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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 21 - 30 of 54 results matching your search criteria
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Paradise Laie

Paradise Beachfront Home in Laie
4 Bedrooms
4 Baths
12 Guests

This 4-bedroom, 3.5-bathroom Island style oceanfront house has breathtaking ocean views and a beautiful beach. Although lovingly weather and beach worn, it is clean and has everything you need for a Hawaiian vacation. This makes the house perfect for both families with children, and those seeking...

Ohana House

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


Hale Ainoni

Hawaiian Paradise in Kailua
3 Bedrooms
3 Baths
6 Guests

This private home is a home away from home, completely enclosed with 3 bedrooms and 3 bathrooms. Wonderfully decorated with the beach in mind, just makes you relax and unwind and enjoy your vacation!

There is a private swimming pool for your enjoyment and a pool fence...

White Pearl

Beachfront Property on Kailua Beach
5 Bedrooms
5 Baths
6 Guests

Escape to this 4,500 sq. ft. open house, featuring 10 ft tall sliding doors leading to a large grassy yard and the beautiful pristine Kailua beach!

Ocean and beach view from living room, dining kitchen and master bedroom. Modern and simple amenities in the house are designed...

Nani’s Cottage

Quaint Cottage Near Kailua Beach
2 Bedrooms
2 Baths
4 Guests

Nani's Cottage is a brand new rental and is now open for your enjoyment! This two bedroom, two bath cottage is within a minutes walk to Kailua Beach. Just perfect for a family of four.

Bedrooms: 2, Sleeps 4

Bathrooms: 2

HI tax id: W01498089-01...

Aloha Nalo

Perfect house for large or multi-generational families
4 Bedrooms
4 Baths
10 Guests

Aloha Nalo means hidden love. The warm ocean breezes; sunrises over the turquoise blue water; clouds rolling over the sheer, emerald green cliffs of Ko'olau Mountains; the slow, friendly pace. Once you stay at this beachfront gem; you too will know you have discovered a great,...

Paradise Point

Paradise Point Estate at Kailua Bay
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...

Sea Suite

Newly Remodeled Studio Near Beach
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.


Martins Hale

Clean & Breezy Cottage In Great Location
1 Bedroom
1 Bath
4 Guests

This is it, this is the one you've been looking for! Enjoy sleeping on a comfortable king size bed conveniently located in Kailua. Clean and breezy, air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice cooker, pots,...

Kahala Mini Resort

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