Luxury Vacation Rentals in Hawaii

Explore the most exclusive Hawaii luxury vacation rentals with our handpicked portfolio of Oahu beachfront estates, Maui private villas, Kauai oceanview homes, and Big Island luxury retreats. These high-end vacation homes feature private pools, chef kitchens, panoramic views, and resort-style amenities – ideal for honeymoons, family reunions, and indulgent island escapes.

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Blue Lagoon Estate at Mauna Lani Resort

Enjoy the best Hawaii has to offer in this luxury 10,000 sq ft Kona Coast tropical estate on The Big Island in the Champion Ridge enclave of Mauna Lani. Enjoy the private heated lagoon pool and spa and access to many of the Mauna Lani resort area amenities including a...

🛏 7 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 18
📍 Waimea, Hawaii

Kuilima Estates West - 3 Bedroom Vacation Home

NEW LISTING! This newly renovated 2-story 3 bedroom condo is located at Turtle Bay in the gated community. This is the ONLY condo with split AC downstairs and central AC upstairs. This beautiful island condo sleeps 8 guests.This condo is just steps away to two...

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

Mauna Kea Villa 3037 - Architectural Island Estate

This dazzling, single-level, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living and Sonos system, a chefs' kitchen with Wolf and Sub-Zero appliances/wine refrigerator, a dining area with adjoining wet bar, a...

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

Kona Hillside Estate - Gated Property with Lap Pool

Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...

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

A 5-Star Estate, Large Groups, Luxury Living

This luxury condo is situated a short walk from the beauty of the beach! A 3,700 square foot, 3 bedroom, 3.5 bath gem, it is the ideal place for a quiet retreat. Features a Master Suite with private lanai and two additional bedrooms with en suite baths, sleeping up to a...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kihei, Hawaii

Beachfront Family Estate. Great for multiple families.

Located in central Kihei, nestled on the northern end of beautiful Halama Street. Family-owned and operated legal short-term rental. There are two dwellings on this beach front property - an apartment building with four units and a detached 2 BR/1BA cottage. The...

🛏 6 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 15
📍 Kihei, Hawaii

Papala Place at Kahakai Estates by Gather: Luxe Poolside Oasis

Welcome to Papala Place at Kahakai Estates by Gather, a stunning four-bedroom, three-and-a-half-bathroom home in the heart of Kailua Kona. The entire house is centrally air conditioned, ensuring a cool and comfortable stay year-round. Accommodating up to eight guests,...

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

Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 9
📍 Honolulu, Hawaii

Makai Estate – Hualalai Luxury Villa with Saltwater Pool

WHY IT'S SPECIALPicturesque, bedroom island suites with outdoor garden showers, premiere resort location, impressive indoor and outdoor chef's kitchen, and oceanside views from the sprawling lanai.Completely relish in the elevated Big Island lifestyle in this...

🛏 4 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

The Bluffs 22 – The Beach House Opulent Oceanview Luxe Estate

Nestled on over an acre in the prestigious Bluffs enclave along the Kohala Coast, The Beach House is an unparalleled sanctuary of luxury and tranquility where indoor-outdoor living takes center stage. This $15 million, 8,141-square-foot estate redefines Hawaiian...

🛏 4 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 10
📍 Kamuela, Hawaii

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Gorgeous and high end 4 bedroom plus bonus (sleeping) loft, located in prime gated community, sleeps 12. Very large landscaped yard, fantastic ocean view, central A/C, plunge pool, top appliances (sub zero) granite kitchen beautiful bedrooms, fabulous artwork and only a...

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

Aloha Sands: Luxury Hawaiian Villa - Puako Beachfront

5 STAR REVIEWS! STUNNING VILLA! TASTE OF OLD HAWAII ON THE BEST BEACH IN PUAKO! This lofty and spacious Hawaiian villa lies on the Gold Coast of Hawaii, the sunniest spot in the state. Aloha Sands is also on the best sandy beach in Puako between the Mauna Kea and Mauni...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 11
📍 Kamuela, Hawaii

Beautiful Oceanfront Estate with heated saltwater pool, Hamakua Coast Acreage.

From the moment you arrive, your every care will melt away at this spectacular gated oceanfront estate. The open floor concept, covered outdoor spaces with BBQ, and poolside gathering areas, are ideal for family vacationing. Hear the sounds of the surf along the rugged...

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

Hale Pakika at Kukui'ula: Exclusive 5BR Estate with Private Pool, Golf & Ocean Vistas

Welcome to Hale Pakika at Kukui’ula by Gather, a luxurious 5-bedroom, 5.5-bathroom Koloa hideaway, perfect for up to 12 guests. Boasting ocean views and an exclusive location off the first tee of Kukuiula Golf Course, this home offers a serene escape on Kauai’s...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Koloa, Hawaii

Hale Koolau Estate - Private Retreat in Haena with Hot Tub & AC

Hale Koolau Estate (Main House + Treehouse), Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018Transient vacation rental is located in the tsunami evacuation zoneOn the north shore of Kauai, Hale Koolau Estate sits behind wooden gates and...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Haena, Hawaii

Dancing Volcano Estate - sleeps 8 Near Hawaii Volcanoes National Park

Dancing Volcano Estate in Volcano, Hawaii is a fantastic place to stay and visit Hawaii Volcanoes National Park just a few minutes drive from our property. Our main house has 3 bedrooms and 2 bathrooms, full kitchen, large dining area, large living area with SMART TV,...

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

Dolphin House Oceanfront Estate

STVR 19-363225 - NUC 19-1616Picture yourself vacationing in this magnificent and upscale 6,000 square foot oceanfront home. The stunning house is comprised of 4 bedrooms and 4½ baths with a variety of features including an atrium entry with cathedral ceilings,...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua Kona, Hawaii

Stunning Ocean View In Luxury Home In Keauhou Estates

Enjoy spectacular 180-degree ocean views from this 3 bedroom, 3700 square foot luxury home in Keauhou Estates on the Big Island of Hawaii. The house has an open floor plan, marble floors throughout most of the main living spaces, and large rooms with tasteful and...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Gorgeous Luxury Estate Home - Hualalai Resort - Spectacular Ocean and Golf Course Views - Private Pool and Spa - 3 Golf Carts Included

Gorgeous, Contemporary, Newer Home Exemplifies Luxury and ease of Living in our Island Paradise. This 5-bedroom, 5 1/2 bath pod-style estate home is exceptionally appointed and designed to take full advantage of the temperate climate and island breezes.Upon arrival to...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua Kona, Hawaii

One Ocean Mauna Lani Golf Estate 4 with Infinity Pool & Spa

Welcome to 5BD Mauna Lani Lux Golf Estate (4) at One Ocean, a brand-new luxurious five-bedroom, six-and-a-half bathroom home built in 2024 nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...

🛏 5 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 10
📍 Waimea, Hawaii

Brand New 4BR Poipu Beach Estates Home

Be among the first to enjoy this brand-new luxury vacation home in the prestigious Poipu Beach Estates neighborhood. Ideally situated between The Shops at Kukui'ula and Poipu Shopping Village, and just a quick five-minute drive to Poipu Beach, this home offers the...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Koloa, Hawaii

Hale Ohia – Private Gated Luxury Estate with Panoramic Ocean Views

Kauai's Premiere Vacation Rental - "Hale Ohia" This private and gated custom estate is like no other. Four suites with private baths lends this home to have constant ocean views. The exceptional out door living area - "Pai Pai" has 2 large drop down TV's for watching...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kaloa, Hawaii

Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean Access

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Laie Beachfront Estate by Gather, a...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Laie, Hawaii

This magnificent, island-style estate truly exceeds all expectations.

Rates shown are for 8 guests; additional guests up to maximum of 11 are $20/night each. This magnificent, island-style estate truly exceeds all expectations. Located on secluded Pakala's Beach on Kauai's west side, this totally serene property borders an orchard and is...

🛏 4 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 8
📍 Waimea, Hawaii

Kona Coast Original Beach Boys 9.5 acre Estate, Pool and Amazing Ocean Views

Kona recalls the Beach Boys playing their pop hits by the pool. The band left but the good vibrations linger. Situated on 9.5 gated acres, gated for with an amazing Hawaiian plantation-style home with separate sleeping quarters and a guest house. Pool hot tub, gas...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 12
📍 Captain Cook, Hawaii

Kahala Beachfront Estate – Private Resort-Style Living

For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.Spacious beachfront estate is situated on lush tropical grounds,...

🛏 7 Bedrooms
🛁 7 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball

Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Koloa, Hawaii

Spacious Historic Estate ~ 5 Min Walk to Hilo & Bay Front

Beautifully appointed historic (once King Kamehameha's private lands) 1930s estate in close proximity to beaches, Botanical Gardens, Akaka Falls, and everything HiloTown has to offer! Walk to the Wailuku River & the Hilo Bayfront in only a few minutes from our home....

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Hilo, 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

Luxury townhouse on Turtle Bay - Kuilima Estates West

Aloha my friend! We invite you to come and experience your tropical paradise...your new home away from home at Turtle Bay Kuilima Estates! Located on the North Shore of Oahu at Turtle Bay, this townhome sits on the Championship Fazio Golf Course with a lake view and a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Kahuku, Hawaii

Ginger Beach House – Anahola Beachfront Estate

Legally licensed short term vacation rental, TVNC#4308 GET Number: GE-136-304-3840-01; TAT Number: TA-136-304-3840-01EXQUISITE FIND!! For those who appreciate the finer things in life, Kauai’s most beloved beach home, known as Ginger Beach House, is your slice of...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Anahola, Hawaii

Hale Minoaka by Destination Kauai - Poipu Beach Estates Exquisite Cottage

E Komo Mai – Welcome to Hale Minoaka!Your serene South Shore retreat in sunny Poipu.Nestled in the prestigious Poipu Beach Estates neighborhood, Hale Minoaka is a thoughtfully designed 1-bedroom, 1-bath private cottage offering the perfect blend of comfort, privacy,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Poipu/ Koloa, Hawaii

Paradisio Ho'o Kumu – Luxury Kukui'ula Oceanfront Estate

A truly stunning oceanfront resort property offering six air-conditioned bedroom suites as well as pool, spa and access to Kukuiula beach park right across the street. Resort living at its best, this casually elegant, island-style private home offers ocean and coastline...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Koloa, Hawaii

Private Garden Cottage on 5 acre country estate /Walk to the Botanic Gardens!

Aloha! Our country estate is in Onomea, 6 miles north of Hilo, on 5 tropical acres with garden and ocean views. Onomea Guest Suite is a private cottage with garden views of flowering royal Poinciana trees, sweeping monkey pod trees, mango, lychee, mountain apple trees,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 3
📍 Hilo, Hawaii

Luxury Mountainview Estate w/Shared Pools/Spa, BBQ Area & AC - Kamilo #407

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.Lovely Mauna Lani KaMilo Home 407 is ideally located in a low-density gated community within the Mauna Lani Resort, on the west coast of the Big Island of Hawaii. This...

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

Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!

The new roof project will take place over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------From the front door, a magical stretch of Maui beach awaits your exploration -...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kihei, Hawaii

Turtle Bay Corner Condo Overlooking the Fairway - Kuilima Estates East

Enjoy the best of what the ‘fabled North Shore’ has to offer in this authentically designed Hawaiian-beach-themed unit, that sleeps up to four (4) adults, with Resort-style amenities at your doorstep, including snorkeling beach access, swimming pool, tennis courts,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kahuku, Hawaii

Blue Oasis - Champion Ridge Estate at Mauna Lani Resort

Experience the best of Hawaii in this luxury 5,600 sq ft estate in the Mauna Lani resort area. Take a dip in the heated pool and hot tub (heated to your desired temperature), drink a beer in the billiards room, have an evening putting competition on the private putting...

🛏 5 Bedrooms
🛁 7 Bathrooms
👤 Sleeps 14
📍 Waimea, Hawaii

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Our very private home, a spacious, 3,500 sq. ft. oceanfront estate, sits on 2/3rds of an acre. It has a large indoor living area, plus an expansive outdoor living area, featuring a 1,000 sq. ft. covered ocean view terrace with a large seating area, a dining table...

🛏 6 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 17
📍 Kihei, Hawaii

Spacious 2 bedroom 2 bathroom on North Shore - Kuilima Estates West

You will enjoy relaxing in this spacious 2 bedroom, 2 bathroom townhome located on the first fairway of the Fazio Golf Course at the Turtle Bay Resort! Beautiful golf course views with ocean view right past the golf course. You may even see some horses grazing in the...

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

HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH

ALOHA & WE WELCOME YOU TO OUR COMFORTABLE HOME AWAY FROM HOME! LOCATED IN THE SUNNY SOUTH SIDE OF THE GARDEN ISLAND OF KAUAI IN POIPU BEACH, THESE 2 HOMES HAVE BEEN RECENTLY CONSTRUCTED WITH TOP OF THE LINE FEATURES, PERFECT FOR A PARADISE FAMILY GATHERING OF MULTIPLE...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 14
📍 Koloa, Hawaii

Palekaiko Estate - Kailua Kona Luxury Home with Ocean View

Palekaiko, meaning paradise, is our 3200+ sq. ft. home away from home situated on over an acre in a gated community. Palekaiko has three bedrooms, three and a half bathrooms, an office and almost 1000 sq. ft. of outdoor living space. On the property, you will enjoy over...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 7
📍 Kailua-Kona, Hawaii

Amazing 180° West Maui Ocean View Estate Pool w/Hot Tub- Central AC

Perched on four lush acres in Launiupoko, this gated estate blends the comfort of a secluded retreat with the feel of a boutique resort. Outside, ocean views stretch toward Moloka’i and Lana’i on the horizon. The main house sleeps 7 across three ensuite bedrooms...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Lahaina, Hawaii

Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and Orchard

The moment you enter the Royal Palm lined driveway of this gorgeous estate, you'll know you have arrived at your new sanctuary! Papa Belle Estate is a 3.5 acre oasis on the South Kona coast offering breathtaking views, wonderful amenities, and lush surroundings.Soak in...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Captain Cook, Hawaii

Kuilima Estates West 3 Bedroom

TMK (1)570010290042 Welcome to Kuilima Estates West. Location! Location! Location!Only steps to the grounds of the famous and newly renovated Turtle Bay Hotel on the North Shore. We are a Legal Vacation Rental.The condos are Surrounded by Two Beautifully manicured golf...

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

Luxury 3br Poipu Estates Home w Private Pool

This home is a true Poipu gem. Located in the Poipu Beach Estates neighborhood, this home features a spacious open floor plan with a covered lanai. The kitchen flows seamlessly into the living area creating the perfect place to gather and “talk story.” All of the...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Koloa, Hawaii

Kahakai Estates Hale: Posh Gold Coast Home w/ Pool, Spa, AC & Sunset Views

Kahakai Estates Hale by Gather – Newly Renovated Luxury Vacation Rental in Kailua-Kona, Big IslandLocation: Kahakai Estates, Kailua-Kona | Sleeps: 6 | Bedrooms: 3 | Bathrooms: 2.5 | Central A/C | Private Pool & Hot TubEscape to paradise in this fully remodeled,...

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

Stunning Estate Property In Gated Community Steps From The Ocean

Welcome to our 5 star rated vacation home. We call our home Forever Sunsets because with just a short walk to the water in our gated community you can watch the sunset every night. You are also a short 600 yard walk to Magic Sands Beach, the most popular sandy beach in...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Kailua-Kona, Hawaii

Beautiful 3 Bed Home in the Wailua Rise Estates, TVNC 1079, 377/night for four

Come to Beautiful Kauai and stay in this immaculate, beautifully furnished Home in the beautiful Wailua Rise Estates. Enjoy the peaceful surroundings while also being only 5 minutes from Golf, Tennis, the Beach, Resturants, and Shopping.Have your coffee on the large...

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

Oasis at Turtle Bay Condo on the North Shore - Kuilima Estates West

This homey one bedroom (cal king bed) with upstairs loft (with one queen and one twin bed)/two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to five! It's close to the public beach at the Turtle Bay hotel, sitting on the 1st hole of PGA Fazio...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Kahuku, Hawaii

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