Kailua Vacation Rentals
<p>Kailua is located on Oahu's east or "windward" shore and is home to two spectacular beaches as well as a lovely town with nice places to eat and shop. Kailua Beach and nearby Lanikai Beach are two of the finest beaches in Hawaii offering clear blue waters lined with white sand and typically enjoying calm conditions and pleasant onshore tropical trade winds.</p><p><b><br></b></p><p><b>Things To Do</b><br>Kailua Beach Park is an excellent place for ocean activities including swimming, bodyboarding, kayaking, surfing and more. Join a guided kayak tour to paddle out to one of the offshore islands, go snorkeling or take a surfing or stand up paddle boarding lesson from a local. Kailua is also quite bike friendly with miles of bike paths along the beach as well as in wetland areas where you can see native waterbirds. Mountain bikers will enjoy the Maunwaili bike trail at the base of the Koolau mountains which is popular for its stunning scenery and lush rainforest areas along a 20-mile route. A relatively easy yet rewarding hike in this area is the Kaiwa Ridge Trail leading up to the "pillboxes" which were shelter bunkers for soldiers guarding the area during World War II. This hike provides great views of Lanikai Beach, Kailua and the Mokulua Islands offshore. A more strenuous hike ascends Mount Olomana providing sweeping views of the windward coast. Another fun hike is the Maunawili Falls trail which leads to a nice waterfall and swimming hole. At Kawai Nui Marsh you can walk a path through wetlands to see native Hawaiian birds in their natural habitat. Golfers can choose from several exceptional courses on Oahu's windward side, all with impressive views of the Koolau mountain range. The scenic Koolau Golf Club is one of Hawaii's toughest courses, and the Olomana Golf Course is considered President Obama's favorite course with great views and memorable signature holes. The municipal Pali Golf Course extends along the foothills of the Koolau range with stunning mount…
16 vacation rentals found. Page 1 of 2 shows 10 properties (10 per page, same as the live site).
Kailua Vacation Rentals
Page 1 of 2 — 16 properties total — 10 per page (matches site listing view).
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
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, OahuRating: 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, OahuRating: 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, OahuRating: 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
Makana's Place
Kailua, OahuRating: 4.9
- 1 Bed
- 1 Full Baths
From $600.00 / night
Makana's Place is a one bedroom, one bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1400 square feet living quarters, which is equivalent to a three bedroom home. Beautifully decorated with fine quality furniture (Koa). Makana's Place features a full kitchen plus an extra queen sofabed and single bed. Wonderful for children. The beach, yes the beach. It is about a 5 minute drive away or 15 minute walk. It has been rated the #1 beach in "best beaches" survey. Most pe
Makana's Place 3 Bedroom 2 bath home
Kailua, OahuRating: 4.7
- 3 Bed
- 2 Full Baths
From $1200.00 / night
Makana's Place is a 3 bedroom, one bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with fine quality furniture (Koa). Makana's Place features a full kitchen plus kitchenette with 2 rooms, 1 bath an extra queen sofabed and single bed located in the extra large spacious living room. There is a very cozy patio area with a fountain and beautiful cooper lighting to enjoy out
Manuela Place
Kailua, OahuRating: 5
- 3 Bed
- 3 Full Baths
From $1485.00 / night
Manuela is a quiet spacious home, in charming Kailua town. This non-smoking home has 1400 square ft of living quarters. It is a 3 bedroom 3 bath home with a front patio and small yard safe for your children. Living and Dining room equipped with a spit A/C for your comfort. All bedrooms have air conditioning as well!!! Kailua beach is about a 3 minute drive or 10-15 minute walk. We take pride in our home and will make sure you enjoy your stay with us. There are many places to go see, ea
