Hawaii Vacation Rentals

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OAHU Vacation Rentals

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Features

4 Bedrooms
3 Bathrooms
10 Guests

Location

OAHU HI
From: $1,250
To: $2,875

HONU HEAVEN
 
Just remodeled, beautiful vacation rental home at the beginning of Oahu's famous Lanikai Beach! 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with privacy and manicured yard space, a generous ocean-facing deck for relaxation and  beautiful landscaping all around

Features

8 Bedrooms
8.5 Bathrooms
14 Guests
Pool

Location

OAHU HI
From: $5,000
To: $8,000

ROYAL BEACH ESTATE
 
Royal Beach Estate is one of the newest , most striking and contemporary executive beachfront estates on world renowned Kailua beach. Constructed in 2008, the estate features two homes (main house and guest house) separated by a resort-style pool with elegant umbrellas and lounge furnishings

Features

6 Bedrooms
7.5 Bathrooms
12 Guests

Location

OAHU HI
From: $2,500
To: $6,250

SWAYING PALMS
 
Luxury, custom home with all the amenities, right on the sands of world renowned Kailua Beach. Enjoy a front row seat for spectacular sunrises, sandcastles, kite surfing and more as you unwind and kick back in this special property

Features

4 Bedrooms
3 Bathrooms
8 Guests

Location

OAHU HI
$500-$1000
per night

This lovely family home is located one house back from the beach! In a short thirty second stroll, you will have your feet in the sand! The Street is quiet and the home is open and airy, perfect for a family beach getaway. It is close to Kalapawai Deli for morning coffee or lunch sandwiches, Kayak rentals, Island Snow and Bob's Pizza .

Bedding Includes: 

-Master bedroom: King bedroom with stone tile flooring



Features

5 Bedrooms
4 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,300
To: $3,125

OLU OLU ESTATE
 
Inspired by the Queen Emma Summer Palace, this is living ' Hawaiian Style'. Barefoot luxury just one-half block from beautiful Lanikai beach

Features

4 Bedrooms
4.5 Bathrooms
10 Guests
Pool, Beachfront

Location

OAHU HI
From: $3,600
To: $6,250

Stunning beachfront home in Diamond Head. The Empress at Diamond Head, located at the slopes of Diamond Head—Honolulu’s most prestigious neighborhood

Features

4 Bedrooms
3.5 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $995
To: $1,995

WAILELE VILLA
 
Seated along a winding, private drive perched on the slopes of Diamond Head, Wailele Villa boasts a breathtaking 180 degree view of Oahu’s south shore. This modern, architect designed home is the epitome of tropical luxury, featuring an indoor water feature, a dramatic pool deck, and private lanai off the kitchen with a spa for quiet relaxation

Features

4 Bedrooms
4 Bathrooms
9 Guests

Location

OAHU HI
From: $995
To: $3,000

Kapoho Hale, situated on Kapoho Cape in the Kaimalino neighborhood of Kailua, Oahu was newly constructed in 2007 and remains in immaculate condition. This amazing home has views of the entire east side of the island- from Makapuu Lighthouse to Kaaawa!

Reef walker foot ware is provided in every size for easy water access

Features

5 Bedrooms
6 Bathrooms
10 Guests
Pool, Beachfront

Location

OAHU HI
From: $3,750
To: $8,000

For those seeking respite, the Paradise Plantation is a Presidential oasis and the anecdote to the stresses of everyday life. 

Paradise Plantation is a rare jewel that comes fully appointed with Plantation style finishes and fu ishings from around the world. Step from a secure entry and motor court into 5 bedrooms all en suite, 5.5 bathrooms of pure beachfront luxury that whispers old Hawaii, yet offers all of the latest amenities and technologies of a mode masterpiece. 

The center courtyard of Paradise Plantation features a secluded lagoon-style pool pavilion including tropical waterfalls and a lavish island spa



Features

5 Bedrooms
6 Bathrooms
12 Guests
Beachfront

Location

OAHU HI
From: $22,000
To: $30,000

KAILANI BEACH HOUSE
 
Stunningly remodeled from roof-to-floor,, this Lanikai vacation residence has been brought back to life, epitomizing the glory of Hawaiian beachfront living. An open concept floor plan melds the two living areas, kitchen, dining area, and bar downstairs

Features

5 Bedrooms
5.5 Bathrooms
14 Guests

Location

OAHU HI
From: $1,800
To: $2,000

Non-Conforming Use Permit Number 90/TVU-0248 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, 
Lic#W-99007836-01.

Beachfront home nestled on Kailua Beach! This house is the perfect place to kick back and enjoy paradise. The tropical dining/living room opens out to breathtaking Kailua beach

Features

4 Bedrooms
5 Bathrooms
6 Guests
Pool, Beachfront

Location

OAHU HI
From: $1,200
To: $3,125

KALANI VILLA
 
Enjoy your morning coffee in comfort on the master lanai and end the day watching the sunset from your own backyard.  Spend days relaxing poolside while listening to your favorite tunes play throughout

Features

4 Bedrooms
3.5 Bathrooms
6 Guests

Location

OAHU HI
From: $875
To: $1,400

COCONUT VILLA
 
Oceanfront living on the Gold Coast of Waikiki.  Located on the Gold Coast, this unique oceanfront home is close to Waikiki's finest restaurants, theaters and shopping

Features

5 Bedrooms
4 Bathrooms
0 Guests

Location

OAHU HI
From: $1,600
To: $1,800

HALE KAI SURF
 
Stunning Kailua beachfront residence, designed with your care-free island lifestyle in mind. Wide turquoise ocean views looking over sandy Kailua Beach and beyond to the Mokulua Islands.
New upgrades make your stay on Kailua Beach effortless and relaxing, completely remodeled gorgeous upstairs ocean view master bathroom, downstairs polished concrete and wood floors, high ceilings, newer windows and fresh paint and fresh furnishings! 
 
Lovely ocean side yard and beautiful tropical landscaping surround this property with a private inner garden courtyard.
 
The Master bedroom along with 3 other bedrooms are upstairs.
One additional bedroom downstairs.
 
Bedding: Master - King bed private bath with ocean view tub and separate shower
Guest bedroom 2 - Queen bed shares hallway bath with bedroom 3, shower only.
Guest bedroom 3 - King (can be split into 2 twins) shares hallway bath with bedroom 2, shower only.
Guest bedroom 4 - King bed with private bathroom, shower only.
Guest bedroom 5-  Double bed with private bath, Japanese soaking tub

Features

5 Bedrooms
6.5 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $7,500
To: $10,000

LANIKAI HILLSIDE ESTATE
 
Your Lanikai Hillside Estate luxury estate awaits you!
Gated and secure, located at the top of a steep driveway with plenty of parking. Air Conditioned garage for 3 cars and space on the driveway for another 9 cars

Features

4 Bedrooms
3.5 Bathrooms
14 Guests

Location

OAHU HI
From: $21,000
To: $25,000

LANIKAI BEACH HOUSE
 
Stunning, rare, sandy Lanikai beachfront location! Two car parking, spacious, beautiful manicured yard with outdoor dining table and chaise lounges await you with a magnificent view of the Mokulua Islands. This home with new interior design catches wonderful, strong tradewinds and sleeps 13 in beds and amazing oceanviews from two bedrooms.
 
Bedding:
Master Suite: King bed, twin bed and master bathroom. 
Ocean-facing guestroom: 2 Twin beds 
Mountain-facing suite: 2 Queen beds, 1 Full bed, bathroom.
Mountain-facing bedroom: 1 Queen bed
 
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1

Features

3 Bedrooms
3.5 Bathrooms
6 Guests
Pool

Location

OAHU HI
From: $1,750
To: $3,000

DIAMOND HEAD SEASIDE HIDEAWAY

Fabulous ocean views, pool and jacuzzi, very private! 1930's Hawaiian Cottage with brand new upgraded kitchen and bathrooms.

 

Located in one of the most prominent neighborhoods on Oahu. This Diamond Head Estate is a hidden treasure only minutes away from Waikiki, allowing a vast choice of restaurants, shopping, and beautiful white sand beaches.
 
Bedding:
1.King master with ocean views, private bath, and ocean view lanai.
2.King room with garden views shares a full bath with walk in shower and 2 sinks
3.Queen room with ocean views. 
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1

Features

2 Bedrooms
2 Bathrooms
4 Guests
Beachfront

Location

OAHU HI
From: $5,500
To: $7,800

KAHALA BEACH APT 
 
Luxurious Kahala beach at its best.  Prestigious Kahala Beach vacation rental apartments

Features

3 Bedrooms
4 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $3,500
To: $5,000

JEWEL OF DIAMOND HEAD
 
TAT#
Jewel of Diamond Head offers tropical contemporary opulence. This brand new Jewel of Diamond Head House is a stunner with "Aman" style and casual island living! 
3 ensuite bedrooms with limited ocean views in a desirable Diamond Head neighborhood, just minutes from Waikiki

Features

7 Bedrooms
7 Bathrooms
14 Guests

Location

OAHU HI
From: $4,650
To: $6,225

KAHALA MINI RESORT

Non-Conforming Use Permit Number 90/TVU-0376 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, 
Lic#W-2010944-01.

 

This spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees.  Enter the grounds thru the privacy gate to enjoy two swimming pools, waterfalls  and your private, tennis court.  Inside the beautiful mansion are gorgeous slate and wooden flooring.  Enjoy the wide-open layout of the kitchen, living room and ocean view dining room.  Located just a short walk down the beach from the Kahala Hotel & Resort.  Shopping and dinning at the Kahala Mall and Waikiki, close by

Features

5 Bedrooms
4 Bathrooms
14 Guests

Location

HAWAII HI
From: $1,000
To: $1,670

This property is a professionally-managed, licensed short-term vacation rental, Non-Conforming Use Permit Number 90/TVU-0042 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#W-87402697-01.

Welcome to the world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall)

Features

3 Bedrooms
2 Bathrooms
6 Guests
Pool

Location

HAWAII HI
From: $550
To: $1,000

KULA LANIKAI
 
TAT#
Charming 1930s cottage in the heart of Lanikai! This newly renovated beach house sits directly across the street from one of Lanikai’s most popular beach access points. Simply cross the street and you’re on the sandiest part of Lanikai beach! Or stay behind and unwind in the brand-new pool. 
 
Designer upgrades—including all new furniture, appliances, and amenities—make this Hawaiian living with style

Features

5 Bedrooms
4 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $795
To: $1,450

HALE MAHINA
 
TAT# W51388984-01
Lovely Island Style home with inviting lanai area and private pool surrounded by beautifully landscaped garden, located within short walking distance to the world famous Kailua beach and short drive to Lanikai Beach.  The main house has four bedrooms and three bathrooms, with modern kitchen and spacious, open dining/living room

Features

4 Bedrooms
4.5 Bathrooms
9 Guests
Pool

Location

HAWAII HI

KAILUA SURF

BEACHFRONT luxury on world renowned Kailua Beach. Ocean and beach views are the focus of this contemporary home with expansive living and dining areas

Features

2 Bedrooms
1 Bathroom
4 Guests

Location

OAHU HI
From: $395
To: $670

COTTAGE AT LANIKAI 
 
Comfortable vacation rental cottage right in the center of beautiful Lanikai Beach on Oahu, Hawaii. Perfect for the ultimate family vacation or a reunion with friends, this home has a magical ocean view and offers spectacular sun and moon rises

Features

4 Bedrooms
5 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,500
To: $3,500

MOKULUA NUI

Fall asleep to the sound of the waves, and wake up to breathtaking sunrises! Mokulua Nui overlooks the sparkling blue-green waters of Lanikai beach, and offers a gorgeous view of the Mokulua Islands. Whether you’re relaxing in the covered cabana by the pool, or soaking up sun on beautifully manicured lawn beside the ocean, this magnificent seaside home is perfect for unwinding. Gaze up at the Ko’olau mountain range and admire the raw beauty of the lush landscape, or turn around and envelop yourself in the breathtaking vista of the Pacific ocean

Features

4 Bedrooms
4 Bathrooms
9 Guests
Pool

Location

OAHU HI
From: $1,600
To: $2,300

DIAMOND HEAD HAWAII LANI
 
Diamond Head Hawaii Lani, remodeled in 2009, is an elegant, contemporary home with beautiful architectural design and panoramic oceanviews in a private tropical setting. The perfect perch for ocean watching and relaxing in luxury, with large pool, surrounding tropical gardens, and lots of lounging space

Features

2 Bedrooms
2 Bathrooms
6 Guests

Location

HAWAII HI
From: $7,500
To: $11,125
** Rate Range Shown Is A Monthly Rate*Please note this home has a very small parking spot that at best fits a compact car.

GOLD COAST HOME

Beautiful, quaint, newly remodeled cottage located steps from the ocean at Diamond Head.
Complete remodel finished December 2013. Perfect location to explore the island from

Features

4 Bedrooms
4 Bathrooms
8 Guests

Location

OAHU HI
From: $795
To: $1,450

HALE LANIKAI
 
Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, 
Lic#W-30525774-01.
 
This comfortable family vacation rental home on a beautiful sandy beach is the perfect antidote to civilization.  Waters protected by off-shore reefs offer swimming and snorkeling year-round

Features

4 Bedrooms
3 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,300
To: $2,000

SANDCASTLE
 
Peaceful beach house with stunning oceanviews on world famous Kailua beach! With white sands and clear shallow waters right outside the door, comfortable, spacious living for the whole family inside, and a beautiful pool with waterfalls, Sandcastle offers an ultimate beach vacation experience year-round.
 
Bedroom and bathroom configuration:
Bedroom 1( master) upstairs- king size bed ocean view - lanai - ceiling fan - A/C -  large screen TV with cable box, private bath only shower no tub full body spray bidet toilet
Bedroom 2-downstairs-king size bed - beach front ocean view - A/C - ceiling fan - no tv - no closet - shared bath in hallway with shower only no tub, but can be a private bath if hallway door is closed
Bedroom 3-downstairs- 2 twins -  ceiling fan - A/C - shared bath with either bedroom with shower only no tub; next bath in hallway has two sinks, and shower no tub
Bedroom 4-downstairs-king size bed - pool/garden view - ceiling fan - A/C - TV - can have private bath or shares with twin size room
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1. Rates and fees are subject to change

Features

6 Bedrooms
5.5 Bathrooms
12 Guests
Pool

Location

HAWAII HI
From: $4,500
To: $6,125

BALI RESORT
 
Relax in the lap of luxury at this exquisite beachfront estate totaling nearly 60,000 sq ft. Spend lazy mornings strolling along the gorgeous stretch of the world-renowned Kailua Beach and sleepy afternoons relaxing beside the resort style pool with its bubbling waterfall and tranquil koi pond

Features

8 Bedrooms
10 Bathrooms
0 Guests
Pool, Beachfront

Location

OAHU HI
From: $8,000
To: $14,000

8 Bedrooms, 10 Baths, Sleeps 16. Highest Level of Luxury, Lagoon Pool, Recreation Cabana, Movie Theater, Concierge, Separate Guest House, Luxurious, Exquisite Interiors, Spacious Yard, Beachfront Estate.

Rarely do opportunities of this magnitude arise -- anywhere

Features

6 Bedrooms
4 Bathrooms
10 Guests

Location

OAHU HI
From: $1,675
To: $1,875

Award winning architecture. Breathtaking views

Features

4 Bedrooms
3.5 Bathrooms
8 Guests
Pool

Location

HAWAII HI
From: $995
To: $1,995
Available only for a small window of time this year! Inquire today!

DIAMOND HEAD DREAM

TAT# W98831613-01

Diamond Head nestles behind this designer appointed, newly renovated, ocean view home. A short walk down the street to Kaalawai Beach or stroll down the road to Diamond Head Beach

Features

5 Bedrooms
4.5 Bathrooms
11 Guests

Location

OAHU HI
From: $3,900
To: $5,575

Gorgeous Meditterranean Island Living
Of the various vacation rentals on Lanikai Beach, The Villa at Wailea Point exists in a class of its own. Originally constructed in 1918, the home has been fully remodeled to combine the casual chic of a contemporary beach house while retaining the soul of an historic Oahu residence.
 
Stepping into the home, once you’ve recovered from the jaw-dropping ocean view, you’ll notice a variety of architectural distinctions and thoughtful amenities

Features

Bedrooms
Bathrooms
12 Guests
Pool

Location

OAHU HI
From: $4,000
To: $10,000

Welcome to the Sullivan Estate & Spa Retreat, the first holistic anti-stress centre on earth. Located directly on the North Shore of Hawaii’s island of Oahu and just 40 minutes from Honolulu’s world class shopping and dining

Features

3 Bedrooms
2 Bathrooms
6 Guests

Location

OAHU HI
From: $1,350
To: $1,700
Coming Soon!!

SECRET SANDS

A Charming Getaway

 

One of the few historic vacation rentals directly on the sands of Lanikai Beach, this uniquely charming home is serenity defined. Surrounded by lush vegetation and open to fresh ocean breezes and incomparable views, this newly remodeled retreat includes a modern kitchen and bathrooms

Features

4 Bedrooms
3.5 Bathrooms
8 Guests

Location

OAHU HI
From: $900
To: $1,000

SONG OF LANIKAI

Exceptional Lanikai oceanfront house for your perfect vacation. This special beach house enjoys glorious views of the Mokulua islands and beautifully landscaped grounds

Features

5 Bedrooms
5.5 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $1,000
To: $1,500

POIPU OCEAN HOUSE

Welcome to Poipu Oceanhouse, a spectacular 5 bedroom, 5.5 bath home perched on the cliffs of Koko Kai. Experience stunning panoramic views of the ocean while listening to the soothing crash of the ocean waves a short distance below

Features

6 Bedrooms
6.5 Bathrooms
12 Guests

Location

OAHU HI
From: $1,950
To: $2,300
COMING SOON!
SECLUDED LANIKAI
 
Sea, Sun and Serenity
For those seeking a Lanikai beach vacation rental with a style matched only by its stunning views, welcome to Hale Kolea. Perched on a hillside overlooking one of the most coveted vistas in all of Hawaii, this extraordinary oceanfront home offers unparalleled access to the very best of Lanikai.
 
Enjoy the best of breezy island living in this architecturally distinctive space, where vaulted ceilings and multi-level design adds an air of openness and community

Features

3 Bedrooms
3 Bathrooms
6 Guests
Pool, Beachfront

Location

OAHU HI
From: $1,050
To: $1,900

NAUPAKA HALE
 
Idyllic classic island style vacation rental home on large lot with huge sandy beach right in front of your very eyes. This beautiful vacation rental home offers breathtaking views of Lanikai Beach, turquoise water and the Mokulua Islands

Features

5 Bedrooms
3 Bathrooms
10 Guests

Location

OAHU HI
From: $15,000
To: $25,000

HALE KEA
 
This beachfront vacation rental home resides on the shimmering sands of the world renowned Lanikai beach, and is the perfect home for a family of all ages to enjoy a relaxing getaway.  Stunning views of the ocean, mountains, beach, and Mokulua islands make this an unforgettable escape. 
 
Upstairs:  King oceanview master. 
Upstairs bedroom #2 with 2 queens shares bath with bedroom #3 with 2 twins.
Downstairs oceanfront Family suite: Queen with an accordian wall separating from 2 twins, shared bath.
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1

Features

3 Bedrooms
4.5 Bathrooms
9 Guests
Pool

Location

OAHU HI
From: $1,850
To: $3,875

HALE HIKINA
 
Ensconce yourself in unpretentious luxury at Hale Hikina, where the indoors flow seamlessly into the outdoors with kingly travertine marble floors and exquisite custom furnishing. Enjoy soft sands, the warm embrace of the Pacific, cooling trade winds, and endless ocean vistas

Features

5 Bedrooms
4 Bathrooms
12 Guests

Location

HAWAII HI
AVAILABLE SOON!
HIDDEN GEM
 
Bed arrangement:
 
Upstairs Master: King
Guest bedroom: Double King (2 kings put together)
Interim space between bedrooms: Twin
Downstairs: 
Queen
2 Twins (could be made into a King)
Queen
 
On sandy beach
No pool
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1. Rates and fees are subject to change
Vacation Rental Guests Beds Baths Amenities City Area Price Range
Honu Heaven 10 4 3 Kailua, $1000-$2500
Royal Beach Estate 14 8 8.5 Pool Kailua, $2500 or more
Swaying Palms 12 6 7.5 Kailua, $2500 or more
Hale Nani 8 4 3 Kailua, $500-$1000
Olu Olu Estate 8 5 4 Pool Kailua, $1000-$2500
Empress At Diamond Head 10 4 4.5 Pool, Beachfront Honolulu, $2500 or more
Wailele Villa 8 4 3.5 Pool Honolulu, $1000-$2500
Kapoho Hale 9 4 4 $1000-$2500
Paradise Plantation 10 5 6 Pool, Beachfront Kailua, $2500 or more
Kailani Beach House 12 5 6 Beachfront Kailua, $1000-$2500
Place In Paradise 14 5 5.5 Kailua, $500-$1000
Kalani Villa 6 4 5 Pool, Beachfront Honolulu, $2500 or more
Coconut Villa 6 4 3.5 Honolulu, $1000-$2500
Hale Kai Surf 0 5 4 Kailua,
Lanikai Hillside Estate 10 5 6.5 Pool Kailua,
Lanikai Beach House 14 4 3.5 Kailua, $1000-$2500
Diamond Head Seaside Hideaway 6 3 3.5 Pool
Kahala Beach Apt 4 2 2 Beachfront Honolulu,
Jewel Of Diamond Head 10 3 4 Pool Honolulu,
Kahala Mini Resort 14 7 7 Honolulu, $2500 or more
Walker's Lanikai Beach House 14 5 4 Kailua,
Kula Lanikai 6 3 2 Pool Kailua,
Hale Mahina 10 5 4 Pool Kailua, $500-$1000
Kailua Surf 9 4 4.5 Pool Kailua,
Cottage At Lanikai 4 2 1 Kailua, less than $500
Mokulua Nui 8 4 5 Pool Kailua, $1000-$2500
Diamond Head Hawaii Lani 9 4 4 Pool Honolulu, $1000-$2500
Gold Coast Home 6 2 2 Honolulu, less than $500
Hale Lanikai 8 4 4 Kailua, $500-$1000
Sandcastle 8 4 3 Pool Kailua, $1000-$2500
Bali Resort 12 6 5.5 Pool Kailua, $2500 or more
Royal Palms 0 8 10 Pool, Beachfront Kailua, $2500 or more
Kailua Bay Estate 10 6 4 Kailua, $1000-$2500
Diamond Head Dream 8 4 3.5 Pool Honolulu,
Point Lanikai 11 5 4.5 Kailua,
Sullivan Estate 12 Pool Hi, $2500 or more
Secret Sands 6 3 2 Kailua,
Song Of Lanikai 8 4 3.5 Kailua,
Poipu Oceanhouse 10 5 5.5 Pool Honolulu, $1000-$2500
Secluded Lanikai 12 6 6.5 Kailua, $1000-$2500
Naupaka Hale 6 3 3 Pool, Beachfront Kailua, $1000-$2500
Hale Kea 10 5 3 Kailua, $500-$1000
Hale Hikina 9 3 4.5 Pool Kailua, $2500 or more
Hidden Gem 12 5 4 Kailua,