Best Airbnb & VRBO Vacation Rentals on the Island of Oahu (December 2023)

Oahu is a beautiful and diverse island in the state of Hawaii. The island is home to the state capital, Honolulu, where the majority of the population resides. Oahu is also the host of a number of surfing competitions on its famed North Shore, where winter waves can climb up to 50 feet high.

Oahu offers tourists a beautiful and unique experience, from whale watching to snorkeling and cultural experiences, the island truly is magical.

There is no shortage of vacation rentals, VRBOs, and Airbnbs where visitors can stay around the island. Below is a brief description of each region along with some of the nicest vacation rentals in that area.


Honolulu is the bustling capital city of Hawaii and home to the majority of Oahu's population. The city is a mixing bowl of cultures and neighborhoods with many diverse restaurants, trendy shops, and thrilling activities. Perhaps the most famous area in Honolulu is Waikiki Beach, which is filled with swanky condo high rises and a vibrant nightlife. This area is a haven for tourists and it has a lively atmosphere year round.

Diamond Head is an upscale neighborhood where you'll find some of the most expensive real estate in the city. There are beautiful and luxurious VRBO and Airbnb vacation rentals that often have private pools, gourmet kitchens, and breathtaking views. Celebrities are known to frequent this area, but there are also options for the more modest travelers as well.

There are a number of local neighborhoods throughout Honolulu, each with its own personality. The University of Hawaii is found in Manoa, so this area has a lively student population. Hawaii Kai has a beautiful beach and Ala Moana is where you'll find a swanky shopping area.

Each neighborhood in Honolulu has at least a handful of vacation rentals available, but there are countless options in Waikiki, where most of the tourists gather. Below are just a few of our favorites.

Diamond Head VRBO Vacation Rental

Honolulu, Hawaii
This stunning house has everything you could need, including a private pool, a full kitchen, and a luxurious setting. This is a family-friendly house with enough room for everyone.

Enjoy a drink by the terrific pool which you'll have all to yourself. The extra space of this 3-bedroom house is an added bonus. With a dining room, porch, and living room, there is enough space for guests to relax and hang out.

3 Bedroom Waikiki Beach Condo

Waikiki, Honolulu, Hawaii
If you're looking for a beach vacation rental in Waikiki, this 3-bedroom, 3-bathroom condo is a great option. This is a family-friendly place with enough room for everyone or it makes a nice option for a group of friends. This property is located conveniently close to the beach. There's also a beautiful balcony where you can enjoy wine or your morning coffee. For those who enjoy cooking, there's a full kitchen with a dishwasher, refrigerator, stove, oven, microwave, and coffee maker. You'll be able to spread out through the dining area, porch, and living room here, as well.

The complex has a fitness center, concierge, and tennis, so plenty to do as well. Also included is laundry, television, parking, a garage, internet, and a coffee maker. With Ala Moana Center located just 1.1 miles away and Diamond Head only 2.1 miles away, you'll find this to be a very convenient place to stay. You'll be close to a number of fun activities including fishing, golf, and surfing.

North Shore

Oahu's North Shore is world famous for its large surfing waves. During the winter season, the waves off of the North Shore can reach has high as 50 feet. These impressive surges bring world class surfers to competitions that attract tourists and locals alike. Sunset Beach, Waimea Bay and the Banzai Pipeline, are all part of the famous Triple Crown Surfing Contest.

During the summer months the water is calmer and families enjoy visiting the area for the beautiful beaches and impressive snorkeling. Turtle Bay Resort is one of the largest and nicest resorts along the North Shore.

Other popular towns on Oahu's North Shore include La'ie and Haleiwa Town. Each town has a charming local vibe with great restaurants, shaved ice, and fun cultural experiences.

There are a number of great VRBO and Airbnb vacation rentals along the North Shore. Options include luxurious beach houses, charming bungalows and cottages, or resort style condos.

Beachfront Oahu VRBO Vacation Rental

Pupukea, Haleiwa, Hawaii
Visitors love this house with its beautiful porch and large windows. The 4-bedroom, 4-bathroom vacation rental has room for up to 11 people so it's great for a larger group of friends or a big family. The fully equipped kitchen has everything you need such as a dishwasher, refrigerator, and stove. Enjoy meals or relaxing in this property's dining area and living room.

Laundry, television, parking, and internet are also included. Places like this get booked up quickly. Nearby is Turtle Bay Beach which is 5.1 miles away and Banzai Pipeline which is 1.1 miles away.

Beachfront La'ie Vacation Rental

Laie, Hawaii
This house is a popular option in Laie, as it has 5 bedrooms and 4 bathrooms. With so much space, everyone can relax, hang out, plan the day's activities, and have a memorable vacation together. With queen-sized beds in several bedrooms, no one will have to fight over which room to stay in. Enjoy cooking your meals in the kitchen, which has modern appliances including a dishwasher, refrigerator, stove, oven, and microwave. There's also plenty of space in the dining area and living room, too.

This is the perfect rental for a beach vacation. Relax on the balcony and enjoy the views. Included with this property is laundry, television, parking, internet, a grill, and a coffee maker. Also nearby is fishing, horseback riding, golf, surfing, and kayaking. Nearby is the Polynesian Cultural Center which is 0.9 miles away and Turtle Bay Beach which is 5.9 miles away. Staying here will make your trip to Laie fun and convenient.

Windward Coast/East Side

Oahu's eastern, Windward side offers stunning scenery and beautiful beaches. The area is a far cry from the hustle and bustle of nearby Honolulu despite its close proximity. The area is known for its slow pace and relaxed atmosphere. Beautiful blue waters meet pristine sandy beaches and dramatic mountains and valleys create a breathtaking backdrop for visitors. The area has been the setting of a number of movies and tv shows including Jurassic Park and Lost.

This area is frequented by such well known celebrities as Barrack Obama and ***, but there are a range of beach houses and vacation rentals available. The areas around Kailua Town and *** have stunning, luxurious homes with custom designed private pools and beautifully landscaped gardens. If luxury is your style, there are countless options to choose from. Below are just a couple of the area's best vacation rentals.

Beachfront Luxury Kailua Estate - Oahu VRBO Vacation Rental

Kailua, Hawaii
This stunning beachfront house is a great place to stay if you want to enjoy everything that the area has to offer. You'll be close to plenty of things to do because nearby you'll find Kailua Beach, Lanikai Beach, and Kaneohe Bay. Fishing, horseback riding, golf, surfing, and boating are all nearby, as well, making this location very convenient. This house has an beautiful private pool which is great for adults and kids alike. The ocean view is also nice, and is a constant reminder that you're on vacation. You can take in the fresh air from the balcony and enjoy relaxing in a luxurious setting. Featuring 6 bedrooms and 7 bathrooms, there's plenty of room for up to 12 people here, so it's perfect for a larger group. Because it's a large space it's perfect for a big family, or multiple families on vacation together. If you just want to eat in, the fully-equipped kitchen with its dishwasher, refrigerator, stove, oven, and microwave will let you cook all of your meals. And with the dining area, porch, and living room, everyone will be able to spread out and relax.

Also on the list for this house is laundry, television, parking, and internet. If you're looking for luxury, comfort and convenience, this is a great house.

Gorgeous Lanikai Villa - Oahu Vacation Rental

Kailua, Hawaii
This large 6-bedroom, 6-bathroom oceanfront villa is delightful, and sleeps up to 15 people. This is a comfortable option for anyone headed to Lanikai and Kailua Beach. It offers a relaxing place to stay where you can take in the fresh air from the balcony and enjoy some time to unwind. With space for the whole group, this is a great vacation rental for the entire family or larger groups.

If you just want to eat in, the fully-equipped kitchen with its dishwasher, refrigerator, and stove will let you cook all of your meals. Everyone can also relax in the dining and living rooms. Multiple bedrooms in this villa have king sized beds, which is a nice luxurious touch that is hard to find elsewhere.

Laundry, television, parking, internet, a grill, and a coffee maker are also on the list of amenities. Also nearby is fishing, horseback riding, golf, and surfing. Not too far away you'll find Kailua Beach, Lanikai Beach, Waimanalo Beach, Hanauma Bay Nature Preserve, and Diamond Head.

Leeward Coast

Oahu's western, Leeward Side is sunny and dry. The area is less developed than nearby Honolulu and offers a more relaxed, off-the-beaten-path destination. There are beautiful beaches, nice surfing spots, and rural landscapes that are fun to explore.

In addition to the rural and local areas on the Leeward Side, there is also the beautiful Ko Olina resort area. This area is where you'll find the famous Aulani Disney Resort & Spa. The area also has a luxurious Four Seasons Resort and Marriott's Ko Olina Beach Club.

Many of the vacation rentals on Oahu's Leeward Coast are found in the Ko Olina resort area, but there are also beautiful homes in the charming towns along the coast that have a more local and less touristy atmosphere. Below are a couple of options along Oahu's Leeward Coast.

Beachfront Oahu VRBO Vacation Rental with Private Pool

Makaha, Waianae, Hawaii
Ideal for a larger group of friends or a big family, this spacious beach house has plenty of room to spread out. The 5-bedroom, 4-bathroom beachfront property is in a great location near Makaha Beach Park, Pokai Bay Beach Park, and Makaha Valley Golf Club. This amazing house has everything you need, and provides it all with a touch of luxury. One of the highlights of this place is the private pool where you'll be able to relax and swim in your own space.

With a view of the blue water, it's hard to beat this location. You can head outside and enjoy a meal on the balcony or sip your morning coffee. Cook all of your meals in the kitchen, as a dishwasher, refrigerator, and stove are provided. This house also has a dining area, porch, and a living room, which will let you relax comfortably on your trip. Laundry, television, and parking are also included.

If you're interested in more accommodation options in Oahu, you should also see Best Airbnb & VRBO Vacation Rentals on Oahu's North Shore.
Share This Page
Budget Your Trip
Budget Your Trip is all about finding out how much everything costs so that you can travel cheaper and longer. With average daily travel costs that are calculated from the budgets of real travelers, you can find out how much money you need to plan your next adventure. On this website you can also find travel advice, accommodation reviews, and activity suggestions.
Share This Page
Pin This Page
Best Airbnb & VRBO Vacation Rentals on the Island of Oahu (December 2023) | Budget Your Trip

Some of the links on this website are sponsored or affiliate links which help to financially support this site. By clicking the link and making a purchase, we may receive a small commission, but this does not affect the price of your purchase.