Kailua lies in the Koʻolaupoko District of Oʻahu on the windward coast at Kailua Bay. It is in the judicial district and the ahupua’a named Ko’olaupoko. It is 12 miles (19 km) northeast of Honolulu – over Nu‘uanu Pali. In the Hawaiian language Kailua means “two seas,” or “two currents,” a contraction of the words kai (meaning sea or sea water) and ʻelua (meaning two); it is so named because of the two lagoons in the district or the two currents which run through Kailua Bay.

Kailua Vacation Rentals

Beach Park Hale

Beach Park Hale

Enjoy tropical island living in this new construction, custom home! Located in a new gated community across from Kailua Beach Park, this beautiful home is complete with a gourmet kitchen and beautiful pool, and is just a short walk to the beach. Lounge around the pool and relax on the large, covered lanai. Enjoy causal evenings at home, cooking in the beautiful new kitchen and hanging out in the large, open great room. Relax in one of the four perfectly appointed bedrooms (two master suites, three with AC and ocean views). Walk to Buzz’s for lunch or dinner, and to the Kalapawai Market for coffee. Luxury in paradise…a perfect combination!

Tranquil Oasis

Tranquil Oasis

Enjoy Kailua Beach sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand…this home is tranquility in paradise. This beautifully decorated three bedroom beachfront home pampers you with a large, well-appointed kitchen, upstairs master suite with soaking tub and killer views, large living room and dining room for gathering, a private den for curling up with a book, and so much more. Nestled among palm trees and tropical gardens, Tranquility sits right on Kailua Beach, and is just steps from the favorite local market and Kailua Beach Park.

Hawaiiana Hale

Hawaiiana Hale

Hawaiiana charm and tropical paradise, beachfront on the sands of world renowned Kailua Beach! Situated right in the middle of Kailua’s beautiful three mile sandy beach, this tropical vacation home puts your toes in the sand from the moment you arrive. A classic Hawaiiana home, Hale Kahakai offers comfortable, spacious living quarters, a large family kitchen, and bedrooms and baths perfectly suited for an active family’s tropical retreat. Whether walking Kailua Beach, testing your surfing skills, creating sandcastles, or just kicking back, this Hawaii vacation home puts you in the middle of paradise.

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Kailua Hale

Built just beyond the breaking waves of Kailua, this spectacular home features exquisite furnishings, stunning architectural detail, and all the creature comforts you would expect. From the moment you enter the front door, the stunning views of the Pacific captivate you. Up the sweeping staircases, step into your own private retreat. Behind the master bedroom doors, sink into the beautiful sitting area and get lost in your favorite book. Soak in the beautiful bath/shower, and settle into bed watching the waves crash just beyond your windows. Enjoy TV in the upstairs loft, or settle into the family room/kitchen for a bite to eat and time with family. Curl up with a glass of wine in the beautiful living room. This enchanting homes offers plenty of room to relax, spread out, and let the ambiance of paradise dictate your next move.

Treasure of Lanikai

Treasure of Lanikai

Fragrant trade winds incessantly sweep cool Pacific breezes through this vaulted, A-framed, Polynesian oceanfront villa decorated in South Pacific splendor. This spacious home provides a slice of heaven in a tropical paradise. Located on the beach that the traveling magazine Conde Naste continually rates as one of the best in the USA, Pua O Lanikai has everything you could desire. It is newly remodeled and very luxurious – from the tropical gardens to the splendid comfort of the Hawaiian decor throughout the home. There is also a guest house, Pua Iki, which sleeps four and can be rented separately or together with the main house.

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Palm Tree Villa

Luxury, custom home with all the amenities, right on the sands of world renowned Kailua Beach. Enjoy a front row seat for spectacular sunrises, sandcastles, kite surfing and more as you unwind and kick back in this special property. Feel the tropical breezes as you relax in the gorgeous great room; enjoy breathtaking sunrises from the front lawn; and kick back around the pool and spa in the lava rock tropical courtyard. This new, custom luxury home offers six spacious bedrooms, including two master suites and a studio suite perfect for extended family and guests. Built around an exquisite courtyard, complete with pool, spa and outdoor kitchen, the property offers the best of both worlds: front row spot on the sand at Kailua beach and the intimacy and privacy of luxurious tropical lazing in the spectacular home and courtyard. This is paradise! Whether walking Kailua Beach at sunrise, testing your surfing skills, creating sandcastles, or just kicking back, this Hawaii vacation home sets the stage for memories that last a lifetime.

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Mokulua View

Perched above Lanikai Beach amidst conservation lands, this luxury Hawaii vacation home offers spectacular vistas across the blue Pacific, the ancient Koolau Mountains, Kailua and Lanikai Beaches, and the famed Mokulua Islands. Gaze out over the reef, watch as kayaks, outrigger canoes and turtles share the Bay, and look for whales off the coast. Enjoy complete seclusion and magnificent sunrises from this hilltop estate. Gated for privacy, this five bedroom Hawaii vacation home offers a large gourmet kitchen, elegant and spacious living and dining areas, and beautifully appointed bedroom suites, each with its own bath. The large, open first floor living areas, dining room and kitchen flow onto the expansive lanai and pool deck, perfect for o’hana (family) living. Escape to the privacy and seclusion of the second floor bedroom suites, including a master suite with a walk-in shower, soaking tub, deck overlooking the ocean, and a private office and huge walk-in closet. The beautiful infinity pool and spa overlook the turquoise water of Kailua Bay and Lanikai Beach. Relax under the stars, enjoy the Hawaiian trade winds and gaze out over the Kailua city lights. The steps below lead to a small, private sandy beach reserved for residents and guests. Famed Lanikai Beach is a short walk, and Kailua Beach a short drive away.

Kailua Alii Villa

Kailua Alii Villa

Welcome to the premier Kailua Beach Oahu estate rental. The Royal Kailua Estate boasts eight beautifully appointed bedrooms and 8 bathrooms and 2 half baths, two luxurious living rooms, a chef’s kitchen, a formal dining room,a pool cabana, and more . . . all overlooking the Pacific Ocean. Hawaiian Koa wood and stone are the theme throughout the estate, imparting a timeless kama aina feel to the property. Exquisite craftsmanship and elegant furnishings throughout offer guests elegant and luxurious comfort. The Royal Kailua Estate Grounds and Pools offer the opportunity to experience Oahus warm sunshine and cool ocean breezes on this sprawling estate, while swimming, strolling, dining, and enjoying the company of friends and family. Wind, stone, wood, and sea coalesce to unite the inside and outside of the estate into a single unified Hawaiian luxury experience, that is The Royal Kailua Estate Oahu. Estate Grounds: fully landscaped grounds and beautifully maintained garden areas overlooking the turquoise ocean. A privacy lava rock wall and hedges surround the estate, and wrap-around viewing decks are ideal for watching the sunrise and catching glimpses of migrating whales and playful dolphins. This Estate rental is distinctive in every detail. The Royal Kailua Estate has three separate living areas surrounding a private pool and poolside cabana with a raised poolside Jacuzzi and cascading waterfall.

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Aqua Dream

A place for friends and family to gather, to share love and laughter, renew relationships, rejuvenate the body and mind, and nourish the soul through the beauty and tranquility that is Lanikai Beach. This spectacular home was designed and built for true o’hana living in paradise. Built right on Lanikai Beach, this brand new home is a showpiece to be admired and enjoyed.