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Live Like a Hawaiian With An Oahu Vacation Rental

An exciting and vibrant island, Oahu is home to most of Hawaii’s residents and has many popular and beautiful vacation rental properties. With legendary big-wave surfing spots such as Waimea Bay and the Banzai Pipeline, and beautiful beaches such as Waikiki and Hanauma Bay, you'll feel like a local on Oahu. Find your ultimate vacation rental with Hawaii Life Vacations.

Beautiful Waikiki Beach on the South Shore is Hawaii’s top visitor destination along with nearby Hanauma Bay, which is Hawaii’s most popular snorkeling spot. Honolulu is Hawaii’s state capitol and also the center of business and commerce. The historical downtown reflects Hawaii's rich cultural past, with sites from Iolani Palace to Kawaiahao Church. Nearby is Pearl Harbor and the U.S.S. Arizona Memorial. Oahu also has a thriving culture and arts community with many music and theater venues, museums, fine restaurants and an abundance of nightly entertainment. 

Come to Play, Come to Stay

If Waikiki isn’t your style and you're looking to rent something more private and secluded, Hawaii Life offers privately owned vacation rentals island-wide. With a few exceptions, zoning laws on Oahu prohibit entire-home vacation rentals outside of resort districts for periods of fewer than 30 consecutive days. Properties that are subject to this restriction have a minimum rental period of 30 days. That means that you will have the right to use the property for the entire 30-day period. Contact us for more information. 

Displaying 81 - 90 of 115 results matching your search criteria
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Ocean Escape

Hawaiiana Home Steps from Kailua Beach
Oahu
4 Bedrooms
 
4 Baths
10 Guests

This 2,800 sq. ft. Hawaiiana beach house is the perfect place to relax and enjoy paradise. The tropical large living room opens onto a spacious private lawn leading out directly via a gate to a sandy walkway, steps to breathtaking Kailua beach. 

A rear private courtyard lanai...

Hale 'Ohana

3+Bedroom, 3 Bath, Oceanview, Pool, Partial A/C
Oahu
3 Bedrooms
 
3 Baths
10 Guests

Hale 'Ohana ~ Oahu, Hawaii Kai

3+Bedroom, 3 Bath, Oceanview, Pool, Partial A/C

Set on the slopes of Koko Head Crater, this spacious two story family-style home offers panoramic ocean views and breathtaking sunsets over Diamond Head. Everyone will enjoy the modern conveniences of this cool and...

Tranquility in Kailua

Beachfront Island Living near Downtown Kailua
Oahu
3 Bedrooms
 
3 Baths
8 Guests

Nestled among palm trees and tropical gardens, Tranquility sits right on Kailua Beach. Enjoy sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand!

This beautifully decorated 3 bedroom beachfront home pampers you with a large, well-appointed kitchen, private den, upstairs...

Premier Beachfront in Kailua

Beachfront Paradise
Oahu
6 Bedrooms
 
5 Baths
12 Guests

There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular! This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua.

The property is secluded...

Shangri La By The Sea

Breathtaking Views & Luxurious Details
Oahu
5 Bedrooms
 
3 Baths
10 Guests

Leave your worries behind as you step into this magical home!

Built just beyond the breaking waves of Kailua, this spectacular home features exquisite furnishings, stunning architectural detail, and all the creature comforts you would expect. From the moment you enter the front door, the stunning views...

Royal Kailua

Stunning Beachfront Home in Kailua
Oahu
8 Bedrooms
 
8 Baths
16 Guests

Fully furnished beach and ocean front executive home to include: 8 bedrooms, 8 full bathrooms, 3 half baths, multi-level interior, no elevator, 2 structures, main 2 story 5 bedrooms, 5 full baths plus 2 half baths, separate single story cottage, 3 bedrooms, 3 full baths and 1 half bath,...

The Sullivan Estate

Private Estate and Spa Retreat
Oahu
6 Bedrooms
 
6 Baths
12 Guests

This property has a minimum rental reserve of 30 days in order to comply with Oahu zoning laws governing vacation rentals. Please contact us for rates and details.

Welcome to the Sullivan Estate & Spa Retreat, the first holistic anti-stress centre on earth. Located directly on the...

Beach Cottage in Laie

Beachfront Cottage on White Sandy Beach
Oahu
3 Bedrooms
 
2 Baths
8 Guests

This beachfront cottage sits on a large lot in Laie. Although a little rustic on the exterior, the interior was recently remodeled and is simple and clean and provides all the amenities needed for a relaxing Hawaiian getaway. The property is on a gorgeous white sand...

Ohana House

Private spacious home with large - deck great for a family fun
Oahu
4 Bedrooms
 
3 Baths
8 Guests

Private spacious home with large - deck great for a family fun filled vacation

Come relax at a private 4 bedroom 3 bath home located in Keolu Hills. This location is in the middle of both well known Kailua

...

Serenity Beachfront Cottage NUC # 90/TVU-0326

Kailua Beachfront Cottage
Oahu
2 Bedrooms
 
1 Bath
4 Guests

This is the beachfront cottage you've been searching for! This delightful cottage is found in the middle of stunning Kailua Beach. Casually lounge in the small but cozy living room and be astounded by breathtaking views of the beach. Step out your front door and onto...

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