Kailua Vacation Rentals

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$2550/nt (avg.)
Location: Kailua
Bedrooms: 5 - KKKQQQQ (sleeps 14)
5 (193 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.
$251/nt (avg.)
Location: Kailua
Bedrooms: 1 - K (sleeps 2)
5 (119 reviews)
Newly built 600 sq. ft. suite with modern beach flair, fully air-conditioned, views of Ko'olau mountains, well-equipped kitchen, private patio, and on-site parking. Walking distance to Kailua and Lanikai beaches, shops, and restaurants.
$996/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.
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.
$1991/nt (avg.)
Location: Kailua
Bedrooms: 4 - KKQQX (sleeps 10)
4.8 (113 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 (143 reviews)
Legal oceanfront Kailua vacation rental with stunning views, tide pooling steps away, 60ft saltwater lap pool, AC, and bed bug protective covers.
$370/nt (avg.)
Location: Kailua
Bedrooms: 1 - (sleeps 3)
4.8 (106 reviews)
Alohawaii Properties by the Sea is a stunning villa located on a private beach lane in Kailua Gardens. It has a pool, hot tub, BBQ, bikes, boogie boards, and is a short walk from Kailua Beach, perfect for swimming, snorkeling, and kayaking.
$517/nt (avg.)
Location: Kailua
Bedrooms: 0 - KT (sleeps 2)
4.7 (140 reviews)
Oceanfront Kailua vacation rental with 60ft saltwater lap pool, upscale neighborhood, and two decks (one with partial ocean view). King bed and loft.
$576/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.
$510/nt (avg.)
Location: Kailua
Bedrooms: 2 - (sleeps 5)
4.7 (102 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 (48 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 (115 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: Kailua
Bedrooms: 1 - Q (sleeps 4)
4.8 (59 reviews)
Large, airy 1BR unit with mountain views, wrap-around deck, A/C, and free WiFi. 7-min drive to Lanikai & Kailua beaches. Minimum 30-day stay required.
$657/nt (avg.)
Location: Kailua
Bedrooms: 5 - KKKKKQTT (sleeps 12)
4.9 (43 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.
$2451/nt (avg.)
Location: Kailua
Bedrooms: 4 - KQQTTD (sleeps 8)
5 (31 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.
$3759/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.
$460/nt (avg.)
Location: Kailua
Bedrooms: 1 - QQX (sleeps 4)
4.8 (56 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.
Location: Kailua
Bedrooms: 5 - (sleeps 15)
5 (28 reviews)
Gorgeous 5bed/4.5bath oceanfront villa with contemporary beach house feel, gourmet kitchen, ocean views from every bedroom, hot tub, outdoor bar & bbq.
$377/nt (avg.)
Location: Kailua
Bedrooms: 0 - Q (sleeps 2)
4.8 (40 reviews)
Private tropical studio steps away from Kailua beach, with garden views, high ceilings, AC, solar-heated water, kitchenette, and beach amenities.
$740/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.
$335/nt (avg.)
Location: Kailua
Bedrooms: 0 - KX (sleeps 3)
4.8 (32 reviews)
Lanikai suite near top-rated beach with king bed, private bath, cooking area, beach chairs, towels & umbrellas. "Old school" Hawaiian decor. No BBQ.
$648/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.
$2937/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.
$775/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.
$126/nt (avg.)
Location: Kailua
Bedrooms: 1 - Q (sleeps 4)
4.9 (16 reviews)
Kailua studio, 3-min from world's most beautiful beach. Private gated courtyard, BBQ, pool, outdoor sitting area, AC, TV, kitchenette, parking.
$981/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.
$1158/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.
$446/nt (avg.)
Location: Kailua
Bedrooms: 2 - QQ (sleeps 4)
5 (4 reviews)
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.
$1183/nt (avg.)
Location: Kailua
Bedrooms: 4 - KKQQ (sleeps 9)
4.5 (2 reviews)
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.