KIHEI Listings

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Monthly $7850.00 - $9920.00

Sugar Beach Resort 415: 1BR Oceanfront | Balcony Kihei, Hawaii, Listing ID: 33161

Snorkel, surf, and swim at this charming Sugar Beach Resort condo! Boasting a prime, walkable location to one of the best beaches in Maui, this resort also offers shared amenities for added fun including a pool, hot tub, sauna, shop, and a grilling area. Wake up the gentle waves...

  • Condo
  • 0
  •  1
  •  1
Monthly $7500.00 - $12400.00

High-End 2BR | Pools | Hot Tub | Tennis | Grill Kihei, Hawaii, Listing ID: 33163

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  2
  •  2
Monthly $4650.00 - $7120.00

Maui Kamaole K110: 1BR | Pool | Hot Tub Kihei, Hawaii, Listing ID: 33164

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  1
  •  2
Monthly $6200.00 - $10190.00

Maui Kamaole B202: Tropical 2BR | Patio | Pool Kihei, Hawaii, Listing ID: 33165

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  2
  •  2
Monthly $4200.00 - $4870.00

Kihei Akahi D613: 1BR Oceanview | Pool Kihei, Hawaii, Listing ID: 33166

Step across the street and enjoy Kamaole Beach Park II, one of Mauis best swimming and stunning beaches. Revel in the spectacular sunsets or stroll along miles of white sandy beach at first light. Kihei Akahi is ideally situated and offers excellent value. This one-bedroom...

  • Condo
  • 0
  •  1
  •  1
Monthly $4200.00 - $4680.00

Kihei Akahi C515: 1BR Oceanview | Pool Kihei, Hawaii, Listing ID: 33167

Step across the street and enjoy Kamaole Beach Park II, one of Mauis best swimming and stunning beaches. Revel in the spectacular sunsets or stroll along miles of white sandy beach at first light. Kihei Akahi is ideally situated and offers excellent value. This one-bedroom...

  • Condo
  • 0
  •  1
  •  1

Similar Properties


Nightly $2500.00 - $29000.00

Luxury Oceanfront Estate: Royal Kahala Estate Honolulu, Hawaii, Listing ID: 30104

Royal Kahala Estate is Oahu’s most luxurious vacation rental near the foot of Diamond Head. The exquisite home features seven bedrooms, eight full baths, and a half-bath, encompassing 14,000 square feet all within a private beachfront estate. This stylish and exclusive...

  • Estate
  • 13000
  •  8
  •  9 1/2
Nightly $327.00 - $4400.00

Historic Home+guest cottage in Kahala near the Beach w/Pool & AC: Ho'okipa Villa Honolulu, Hawaii, Listing ID: 30105

Kahala Luxury Living Welcome to Ho'okipa Villa! Built in 1938 and recently renovated, this luxury home offers a unique combination of vintage and modern beach charm. Four bedrooms and three bathrooms comprise the main home, including the Master Bedroom with an ensuite bath as...

  • House
  • 3010
  •  5
  •  4
Nightly $200.00 - $1200.00

Immersed in nature Home w/ A/C, bbq area, Hale Poola Honolulu, Hawaii, Listing ID: 30106

This five-bedroom, three-bathroom home sits in the wonderful quiet neighborhood of Aina Haina. The home offers the perfect retreat for families hoping to avoid the hustle and bustle of Waikiki, yet remain close to all the attractions of south Oahu. Unassuming, Private...

  • House
  • 1678
  •  5
  •  3
Nightly $1335.00 - $5000.00

Gorgeous Oceanfront Home w/Private Pool, Jacuzzi, & Sunset Views. Moana Lani Honolulu, Hawaii, Listing ID: 30107

Welcome Home to 'Moana Lani'! Are you ready for a truly private and awe-inspiring waterfront vacation? This oceanfront estate designed by Philip 'Pip' White, offers sunsets and views galore! All while being centrally located 10 minutes to Kahala and 5 minutes to Hawaii Kai!!...

  • House
  • 5103
  •  5
  •  5 1/2
Nightly $175.00 - $1500.00

Family fun Cottage w/Private Pool,A/C, walk to Beach and shops, Kahala Cottage Honolulu, Hawaii, Listing ID: 30108

This home-away-from-home exudes island style and comfort! Open, airy Kahala Cottage features two charming living spaces, a nicely-appointed kitchen, and a dedicated dining area that allow guests to enjoy quality time together at home. Flexible sleeping options enable it to...

  • House
  • 1628
  •  2
  •  2
Nightly $667.00 - $3000.00

Luxurious Kailua Home w/Pool Oasis & A/C, Near Beaches and Shopping - Maluhia Kailua, Hawaii, Listing ID: 30109

Let the tranquil atmosphere of Maluhia whisk you into vacation mode. A favorite of many celebrities and families for the perfect, peaceful getaway, Maluhia is the definition of island contemporary. Its remodeled, modern interior features nearly 5,000 sq. ft. of living space. The...

  • House
  • 4919
  •  4
  •  4
Nightly $400.00 - $1024.00

Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach - Lanikai Cottage Kailua, Hawaii, Listing ID: 30110

Charming Lanikai Cottage features two dwellings on the same property, providing a total of three bedrooms and two bathrooms. Although separate, the dwellings share a private fenced-in yard with a new pool. Furnished in a beach-chic style, both offer the option of relaxing in air...

  • House
  • 1469
  •  3
  •  2
Nightly $433.00 - $3500.00

Luxury Home w/Cottage, Private Saltwater Pool & Observatory Deck: Villa Luana Honolulu, Hawaii, Listing ID: 30111

Villa Luana (meaning happy or content) provides an ideal setting for relaxing in blissful comfort. With several living spaces, a gourmet kitchen, and a large dining area, high speed WIFI, this elegant home perfectly accommodates everything from multi-generational families to...

  • House
  • 4500
  •  6
  •  6
Nightly $550.00 - $2200.00

One-of-a-Kind Home w/Pool, A/C, chef's kitchen and Mountain Views - Hale Laulea Honolulu, Hawaii, Listing ID: 30112

Heavenly Hale Laulea, or “house of peace and happiness,” rests on Kamehame Ridge in South Oahu’s exclusive Hawaii Kai neighborhood. Unpack and unwind in this spacious contemporary four-bedroom, three-bathroom home. A Private Oasis Hale Laulea features sleek, modern...

  • House
  • 2990
  •  4
  •  3
Nightly $380.00 - $1812.00

Beautiful Tropical Home Close to Beach w/Pool, Yard & AC: Hale Nani Lanikai Kailua, Hawaii, Listing ID: 30113

Nestled in the highly sought after wonderful Lanikai community, this beautiful executive home was newly built in 2014. This home is a perfect vantage point. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the...

  • House
  • 0
  •  3
  •  3 1/2
Nightly $1735.00 - $5039.00

Gorgeous Banzai Beachfront Home w/AC & Stunning Ocean Views - Pipeline House Haleiwa, Hawaii, Listing ID: 30114

The Pipeline House is a uniquely designed piece of paradise that sits on the beach, front and center at the world famous Bonzai Pipeline! Pipeline or Ehukai Beach which means sea spray is located on the best stretch of beach throughout all of Hawaii and is referred to as the...

  • House
  • 2386
  •  3
  •  3 1/2
Nightly $300.00 - $1995.00

Charming Spanish Colonial Historic Home,Ocean Views,A/C,Near Waikiki. Hale Mahie Honolulu, Hawaii, Listing ID: 30115

A 10-minute walk from Waikiki, discover your own private paradise nestled at the base of Diamond Head in Honolulu’s renowned Gold Coast. Built in 1926 and beautifully remodeled with modern luxuries, Hale Mahie is notable as an example of the Spanish Colonial Revival style,...

  • House
  • 3795
  •  4
  •  3 1/2
Nightly $230.00 - $1083.00

Gorgeous Hilltop Home Overlooking Miles of Water and Coastline. Private Pool & Courtyard - Hale Maluhia (Big Island Kailua Kona, Hawaii, Listing ID: 30116

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Hale Maluhia Nestled near the top of the hill overlooking the ocean, this home is just a few minutes from Kailua Kona town center. Perched upon a knoll at the perfect...

  • House
  • 2230
  •  3
  •  3
Nightly $226.00 - $672.00

Perfect Family Getaway! Private Lanai & Pool Overlooking the Water - 7 C's Kona (Big Island) Kailua Kona, Hawaii, Listing ID: 30117

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Welcome to 7C's Kona, where you'll experience amazing Hawaiian sunsets from the back lanai! This beautifully decorated 3 bedroom, 2.5 bath home is the perfect place for your...

  • House
  • 2106
  •  3
  •  3
Nightly $333.00 - $3200.00

Tropical Home w/Pool, Yard, Outdoor Lanai for Entertaining, & A/C. Hale Niuiki Honolulu, Hawaii, Listing ID: 30118

High Class Luxury E komo mai (welcome) to Hale Niuiki! The home's expansive open floor plan seamlessly connects the living and dining spaces to the newly-remodeled kitchen, allowing large groups endless options for spending time together. Stone floors, elegant wood-beam...

  • House
  • 3265
  •  4
  •  4
Nightly $250.00 - $464.00

Oceanfront Condo w/Views of Diamond Head & Seaside Pool. Executive Gold Coast Honolulu, Hawaii, Listing ID: 30120

This exquisitely decorated two bedroom Coral Strand suite provides nearly 360 degree panoramic views along the Gold Coast beyond Waikiki Beach and back around to the notorious Diamond Head. Spectacular oceanfront unit provides tropical elegance overlooking the blue Pacific...

  • Condo
  • 1456
  •  2
  •  2
Nightly $450.00 - $3200.00

Oceanfront Home w/Pool, A/C, and stunning Sunset Views, Hale Kai Honolulu, Hawaii, Listing ID: 30121

Hale Kai offers space and comfort in a chic oceanfront setting. The pristine, private ocean front house has its own staircase leading down to the stunning shoreline of Maunaloa Bay. Centrally located in Portlock, just a few minutes' walk or drive from marina-front dining and...

  • House
  • 0
  •  5
  •  3 1/2
Nightly $280.00 - $2250.00

Large Tropical Modern Home w/Pool, Ocean / Koko Head Views, & A/C. Makani Lani Honolulu, Hawaii, Listing ID: 30122

Make lasting memories with your family in this tropical retreat. Located in Hawaii Kai on a quiet cul-de-sac, Makani Lani provides expansive views and a spa-like setting near all the attractions of south Oahu. The main floor of Makani Lani offers commanding views of Koko Crater...

  • House
  • 2567
  •  5
  •  3 1/2
Nightly $167.00 - $1100.00

Oceanfront Cottage w/Panoramic Views, Yard, & Private Beach Access. Waipuna Laie, Hawaii, Listing ID: 30123

Welcome to Waipuna Cottage, a charming oceanfront property located on a private secluded estate with panoramic coastline views. This oceanfront home is kept in its originally built state with much of the original hardware and fixtures present. The main bedroom is completely...

  • House
  • 1272
  •  2
  •  2
Nightly $167.00 - $540.00

Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool. Ohana Kai Honolulu, Hawaii, Listing ID: 30124

Enjoy your own waterfront slice of Hawaii at Ohana Kai! Located in a gated community along Hawaii Kai’s stunning waterway, you’ll enjoy marina and Koko Head views from every room. Unwind in the casual charm of this peaceful paradise with its open floor plan and stylish...

  • Condo
  • 1464
  •  3
  •  2 1/2
Nightly $450.00 - $3150.00

Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head Views,Aloha Nalu Honolulu, Hawaii, Listing ID: 30126

Discover one of Oahu's luxury vacation rentals with its gorgeous private pool terrace overlooking the Pacific Ocean and Diamond Head, Aloha Nalu (meaning “warm, welcoming sea”) will surely sweep you into the spirit of aloha. The villa sits on the side of Koko Crater among...

  • House
  • 3387
  •  4
  •  3 1/2
Nightly $416.00 - $3600.00

Modern Tropical Home w/Pool, Private Yard, & A/C. Kahala Breeze Honolulu, Hawaii, Listing ID: 30127

Experience the laidback luxury and authentic island living of Kahala Breeze, a spacious four-bedroom home that features elegant decor and design cohesive with the natural beauty that surrounds it.  An abundance of windows in the living area allows for maximum light and fresh...

  • House
  • 3022
  •  4
  •  4 1/2
Nightly $650.00 - $4078.00

Gorgeous Oceanfront Home w/Mokulua Isle Views, Yard & AC: Lanikai Oceanside Kailua, Hawaii, Listing ID: 30128

With front row seats to the ocean and the famous Mokulua Islands of Kailua, Lanikai Oceanside offers the best seats in the house. Newly renovated, this tropical chic and modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea,...

  • House
  • 4880
  •  5
  •  4
Nightly $2125.00 - $946000.00

Luxury Oceanfront Estate: Maunalua Bay Estate Honolulu, Hawaii, Listing ID: 30129

Oahu's Newest Luxury Estate Maunalua Bay Estate is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego based developer Mark Gosselin. This estate is a modern take on Oahu's well-known Banyan House....

  • House
  • 8800
  •  6
  •  7 1/2
Nightly $225.00 - $6000.00

Posh Oceanview Condo w/Resort Pool & Spa, AC & Spacious Lanai - Park Lane Palm Honolulu, Hawaii, Listing ID: 30130

Intentional Interiors The Park Lane Palm Resort suite is equipped with a full modern living, kitchen and dining area which comfortably accommodates six. In the evening, lounge on the sofa for some television time. The primary suite features a sumptuous king-size bed and spa-like...

  • Condo
  • 1635
  •  2
  •  2
Nightly $500.00 - $2599.00

Stunning Secluded Fmaily Oasis w/ Private Pool and Courtyard - Lanikai Breeze Kailua, Hawaii, Listing ID: 30131

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze. Built in 2017, this brand new construction boasts upgraded appliances and...

  • House
  • 3240
  •  5
  •  4 1/2
Nightly $525.00 - $1300.00

Gorgeous Oceanview Estate w/Private Pool, Spa & AC: Breathtaking Mango Sunsets Kamuela, Hawaii, Listing ID: 30132

We invite you to sit back, relax and experience the dazzling sunsets, tropical breezes and never ending ocean views from "Mango Sunsets", our private 3-acre Kohala Ranch estate where modern elegance meets traditional quality craftsmanship. This previous popular vacation rental...

  • House
  • 2924
  •  3
  •  3
Nightly $227.00 - $1300.00

Elegant Home overlooking the Marina w/Jacuzzi, Outdoor space, AC, Holoholo Hale Honolulu, Hawaii, Listing ID: 30133

Discover one of our most recent additions to the vacation rental market on Oahu! Enjoy your own slice of Hawaii waterfront at Holo Holo Hale, located in safe and small community along Hawaii Kai’s stunning waterway... Unwind in the casual charm of this peaceful paradise with...

  • House
  • 1890
  •  4
  •  2
Nightly $2300.00 - $16124.00

Expansive Beachfront Kailua Shores Estate w/Pool, Spa, AC & Breathtaking Views Kailua, Hawaii, Listing ID: 30134

One of the largest, most private and secluded vacation rental residences on the island of Oahu, Kailua Shores Estate provides a spectacular beachfront location and all the amenities of a luxury resort, making it ideal for a family reunion, an escape to paradise with a group of...

  • Estate
  • 7500
  •  8
  •  9
Nightly $198.00 - $1083.00

Spectacular Oceanview Home w/Private Pool & Spa, AC & Lanai - Sunset Hale Kailua Kona, Hawaii, Listing ID: 30135

Sunset Hale is a stunning tropical escape situated above downtown Kona. Luxuriously appointed, this residence is nestled within the lush green hillside overlooking Kamakahou Bay, features a 900 sq. ft. lanai and can accommodate up to six guests. Tropical luxury awaits you at...

  • House
  • 2230
  •  3
  •  2 1/2
Nightly $3000.00 - $13590.00

Luxury Beachfront Kai Moena Estate w/Pool, Spa, AC, Sauna, Tennis Court & More! Kailua, Hawaii, Listing ID: 30136

This luxury vacation rental sits on nearly 60,000 sq. ft. of prime Kailua Beach property with 225+ sq. ft. of linear beach frontage featuring soft sand, blue water and spectacular views of Kailua Bay. Two separate rental houses by award winning architect James McPeak are laid...

  • Estate
  • 8600
  •  9
  •  7 1/2
Nightly $312.00 - $949.00

Luxurious Oceanview Getaway w/Private Pool & Spa and Serene Lanai - Piko Nani Kailua Kona, Hawaii, Listing ID: 30137

Please note that the neighboring property is under construction and the construction team is actively working on the property Monday through Friday from 8-5. To assist in ensuring tranquility we have programmed the pool waterfall to drown out the noise. Feel free to inquire to...

  • House
  • 2740
  •  3
  •  3 1/2
Nightly $667.00 - $3930.00

Luxurious Kahala Grand Splendor: Private Home w/Pool, Spa, AC & Lush Landscaping Honolulu, Hawaii, Listing ID: 30138

Admiration starts at first glance with this contemporary vacation residence, located in a luxury residential area in Kahala, right at the slopes of Diamond Head. The luxury residence was completed in 2015, boasting a huge pool, luxurious rooms with extravagant details, and...

  • House
  • 5002
  •  5
  •  4 1/2
Nightly $350.00 - $4219.00

Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa: Kahala Seaside Honolulu, Hawaii, Listing ID: 30139

Welcome to Kahala Seaside, a spacious two-story garden view home featuring four bedrooms, three-and-a-half bathrooms, and lush garden views. Nestled in the upscale seaside burg of Kahala, you’ll have access to all the fun and excitement of Waikiki, including luxury shopping,...

  • House
  • 2355
  •  4
  •  3 1/2
Nightly $600.00 - $3500.00

Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset Honolulu, Hawaii, Listing ID: 30140

Situated in the famed oceanside neighborhood of Portlock on a rare double-sized ocean lot, this Hawaii Kai vacation rental home provides the ultimate in privacy and accommodations for your large group. Multiple estate structures surround a tropical courtyard and...

  • House
  • 3339
  •  6
  •  6 1/2
Nightly $400.00 - $667.00

Newly Remodeled Ocean-View Home With A/C, Steps From Pipeline: Ehukai Beach Hale Haleiwa, Hawaii, Listing ID: 30141

This updated Haleiwa vacation rental home is just steps from the sand at Ehukai Beach Park and world-famous Banzai Pipeline. Complete with ocean views and air conditioning in the living areas, it has a chic, modern beach house feel with elegant finishes and all the amenities...

  • House
  • 1704
  •  3
  •  2
Nightly $1667.00 - $25000.00

Extravagant Kahala Beachside Estate w/Pool, Jacuzzi, AC & Spacious Yard Honolulu, Hawaii, Listing ID: 30142

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Boasting an extraordinary beachfront location, this private Kahala vacation rental estate provides all the modern luxury features your large group requires, with the charm of...

  • House
  • 7860
  •  7
  •  8
Nightly $583.00 - $4465.00

Exquisite Oceanfront Retreat w/Mokulua Views, AC & Lush Yard: Lanikai Seashore Kailua, Hawaii, Listing ID: 30143

Experience luxurious coastal living at Lanikai Seashore, a tropical two-story vacation rental just steps away from the renowned Lanikai Beach. This villa’s spacious open floor plan and unobstructed ocean views makes one feel they’re almost on their own private isle; away...

  • House
  • 2100
  •  4
  •  3 1/2
Nightly $533.00 - $7000.00

Gold Coast Oceanfront Home w/AC & Gorgeous Views: Diamond Head Surf House Honolulu, Hawaii, Listing ID: 30144

Completely immerse yourself into the island life in this brand-new, picturesque Diamond Head luxury vacation rental. With its striking ocean views and ideal location nestled between Diamond Head and Waikiki, it’s no wonder that time moves a little more slowly in this coveted...

  • House
  • 3047
  •  3
  •  3 1/2
Nightly $334.00 - $2160.00

Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua Kailua, Hawaii, Listing ID: 30145

Let the relaxing atmosphere of Lokomaika’i Kailua (meaning Gracious Kailua) whisk you into vacation mode. The home includes 2 primary suites that beckon you to the outdoor areas of the pool and garden. There are also 2 additional bedrooms and bonus sitting room located off of...

  • House
  • 2680
  •  5
  •  3
Nightly $470.00 - $1848.00

Bright Kailua Retreat w/hot tub, Lush Pool, Walk to Beach: Hale Ohana Kailua, Hawaii, Listing ID: 30146

Hale Ohana meaning Family House is just that! With multiple lounge areas, pool, hot tub, game room inclusive of a spider man pinball game, ping pong table and much more this home is perfect for a family get away! The home includes 3 bedrooms in the main house and a separate...

  • House
  • 2987
  •  4
  •  3
Nightly $233.00 - $1400.00

Private & Quiet Oceanfront Home w/ Stunning Ocean/Mountain Views: Hale Ula Ula Kahuku, Hawaii, Listing ID: 30147

Please note: This property is currently for sale. The property manager may contact you to make arrangements to schedule showings at a convenient time if necessary. Welcome to old Hawai'i. Hale Ula Ula sits on a white sandy beach with calm blue waters right in front. Private,...

  • House
  • 1292
  •  3
  •  2
Nightly $1666.00 - $5500.00

Lavish Oceanview Estate w/Pool, Spa, AC & Mokulua Isle Views: Lanikai Hillside Kailua, Hawaii, Listing ID: 30148

Welcome to Lanikai Hillside Estate, a premier vacation rental nestled on the world’s most isolated chain of islands. While residing here, you’ll delight in the near heaven-like beauty of this small, coastal community which is truly the envy of all paradises. Lanikai Hillside...

  • Estate
  • 6296
  •  5
  •  6 1/2
Nightly $750.00 - $4095.00

Balinese-inspired decor Home immersed in nature w/ Private Pool, Kahala Lani Honolulu, Hawaii, Listing ID: 30150

Ideal for multi-generational families and golf enthusiasts, this exquisite five bedroom, four bath home blends both island-style and Balinese touches to create the ultimate vacation home. Spread over 20,000 square feet, this property sleeps 14 guests and boasts incredible...

  • House
  • 4339
  •  5
  •  4
Nightly $480.00 - $3302.00

Modern Beachfront Home w/Ocean views covered Lanai and AC: Hale Waimanalo Waimanalo, Hawaii, Listing ID: 30151

Commonly known as the Paniolo countryside, you could pass right through the small town of rural Waimanalo on the southeastern corner of O’ahu and never realize what you missed. Nestled in this quaint village is a hidden gem, Hale Waimanalo, where you will wake up every morning...

  • House
  • 2440
  •  4
  •  4
Nightly $931.00 - $8333.00

Hidden Mountainside Home w/ Private Pool, Ocean Views & soaking tub, Hale Lani Kailua, Hawaii, Listing ID: 30152

Find your next dream vacation here at Hale Lani, situated on the picturesque northern shores of Oahu, Hawaii. Hale Lani in Hawaiian translates to “house in the heavens”, and this heavenly home surely lives up to its name. Nestled atop the lush mountainside of the...

  • House
  • 2888
  •  3
  •  4
Nightly $1000.00 - $9532.00

Ocean View Home w/ Oahu beach in the backyard, Hale Nalu Haleiwa, Hawaii, Listing ID: 30153

Not only are you surrounded by the world famous beaches of the North Shore of O’ahu at Hale Nalu, your backyard extends out into the Pacific Ocean, making for an unforgettable beach vacation. Sleeping up to 14 guests and with two separate kitchens and living spaces, this six...

  • House
  • 2682
  •  6
  •  4
Nightly $200.00 - $911.00

North Shore little Paradise w/ AC, Mountain & Ocean Views: Pali Kai Kaaawa, Hawaii, Listing ID: 30154

From the moment that you walk through the cozy wooden gates, you can settle into the pleasantries of your Hawai’i vacation home at Pali Kai. Nestled into the quiet side streets off of the Kamehameha Highway in the small town of Ka’a’awa on the North coast of Oahu, you’ll...

  • House
  • 729
  •  2
  •  1
Nightly $300.00 - $3242.00

Unique Luxury Oahu Villa w/ AC,Private Yard & Mountain View:Hawaii Hobbit House Waimanalo, Hawaii, Listing ID: 30155

Take a journey back in time at Hawaii Hobbit House. This cozy, yet abundant luxury villa is shrouded in charm as well as amenities for your whole party to enjoy. Equipped with 3 bedrooms, 3 full bathrooms and accommodating 12 people, you and your party will feel enveloped in...

  • Villa
  • 2691
  •  3
  •  3
Nightly $584.00 - $3796.00

Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi Honolulu, Hawaii, Listing ID: 30156

Let your dream tropical vacation begin when you step into the olden days of Hawai’i here at Hale Le’ahi, an illustrious and expansive 3 story plantation board and baton wood-framed estate located on the lower slopes of the world famous Diamond Head Crater on the southern tip...

  • Estate
  • 4200
  •  5
  •  4
Nightly $200.00 - $620.00

New Listing! Serene Ocean View Home w/Private Pool, Yard & AC: Malulani Retreat Kailua Kona, Hawaii, Listing ID: 30157

New on the Rental Market Special! If you are searching for the perfect Hawaiian vacation rental home that combines style, comfort, tranquility and access to nightlife, then look no further than Malulani Retreat. This hidden gem of a home is located on the western side of the...

  • House
  • 1340
  •  2
  •  2
Nightly $383.00 - $2250.00

Modern Private Oasis w/ Private Pool/Hot Tub, Sauna, AC & BBQ: Hale Ho'omaha Honolulu, Hawaii, Listing ID: 30158

E komo mai (welcome) to Hale Ho’omaha, the house of relaxation! The home's expansive open floor plan seamlessly connects the living and dining spaces to outdoors, allowing large groups endless options for spending time together. Modern island furnishings and tropical...

  • House
  • 3069
  •  5
  •  3 1/2
Nightly $480.00 - $5000.00

Ocean View Villa w/Beach as Backyard, Walk to Attractions: Kailua Hale Kahakai Kailua, Hawaii, Listing ID: 30160

Let the tranquil atmosphere of Kailua Hale Kahakai whisk you away into vacation mode! Located on one of the most beautiful stretches of Kailua Beach, this spacious villa boasts gorgeous ocean views from four of the six bedrooms. This villa also sits on a quiet flag lot, offering...

  • Villa
  • 4326
  •  6
  •  5
Nightly $1440.00 - $9500.00

Stunning Beachfront Estate w/Private Pool/Spa, Ocean View & AC, Kailua Beach Villa Kailua, Hawaii, Listing ID: 30161

Welcome to Kailua Beach Villa, the perfect luxury Hawaiian home for your next beachfront getaway. This large, 2-level clean and contemporary villa comes with 5 bedrooms (and 1 additional optional bedroom), 5 bathrooms and sleeps up to 12 guests. With a spacious and open-air...

  • Villa
  • 4000
  •  5
  •  5
Nightly $650.00 - $6000.00

Luxury Condo w/ Resort Pool/Spa, AC, Ocean View & Spacious Lanai: Park Lane Sky Honolulu, Hawaii, Listing ID: 30162

Intentional Interiors The Park Lane Sky Resort suite is equipped with a full modern living, kitchen, and dining area which comfortably accommodates six. In the evening, lounge on the sofa or additional seating in the living area for some television time or catch up with family...

  • Condo
  • 2700
  •  3
  •  3 1/2
Nightly $450.00 - $1750.00

Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate Kailua, Hawaii, Listing ID: 30163

Ranch Beach House Estate is a hidden Hawaiian gem, just steps away from Kailua’s powder white sand beaches. Located on one of Kailua’s most coveted loops, you will find its location ideally accessible to numerous cafés, boutiques and farmers’ markets. A well-manicured...

  • Estate
  • 3800
  •  4
  •  3 1/2
Nightly $517.00 - $1434.00

Oceanview Estate w/ Pool/Spa, Tennis Court, Fitness Pavilion & AC: Olomana Hale Kamuela, Hawaii, Listing ID: 30164

Come settle into your relaxing Hawaiian vacation here at Olomala Hale at Kohala Ranch, a luxurious 5-bedroom, 3.5-bathroom gated estate located in the upscale gated community of Kohala Ranch on the sunny slopes of the majestic Kohala Mountains. Enjoy total tranquility and...

  • Estate
  • 3850
  •  5
  •  3 1/2
Nightly $667.00 - $7994.00

Oceanfront Luxury Home w/Hot Tub, A/C & Views of Lanikai Beach: Na Makana Villa Kailua, Hawaii, Listing ID: 30165

Welcome to Na Makana Villa, the perfect luxury Hawaiian home for your next beachfront getaway. This expansive villa comes with 4 bedrooms in the main house and a 2 bedroom attached guest cottage, providing enough space to sleep up to 13 guests. With a spacious and open-air...

  • Villa
  • 4098
  •  6
  •  4 1/2
Nightly $300.00 - $1812.00

Peaceful Oceanfront Home Near Downtown Kailua w/ BBQ & AC: Kai Mele Kailua, Hawaii, Listing ID: 30166

Welcome to Kai Mele, your next charming beachfront getaway filled with all the historic charm and character. Nestled on the picturesque Kailua shores of Oahu, this quaint island home with its antique quirks is full of cozy comforts that are sure to relax and revitalize its...

  • House
  • 1690
  •  3
  •  2
Nightly $934.00 - $7475.00

Luxury Villa w/ Ocean View, Private Pool, Superb Design: Diamond Head Grandeur Honolulu, Hawaii, Listing ID: 30167

Find peace and tranquility in your very own 5-bedroom, 5.5-bathroom villa here at Diamond Head Grandeur in the centralized neighborhood of Kahala on Oahu. Around the corner from the Diamond Head State Monument, this stunning property is just 15 minutes from downtown Honolulu and...

  • Villa
  • 5727
  •  5
  •  5 1/2