Kailua Vacation Homes

Kailua Vacation Homes Kailua, the bustling beach town of Oahu - the heart of Hawaii - is only 30 minutes away from Honolulu and Waikiki and a favorite destination for visitors to soak up some Hawaiian fun and sun. If you're one of the many lured by Kailua's green cliffs, turquoise waters, botanical gardens, and soft white sands, we've got the perfect Kailua vacation home for you so you can explore this Windward Coast town that's the perfect blend of beautiful city and country island attractions. Experience Kailua With our selection of first-class Kailua vacation homes, you'll find properties that boast both sophisticated elegance and untapped island elements. Choose from modern beachfront accommodations that are steps to the beach or pick a plantation cottage that provides you that perfect Hawaiian retreat. Luckily, all of our Kailua homes are in close proximity to the world's best beaches so you can shop, snorkel, windsurf, or just read a good book. When you've had enough sun and sand, opt for a jaunt into Kailua Town for some shaved ice or a souvenir from one of Kailua's unique boutiques. Finally, don't forget to get some picture perfect photos on the one-hour Lanikai Pillbox hike, a great trail with stunning vistas that overlook Kailua and Lanikai. Oceanfront Kailua Homes The perfect ambiance for adventure and fun, Kailua Beach is one of the world's ultimate windsurfing and sailing destinations. Ocean lovers will appreciate the warm Pacific that invites them to try a variety of water activities including kiteboarding, kayaking, and scuba diving. With a gorgeous Kailua vacation property to call home, all of the town's main attractions are within reach. If you prefer to eat, savor the delectable cuisines from a number of top-rated Kailua restaurants. Many feature farm-to-table dishes so you can taste the fresh offerings unlike anywhere else in the world. If shopping is on your agenda, head to the…

20 vacation rentals found. Page 1 of 2 shows 10 properties (10 per page, same as the live site).

Kailua Vacation Homes

Page 1 of 2 — 20 properties total — 10 per page (matches site listing view).

77-6386 Hale Alii Honu Kai

Kailua Kona, HI, US

3 Bed
3.5 Full Baths

From $4025.00 / night — Total price: $12075.00

Luxury Oceanfront Stay in Kona

FWN1 Hale 'O Ka La

Kamuela, HI, US

5 Bed
6.5 Full Baths

From $9228.75 / night — Total price: $27686.25

Hale ‘O Ka La, a Luxury Mauna Kea Home

Kai Nani Kailua Beach

Kailua, Oahu

6 Bed
6 Full Baths

From $3094.83 / night — Total price: $9284.49

Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking at your front doorstep. 6 bedrooms, 6.5 baths wrap around a sparkling solar heated swimming pool with spacious grounds for sunbathing and gathering. The living, dining and 2 primary bedrooms enjoy gorgeous ocean sunrises. A one bedroom attached guest qu

Koohoo Place - 2BR Home Ocean View

Kailua, Oahu

2 Bed
2 Full Baths

From $426.00 / night — Total price: $1278.00

Two bedroom, two bath private residence at the top of Lanikai with spectacular, panoramic views of the Kailua coastline. Feel on top of the world in this truly unique hilltop bungalow. Nestled just beneath the Lanikai Pillboxes, a popular hiking trail, Koohoo provides unobstructed views of the Mokulua Islands and the deep blue Pacific beyond. A large lanai provides the perfect outdoor space to soak in colorful sunrises and to entertain your guests. Enjoy the fragrant plumeria trees and tropical

PSV33 Pacific Sunset Villa

Waikoloa, HI, US

4 Bed
5.75 Full Baths

From $6512.45 / night — Total price: $19537.35

Experience luxury in Waikoloa at the spacious 4-bedroom Pacific Sunset Villa!

Hale Ainoni - 3BR Home

Kailua, Oahu

3 Bed
3 Full Baths

From $625.00 / night — Total price: $1875.00

This 3 bedroom, 3 Bath property is completely enclosed. You get a calm serene feeling when you walk in. There is a private swimming pool for your enjoyment. Kailua Beach is jus a 1-2 min walk away to the beach access. The space The property will be made exclusively available to the renter for a full period of 30 days and no one else may occupy the property during that period. The 30-day rental period will be communicated to guest upon booking. All rates quoted will be based on a 30 day perio

Hale Alapi 'i - 4BR Home

Kailua, Oahu

4 Bed
3 Full Baths

From $2100.00 / night

Welcome to Hale Alapi'i, our home in fabulous Lanikai! This is a 3b/2b 1,400 sq. ft. main house that sleeps 4 adults or 2 adults + 2 kids comfortably, on a slight uphill to enjoy beautiful Hawaiian scenery, tropical birds and island breezes. It has been recently fully renovated and has all the necessities to enjoy a wonderful vacation for an extended family. The studio with queen and full bathroom (350 sq. ft.) accommodates 2 extra people and rents for an additional fee. The space The ho

Kaapuni Kainani- Steps away from beach

Kailua, Oahu

Rating: 5

3 Bed
3 Full Baths

From $800.00 / night — Total price: $2400.00

Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is designed for a comfortable, casual way of life, whether you just want to kick-back and relax at world-famous Kailua Beach (consistently voted one of the worlds top beaches) or participate in the many ac

Kakela Kai - 4BR Home

Kailua, Oahu

Rating: 4.9

4 Bed
3 Full Baths

From $1700.00 / night — Total price: $5100.00

MINIMUM RENTAL PERIOD: Minimum stay requirements vary by property. On Oahu, the City and County of Honolulu regulations require a minimum 30-day rental agreement for properties outside of resort-zoned areas. Therefore your rental agreement will be for a minimum of 30 days. Monthly rates range from $26,000 - $30,000, depending on season. Well maintained beachfront home set in a security-gated neighborhood. Decorated with island style rattan furnishings, ceiling fans through out. Complemente

Lanikai Cottage - 2BR Home

Kailua, Oahu

Rating: 5

2 Bed
2 Full Baths

From $1350.00 / night

This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean, open tranquil feel. Lanikai is the place to stay in Kailua, still close to all amenities such as restaurants, shopping. Honolulu is but a drive over the mountain about 15-20 minutes and your back in th