanning 1000 square feet, it comfortably sleeps up to four guests, with a bedroom and a loft, each furnished with a cozy queen bed.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Hawi
from $277 
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Kauai North Shore Vacation Hideaway with Ocean Views
Kauai North Shore Vacation Hideaway with Ocean Views
Kauai North Shore Vacation Hideaway with Ocean Views

Kauai North Shore Vacation Hideaway with Ocean Views

Welcome to Kauai's enchanting North Shore! This expansive 3-acre property features a charming main house and a separate guest house, offering ultimate privacy and stunning ocean views. A private path leads directly to a secluded white sand beach, perfect for peaceful escapes.

  • 3 bedroom
  • 1 bathroom
  • Sleeps 8
Hawaii> Kilauea
from $1,024 
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Luxury Oceanview Estate at Mauna Kea Residences
Luxury Oceanview Estate at Mauna Kea Residences
Luxury Oceanview Estate at Mauna Kea Residences

Luxury Oceanview Estate at Mauna Kea Residences

This stunning single-level gated estate offers breathtaking ocean views and luxurious island living. The spacious sunken great room features sliding glass pocket doors that seamlessly connect indoor and outdoor spaces, perfect for relaxing or entertaining.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kamuela
from $2,649 
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