Kailua Listings

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Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 18,000

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
Monthly Rent $ 27,480

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
Monthly Rent $ 0

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
Monthly Rent $ 75,000

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
Monthly Rent $ 140,010

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
Monthly Rent $ 28,500

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
Monthly Rent $ 0

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
Monthly Rent $ 84,990

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
Monthly Rent $27,930 - $108,000

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
Monthly Rent $ 30,000

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
Monthly Rent $ 0

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
Monthly Rent $ 22,500

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
Monthly Rent $ 45,000

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
Monthly Rent $ 15,000

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
Monthly Rent $ 17,490

Superbly Designed Home w/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise Kailua, Hawaii, Listing ID: 30173

Enjoy top-tier luxurious living on your next Hawaiian vacation at the Mokulua Sunrise ocean villa, located in the world famous neighborhood of Lanikai on the eastern shores of the vibrant island of Oahu. This 4-bedroom, 3.5 bath home lets you escape to the privacy and...

  • House
  • 4385
  •  4
  •  3 1/2
Monthly Rent $ 39,990

Luxurious Villa w/ Private Pool, Jacuzzi & Stunning Ocean Views: Lanikai Villa Kailua, Hawaii, Listing ID: 30175

Make your tropical fantasy vacation a reality with this seamlessly designed coastal villa just minutes away from the world famous Lanikai Beach. On the eastern shores of Oahu, this luxurious 4 bedroom and 4.5 bathroom home hosts tons of stunning features such as a large...

  • Villa
  • 4800
  •  4
  •  4 1/2
Monthly Rent $ 0

New to the market! Private Villa w/Pool, AC, walk to beach: Villa Hui Hou Kailua, Hawaii, Listing ID: 30180

The ultimate beach lifestyle awaits you at idyllic Villa Hui Hou on O’ahu’s scenic windward coast. Located off the main strip in the exclusive neighborhood of Lanikai, this recently remodeled five bedroom, four and a half bathroom property boasts a backyard oasis,...

  • House
  • 4920
  •  5
  •  4 1/2
Monthly Rent $ 0

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

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Monthly Rent $2,000 - $3,150

Waikiki condo w/ lanai, mountain/city views & shared pool/hot tub/gym/sauna! Honolulu, Hawaii, Listing ID: 26803

Wake up to views of Honolulu's lush mountains, glittering cityscape, and Ala Wai Canal at this comfortable high-rise condo in the heart of Waikiki! You'll have a private lanai, easy walking access to shopping and dining, and shared use of an outdoor pool, a hot tub, a sauna, a...

  • Condo
  • 678
  •  1
  •  1
Monthly Rent $1,800

Amazing Tropical Condo w/Shared Pool, Private Washer/Dryer, Free WiFi, Lanai Maunaloa, Hawaii, Listing ID: 28522

This two-story condo sits over the pool. The upper level includes the main bedroom, and there are two bathrooms, one on each floor. This condo is about 1,000-square-feet and features open beam ceilings with ceiling fans, beautiful burnished floors, and a large screened-in lanai....

  • Home
  • 500
  •  1
  •  2
Monthly Rent $1,800

Ground-Floor Condo w/ Ocean View, Lanai, Shared Pool/Hot Tub - Walk to Beach! Maunaloa, Hawaii, Listing ID: 28612

Enjoy views that reach the Pacific Ocean at Ke Nani Kai 113, a bright and cheery two-bedroom, two-bathroom condo on Molokai's west end. Here on the ground floor of Ke Nani Kai, you'll have sliding glass doors that open to your private lanai, where you can relax in a lounge chair...

  • Condo
  • 950
  •  2
  •  2
Monthly Rent $1,800

Garden View, Ground-Floor Condo w/ Lanai & Shared Hot Tub/Pool - Walk to Beach! Maunaloa, Hawaii, Listing ID: 28617

With views of the surrounding garden property from the living room, both bedrooms, and the private lanai, this ground-floor condo at Ke Nani Kai offers a relaxing escape on the serene west side of Molokai. Step inside to find a thoughtfully upgraded living space with a fully...

  • Condo
  • 950
  •  2
  •  2
Monthly Rent $1,800

Secluded Corner Condo w/Nature Views, Wrap-Around Lanai, Free WiFi, Shared Pool Maunaloa, Hawaii, Listing ID: 28621

Your next escapade to Maunaloa will be unforgettable thanks to this 1,000+ sq. ft., garden/ocean view condo featuring an open floor plan, hardwood floors, wood-planked cathedral ceilings, two skylights, and a magnificent fully-screened, wrap-around 400+ sq. ft. lanai) in Paniolo...

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  • 0
  •  1
  •  1
Monthly Rent $1,800

Oceanfront Studio w/Free WiFi, Lanai, & Shared Pool, Grills - Walk to the Beach! Maunaloa, Hawaii, Listing ID: 28622

This lovely, oceanfront studio is the ideal place for a relaxing getaway to Hawaii! It has a screened-in lanai with furniture to lounge on and is within walking distance to all our beautiful white sand beaches and a sundry shop located in the old hotel. It's quite a large studio...

  • Condo
  • 0
  •  0
  •  1
Monthly Rent $ 159,990

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 30,960

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
Monthly Rent $88,710 - $98,340

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 7,500

Oceanfront Custom Home w/A/C, Large Yard, & Lanai for Entertaining. Makaha Hale Waianae, Hawaii, Listing ID: 30119

Located on Oahu's Leeward coast, this private oceanfront estate in West Oahu boasts views of the Waianae mountain range and Pacific Ocean. Enjoy spectacular sunsets and dramatic surf from this custom west side getaway. Beautifully remodeled and upgraded in 2007 this 6 BD/4 BA...

  • House
  • 2974
  •  6
  •  3 1/2
Monthly Rent $ 7,500

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
Monthly Rent $ 28,500

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 17,490

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
Monthly Rent $ 124,980

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
Monthly Rent $ 16,020

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 12,000

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
Monthly Rent $ 21,000

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
Monthly Rent $ 0

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
Monthly Rent $ 69,990

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
Monthly Rent $ 15,990

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
Monthly Rent $ 7,020

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
Monthly Rent $ 0

Paradisiac Oceanfront Home on Oahu's North Shore with Hot tub, Hale Oka Nunu Waialua, Hawaii, Listing ID: 30149

Your dreams of staying oceanfront on O’ahu’s North Shore come true at Hale Oka Nunu. When you stay at this 4-bedroom, 3-bathroom home located in rural Mokuleia, the clear, aqua ocean is your backyard and with its lapping waves, it beckons you to come out and play. The house...

  • House
  • 1832
  •  4
  •  3
Monthly Rent $ 90,000

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
Monthly Rent $ 18,000

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
Monthly Rent $ 180,000

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
Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $ 22,500

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
Monthly Rent $ 0

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
Monthly Rent $ 19,500

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
Monthly Rent $ 58,500

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
Monthly Rent $ 7,500

Newly Renovated Home w/Gate to Ocean, Beachview Patio & Private Yard: Pikai Hale Haleiwa, Hawaii, Listing ID: 30168

Welcome to Pikai Hale, your tropical beachfront getaway located along the idyllic north shore of Oahu. This newly decorated 2 bedroom, 1 bathroom home not only overlooks the sparkling blue shoreline from the comforts of a quiet neighborhood, but it is also within a short walking...

  • House
  • 850
  •  2
  •  1
Monthly Rent $ 0

Gorgeous Remodeled Home w/ Private Hot Tube & Ocean Views: Hale Mahina Haleiwa, Hawaii, Listing ID: 30177

Hale Mahina is a beautiful 4 bedroom, 3.5 bathroom home located in a private, very quiet neighborhood in the hills of Pupukea, on Oahu's North Shore. Enjoy panoramic ocean views while still being within minutes of first-rate beaches and other activities. The grounds of this...

  • House
  • 3798
  •  4
  •  3 1/2
Monthly Rent $ 10,500

Luxury Gold Coast Home w/ AC and Backyard: Hale Nui Honolulu, Hawaii, Listing ID: 30178

Nestled into a peaceful neighborhood on the Gold coast beside Diamond Head Crater, this luxury vacation rental will give you the island feel you’ve been waiting for. Surrounded by lush greenery and swaying palm trees, this stunning beach house sits elegantly in Hawaii’s...

  • House
  • 2096
  •  4
  •  3
Monthly Rent $ 0

New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai Honolulu, Hawaii, Listing ID: 30179

Located in the upscale neighborhood of Hawai’i Kai, Nani Wai is a 5-bedroom, 4-bathroom gated home located on a marina and with views of the majestic Koko Crater. This spacious home is ideal for larger groups, with lots of room to spread out both indoors and out, so you can...

  • House
  • 3206
  •  5
  •  4
Monthly Rent $ 30,000

Luxury, Pool, AC & Stunning Ocean Views: Hale Makana Honolulu, Hawaii, Listing ID: 30181

Hale Makana is a luxurious, single-level estate in Hawaii Kai’s most coveted oceanfront neighborhood. This five-bedroom, seven-bathroom property is the perfect getaway for single and joint families. With front yard views worthy of a postcard, you can expect to find paradise in...

  • House
  • 4643
  •  5
  •  7
Monthly Rent $4,500 - $5,500

Beautifully Restored Cottage | AC in Bedrooms | 2 Blocks to Beach & Harbor Haleiwa, Hawaii, Listing ID: 30194

Located 2 blocks from the beach in the heart of Haleiwa Town, this beautifully restored 3BR/2BA cottage is an ideal home base for island exploration. Walk just 2 minutes to hop aboard a fishing charter at Haleiwa Harbor, or stroll 3 minutes to surf at Ali‘i Beach Park....

  • Home
  • 1012
  •  3
  •  2
Monthly Rent $4,500 - $5,500

Waterfront Kuapa Isle Gem | Koko Crater Views & Pool | By the Beach Honolulu, Hawaii, Listing ID: 30196

This dreamy 2BR/2.5BA waterfront rental overlooks Koko Crater and a glittering blue lagoon. Take in the views on two breezy decks -- one off the kitchen and the other off the primary suite. This sun-soaked getaway offers two spacious floors and a modern kitchen. Located in...

  • Apartment
  • 0
  •  2
  •  2 1/2
Monthly Rent $4,500 - $5,500

Ocean View Condo w/ Shared Pool/Hot Tub/Gym & Free WiFi - Snowbird-Friendly Honolulu, Hawaii, Listing ID: 30205

Soaring above Oahu on the 37th floor, this condo boasts panoramic views of it all - the sparkling Pacific, and every angle of the city. You won't miss a thing! Hawaii's tropical beaches are just one street away from this little slice of paradise and its resort-style amenities....

  • Apartment
  • 953
  •  2
  •  2
Monthly Rent $3,000

Stellar Mountain, River & City Views! Luxe Condo - Shared Pool, Hot Tub & Sauna Honolulu, Hawaii, Listing ID: 30208

Enjoy the best views in the city when you stay at this luxe condo, conveniently located in the Four Paddle community. From the living area and private balcony, you can soak in unparalleled views of the mountains, city, and river! After fun-filled days, cozy up for movie nights...

  • Condo
  • 553
  •  1
  •  1
Monthly Rent $4,500 - $5,500

Beachfront Hideaway with Breathtaking Views & Modern Updates | Steps to Sand Hauula, Hawaii, Listing ID: 30209

Escape to the islands at this charming 1BR hideaway! Enjoy a stunning beachfront locale with breathtaking coastal and lagoon views as well as direct ocean access. Stroll directly from your backyard onto the sand and into the ocean for a delightful dip. Witness majestic turtles,...

  • Cabin
  • 576
  •  1
  •  1
Monthly Rent $2,700

Inviting Apartment w/City Views, Free WiFi, Partial A/C, Washer/Dryer, Balcony Honolulu, Hawaii, Listing ID: 30214

Relax in style at this well-equipped aparthotel minutes away from Honolulu's picturesque beaches, ocean adventures, and unforgettable restaurants! This retreat is ideal for a romantic escapade or even a solo trip for the adventurous. The balcony is the ideal place to lounge...

  • Apartment
  • 643
  •  1
  •  1
Monthly Rent $2,400

Waikiki condo with lanai, mountain views, pool, hot tub, & sauna Honolulu, Hawaii, Listing ID: 30216

Wake up to views of Honolulu's lush mountains, glittering cityscape, and Ala Wai Canal at this comfortable high-rise condo in the heart of Waikiki! You'll have a private lanai, easy walking access to shopping and dining, and shared use of an outdoor pool, a hot tub, a sauna, a...

  • Condo
  • 678
  •  1
  •  1
Details No Image Available

$Multi-Month Discount!

Monthly Rent $10,000

Ocean Front luxury Condo on Ala Moana, Diamondhead,Waikiki,Magic Island,Ala Moana Beach, park and pool views. Walkable Honolulu, Hawaii, Listing ID: 30243

Ocean front luxury condo across from the Ala Moana beach park. Unobstructed Ocean views in an exceptional location, walking distance to shopping, restaurants, beach, harbor, Waikiki, parks, theatre and convention center. Functional kitchen with Subzero refrigerator freezer...

  • Condo
  • 940
  •  1
  •  1
Monthly Rent $2,985 - $3,787

Superb Studio Oceanview 43rd-Floor | Balcony Honolulu, Hawaii, Listing ID: 33040

Island Colony is nestled on the shores of beautiful Waikiki. Take a dip in the pool or hot tub, relax on the sundeck, or enjoy the view from your private lanai. Check out the shops at the Aloha Marketplace or Ala Moana Shopping center, just a few miles away. Take a one-mile walk...

  • Studio
  • 419
  •  0
  •  1
Monthly Rent $2,480 - $3,680

Studio Waterview 35th-Floor | Balcony | Pool Honolulu, Hawaii, Listing ID: 33041

Welcome to Island Colony -- the perfect choice for travelers looking to be immersed in the culture of Waikiki. This building offers guests convenient access to everything the neighborhood has to offer as well as luxury on-site amenities to help make your stay that much more...

  • Studio
  • 316
  •  0
  •  1
Monthly Rent $2,920 - $3,850

Luxe Studio Oceanview 42nd-Floor | Balcony Honolulu, Hawaii, Listing ID: 33042

Find yourself in paradise at this family-friendly, deluxe studio by the water complete with a furnished lanai and access to several on-site amenities including a shared pool, hot tub, dry sauna, fitness center, and a BBQ area. Those looking to swim, surf, stroll along the...

  • Studio
  • 400
  •  0
  •  1