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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Tropical Turtle Bay Condo - Kuilima Estates East

This newly listed unit features a loft bedroom, with a large kitchen and living room. Unit is located right on the Arnold Palmer golf course and a 5 minute walk or 2 minute drive from Turtle Bay Resort. Enjoy luxury gated community amenities featuring gated access,...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kahuku, Hawaii

Davidson Point Oceanfront Estate by Destination Kauai, Sunset Views, Heated Pool, AC

TVRNC-1099E Komo Mai, Welcome to Davidson Point Beach House!Experience the peace and tranquility of this oceanfront estate size lot offering privacy and a front row seat to the surfers at Davidson's Surf Break. Enjoy views of the island of Ni'ihau in the distance and...

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

One of a kind private Luxury beachfront Estate with oceanfront pool & jacuzz

TVNC #4224This is truly a one of a kind Hawaiian dream home. Stroll down the sand beach and find Hawaiian Paradise set on over an acre of beautiful tropical beachfront landscaping. This approx 5000 sq ft gated home has all the comforts one could need from a gourmet...

🛏 3 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 6
📍 Kekaha, Hawaii

Kihei Garden Estates C-105 - Stunning Renovation, AC, Steps from the Beach!

The new roof project will take place on building C from 7/14 to 7/23 and over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------Welcome to Kihei Garden Estates C-105, where...

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

Immaculate maintained Turtle Bay Condo - Kuilima Estates West

ALOHA! Perfect North Shore getaway! This surf inspired condo is bright and clean, and stocked with all you should need for a great stay! Located in the Turtle Bay Area, it's very close to beaches (about a 5 minute walk), golf coarse, and some amazing restaurants. This...

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

Turtle Bay Penthouse 164 - Kuilima Estates West

Panoramic golf course views and gorgeous mountains surrounding the Turtle Bay Resort welcome you at the Kuilima Collection | 146 WEST The set up:1 BEDROOM | Super cozy, plush, pillow-top Queen sized bed with A/C and smart TV. Ample closet space and charming garden view,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kahuku, Hawaii

Guest house on gated acre estate, Sleeps up to 7; Great for Events, too

Beautiful, elegantly furnished and fully-equipped 2 bedroom, two bath guest house, with antiques and open beam ceiling, on a 1 acre gated estate, with koi pond, waterfall, fountain, chlorine-free pool and hot tub, and 180 degree ocean-view lanai. Fully furnished and...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Kailua-Kona, Hawaii

North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West

Aloha and welcome to our spacious and beautifully renovated North Shore Turtle Bay Resort 2 Bedroom condo that includes an additional 3rd loft room + 2 bathrooms. Directly outside the living room is a large manicured grassy lawn and the Fazio Golf Course. This gated...

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

Turtle Bay Hale Lani - Kuilima Estates East

This beautiful, modern 1 bedroom w/loft bath and a half. Upgraded unit has new kitchen cabinets & appliances, ceramic tile floors and granite countertops. The extended living room has a large flat-screen TV, internet and WIFI, TV in master bedroom as well. Window a/c in...

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

Gorgeous Estate w/AC & Heated Salt Water Pool!

Bright, cheerful and tastefully designed, this 5 bedroom home sleeps 10 comfortably. Each room has its own unique personality, while the estate is coordinated with aquamarine color schemes, hardwood accents and inspiring details. Cooking for many is an easy task with a...

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

Oceanfront Gated Estate Retreat - Banyan Tree B&B Suite w/ Horses-Beach 10m Walk

Aloha and welcome to our Hawaiian Celebration, our Ho'olaule'a. Hale Laule'a at Opihi Point is a +l$10+M, one-of-a-kind, World Class, 5-acre private, Estate Retreat sitting on the cliff edge of the Pacific Ocean with an unmatched view of the Hamakua Coast. Hale Laule'a...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Hakalau, Hawaii

Delightful Artful Bungalow on Historic Estate Property. Choice Holualoa!

A charming 1930-era cottage, with a screened-in sitting area on the lanai, well-stocked kitchen, bath, will sleep two in a comfy queen-sized bed. Perfect for single or double occupancy. Covered parking close by. An outdoor patio fronting the cottage lanai, is a private...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Holualoa, Hawaii

Turtle Bay Condo - Kuilima Estates East

This is a legal vacation rental located on the Legendary North Shore of Oahu!Permit #: 2211-CCH-0353TA #: TA-106-244-7616-01GE #: GE-106-244-7616-01Famous North Shore Beaches, Two beautiful Swimming pools, Free Parking, No Resort Fees, AC, wireless internet, second...

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

Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West

Enjoy the North Shore by staying close to everything when you stay at this centrally-located place. The townhouse is right next to the famous Turtle Bay Resort.Our two-level, one-bedroom plus loft, end unit condo is located on the second floor for full privacy. ***($20...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Kahuku, Hawaii

Beautiful Private Cottage w/ AC in Sunny Poipu Beach Estates 5 Minutes to Beach!

This new, air-conditioned suite is in an exclusive neighborhood of Poipu, offering you the most rare and impressive accommodation the sunny South Shore has to offer. The rolling golf course greens that surround this property provide an open and airy feel. Enjoy the...

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

Hale Makai at Diamond Head – Oceanfront Estate

We want to inform our valued guests that there is ongoing construction next door to Hale Makai at Diamond Head. This construction is expected to last into 2026. We apologize for any inconvenience and appreciate your understanding in this matter.This Diamond Head...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Keauhou Bay Oceanfront Estate

Spectacular oceanfront estate at Keauhou Bay. This fabulous home with soaring vaulted ceilings throughout the living room and into the Grand Master Suite, opens to the wonderfully landscaped yard fronting Keauhou Bay. The grand living room offers various seating and...

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

Amazing Turtle Bay Condo - Kuilima Estates East

Look no further for your perfect escape to Hawaii! Nestled in the resort community of Turtle Bay, this newly updated 1 bedroom condo w/ a loft is outfitted with LUTRON Ketra lighting technology & LUTRON motorized shades and can easily sleep 4-5 guests the Kuilima...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

Turtle Bay - Relax In Paradise - Kuilima Estates West

Aloha ! Welcome to my condo located at 57-101 Kuilima Dr. Kahuku Hawaii 96712. My condo is clean, well maintained, and comes with many amenities . Some amenities are Tennis rackets, bodyboards, snorkel and mask sets , beach towels, beach chairs, and more. Full access to...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kahuku, Hawaii

Townhome at Kuilima Estates at Turtle Bay

Welcome to this spacious second story townhome at Kuilima Estates at Turtle Bay. This condo is located on the eastern side of Kuilima Estates, making this condo one of the closest units to the Turtle Bay beach. .With a completely updated interior, guests enter into the...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

Hale Kahili: 8BR Ocean View Estate w/Pools+Spa!

This spacious, sparkling compound offers ideal large-group accommodations in an idyllic setting. Two elegant new villas nestle on an expansive 1-acre lot, with views that might have been plucked from a rack of curated postcards: glittering swatches of ocean, craggy...

🛏 8 Bedrooms
🛁 8 Bathrooms
👤 Sleeps 16
📍 Koloa, Hawaii

Sandcastles - Anahola Beachfront Estate with Hot Tub & Enclosed Yard

Sandcastles TVNCU#1305Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This majestic home, Sandcastles, has vaulted ceilings and large sliding glass doors that open to a spacious...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Anahola, Hawaii

Panoramic Ocean Views! Luxury Estate - Pool, Hot Tub, Jacuzzi & Air Conditioning

On the main floor of the home, there is a large lanai with a pool, jacuzzi, outdoor eating area and a fire pit with lounge area. Inside, on the main floor, you will find a **newly renovated** kitchen, large eating area, living room area, and the mother-in-law suite. The...

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

6.5 acres Oceanfront Estate with180-degree views of the deep blue Pacific Ocean!

Kailani Villa is the epitome of privacy, comfort and style and far away from the fray of normal life. The six-and-one-half acre estate is beautifully landscaped and offers unobstructed 180-degree views of the deep blue Pacific Ocean. Retreat to the immense oceanfront...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Ninole, Hawaii

Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East

Panoramic Arnold Palmer golf course views and gorgeous mountains surrounding the Turtle Bay Resort welcome you at the Kuilima Collection | 101 East The set up:1 BEDROOM | Super cozy, plush, pillow-top Queen sized bed with A/C and smart TV. Ample closet space and...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kahuku, Hawaii

A beautiful Turtle Bay condo on the golf course - Kuilima Estates East

Welcome to paradise, enjoy this North Shore Turtle Bay condo. Brand new state of the art air conditioner in master bedroom, living room, and loft. Private master bedroom with A/C and king sized bed and bathroom. Upstairs find two queen size beds in a loft and fan. This...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates

*NEW A/C : LIVING ROOM AND PRIMARY SUITE (2024).Wish You Were Here... on Oahu's famous North Shore at the world class Turtle Bay Golf and Tennis Resort. Spacious 2 bedroom, 2 Full Bath west side condo also has a bonus loft (w/2 twin beds). Kitchen/bathrooms remodeled in...

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

PRIVATE OCEAN FRONT ESTATE ON TURTLE COVE, NAPILI. nMOST SPECTACULAR LOCATIONn

THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES, WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING, TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna .....

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

Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach

Welcome to Palione Papalani – “Heavenly Sands”Just steps from world-famous Kailua Beach, this newly renovated 6-bedroom tropical estate offers the privacy, comfort, and amenities of a high-end resort — all to yourself. ?? Why You’ll Love It:Exclusive Location:...

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

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...

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

Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West

Located on the North Shore of Oahu at Turtle Bay, our condo sits on the Championship Fazio Golf Course. There are multiple walking trails and paths that lead to quiet secluded beaches or world-famous beaches such as Sunset Beach, Waimea Bay, and Pipeline. A large pool...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 5
📍 Kahuku, Hawaii

Hale La'i: Dreamy Oceanfront Estate w/Pool, Spa & AC, Hale La’i

Aloha & Welcome to Hale La’i - House of Peace and TranquilityFor years, visitors from around the world have traveled in search of a tropical destination offering a relaxing transcendent experience. Our family has found that here, on the Big Island of Hawaii. We have...

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

Honu Hale: Exquisite Kona Vacation Home with Pool, Hot Tub & Oversized Chess Set

Aloha and welcome to Honu Hale by Gather, your Hawaiian home away from home. This luxury Kona vacation home is located in an upscale neighborhood just 2 miles away from Magic Sand Beach, Kahaluu Beach Park, and downtown Kona. Honu Hale has 5 bedrooms, 3.5 bathrooms and...

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

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 views of the Pacific and 15...

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

Oahu North Shore Vacation Home @ Kuilima Estates West

Elegant Hawaiian Home: A Spacious Retreat with Resort-Style Living on Oahu’s North ShoreWelcome to this beautifully appointed 3-bedroom, 2-bathroom Hawaiian home, where elegance meets comfort. Located in a prime North Shore setting, this fully air-conditioned home has...

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

Waimea Bay Luxury Estate Views & Hot tub

Summary:Immerse yourself in the ultimate Hawaiian experience at Waimea Bay Luxury Estate, located on a corner bluff lot in the peaceful neighborhood of Pupukea on Oahu's North Shore. This expansive estate boasts breathtaking ocean views from every angle and is just...

🛏 9 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 20
📍 Haleiwa, Hawaii

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. The...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Hawi, Hawaii

Beachfront Estate North Shore Oahu – Surf & Sunsets Await!

A Rare Opportunity To Stay in Hawaiian ParadiseNestled on the world-famous North Shore of Oahu, this stunning beachfront estate offers an unparalleled blend of luxury, comfort, and adventure. Whether you're looking to come to paradise with a group of friends or enjoy a...

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

Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates

We welcome short term rentals Welcome to this nicely updated two bedroom condo located on the peaceful East side of Kuilima Estates at Turtle Bay. The condo features brand new tile flooring in the living room and kitchen along with new kitchen cabinetry!This unit has a...

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

Jungle Estate - 3 Cottages, 1.5 Acres and a POOL Sleeps 9

If you are dreaming of your own private getaway for up to nine guests in the verdant landscapes on the east side of Hawaii Island, you've come to the right place! Jungle Estate offers three cottages spread over a 1.5 acre parcel in Hawaiian Paradise Park, just south of...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 9
📍 Keaau, Hawaii

Luxury Fairwayfront Estate w/Private Pool, Spa, AC & Stunning Views: Kamilo #217

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.Welcome to Mauna Lani KaMilo #217 by Gather, a cozy and inviting four-bedroom, three-bathroom home in Kamuela, HI. Nestled on the stunning Kohala Coast within the...

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

Hale O Ka Nalu Po'i: Oceanfront Estate on Poipu Coastline

Breathtaking, magnificent, superlative, sublime: there’s simply no way to overstate the extraordinary appeal of this uniquely situated, strikingly beautiful oceanfront estate. Hale O Ka Nalu Po'i (poetically named for the waves that crash dramatically against...

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

Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)

***WE ARE ON OAHU, AND CONTINUE TO WELCOME VISITORS***Fully remodeled 2 bedroom ( 2nd bedroom is large loft) beautiful condo with 2 full bathrooms. We are in Kuilima Estates West, which is next to , but not a part of, the Turtle Bay resort. We have 3 pools for your use....

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

Hualalai Hainoa Estate | Private Residence | Pool | Panoramic Ocean Views

Spectacular sunset and panoramic view highlight this large estate home with private heated pool and spa at Hualalai Resort. Located along the first fairway of the Tom Weiskopf-designed member's golf course, the home features 4 bedrooms and 4.5 bath on one level, with...

🛏 4 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Surfer Hale - Kuilima Estates East # 1

TA/155037900801-01Short Term License STR#2034Kuilima Estates East57-120 Lalo Kuilima #1Beautiful downstairs end unit condo. Step into old Hawaii. Hawaiian decor with natural wood and rattan furniture and tropical colors. 2021 brought new floors, quartz countertops in...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kahuku, Hawaii

Pulelehua Kuilima Estates West #142: Bright & Lively w/ Community Pool & A/C

A restful retreat on the North Shore of O’ahu awaits either couples or small families in the one bedroom, one bath ground floor condominium unit of Pulelehua Kuilima Estates West #142. Located on the grounds of the Turtle Bay Resort, the swaying palm trees, colorful...

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

3-bedroom estate in peaceful Haleiwa Hawaii

Haleiwa is waiting for you at this marvelous 3-bedroom estate. With 2 queen beds and 1 king bed, this brilliant property offers a cozy retreat for guests. Enjoy the bathtub, hair dryer, and WiFi during your stay. We're happy to assist with any questions while you stay...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Haleiwa, Hawaii

Kukuna Estate – Luxury Kailua-Kona Coast Villa

WHY IT'S SPECIALElevate your vacation at Kukuna Estate, a peaceful retreat with plenty of relaxation at a cool 1300 feet above sea level. This stunning property offers superb panoramic beach and ocean views from its elegantly designed living room and sprawling multiple...

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

Private Townhouse on the North Shore - Kuilima Estates West #131

The perfect mixture of resort life in a private home. This spacious 3 bedroom, 2 bath townhome is located adjacent to the Turtle Bay Resort and its two golf courses, the Fazio and Palmer Courses. This unit is located in the Kuilima Estates, which provides access to the...

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

Beautiful Turtle Bay Condo - Kuilima Estates East

Beautiful Turtle Bay and Kuilima Estates is located on 840 acres of landscaped gated grounds, the only tropical resort on Oahu's tranquil and iconic North Shore!Get away from busy Waikiki and other crowded vacation spots with our tastefully decorated one bedroom condo...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

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