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Kailua Vacation Rentals In Hawaii

We offer a spectacular selection of private Kailua Island rentals and beachfront homes in Kailua. Search Kailua beach rentals, private home rentals in Kailua, Hawaii on the Island of Oahu.

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There are 42 listings in Kailua




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Kailua Featured Listing

 

Hillside Terrace Vacation Home with Hot

Listing Main Photo
Shared Game Room
Living Room
Kitchen
Master Bedroom
2nd Bedroom
Lanai off Master Bedroom
3rd Bedroom

Kailua, Hawaii

  • Type: Home
  • Beds: 3
  • Baths: 2.5
  • Capacity: 8
  • Rate: Over $250

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 an...

Kailua Vacation Rentals

Hillside Terrace Vacation Home with Hot Tub near Kailua

Kailua, Hawaii

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...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night

Hillside Guest House, Quiet 1 Bedroom on Private Estate

Kailua, Hawaii

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...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night

Coconut Corner, Full Kitchen, A/C and Half-mile away

Kailua, Hawaii

View Coconut Corner Full Kitchen

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 a shopping center and restu...


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Availablity

My Favorites

  • Type: Home
  • Max Cap.: 5
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night

Absolutely Oceanfront-Kailua Vacation Rental

Kailua, Hawaii

View Absolutely OceanfrontKailua

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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My Favorites

  • Type: Home
  • Max Cap.: 3
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night

Kakela Kai

Kailua, Hawaii

View Kakela Kai

Executive type beachfront home set in a security-gated nieghborhood. Docorated with island style rattan furnishings, ceilng fans throughout, cool white tile and wooden flooring. Gourmet kitchen and...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: Over $250 Per Night

Ginger Cottage

Kailua , Hawaii

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...


Reviews (0)

My Favorites

  • Type: Apartment
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $99 or Less Per Night

STAY AT ONE OF THE BEST BEACHES IN THE WORLD

Kailua, Hawaii

Escape to the REAL Hawaii - a friendly place of breathtaking beauty and small-town charm. Kailua Beach has been voted World's Number One Beach. You can body-surf, swim, kayak to an offshore island, bo...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 14
  • Bedrooms: 5
  • Rate: Over $250 Per Night

Pineapple Beach House

Kailua, Hawaii

Aloha and welcome to Pineapple Beach House. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself co...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night

Kailua Paradise

Kailua, Hawaii

This is a beatifully upgraded 3 Bedroom, 3 Bath Executive home which boasts the following: 2 Master Suites with Private "Spa like"custom made Baths 3rd Bedroom has its own bath that can be accessed...


Reviews (0)

Availablity

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night

Beachside Paradise

Kailua, Hawaii

2 Bedroom, 2 Bath completely remodeled with comfort in mind. This house is located on a private street which dead ends at the beach, There is private, gated access to the beach. The house consists ...


Reviews (0)

Availablity

My Favorites

  • Type: Home
  • Max Cap.: 6
  • Bedrooms: 2
  • Rate: Over $250 Per Night

Decked Out in Kailua Hawaii

Kailua, Hawaii

Plenty of indoor/outdoor living in this 3bd 3 bath home. Decks above decks below decks in front decks in back. Beautifully landscaped. The home has just been completely redone. Granite, natural stone,...


Reviews (0)

Availablity

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night

Margies Pink Kailua Beach House

Kailua, Hawaii

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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Availablity

My Favorites

  • Type: Home
  • Max Cap.: 10
  • Bedrooms: 3
  • Rate: Over $250 Per Night

Kailuana Beachfront Vacation Rental

Kailua, Hawaii

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, situat...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 4
  • Rate: Over $250 Per Night

Kailua Beach Estate

Kailua, Hawaii

Kailua Beach Estate features secluded grounds with expansive lawns and sandy beaches right in the backyard, yet is only 25 minutes from the bustle and crowds of Waikiki. The Kailua Beach Estate is ...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 5
  • Rate: Over $250 Per Night

Villa D Este - Lanikai Beach

Kailua, Hawaii

Imagine waking in a tropical paradise with swaying palm trees and white sand beaches, where the ocean miraculously changes hues from soft teal to bright turquoise and shades of emerald. Watch the s...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 16
  • Bedrooms: 8
  • Rate: Over $250 Per Night

Hale'ohe - Kailua Beach

Kailua, Hawaii

Beachside living awaits you in this large family style home with it's bamboo floors and all new furniture. Master Craftsmanship abounds in the artistic Koa pieces custom made just for this home. Lo...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: $100 to $250 Per Night

Honukai - Kailua Beach Front Home

Kailua, Hawaii

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...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: $100 to $250 Per Night

The Casa - Lanikai

Kailua, Hawaii

A peaceful white and red stucco oasis deep in Lanikai with Hawaiian charm, breezes and comfort awaiting you. Across the street from the sparkling turquoise blue waters and fine white sand of famous...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 4
  • Bedrooms: 2
  • Rate: $100 to $250 Per Night

Treetops

Kailua, Hawaii

"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 qual...


Reviews (0)

My Favorites

  • Type: Apartment
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night

Koolau Vista Villa

Kailua, Hawaii

Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, executive, two-story, four-bedroom plus bonus room, four-bath property located in beautiful Kailua,...


Reviews (0)

My Favorites

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 4
  • Rate: Over $250 Per Night
Currently displaying listings 1 through 20 of 42 listings.
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