Oahu Vacation Homes

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$4250/nt (avg.)
Location: Kahala
Bedrooms: 7 - KQQQDDKK (sleeps 14)
 
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.
$2500/nt (avg.)
Location: Kailua
Bedrooms: 5 - KKKQQQQ (sleeps 14)
5 (190 reviews)
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.
Location: Haleiwa
Bedrooms: 4 - QTTK (sleeps 8)
4.9 (221 reviews)
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.
$740/nt (avg.)
Location: Kailua
Bedrooms: 3 - KFK (sleeps 6)
5 (102 reviews)
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.
$1485/nt (avg.)
Location: Honolulu
Bedrooms: 4 - KKKKQQ (sleeps 14)
4.6 (243 reviews)
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.
$550/nt (avg.)
Location: Turtle Bay
Bedrooms: 3 - QTQTDT (sleeps 8)
4.7 (179 reviews)
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.
$1460/nt (avg.)
Location: Waimanalo Beach
Bedrooms: 4 - KQTQ (sleeps 9)
4.9 (96 reviews)
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.
Location: Kailua
Bedrooms: 1 - Q (sleeps 2)
4.9 (87 reviews)
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.
$1800/nt (avg.)
Location: Kailua
Bedrooms: 4 - KKQQX (sleeps 10)
4.8 (111 reviews)
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.
Location: Kailua
Bedrooms: 1 - Q (sleeps 2)
4.7 (142 reviews)
Legal oceanfront Kailua vacation rental with stunning views, tide pooling steps away, 60ft saltwater lap pool, AC, and bed bug protective covers.
$650/nt (avg.)
Location: Turtle Bay
Bedrooms: 3 - KQTT (sleeps 8)
4.7 (141 reviews)
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.
$399/nt (avg.)
Location: Kailua
Bedrooms: 0 - KT (sleeps 2)
4.7 (139 reviews)
Oceanfront Kailua vacation rental with 60ft saltwater lap pool, upscale neighborhood, and two decks (one with partial ocean view). King bed and loft.
Location: Honolulu
Bedrooms: 2 - QQT (sleeps 6)
4.9 (76 reviews)
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.
$2200/nt (avg.)
Location: Laie
Bedrooms: 3 - KKKTT (sleeps 8)
5 (49 reviews)
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.
Location: Waimanalo Beach
Bedrooms: 3 - KQQFF (sleeps 8)
5 (48 reviews)
Hale Pohaku is a historic beachfront home on Waimanalo beach, Oahu. Sleeps 8, with ocean views, swimming, snorkeling, and boogie boarding.
$650/nt (avg.)
Location: Turtle Bay
Bedrooms: 3 - KTT (sleeps 8)
4.7 (116 reviews)
Beachfront 3-bedroom + loft, 3-bath home with ocean views, AC, and outdoor shower. Ideal for family reunions or weddings. Close to attractions.
$439/nt (avg.)
Location: Kailua
Bedrooms: 3 - (sleeps 6)
4.9 (61 reviews)
Private tropical rental near Keauhou Bay, Kailua-Kona, HI. Features ocean golf course views, pool, Pacific decor, and walking distance to dining and activities.
$375/nt (avg.)
Location: Turtle Bay
Bedrooms: 2 - QTT (sleeps 4)
4.6 (141 reviews)
Beachfront 2-bedroom cottage with A/C, Wi-Fi, cable TV, outdoor shower, grill, and covered lanai. Ideal for family reunions or small weddings.
$395/nt (avg.)
Location: Kailua
Bedrooms: 2 - (sleeps 5)
4.7 (99 reviews)
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.
Location: Kailua
Bedrooms: 4 - QQQQ (sleeps 6)
4.9 (47 reviews)
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.
Location: Kailua
Bedrooms: 3 - KQQTT (sleeps 7)
4.6 (113 reviews)
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.
Location: Kailua
Bedrooms: 2 - (sleeps 4)
4.9 (46 reviews)
Charming 2BR/1BA beachfront cottage on Kailua Beach with ocean views, full kitchen, and tropical outdoor shower. Available for weekly/monthly rentals.
Location: Honolulu
Bedrooms: 4 - QQQQX (sleeps 10)
4.9 (46 reviews)
Historic Gingerbread House: Gated property across from Kahala beach, saltwater pool, jacuzzi, BBQ, outdoor dining, cathedral ceilings, AC, TV in all rooms.
$500/nt (avg.)
Location: Kailua
Bedrooms: 5 - KKKKKQTT (sleeps 12)
4.9 (42 reviews)
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.
$2532/nt (avg.)
Location: Kailua
Bedrooms: 6 - KKKKQQTXX (sleeps 12)
4.8 (56 reviews)
Palione Papalani is a spacious six-bedroom estate with three private entrances, multiple kitchens, and a pool. Steps away from Kailua Beach, the estate offers stunning views, hammocks, and an outdoor tiki bar.
$350/nt (avg.)
Location: Kailua
Bedrooms: 1 - QQX (sleeps 4)
4.8 (54 reviews)
Viewhouse in Lanikai: Best view, 5 min walk to beach, licensed vacation rental, renovated, private large lanai, one-bedroom, full kitchen, bikes, beach gear.
$875/nt (avg.)
Location: Honolulu
Bedrooms: 3 - KTQQ (sleeps 10)
4.9 (33 reviews)
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.
$2204/nt (avg.)
Location: Kailua
Bedrooms: 4 - KQQTTD (sleeps 8)
4.9 (29 reviews)
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.
$420/nt (avg.)
Location: Honolulu
Bedrooms: 2 - FK (sleeps 6)
4.8 (39 reviews)
Legal vacation rental with stunning ocean and Diamond Head views from the 11th floor. 2 bedrooms, fully equipped kitchen, free internet, and beach access.
$571/nt (avg.)
Location: Kailua
Bedrooms: 1 - (sleeps 4)
4.8 (36 reviews)
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.
$2222/nt (avg.)
Location: Honolulu
Bedrooms: 3 - KKQQ (sleeps 8)
4.8 (34 reviews)
Luxury oceanfront vacation rental with pool, AC, and stunning Diamond Head views. Fully stocked kitchen, en-suite bathrooms, and beach toys included.
$1923/nt (avg.)
Location: Honolulu
Bedrooms: 5 - KKTQKKT (sleeps 16)
5 (16 reviews)
Moana Lani is a luxurious six-bedroom, six-bathroom oceanfront villa with stunning sunset views, private pool, media room, guest cottage, and fitness area.
$471/nt (avg.)
Location: Kailua
Bedrooms: 3 - KTKX (sleeps 6)
5 (16 reviews)
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.
$2546/nt (avg.)
Location: Kailua
Bedrooms: 4 - TQTQTKK (sleeps 10)
5 (15 reviews)
Hale Kai is a historic Hawaiian estate on 3 acres of oceanfront property with a private dock, pool, tennis court, and lush tropical gardens.
$785/nt (avg.)
Location: Honolulu
Bedrooms: 6 - QTQQKF (sleeps 12)
4.9 (19 reviews)
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.
$198/nt (avg.)
Location: Pupukea
Bedrooms: 3 - TXQKX (sleeps 6)
4.7 (32 reviews)
Charming 3BR/2BA upstairs unit 1 house back from Sunset Beach. Sleeps 6, ocean view lanai, minutes from famous surf spots & hiking trails. Quiet, gated property. No AC needed. Perfect for working nomads or families seeking a North Shore getaway. Minimum stay of 30 days.
$626/nt (avg.)
Location: Kailua
Bedrooms: 4 - KQQQTTTTX (sleeps 14)
5 (12 reviews)
Private beach access, luxurious privacy, open floor plan, private swimming pool, covered lanai, 4BD/4BA, fully equipped kitchen, and just a few houses off the famous Kailua Beach.
$1043/nt (avg.)
Location: Honolulu
Bedrooms: 4 - KKQT (sleeps 10)
5 (12 reviews)
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.
$525/nt (avg.)
Location: Kailua
Bedrooms: 3 - KQF (sleeps 8)
5 (11 reviews)
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.
$863/nt (avg.)
Location: Kailua
Bedrooms: 5 - KKQQQX (sleeps 10)
5 (10 reviews)
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.
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