Oahu Vacation Homes

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.

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.

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.

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.

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.

South Shore 35 is a spacious beachfront house with 4 bedrooms, 4 bathrooms, stunning ocean views, a beachfront jacuzzi, and a large lanai. It sleeps up to 15 guests and has amenities such as central air conditioning, ultra high-speed Wi-Fi, and televisions in every bedroom.

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.

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.

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.

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

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.

Oceanfront Kailua vacation rental with 60ft saltwater lap pool, upscale neighborhood, and two decks (one with partial ocean view). King bed and loft.

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

Spectacular beachfront Kailua retreat with a renovated 4-bedroom main home and private 1-bedroom cottage, floor-to-ceiling ocean views, a chef’s kitchen, and breezy indoor-outdoor dining.

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

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.

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.

Refreshed 3-bedroom, 3-bath Kailua beachfront home on .9 acres, with a large pool, private oceanfront lawn and two miles of white-sand beach for swimming, paddling, bodysurfing and kitesurfing.

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

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.

Remodeled Kailua beachfront estate on nearly an acre with prime wide-sand frontage. Two homes sleep 8-12, with AC, modern kitchens, sun decks, and a vast oceanfront lawn. Walk to Kailua Town and water-sport rentals.

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

Private North Shore beachfront estate with direct beach access, 3 ensuite bedrooms, open-plan living, a lanai, landscaped grounds, and a brand-new hot tub and sauna.

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.

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.

Oceanfront Haleiwa retreat with panoramic views, direct beach access, and a spacious deck and private yard. Newly renovated for up to eight, with two living areas and A/C in every bedroom.

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.

Newly built executive home in Lanikai with 3 en suite bedrooms, spacious living area, fully equipped kitchen, large lawn with Ka'Iwi ridge views, 3 min walk to Lanikai beach, close to Kailua town center. Split AC in each bedroom and common living area. Minimum 30-day rental.

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.

Unwind in a serene gated community with mountain and ocean views from every room. Near uncrowded beaches, turtle and dolphin spots, hiking, world-famous Makaha surfing, diving, and scenic golf.

Penthouse in Lanikai has the best view, is close to the beach, and has a private large wrap-around balcony. It's a tropical oasis with renovated interiors, beach chairs, umbrellas, and bikes. It has a queen bed, semi-private room, and a bathroom with a shower.

Lanikai Oceanside is a newly renovated oceanfront home in Kailua, Oahu. It offers stunning views of the ocean and Mokulua Islands. The property has 4 bedrooms, 3 bathrooms, a guest house, two living/dining rooms, and a spacious yard.

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.

Modern 4BR home in 24/7 gated Makaha Valley with mountain/ocean views. 5 mins to Makaha Beach. Sleeps 10. Patio with misters, fire pit & BBQ, AC in every room, pool/gym access, arcade games. Peacocks add island charm.

Charming 3BR/2.5BA home with panoramic ocean views, spacious living areas, AC, and modern kitchen. Enjoy the whirlpool tub, BBQ on the back patio, and proximity to shopping, dining, beaches, and attractions. Sleeps up to 8.

Royal Kahala Estate is a luxurious 7-bedroom, 8.5-bath beachfront vacation rental near Diamond Head. It features a pool, gym, game room, and stunning ocean views.

Nani Wai is a gated 5-bed, 4-bath home in Hawai’i Kai with marina views, a pool, outdoor kitchen, and a large yard. Ideal for larger groups.

Two private king-bed studios, each with a kitchenette, full bath, sofa, and balcony, just a 60-second walk from world-famous Lanikai Beach. Enjoy room-by-room A/C and two separate patios.

Kahala Breeze is a luxurious 4-bedroom home with a pool, barbecue grill, and expansive terrace for dining. It features elegant decor, open floor plan kitchen, and two lanais. It is located near beaches, outdoor activities, shopping, and dining. Maximum occupancy is 8 guests.

Maluhia is a celebrity favorite vacation rental with 4 bedrooms, 4 bathrooms, a pool, and a waterfall. It has direct beach access and a modern interior.