Kailua Hawaii Vacation Rentals

Search 21 Kailua vacation beach homes and condo rentals.

Hawaii Areas

Oahu - Hawaii Cities

Kailua Vacation Rentals

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Kakela Kai
This Listing Qualifies for the Trusted Seal - All Information is up to date and the Owner in good standing.

Kailua Hawaii

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  • Home,
  • 4 Bedrooms,
  • Capacity 10,
  • Over $250 Per Night
View Kakela Kai

Executive beachfront home set in a security-gated nieghborhood. Decorated with island style rattan furnishings, ceilng fans throughout, cool white tile and wooden flooring. Gourmet kitchen and bath...
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Coconut Corner Rental-Full Kitchen-Covered Patio-Split
This Listing Qualifies for the Trusted Seal - All Information is up to date and the Owner in good standing.

Kailua Hawaii

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  • Home,
  • 1 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
View Coconut Corner RentalFull KitchenCovered

Leave the hustle and bustle of Waikiki behind - come stay in a tropical hideaway in a quiet residential neighborhood, just a half-mile from beautiful Kailua Beach. Close to shopping and resturants ...
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Reviews (2)
Rating 5 Stars

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Margies Pink Kailua Beach House

Kailua Hawaii

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  • Home,
  • 3 Bedrooms,
  • Capacity 10,
  • Over $250 Per Night
View Margies Pink Kailua Beach House

Just a QUICK 100 YARD DASH to KAILUA BEACH from this Charming retro 50ties Hawaiian Style Open Plan BEACH HOUSE located right across from Kailua Beach With a VIEW OF KAILUA BEACH AND KAILUA BEACH ...

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Ginger Cottage

Kailua Hawaii

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  • Apartment,
  • 1 Bedrooms,
  • Capacity 4,
  • $99 or Less Per Night
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This new remodeled 1 bedroom Cottage is surrounded all year by green and blooming tropical plants. The bedroom has a queen bed, ceiling fan and also a safe.The living room with eating and kitchen...
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Absolutely Oceanfront-Kailua Vacation Rental-$220

Kailua Hawaii

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  • Home,
  • 1 Bedrooms,
  • Capacity 3,
  • $100 to $250 Per Night
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Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, ba...
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Kailua Beach Escape, 5 Bedroom, Pool, Sleeps 13

Kailua Hawaii

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  • Home,
  • 5 Bedrooms,
  • Capacity 13,
  • Over $250 Per Night
View Kailua Beach Escape 5 Bedroom

5 bedroom home that was recently remodeled and comfortably sleeps up to 13.  It is located on a quiet street with no traffic and you can walk to Kailua beach entrance 2 short blocks away.  The beach e...
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2 Bedroom Kailua Beachside

Kailua Hawaii

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  • Home,
  • 2 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
View 2 Bedroom Kailua Beachside

This house is just 2 houses away from the white sands fo Kailua Beach.  The Master Suite in this house will take your breath away and is on a third story all to its own. It is hard to decide what is ...
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Hillside Terrace Vacation Home with Hot Tub near Kailua

Kailua Hawaii

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  • Home,
  • 3 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
View Hillside Terrace Vacation Home

The 3 bedroom Terrace vacation home is located on a 2 acre estate with a beautiful view of the Bay and Ocean. You'll enjoy a newly remodeled kitchen and living room looking out on the lanai...
Hot Tub

Hillside Guest House, Quiet 1 Bedroom on Private Estate

Kailua Hawaii

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  • Home,
  • 1 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
View Hillside Guest House Quiet 1

Get above it all on your vacation! It is great to walk to the beach, but you're in another world up on our Hillside. Enjoy great views and ocean breezes on this vacation. We have all the bea...

Six month Lease - Kailua Execitive Home near Beach

Kailua Hawaii

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  • Home,
  • 2 Bedrooms,
  • Capacity 4,
  • $99 or Less Per Night
View Six month Lease Kailua Execitive

A six month lease, Jul-Dec 2013 ..................Executive Home near beach & town w/pool&spa - Util Incl - Fully furnished. Close to Kailua Beach (often chosen as "Best Beach in the World") and Ka...
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Hale Kai

Kailua Hawaii

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  • Suites,
  • 1 Bedrooms,
  • Capacity 3,
  • $100 to $250 Per Night
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This large vacation studio with full bath is located near many shops and restaurants. It has a nice pool, large covered lanai, with a canal in the back yard that goes to Lovely Kailua beach. It w...
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Koolau Vista Villa

Kailua Hawaii

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  • Home,
  • 5 Bedrooms,
  • Capacity 12,
  • Over $250 Per Night
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Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story, four-bedroom plus bonus room ( can act as 5th bedroom), four-bath single home in beauti...
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Waioha Kailua

Kailua Hawaii

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  • Studio,
  • 1 Bedrooms,
  • Capacity 2,
  • $100 to $250 Per Night
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You will feel Waioha "joy" and happiness as you enter into your private tropical retreat. Waioha is a charming studio perfect for a single on a work exchange or a couple wanting to escape on a qu...
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Kailuana Beachfront Vacation Rental

Kailua Hawaii

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  • Home,
  • 4 Bedrooms,
  • Capacity 12,
  • Over $250 Per Night
View Kailuana Beachfront Vacation

Aloha! Welcome to our Kailua Beachfront Vacation Estate located on the pristine shores of Kailua Beach on the Island of Oahu, Hawaii. Kailuana estate is nestled within towering palms, situated perf...
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Treetops

Kailua Hawaii

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  • Apartment,
  • 1 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
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"Treetops" is clean, and comfortably furnished......it is private, spacious and offers cool breezes and everchanging views of the Koolau mountain range. This one-bedroom apartment boasts a high ...
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Dolphin Manor

Kailua Hawaii

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  • Home,
  • 3 Bedrooms,
  • Capacity 8,
  • Over $250 Per Night
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This is an exquisite oceanview 3 bedroom, 4 bath home with a gorgeous swimming pool and less than a 2 minute walk to Kailua Beach through beautiful Kailua Beach Park....
Pool Hot Tub

The Ocean House

Kailua Hawaii

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  • Home,
  • 3 Bedrooms,
  • Capacity 7,
  • Over $250 Per Night
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This is a fabulous, newly remodelled, beachside home which can be rented with 2 or 3 bedrooms and 2 or 3 baths.There is a beautifully tiled swimming pool and jacuzzi and it is less than a two minute w...
Pool Hot Tub

The Palm Villa

Kailua Hawaii

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  • Hotel,
  • 2 Bedrooms,
  • Capacity 4,
  • $100 to $250 Per Night
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This pristine villa can be rented as a one bedroom, one bath or as a 2 bedroom, 2 bath villa with a gorgeous fully tiled swimming pool and outdoor jacuzzi. And its only a short one minute walk to famo...
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Honukai - Kailua Beach Front Home

Kailua Hawaii

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  • Home,
  • 4 Bedrooms,
  • Capacity 8,
  • $100 to $250 Per Night
View Honukai Kailua Beach Front

This great family style two story beachfront home is the ultimate in tropical comfort. The gourmet kitchen with its sitting area/library is the perfect gathering place and has been placed in the pe...
Pool Hot Tub

On Beautiful Kailua Beach-from 1 to 5 bedroom units

Kailua Hawaii

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  • Home,
  • 5 Bedrooms,
  • Capacity 12,
  • $100 to $250 Per Night
View On Beautiful Kailua Beachfrom

Relax in the comfort of a beautiful vacation home on Kailua Beach, Oahu, Hawaii. Swim in warm, turquoise water, walk on soft, white sands, enjoy tropical gardens away from the big city. Our bright ...

Currently displaying listings 1 through 20 of 21 listings.

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