Oahu Vacation Homes

5-bedroom oceanfront home on Kailua Beach, voted "Best Beach in the United States." Large outdoor deck, fully equipped kitchen, and water sports equipment provided. Access to Hale Kai Surf and Racquet Club.

Gated beachfront mini resort in Kahala with 2 swimming pools, Jacuzzi, private tennis court, A/C. Main house has 5 bedrooms, while cottage has two bedrooms. Sleeps 12-14.

Beachfront 4BR/3BA house on Oahu's Sunset Beach with private volleyball court, hot tub, 2 BBQs, AC in each bedroom, and ocean views. Sleeps 8.

Kaimalino Kai is a 2-story, 3BR/4BA oceanfront rental with a private heated saltwater pool, ocean views, and lush tropical gardens. Short drive to Kailua town.

Beachfront 4BR/3BA Hawaiian-style house with ocean views, private beach access, modern kitchen, bamboo & koa floors, jacuzzi tub, HDTVs, & BBQ pit. Sleeps 8. No rocks or coral in the water. Magnificent views of pali cliffs & sunrise over the ocean.

Beachfront, 3-bedroom, 2-bath home with panoramic ocean and sunset views. Upstairs master suite with ocean views, loft with twin beds, and two bedrooms on the ground floor. Outdoor hot/cold shower, free Wi-Fi, cable TV, and outdoor dining area. Short drive to attractions.

Hawaii Sheffield House's Ginger Studio is a legal B&B with a private entrance and a large walk-in shower. It has a breakfast bar, a queen-sized bed, and a bubbling fountain in the garden.

Island living at its finest, this casual Kailua beachfront home is located on the Windward side of Oahu, 30 minutes from Honolulu and approximately 1 mile from the center of Kailua Town. Enjoy spectacular sunrises over Kailua Bay, the scenic Ko'olau Mountain Range.

Beachfront 2-bedroom cottage with A/C, Wi-Fi, cable TV, outdoor shower, grill, and covered lanai. Ideal for family reunions or small weddings.

Legal oceanfront Kailua vacation rental with stunning views, tide pooling steps away, 60ft saltwater lap pool, AC, and bed bug protective covers.

3-bedroom 3-bath beachfront home with ocean views, AC, outdoor shower, free Wi-Fi, fully equipped kitchen, and a private lanai. Ideal for family reunions or small weddings. Conveniently located near attractions. Minimum stay of 5 nights.

This first class accommodations in the world famous Ilikai Hotel is located at the gateway to Waikiki. This location is complete with a fully remodeled, spacious 2 bedroom, 2 bathroom and a beautiful views of the Pacific Ocean & City View of Honolulu.

Charming 2BR/1BA beachfront cottage on Kailua Beach with ocean views, full kitchen, and tropical outdoor shower. Available for weekly/monthly rentals.

Beachfront 3-bedroom + loft, 3-bath home with ocean views, AC, and outdoor shower. Ideal for family reunions or weddings. Close to attractions.

Beachfront 3BR/4BA home on Oahu's North Shore. Lovely views of the Pacific and nearby beach. Private paddle tennis courts, basketball court, and bike path. Outdoor showers. Perfect for families or romantic retreats. Close to Kahuku, Laie, and Turtle Bay Resort.

Hale Pohaku is a historic beachfront home on Waimanalo beach, Oahu. Sleeps 8, with ocean views, swimming, snorkeling, and boogie boarding.

Alohawaii Properties by the Sea is a winner of 2021 Best of Kailua Awards. Their villa has a pool, hot tub, A/C in every room, free WiFi, and is just a short walk from Kailua Beach. They provide bikes, boogie boards, coolers, beach chairs, mats, and towels.

Private tropical rental near Keauhou Bay, Kailua-Kona, HI. Features ocean golf course views, pool, Pacific decor, and walking distance to dining and activities.

The Pink House is a Hawaiian-style beach house with ocean views, 100 yards from Kailua Beach. It has 3 bedrooms, 2 baths, a large backyard, and a lanai. Amenities include WiFi, cable tv, washer/dryer, and outdoor shower.

Hale Lanikai is a Hawaiian-style vacation home with stunning ocean and mountain views, located on a sandy beach. It has 4 bedrooms, a guest cottage, and a fabulous ocean deck.

Viewhouse in Lanikai: Best view, 5 min walk to beach, licensed vacation rental, renovated, private large lanai, one-bedroom, full kitchen, bikes, beach gear.

Pet-friendly home in Manoa Valley with stunning views of Diamond Head. Features a large lanai with BBQ, stylish Old Hawaii interior, and easy access to beaches, cafes, and hiking. Includes central AC and elegant furnishings.

Spacious 2-story home on Koko Kai slopes with panoramic ocean views and sunset over Diamond Head. Private pool, island decor, large kitchen, and lanais. Close to beaches and attractions.

Helen's Beach House is a 5BR/5BA vacation rental just four houses away from Kailua Beach. Bedrooms have AC and en suite bathrooms, and there are two kitchens and living areas. The exterior features a private pool, gazebo, and BBQ area.

Legal vacation rental on over an acre of land steps from the best white sand beach in Hawaii. Ocean and mountain views, sleeps 8, A/C in master bedroom.

Charming 2BR duplex with Craftsman details, pet-friendly, and a lanai with panoramic views. Close to beaches, hiking, and cafes. Enjoy two living areas, a unique kitchen, and outdoor shower. Perfect for families up to five.

Legal vacation rental with stunning ocean and Diamond Head views from the 11th floor. 2 bedrooms, fully equipped kitchen, free internet, and beach access.

Newly renovated unit steps from Waikiki Beach and Ala Moana Mall. Enjoy a pool, Jacuzzi, gym, café, and BBQ grills. Stunning city, mountain, and ocean views. Beach gear available. 24-hour security.

Renovated Lanikai cottage with new furnishings, short walk to beach, efficient kitchen, washer/dryer, large lanai, small pool with waterfall, tropical garden, privacy, licensed. Ideal for 2 adults, small pool suitable for small children.

Luxurious 5BR, 4BA estate near Diamond Head. Features pool, garden, game room, spacious kitchen, and outdoor dining. Minutes from beaches and Waikiki. Perfect for a tropical getaway for up to 10 guests.

Newly renovated 3-bed, 2-bath condo sleeps 10+ on O'ahu's North Shore. Walk to Turtle Bay beaches, golf course, plus 3 pools, pickleball, and tennis. Close to top beaches and dining. Perfect for beach and surf lovers!

Luxury oceanfront vacation rental with pool, AC, and stunning Diamond Head views. Fully stocked kitchen, en-suite bathrooms, and beach toys included.

Ohana Paradise is a luxurious 6-bedroom vacation rental in Diamond Head-Kahala, Oahu. It has a private pool & spa, outdoor living & dining, and is walking distance to the beach, mall, and restaurants.

Charming Lanikai Cottage has 2 dwellings with a total of 3 bedrooms and 2 bathrooms. They share a private fenced-in yard with a new pool, bikes, kayaks, and snorkel gear. It has a partial ocean view, beach access, AC, Wi-Fi, and laundry.

Moana Lani is a luxurious six-bedroom, six-bathroom oceanfront villa with stunning sunset views, private pool, media room, guest cottage, and fitness area.

Hale Kai is a historic Hawaiian estate on 3 acres of oceanfront property with a private dock, pool, tennis court, and lush tropical gardens.

Spacious 4BR/2BA duplex in a secluded historical area near Waianae, ideal for cultural immersion. Enjoy stargazing, private hiking, and breathtaking views. Close to Koolina resorts. Perfect for family gatherings and cultural events.

Legal vacation rental with amazing ocean views, full kitchen, private lanai, and communal oceanfront gardens. Perfect for couples on business or pleasure. Onsite parking available for standard/mid-size cars only.

Luxury Oahu vacation rental with private pool terrace and stunning ocean and Diamond Head views in prestigious Portlock neighborhood. Modern open floor plan, air conditioning, and upscale finishes. Centrally located in Hawaii Kai area with nearby beaches, dining, and shopping.

Oceanfront home on Oahu's south shore with private dock, remodeled 4BR, 3BA for up to 8 guests. Enjoy sunsets from the lanai, BBQ on the sundeck, and explore nearby attractions like Hanauma Bay and Waikiki Beach. Fully air-conditioned.