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Kailua Vacation Rental Listings

Our Kailua Vacation Rentals selection includes only the best Kailua homes, condos, villas, hotels, bed & breakfasts, cabins, and cottages.

Listed below, you will find numerous Kailua lodging and accommodations to suit your needs. Click on the view details button to explore any of the Kailua rentals you see listed for more information. Oahu, Kailua Vacation Rentals are continuously added and modified, so if you do not find what you are looking for in our Kailua Vacation rental inventory, make sure you bookmark us and come back frequently.

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Kailua Beach Home - Vladmir Ossipoff Home - Vacation Rental in Kailua

Kailua Beach Home - Vladmir Ossipoff Home - Kailua

6 Bedrooms
Sleeps 12
From USD25000.0 mt

• Full Kitchen
• Ice Maker
• Dishwasher
• Full Kitchen
• Coffee Maker
• Dishwasher

Details: Six Bedrooms Five Baths Pool, Hot Tub, and Suana 100 feet of beach front Air conditioned Sleeps up to twelve High Speed Internet Access Flat Screen TV Snorkeling, fishing, surfing, windsurfing, bodysurfing and kayaking are just a few of the a
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Beachfront Elegant 4 Bedroom Home - Kailua - Vacation Rental in Kailua

Beachfront Elegant 4 Bedroom Home - Kailua - Kailua

5 Bedrooms
Sleeps 14
From USD1050.0 nt

• Pool
• Jacuzzi/Hot Tub
• Garage
• BBQ
• Utensils
• Stove - Electric

For the best rates, this site is managed by the owners. This beautiful vacation rental home, located directly on the white sand three mile long beach of Kailua, offers all the comfort and amenities of Island Living in an exotic setting. The large open
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Your Beach House - Kailua Vacation Rental - Vacation Rental in Kailua

Your Beach House - Kailua Vacation Rental - Kailua

3 Bedrooms
Sleeps 8
From USD250.0 nt

• Pool
• BBQ
• Utensils
• Stove - Gass
• Stove - Electric
• Refrigerator

This charming Kailua vacation home has everything you need for your dream Hawaii vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life
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SPECIAL OFFER
Kwai Sim's....When the ordinary just won't do - Vacation Rental in Kailua
18.52% OFF
From: Jun 30, 2008
To: Jul 07, 2008

Kwai Sim's....When the ordinary just won't do - Kailua

3 Bedrooms
Sleeps 8
From USD396.0 nt

• Pool
• Jacuzzi/Hot Tub
• Covered Parking
• BBQ
• Utensils
• Stove - Electric

Private. No other rental units on site. Enjoy exclusive use of Kwai Sim's. Gated, fenced and landscaped for privacy. The entire vacation rental home, grounds, pool and spa just for you. Quiet central air conditioning and ceiling fans keep you cool on
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ISLAND RENTALS - Vacation Rental in Kailua

ISLAND RENTALS - Kailua

Studio
 
From USD75.0 nt


Island Rentals welcomes you to the beautiful islands of Hawaii. We offer you an Affordable Paradise Vacation at one of our many local estates and homes throughout the state of Hawaii. We can find you the perfect get-away to make your Hawaiian vacation
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Kailua Beach Vacation Rental - Vacation Rental in Kailua

Kailua Beach Vacation Rental - Kailua

6 Bedrooms
Sleeps 13
From USD600.0 nt

• Pool
• BBQ
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Experience the Hawaiian cultural and tropical setting of this spacious 3200 square foot island-style vacation rental home. Located 250 yards from the sand of the highly-rated Kailua Beach, this fully furnished, private, single-level home can comfortab
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BEACH COTTAGE - BREATHTAKING OCEAN VIEWS! - Vacation Rental in Kailua

BEACH COTTAGE - BREATHTAKING OCEAN VIEWS! - Kailua

4 Bedrooms
Sleeps 8
From USD1250.0 nt

• Coffee Maker
• TV/VCR
• Stereo
• Phone
• Linens provided
• High Speed Internet

BREATHTAKING VIEWS FROM EVERY ROOM in this beautiful Oahu Beach Rental. ON A BEAUTIFUL BEACH yet only 20 minutes from vibrant Honolulu. Considered a landmark on Kailua Beach; this Kailua waterfront home was designed for oceanside living and to reflect
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3-bedroom vacation home & guest house - Vacation Rental in Kailua

3-bedroom vacation home & guest house - Kailua

4 Bedrooms
Sleeps 12
 

• Garage
• BBQ
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Both Mala Pua Hale main house and guest house are fully equipped Kailua vacation rentals and can be rented separately or together. Main House: Lush tropical gardens make this 3-bedroom, 2-bath private home into a quiet, comfortable retreat. Large enou
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Maunawili Guesthouse - Vacation Rental in Kailua

Maunawili Guesthouse - Kailua

2 Bedrooms
Sleeps 4
 

• High Speed Internet
• Phone
• TV/VCR
• Coffee Maker
• Microwave
• Refrigerator

Looking for the ideal Hawaii vacation rental? This Hawaii accommodation located in Kailua on Oahu is perfect for a tropical getaway and Hawaiian holiday. A tropical home away from home decorated with style and comfort. If you are a family of four (+ o
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Hawaiian Oasis - 3 BR/2BA with Pool - Vacation Rental in Kailua

Hawaiian Oasis - 3 BR/2BA with Pool - Kailua

3 Bedrooms
Sleeps 6
From USD375.0 nt

• Pool
• Covered Parking
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

You can't get much closer to Heaven than you will be in our spacious 3 bedroom, 2 bath home with solar-heated pool. All of your troubles will fade away once you set foot in this beautiful oasis. Short stroll to Kailua Beach. Heavenly Splendor is great
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Makana's Place - Vacation Rental in Kailua

Makana's Place - Kailua

1 Bedrooms
Sleeps 7
From USD175.0 nt


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 well quality furniture. Makana'
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Hale ' Ohe - Beachside, Kailua, Oahu - Vacation Rental in Kailua

Hale ' Ohe - Beachside, Kailua, Oahu - Kailua

4 Bedrooms
 
From USD3500.0 wk

• TV/VCR
• Fireplace

Beachside living awaits you in this large family style Kailua vacation rental home with its bamboo floors and all new furniture. Master Craftsmanship abounds in the artistic Koa pieces custom made just for this Kailua vacation home. Lounge on the lana
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Kailua Vacation Rental - Vacation Rental in Kailua

Kailua Vacation Rental - Kailua

3 Bedrooms
Sleeps 8
From USD399.0 nt

• Cable/Satellite TV
• CD Player
• High Speed Internet
• Linens provided
• Phone
• Stereo

Hale Kai is beach side, 30 yards to the water and nothing is shared or split. You have the entire home to your self. The home features fine furnishings, including Koa wood cabinets, marble baths, hardwood floors, crown moldings, and antique fixtures.
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An Aloha Experience: Kailua Beach Vacation Accomm. - Vacation Rental in Kailua

An Aloha Experience: Kailua Beach Vacation Accomm. - Kailua

2 Bedrooms
Sleeps 4
From USD115.0 nt


Lovely, modern studios to two bedroom units right on Kailua Beach or only steps to the beach. Surrounded by tropical yards with endless views of the Pacific Ocean. Miles and miles of sandy beach to walk or just relax in the sun. Reasonably priced!...
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Charming Kailua Beachside Vacation Villas & Homes - Vacation Rental in Kailua

Charming Kailua Beachside Vacation Villas & Homes - Kailua

5 Bedrooms
Sleeps 11
 

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

Enjoy these beautiful Kailua Oahu Beachside rentals with sparkling fully tiled swimming pools and jacuzzi surrounded with lush tropical gardens. Stay in one of our beautiful Oahu Hawaii private vacation villas, each with 1-5 bedrooms, each with its ow
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