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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 31 - 40 of 57 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...

Kaimana In Kailua

Ecofriendly Home In Great Location
Oahu
4 Bedrooms
 
2 Baths
9 Guests

Create life long memories and experience Hawaiian local living in the comfortable and beautiful "Kaimana in Kailua". Kaimana (Diamond) in Kailua is an ecofriendly 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in...

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...

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...

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...

Paradise Laie

Paradise Beachfront Home in Laie
Oahu
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...

Makanas Place

Quaint Home Near Kailua Beach
Oahu
3 Bedrooms
 
2 Baths
10 Guests

Located in quaint Kailua Town is Makana's Place! This over 1500 sq. ft. home is very spacious and beautifully decorated. Enjoy a full kitchen along with a kitchenette plus an extra queen sofabed and single bed. Makana's Place can be rented as a one (1),two(2) or three (3) bedroom...

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...

Koko Head Estate

Private 3 Story Estate
Oahu
4 Bedrooms
 
3.5 Baths
8 Guests

Just 20 minutes from Waikiki and Honolulu, this private estate is part of a very small class of Oahu homes that sits at the top of Hawaii Kai Cliffs. This 3 story, 5,700 square foot home has phenomenal panoramic views of the Pacific Ocean. While lounging...

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...

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