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: $1,600
To: $2,875

HONU HEAVEN
TA-006-302-3104-01
 
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

7 Bedrooms
8.5 Bathrooms
14 Guests
Pool

Location

OAHU HI
From: $6,500
To: $10,000

ROYAL BEACH ESTATE
TA-016-888-2176-01
 
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: $3,750
To: $6,250

SWAYING PALMS
TA-192-192-7168-01
 
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

7 Bedrooms
9 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $8,000
To: $12,500

BANYAN HALE

 TA-199-064-7808-01

This stunning executive estate at the base of Diamond Head offers complete privacy and a luxurious, romantic experience for even the most discriminating guests. Beautiful manicured tropical gardens greet you at the entrance through a gated driveway

Features

4 Bedrooms
4.5 Bathrooms
10 Guests
Pool, Beachfront

Location

OAHU HI
From: $4,500
To: $7,825

EMPRESS AT DIAMOND HEAD

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
Bathrooms
8 Guests

Location

HAWAII HI
From: $4,000
To: $7,000

DIAMOND HEAD BREEZES
 
Architectural Digest featured home. Unparalleled property and oceanfront location

Features

3 Bedrooms
2 Bathrooms
10 Guests

Location

OAHU HI
From: $1,350
To: $1,700

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

5 Bedrooms
4 Bathrooms
14 Guests

Location

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

WALKERS LANIKAI BEACHOUSE

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

4 Bedrooms
4 Bathrooms
0 Guests

Location

OAHU HI
From: $2,000
To: $3,500

LANIKAI SEASIDE
TA-046-903-0912-01
 
Relax in this charming Hawaiian island style vacation rental home while taking in some of the best ocean views on the East Shore! Inside, Lanikai Seaside offers the color and cheer of Polynesian decor along with every convenience from a fantastic open layout kitchen with ocean views to a lava-rock hot tub inspired by the natural tide pools along the coast.
This Hawaiian vacation rental is just minutes away from Kailua beach and Lanikai beach, Lanikai Seaside offers incredible access to both hot spots while still preserving the sense of privacy and quiet for a restful and fun vacation!
Gated off street parking with 2 car garage.
Come feel the gentle breezes of Oahu’s Eastern Shores…. Best beaches in Hawaii!
 
Upstairs:
King master w/ ocean views, ensuite bath -
bathtub, shower, double sinks, walk in closet, A/C.
Bedroom 2 - Queen Bedroom with Ocean Views, A/C.
Bedroom 3 - Queen Bedroom, A/C.
Bedroom 4 - Downstairs Double Bed (no A/C downstairs.)
 
Amenities:
3 one-man kayaks 
2 kayak rollers 
2 bikes 
2 long surf boards (not soft top) 
Short 3 to 5 minute walk to both Lanikai and Kailua Beach
Lava Rock Hot Tub
Panoramic Ocean Views
Sea Turtles regularly swim off this Lanikai Point.
WiFi
 
 
 
OTHER FEES:
Oahu Tax (calculated against rent only): 13.962%
Departure Cleaning Fee: $850.00 
Refundable Security Deposit: $3,000.00 
Reservation fee: 2.5% on entire amount.
14 night minimum stay applies.
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1

Features

7 Bedrooms
10 Bathrooms
16 Guests
Pool, Beachfront

Location

OAHU HI
From: $7,750
To: $8,600

PAUL MITCHELL ESTATE

TA-162-678-7840-01

Only 30 minutes from downtown Honolulu, a serene and enchanting hideaway exists beside the sea in Lanikai. Situated opposite the Mokulua Islands in Lanikai Bay with 230 ft

Features

5 Bedrooms
4 Bathrooms
0 Guests

Location

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

HALE KAI SURF
TA-126-930-9440-01
 
Stunning Kailua beachfront vacation rental residence, designed with your care-free Hawaiian island lifestyle in mind. Enjoy expansive turquoise ocean views looking over sandy Kailua Beach and beyond to the Mokulua Islands.
New upgrades make your stay at this vacation rental on Kailua Beach effortless and relaxing

Features

4 Bedrooms
5 Bathrooms
9 Guests
Pool

Location

OAHU HI
From: $995
To: $5,000

WAILEA LANI

TA-019-146-9568-01

Fantasy 4 bedroom plus office and library, 5 bathroom, sleeps 8-9 celebrity vacation rental retreat in Lanikai. You will experience the most magical view of the Pacific Ocean, the Mokulua Islands and enchanting Lanikai! The ultimate in privacy and luxury, this exquisite vacation rental property is surrounded by Royal Palms and colorful tropical foliage

Features

4 Bedrooms
4 Bathrooms
0 Guests

Location

OAHU HI
From: $1,850
To: $2,500

PALM OASIS ESTATE
TAT  #W20885750-01
 
This four bedroom, four bathroom home is ideal for families. It features high vaulted ceilings, a large open living space, plenty of dining areas, a perfectly manicured yard, and access to a gorgeous white sand beach just yards away. 
 
The gourmet kitchen is fully appointed and has all brand new stainless steel appliances including a wine fridge and double oven

Features

4 Bedrooms
Bathrooms
8 Guests

Location

OAHU HI
From: $1,950
To: $3,500

SURF SHACK

 

Oceanfront. Steps into the water

Features

0 Bedrooms
0 Bathrooms
4 Guests
Pool

Location

OAHU HI
From: $450
To: $650
Our newest, most modern studio directly on Lanikai beach at a SPECIAL RATE!
SUNRISE SANDS VILLA STUDIO
 
This intimate studio connects to one of the iconic Lanikai Villas offers a modern, tasteful space with unbeatable access to a world famous beach! 
 
The studio rental includes exclusive use of the villa parking, gorgeous covered pool and lawn, creating the perfect way to enjoy the splendor of the white sandy beach while keeping the privacy of a personal home in a prime location. 
 
The fully furnished studio includes all the necessities - two queen beds, full bathroom with double sinks and showers and kitchenettes with dining areas. A couch and TV complete the suite of amenities for a perfectly simplified compliment to the vibrant lifestyle of Kailua with a plethora of vibrant water activities, sunshine hikes and plenty of local stores and restaurants.
 
OTHER FEES:
 
Oahu Tax (calculated against rent only): 13.962%
 
Departure Cleaning Fee: $300.00 
 
Refundable Security Deposit: $2,000.00 
 
Reservation fee: 2.5% on entire amount.
 
ADDITIONAL INFORMATION AND DISCLOSURES:
 
1

Features

6 Bedrooms
6.5 Bathrooms
12 Guests

Location

OAHU HI
From: $1,950
To: $2,300

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

4 Bedrooms
4.5 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $2,750
To: $3,875

HALE HIKINA
TA-073-025-3312-01
 
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 Hawaii’s soft sands, the warm embrace of the Pacific, cooling trade winds, and endless ocean vistas

Features

6 Bedrooms
4 Bathrooms
10 Guests

Location

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

KAILUA BAY ESTATE

Award winning architecture. Breathtaking views

Features

4 Bedrooms
6 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $18,000
To: $25,000
** Rate Range Shown Is A Monthly Rate**THIS PROPERTY RENTS AT THE MONTHLY RATE ONLY*

ISLAND MOUNTAIN RETREAT

TA-155-695-7184-01
 
Perched high above the Honolulu City lights in a lush tropical valley, home to Manoa Falls, is a  modern masterpiece retreat. The 6400 sq

Features

4 Bedrooms
3.5 Bathrooms
14 Guests

Location

OAHU HI
From: $21,000
To: $27,750
** Rate Range Shown Is A Monthly Rate**THIS PROPERTY RENTS AT THE MONTHLY RATE ONLY*
LANIKAI BEACH HOUSE
TA-105-568-8704-01
 
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

5 Bedrooms
4 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $800
To: $1,450
NEW LOW NIGHTLY RATE NOW THROUGH NOVEMBER 16th, 2017!!
HALE MAHINA
TA-014-244-2496-01
 
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

6 Bedrooms
7 Bathrooms
12 Guests
Pool

Location

OAHU HI
From: $10,000
To: $15,000

SOUTHSIDE ESTATE
 
TA-
BEACH ESTATE. Stunning, sophisticated and modern 1.43-acre oceanfront estate w/ 185 linear feet of beach frontage, tennis court/ tennis pavilion, sparkling pool, Jacuzzi and pool pavilion + lush, tropical landscaping

Features

5 Bedrooms
10 Bathrooms
12 Guests
Pool

Location

OAHU HI
From: $2,800
To: $5,000
BRAND NEW BIG ISLAND RENTAL!
 BIG ISLAND WATERFALLING ESTATE
 
Ocean View! Private pool! 10,942 sq ft.
 
Hawaii’s Waterfalling Estate is a luxury vacation rental property unlike any other.  Noted by MSNBC as one of the “seven best backyards in the world”, Waterfalling sits on ten private, gated acres and features an Olympic swimming pool, a (private) 9-tee golf course, a tennis (or basketball)  stadium, the world’s largest residential pneumatic elevator (wrapped in Louis Vitton leather), and rooftop and lawn helipad.
 
Waterfalling Estate is blessed with a natural waterfall that cascades into the ocean

Features

3 Bedrooms
4 Bathrooms
6 Guests

Location

OAHU HI
From: $650
To: $1,000

BAY VIEW
TA-185-192-8576-01
 
Peaceful Kaneohe Bay Views … what a wonderful vacation rental to relax and unwind in.
 
Brand new Hawaiian home built in 2017, not a detail has been overlooked.  Luxury Hawaii living at a fraction of the cost if you were to rent on a sandy beach

Features

5 Bedrooms
5.5 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $2,000
To: $2,500

PORTLOCK PARADISE
 
Luxury estate just one home from the beach in Portlock. This unique home features deep wrap around lanais, mahogany doors that disappear creating a seamless blend of indoor/outdoor living, a great room with vaulted Balinese style ceilings, reclaimed wide plank pine floors, gourmet kitchen with top-of-the-line appliances, family room, heated tiled pool and spa, 5 huge en-suite bedrooms, a spacious second level den, central AC, energy saving PV system, 2 car garage.
OPTIONAL Escalade and driver
OPTIONAL 30 foot yacht and captain

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

TA-163-309-3632-01

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

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

4 Bedrooms
4.5 Bathrooms
9 Guests

Location

OAHU HI
From: $1,800
To: $2,500

LANIKAI SANDS

 

Spectacular 2015/2016 remodel in a sandy Lanikai beach location. Set back from the beach amidst an oasis of tropical foliage, a wide, private access path connects the back yard with the sandiest part of the beach

Features

4 Bedrooms
3 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,500
To: $2,225

SANDCASTLE
TA-108-173-7216-01
 
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. A/C in all bedrooms, den and dining room.
2

Features

2 Bedrooms
2 Bathrooms
6 Guests

Location

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

GOLD COAST HOME

TA-036-705-0752-01

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

6 Bedrooms
5.5 Bathrooms
12 Guests
Pool

Location

HAWAII HI
From: $4,500
To: $7,650

BALI RESORT II
TA-130-529-4848-01
 
Come enjoy the luxurious Bali Resort on Oahu’s Easter Shore, Hawaii’s best beaches!! This Hawaiian luxury vacation rental sits on 60,000 sq ft of prime Kailua Beach property with 225+ feet 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 out on a lush tropical Hawaiian estate including a volcanic-rock waterfall and swimming pool, koi pond, tennis court, hitting wall, BBQ and bar area for a private resort style vacation

Features

6 Bedrooms
5 Bathrooms
13 Guests
Pool

Location

OAHU HI
From: $2,500
To: $3,900

HOUSE ON THE GREEN
 
 
 
Island luxury at its best, enjoy ocean and golf course views from this newly remodeled contemporary home. This 6 bedroom / 5 bathroom villa is a vacationer’s dream, steps to world famous Kahala beach and resort with over 130 linear feet of Waialae golf course frontage, home of the Sony Open

Features

5 Bedrooms
5.5 Bathrooms
9 Guests
Pool

Location

HAWAII HI
From: $2,750
To: $5,475

KAILUA SURF

TA-122-016-5632-01
 
Treat yourself to 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

Bedrooms
Bathrooms
12 Guests
Pool

Location

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

SULLIVAN ESTATE

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

4 Bedrooms
3.5 Bathrooms
6 Guests

Location

OAHU HI
From: $975
To: $1,400

COCONUT VILLA
TA-023-127-2448-01
 
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

4 Bedrooms
5 Bathrooms
6 Guests
Pool, Beachfront

Location

OAHU HI
From: $1,600
To: $3,125

KALANI VILLA
TA-105-568-8704-01
 
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

5 Bedrooms
6 Bathrooms
12 Guests
Beachfront

Location

OAHU HI
From: $22,000
To: $33,500
** Rate Range Shown Is A Monthly Rate**THIS PROPERTY RENTS AT THE MONTHLY RATE ONLY*
KAILANI BEACH HOUSE
TA-108-173-7216-01
 
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

2 Bedrooms
2 Bathrooms
4 Guests
Beachfront

Location

OAHU HI
From: $4,900
To: $7,800
** Rate Range Shown Is A Monthly Rate*
KAHALA BEACH APT
TA-004-895-1296-01
 
 Enjoy the prestigious Kahala Beach vacation rental apartment with beach living at it's best. Beautifully upgraded apartment with 2 bedrooms, 2 bathrooms, A/C, fully furnished with garden view and 1 designated underground parking spot

Features

3 Bedrooms
2 Bathrooms
6 Guests
Pool

Location

HAWAII HI
From: $575
To: $800
*MINIMUM STAY IS REQUIRED*
KULA LANIKAI
TA-202-866-8928-01
 
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

9 Bedrooms
7.5 Bathrooms
0 Guests
Pool

Location

OAHU HI
From: $6,500
To: $10,000

ROYAL HAWAIIAN ESTATE
 
Experience Hawaii in an exquisite beachfront mansion with panoramic ocean views on beautiful Waimanalo Beach (famous filming locale for Magnum P.I., Hawaii 5-0, & Lost).  Waimanalo's small town doesn’t allow hotels, making it the perfect getaway from the busy tourist spots, yet still close to so many great activities and attractions! The countryside of Waimanalo is slow moving and filled with Aloha, beauty, and authentic Hawaiian experiences.

The Royal Hawaiian Estate offers a luxurious and relaxing open floor plan maximizing the breathtaking scenic views from floor to ceiling windows and doors which open up to the beautiful surroundings. The multiple levels of the estate provide 6 bedrooms boasting beautiful ocean views while the other 3 rooms overlook the spectacular Ko’olau Mountains. The entryway to the guest wing at the top of the second floor creates options to suit your needs for community living or close it for a more private experience among guests

Features

5 Bedrooms
5 Bathrooms
6 Guests
Pool

Location

OAHU HI
From: $2,500
To: $3,000

OCEAN HOUSE
 
Along the white sandy beach of Kailua, Ocean House offers the best of the location. Two stories of panoramic picture windows highlight the gorgeous blue horizon while you relax in the spacious and comfortable living room

Features

3 Bedrooms
3 Bathrooms
6 Guests
Pool, Beachfront

Location

OAHU HI
From: $1,350
To: $2,125

NAUPAKA HALE
TA-151-566-1312-01
 
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

2 Bedrooms
2.5 Bathrooms
4 Guests

Location

OAHU HI
From: $12,500
To: $16,000

CLEARWATER COTTAGE
 
Celebrate the restorative power of nature as you relax while being surrounded by Lanikai's glorious panoramic views. Revitalise your mind and renew your spirit at this peaceful tropical retreat which offers nurturing surroundings just perfect to rejuvenate yourself. 
 
BEDDING: 
Upstairs Master Bedroom:  King
Upstairs Guest Bedroom:  Queen 
Downstairs Studio Bedroom:  Queen and Full-size sleeper sofa (on request) 
 
LINK to interactive floorplan and virtual tour: 
www.us.open2view.com/tour/unbranded/plan/2037
 
OTHER FEES:
Oahu Tax (calculated against rent only): 13.962%
Departure Cleaning Fee: $400.00 
Refundable Security Deposit: $2,000.00 
Reservation fee: 2.5% on entire amount.
30 night minimum stay applies.
 
ADDITIONAL INFORMATION AND DISCLOSURES:
1

Features

5 Bedrooms
7 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $60,000
To: $85,000
**Rate range shown is a MONTHLY range.**

NOELA ESTATE

 

The wait is finally over! A botanical tapestry w/over 28,000 sq. ft

Features

5 Bedrooms
4.5 Bathrooms
11 Guests

Location

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

POINT LANIKAI
 
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

4 Bedrooms
3.5 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,225
To: $2,625

WAILELE VILLA
TA-004-170-5472-01
 
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

2 Bedrooms
1 Bathroom
4 Guests

Location

OAHU HI
From: $475
To: $670

COTTAGE AT LANIKAI
TA-176-161-3824-02
 
Magical Hawaiian ocean views await you from this Lanikai Beach front Cottage. One of the very few vacation rentals of this size, 2 bedroom cottage, left in the area

Features

5 Bedrooms
4 Bathrooms
8 Guests
Pool

Location

OAHU HI
From: $1,800
To: $2,500

HALE CAPRI 
TA-091-570-5856-01
 
Hale Capri is a newly built plantation inspired contemporary home just 200 yards from Lanikai Beach. Enjoy your stay in this magnificent five bedroom property which includes a 40-foot swimming pool with spa and spacious garden facing the scenic Ka’iwa Ridge above Lanikai Beach

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

4 Bedrooms
4 Bathrooms
8 Guests

Location

OAHU HI
From: $995
To: $1,450

HALE LANIKAI
Lic# TA-176-161-3824-01
Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.
 
This Hawaiian style family vacation rental home on a beautiful sandy beach is the perfect antidote to civilization.  Waters protected by off-shore reefs offer safe swimming and snorkeling year-round

Features

5 Bedrooms
Bathrooms
10 Guests
Pool

Location

HAWAII HI
From: $1,750
To: $2,800

DIAMOND HEAD RETREAT

 

This is a high end, modern, relaxed home situated at the base of world famous Diamond Head and walking distance to Waikiki.

This property is arguably the best location on Oahu just a block away from Kapiolani Park with beautiful city skyline views. Minutes from beautiful white sandy beaches, zoo, aquarium, and all the excitement of Waikiki.

 

ADDITIONAL INFORMATION AND DISCLOSURES:

1

Features

5 Bedrooms
6 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $5,000
To: $10,000
Obama's NEW Winter White House!
OBAMA WHITE HOUSE RETREAT
 
The gorgeous wooden gateways of Obama's Winter White House Retreat open to reveal a lush grotto area with a web of turquoise pools and hot tub ringed with lava rocks, waterfalls, stone bridges and green rainforest foliage - a world unto itself!
 
The spacious luxury house is laid out for luxury living with privacy, comfort and a special south eastern flare, punctuated by exquisite wood carvings which add a richness and mystic to compliment the special grounds and exotic location.
 
The lawn sits along the shoreline overlooking all of Kailua bay with views of the Mokulua Islets and even the neighbor islands of Lanai and Molokai on a clear day. An expansive, open lawn creates the perfect area to sun bathe and enjoy the clear evening skies.
 
The main house includes a gourmet kitchen, dining room, two seating areas and three bedrooms with en-suite baths

Features

5 Bedrooms
5.5 Bathrooms
14 Guests

Location

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

PLACE IN PARADISE
 
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

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, 
TA-005-323-3664-01 

 

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

4 Bedrooms
4 Bathrooms
9 Guests
Pool

Location

OAHU HI
From: $1,600
To: $2,875

DIAMOND HEAD HAWAII LANI
TA-107-635-5072-01
 
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

5 Bedrooms
3 Bathrooms
10 Guests

Location

OAHU HI
From: $21,000
To: $27,750
** Rate Range Shown Is A Monthly Rate**THIS PROPERTY RENTS AT THE MONTHLY RATE ONLY*
HALE KEA
TA-033-652-7360-01
 
*THIS HAWAIIAN VACATION RENTAL PROPERTY RENTS AT THE MONTHLY RATE ONLY*
 
This Hawaiian 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 Hawaii getaway.  Stunning views of the ocean, mountains, beach, and Mokulua islands make this an unforgettable escape.
Comfortable Hawaiian beach home is bringing repeats back time and time again to stay here on Lanikai Beach

Features

5 Bedrooms
6 Bathrooms
10 Guests
Pool, Beachfront

Location

OAHU HI
From: $4,375
To: $8,000

PARADISE PLANTATION

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

3 Bedrooms
4 Bathrooms
10 Guests
Pool

Location

OAHU HI
From: $2,500
To: $5,475

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
Vacation Rental Guests Beds Baths Amenities City Area Price Range
Honu Heaven 10 4 3 Kailua, $1000-$2500
Royal Beach Estate 14 7 8.5 Pool Kailua, $2500 or more
Swaying Palms 12 6 7.5 Kailua, $2500 or more
Banyan Hale 10 7 9 Pool Honolulu, $2500 or more
Empress At Diamond Head 10 4 4.5 Pool, Beachfront Honolulu, $2500 or more
Diamond Head Breezes 8 4 Honolulu,
Secret Sands 10 3 2 Kailua,
Walker's Lanikai Beach House 14 5 4 Kailua,
Lanikai Seaside 0 4 4 Kailua,
Paul Mitchell Estate 16 7 10 Pool, Beachfront Kailua, $2500 or more
Hale Kai Surf 0 5 4 Kailua,
Wailea Lani 9 4 5 Pool Kailua, $1000-$2500
Palm Oasis Estate 0 4 4 Kailua,
Surf Shack 8 4 Honolulu,
Sunrise Sands Villa Studio 4 0 0 Pool Kailua, $500-$1000
Secluded Lanikai 12 6 6.5 Kailua, $1000-$2500
Hale Hikina 8 4 4.5 Pool Kailua, $2500 or more
Kailua Bay Estate 10 6 4 Kailua, $1000-$2500
Island Mountain Retreat 8 4 6 Pool Honolulu,
Lanikai Beach House 14 4 3.5 Kailua, $1000-$2500
Hale Mahina 10 5 4 Pool Kailua, $500-$1000
Southside Estate 12 6 7 Pool Honolulu, $2500 or more
Big Island Waterfalling Estate 12 5 10 Pool
Bay View 6 3 4 Kaneohe,
Portlock Paradise 10 5 5.5 Pool Honolulu, $1000-$2500
Diamond Head Dream 8 4 3.5 Pool Honolulu,
Diamond Head Seaside Hideaway 6 3 3.5 Pool
Lanikai Sands 9 4 4.5 Kailua,
Sandcastle 8 4 3 Pool Kailua, $1000-$2500
Gold Coast Home 6 2 2 Honolulu, less than $500
Bali Resort 12 6 5.5 Pool Kailua, $2500 or more
House On The Green 13 6 5 Pool
Kailua Surf 9 5 5.5 Pool Kailua,
Sullivan Estate 12 Pool Hi, $2500 or more
Coconut Villa 6 4 3.5 Honolulu, $1000-$2500
Kalani Villa 6 4 5 Pool, Beachfront Honolulu, $2500 or more
Kailani Beach House 12 5 6 Beachfront Kailua, $1000-$2500
Kahala Beach Apt 4 2 2 Beachfront Honolulu,
Kula Lanikai 6 3 2 Pool Kailua,
Royal Hawaiian Estate 0 9 7.5 Pool
Ocean House 6 5 5 Pool Kailua,
Naupaka Hale 6 3 3 Pool, Beachfront Kailua, $1000-$2500
Clearwater Cottage 4 2 2.5 Kailua,
Noela Estate 10 5 7 Pool Honolulu, $2500 or more
Point Lanikai 11 5 4.5 Kailua,
Wailele Villa 8 4 3.5 Pool Honolulu, $1000-$2500
Cottage At Lanikai 4 2 1 Kailua, less than $500
Hale Capri 8 5 4 Pool Kailua,
Poipu Oceanhouse 10 5 5.5 Pool Honolulu, $1000-$2500
Hale Lanikai 8 4 4 Kailua, $500-$1000
Diamond Head Retreat 10 5 Pool Honolulu,
Obama White House Retreat 10 5 6 Pool
Place In Paradise 14 5 5.5 Kailua, $500-$1000
Kahala Mini Resort 14 7 7 Honolulu, $2500 or more
Diamond Head Hawaii Lani 9 4 4 Pool Honolulu, $1000-$2500
Hale Kea 10 5 3 Kailua, $500-$1000
Paradise Plantation 10 5 6 Pool, Beachfront Kailua, $2500 or more
Jewel Of Diamond Head 10 3 4 Pool Honolulu,