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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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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 and the view. The Lanai has a cocktail table and chairs for two, a table for 4 and a grill. There are ...

Kailua Vacation Rentals

View Hillside Terrace Vacation Home

Hillside Terrace Vacation Home with Hot Tub near Kailua

Kailua, Hawaii

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 and the view. The Lanai has a cocktail table and chairs...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night
  • Viewed: 5941

Top Listing

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View Hillside Guest House Quiet 1

Hillside Guest House, Quiet 1 Bedroom on Private Estate

Kailua, Hawaii

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 beach gear you'll need and you're just a 5 minute drive to...

  • Type: Home
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night
  • Viewed: 4942

Top Listing

View Hillside Guest House Quiet 1

View Absolutely OceanfrontKailua

Absolutely Oceanfront-Kailua Vacation Rental

Kailua, Hawaii

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, bathrooms, and kitchenette facilities. These are deluxe...

  • Type: Home
  • Max Cap.: 3
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night
  • Viewed: 1929

Top Listing

View Absolutely OceanfrontKailua

View Coconut Corner Full Kitchen

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

Kailua, Hawaii

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 resturants. Cancellations are rare, however, they sometimes...

  • Type: Home
  • Max Cap.: 5
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night
  • Viewed: 7509

Top Listing

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View Kakela Kai

Kakela Kai

Kailua, Hawaii

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 bathrooms with granite & marble accents. Fenced-in...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: Over $250 Per Night
  • Viewed: 4738

Top Listing

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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 kitchenette features a comfortable fold out couch and 2 chairs,...

  • Type: Apartment
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $99 or Less Per Night
  • Viewed: 1851
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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, body-board, surf, windsurf, kite-board, snorkel, spearfish,...

  • Type: Home
  • Max Cap.: 14
  • Bedrooms: 5
  • Rate: Over $250 Per Night
  • Viewed: 512
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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 comfortable. As soon as you walk through the door the...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night
  • Viewed: 5522
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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 via the bedroom or the hallway. The interior of the...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night
  • Viewed: 2604

 Availablity Calendar

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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 of 2 suites, each with its own private bath. It has...

  • Type: Home
  • Max Cap.: 6
  • Bedrooms: 2
  • Rate: Over $250 Per Night
  • Viewed: 2779

 Availablity Calendar

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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, cherry wood cabinets and floors, etched glass. Just...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 3
  • Rate: Over $250 Per Night
  • Viewed: 2350

 Availablity Calendar

View Decked Out in Kailua Hawaii

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 PARK Charming 50ties old HAWAIIAN STYLE 3 BEDROOM...

  • Type: Home
  • Max Cap.: 10
  • Bedrooms: 3
  • Rate: Over $250 Per Night
  • Viewed: 3655

 Availablity Calendar

View Margies Pink Kailua Beach House

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, situated perfectly on beautiful Kailua Beach. Here you can...

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 4
  • Rate: Over $250 Per Night
  • Viewed: 3942
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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 comprised of the Beach House and the Tennis House,...

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 5
  • Rate: Over $250 Per Night
  • Viewed: 2712
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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 sun dance on the sea like millions of sparkling diamonds...

  • Type: Home
  • Max Cap.: 16
  • Bedrooms: 8
  • Rate: Over $250 Per Night
  • Viewed: 2103
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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. Lounge on the lanai with your favorite island beverage...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: $100 to $250 Per Night
  • Viewed: 2797
View Haleohe Kailua Beach

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 perfect position - Beachfront! Feel private in the courtyard...

  • Type: Home
  • Max Cap.: 8
  • Bedrooms: 4
  • Rate: $100 to $250 Per Night
  • Viewed: 2751
View Honukai Kailua Beach Front

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 Lanikai Beach. 2 bedrooms (one queen, one double bed)...

  • Type: Home
  • Max Cap.: 4
  • Bedrooms: 2
  • Rate: $100 to $250 Per Night
  • Viewed: 2753
View The Casa Lanikai

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 quality King size bed, which is so comfortable that several...

  • Type: Apartment
  • Max Cap.: 4
  • Bedrooms: 1
  • Rate: $100 to $250 Per Night
  • Viewed: 761
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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, Hawaii. Known for its small town charm and friendliness, Kailua...

  • Type: Home
  • Max Cap.: 12
  • Bedrooms: 4
  • Rate: Over $250 Per Night
  • Viewed: 8096
View Koolau Vista Villa
Currently displaying listings 1 through 20 of 42 listings.
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