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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, but will not be obligated to stay for the entire time if you choose not to. Contact us for more information. 

Displaying 41 - 50 of 56 results matching your search criteria
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Kaapuni Kainani

Beachside Paradise: One House From Kailua Beach
Oahu
3 Bedrooms
 
3 Baths
8 Guests

Enjoy a Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. This home is designed for a comfortable, casual way of life, whether you just want to “kick-back” and relax at world-famous Kailua...

Beachside Zen

Just steps to the most beautiful Beach
Oahu
3 Bedrooms
 
2 Baths
8 Guests

Private 3 bedroom 2.5 baths just steps to the most beautiful Beach

Imagine lying on a stretch of powder-white soft sands of Kailua Beach, with clear turquoise waves lapping by your feet, sea breezes gently swaying the nearby palms

...

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...

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...

Sea Suite

Newly Remodeled Studio Near Beach
Oahu
0 Bedrooms
 
1 Bath
2 Guests

This Brand new Vacation Rental is now available! Newly remodeled and furnished with the ocean in mind. The beach is just a little walk down the street to the beach access or for a short drive you can be at the famous Sandy's Beach or Hanauma Bay.

This...

Kahala Mini Resort

Beachfront, 2 Pools (cottage pool heated), Jacuzzi, Tennis Court
Oahu
7 Bedrooms
 
7 Baths
14 Guests

5 Bedroom, 5+ Bath Main House and 2 Bedroom, 2 Bath Cottage, 

Beachfront, 2 Pools (cottage pool heated), Jacuzzi, Tennis Court, Air Conditioning

Main House: Enter the lush tropical grounds thru the privacy gate and enjoy a swim in one of the sparkling pools or a game...

Kolea Estate

Large Estate with Breathtaking View of Ko'olau Mountain Range
Oahu
6 Bedrooms
 
4 Baths
19 Guests

Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home! This property is uniquely expansive and gorgeously designed with beautiful Koa wood, granite stone and stainless steel accents. 

This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot...

Kailua Beachfront

Unforgettable Beachfront Oasis
Oahu
6 Bedrooms
 
5 Baths
12 Guests

Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with...

The Sullivan Estate

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

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. Private, secure and inviting we tempt you to indulge...

Paradise Point

Paradise Point Estate at Kailua Bay
Oahu
5 Bedrooms
 
6 Baths
10 Guests

The Plantation Estate at Paradise Point on Kailua Bay is a single level 5 bedroom/6 bed, 5.5 bath beachfront luxury rental home. Located on Kailua Beach on the windward shore of Oahu, the elegant, yet comfortable estate is recognized for its presidential and celebrity-level security and...

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