Luxury Kailua Vacation Rentals, Beachfront Homes & Villas

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From $10,000.00 / daily
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Lanikai_Hillside_Estate

Lanikai Hillside Estate

Kailua

Beds: 5   Baths: 6.5   Sleeps: 10
From $9,500.00 / daily
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Oahu_Lani

Oahu Lani*

Kailua

Beds: 10   Baths: 11.5   Sleeps: 12
From $7,500.00 / daily
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Kailuas_Kai_Moena_Estate

Kailua's Kai Moena Estate

Kailua

Beds: 9   Baths: 7.5   Sleeps: 14
From $7,000.00 / daily
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Kailuas_Kai_Moena

Kailua's Kai Moena

Kailua

Beds: 7   Baths: 6.5   Sleeps: 12
From $6,500.00 / daily
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Kailua_Shores_Estate_8_Bedroom

Kailua Shores Estate 8 Bedroom

Kailua

Beds: 8   Baths: 9   Sleeps: 18
From $6,500.00 / daily
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Kailua_Shores_Estate_5_Bedroom

Kailua Shores Estate 5 Bedroom

Kailua

Beds: 5   Baths: 5   Sleeps: 10
From $2,445.00 / daily
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Maluhia

Maluhia

Kailua

Beds: 4   Baths: 4   Sleeps: 9
From $1,500.00 / daily
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Place_in_Paradise

Place in Paradise*

Kailua

Beds: 5   Baths: 5.5   Sleeps: 14
From $1,250.00 / daily
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Kailua_Beach_House

Kailua Beach House

Kailua

Beds: 4   Baths: 4   Sleeps: 8
From $1,075.00 / daily
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Hale_Ohana

Hale Ohana

Kailua

Beds: 4   Baths: 3   Sleeps: 10
From $1,000.00 / daily
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Lokomaikai_Kailua

Lokomaika'i Kailua

Kailua

Beds: 5   Baths: 3   Sleeps: 10
From $792.00 / daily
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Hale_Kalio

Hale Kalio

Kailua

Beds: 6   Baths: 4   Sleeps: 11

Captivating Kailua is Home to Top Beaches and Brimming with Charm

The quaint beach community of Kailua, located on windward Oahu just 20 minutes from downtown Honolulu, offers an alternative to busy city life. Neighborhoods boast tree lined streets, bicycle lanes, and ample access to white sandy beaches. Kailua residents have a true sense of community which gives the town of 38,600 its small-town look and feel.

Kailua received international attention when President Barack Obama came to Kailua for his annual family vacations propelling the sleepy beach community into the spotlight. But, Kailua residents take it all in stride. Consistently named one of the top beaches in Hawai’i, Kailua Beach Park is an expansive 2.5-mile-long white sand beach with crystal clear sapphire blue water. The morning sunrise peaks over the iconic Mokulua Islands as residents stroll the powdery sand- a ritual for many who call the town home Kailua residents enjoy an active outdoor lifestyle. From land to sea there is something for everyone- parks, hikes, walking and cycling paths, tennis courts, kayaking, fishing, kite surfing, canoe clubs, and so much more. Small waves make body boarding a favorite pastime for young and old. While the steady trade winds make Kailua a popular destination for windsurfing and kitesurfing.

Kailua was but a small village up until the 1950s when many of the quaint beach bungalow style homes of the Coconut Grove and Kalama area were built. By 1960s Kailua’s population boomed to be nearly what it is today. The eclectic Lanikai area, with its beachside estates, hillside modern houses, and the playful intermix of kama’aina cottages had a fraction of the homes seen today.

Outside of the town center, neighborhoods are tucked away forming attractive communities unto themselves. The beachside area is one of the most sought-after locations due to proximity to the beach and the breathtaking views of Kailua Bay. Kaimalino is a comparable area though perched on rocks and limited beachline it is an area with a strong sense of community. Just back from the beach is the Kalama and Coconut Grove area. The Aikahi neighborhood is near the back gate of Marine Corps Base Kaneohe Bay overlooks the waterway between Kailua Bay and the Kawainui Marsh. On the other side of Kailua town, across a small bridge is the famed Lanikai neighborhood. Home to many celebrities, Lanikai Beach is consistently on Forbe’s best beaches list year after year. The exclusive community boasts sweeping views and tree lined streets. The Lanikai neighborhood association is very active coordinating neighborhood events, community park, and the Lanikai Canoe Club.

As Kailua continues to offer the charm of a small town, modern amenities blend seamlessly with the established architecture. Whole Foods, CorePower Yoga, and Target deliver contemporary comforts. Most of Kailua’s residents live in homes, however there are several townhouse communities that offer resort style facilities. There are no hotels, instead visitors stay in luxury beach rentals or local B&B’s. Boutiques offer a range of shopping experiences from stylish bikinis to island inspired home furnishings. Kailua even has its own microbrewery complete with tasting room.  Most residents cycle on beach cruisers to do their daily shopping and pedal home with baskets brimming with ingredients. On Thursday, enjoy the local Farmer’s Market in the Long’s parking lot, and get the freshest food and produce. Lanikai’s Craft Fair, an annual occurrence, showcases the best of local artists with clothing, jewelry, art pieces, and even pet supplies made by local artists.