Kailua Vacation Rentals

Kailua is one of the most famous vacation rental destinations on Oahu, featuring a fantastic white-sand beach. Many of the vacation rental properties in Kailua are oceanfront, which makes Kailua the perfect destination for those looking for privacy or a romantic getaway. You can have your privacy here and in the same time enjoy easy access to shopping malls, restaurants and services. Kailua Beach is ideal for swimming, kayaking and windsurfing and was nominated the best beach in the U.S. by Condé Nast magazine in 1998.

  • Nice Studio. Covered Patio. 3 Blks To Beach. Air Cond. Wifi. Parking. Pay Washer

    Studio unit in a private home. Private entrance and private bathroom. Quiet, laid back owners prefer similar, like minded guests. Air conditioner, ceiling fan. Free parking, WIFI and bike use. Pay washer, dryer on property. No singles parti...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    85 USD - 92 USD

    nightly

    575 USD - 630 USD

    weekly

    2,250 USD - 2,500 USD

    monthly

  • Tropical Hide Away for Two

    If you're looking for a quiet getaway in residential Kailua just a few blocks from the ocean, here it is. Attached to our house is a remodeled one bedroom/bath with separate living room and small kitchenette to make your vacation a dream co...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    100 USD - 100 USD

    nightly

    700 USD - 700 USD

    weekly

    2,500 USD - 2,500 USD

    monthly

  • Honu Haven: A Tropical Garden Setting with a Pool

    Honu Haven is just a 10 minute walk to Kailua Town and world famous Kailua Beach where windsurfers, kiteboarders and beachcombers from around the world converge to enjoy the beautiful water. In Kailua Town there is great dining and shopping. Ke...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    125 USD - 125 USD

    nightly

    875 USD - 875 USD

    weekly

  • Cottage with free WIFi & Parking, Central AC, Pool on property

    This Air Conditioned 1 bedroom Cottage is surrounded all year by green and blooming tropical plants. The Aloha Cottage offers a tropical “Hawaiian” style retreat, at a truly affordable price. Ideal for couples, or small families, this comfortable ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    139 USD - 139 USD

    nightly

    950 USD - 950 USD

    weekly

  • Tropical Beach Cottage, 1 house from Beachfront, 20 Steps to the ocean

    Our beautiful Kailua beach cottage rental, is located on a private lane, and just one house from beachfront. From your gate to the ocean, you're just 20 steps away from the world renowned Kailua Beach. This 1 bedroom, features a queen bed, bathroo...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    140 USD - 140 USD

    nightly

    4,500 USD - 4,500 USD

    monthly

  • Cozy Kailua Cottage 1 Block To Beach

    Our place is only 1 block from beautiful Kailua Beach, and a short walk or bike ride to Kailua Town for restaurants and dining. You’ll love my place because of private, separate entry, newly renovated, private outside living space, granite counter...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    140 USD - 145 USD

    nightly

    910 USD - 910 USD

    weekly

    3,200 USD - 3,200 USD

    monthly

  • Tropical Retreat, Short Walk to Kailua Beach!

    Our tropical retreat offers you a place you can relax and enjoy. Watch the beautiful sunrise on a morning Kailua Beach walk, only a short block from our cottage. Enjoy a cup of coffee or glass of wine on your private lanai. Our island style c...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    140 USD - 140 USD

    nightly

    980 USD - 980 USD

    weekly

  • Heavenly Haven - From $950. Weekly/$140. Nightly

    Aloha! Stay in comfort and luxury while enjoying all Hawaii has to offer. Beautiful beaches, lush landscapes, tropical breezes, and crystal clear oceans will take your breath away! Our one-bedroom rental, with its own private entrance and off-str...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    140 USD - 140 USD

    nightly

    950 USD - 950 USD

    weekly

    3,200 USD - 3,200 USD

    monthly

  • 1 Block to Kailua Beach Park/Private Patio/Blue Water Haven/washer/dryer/WIFI

    Enjoy the beauty and privacy of your own shaded, tropical patio or walk one block to Kailua Beach Park with its lawns, trees, and three-mile, white-sand beach. It is an easy walk to Lanikai Beach which Conde Nast Magazine has called the number one...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    145 USD - 145 USD

    nightly

    910 USD - 910 USD

    weekly

    3,600 USD - 3,600 USD

    monthly

  • As close as you can get to Kailua Beach

    Enjoy our Hawaiian sunshine and one of the most beatuiful beaches in the world. Our studio has high ceiling with a Monet- designed decor. A Large queen size 4 poster bed, with a sitting area and dining area. There is a breakfast bar which inclu...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    145 USD - 145 USD

    nightly

    1,015 USD - 1,015 USD

    weekly

  • Your Private Place in Paradise - Sleeps 2 to 4!

    The dramatic Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home. Tranquil, and safe, this ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    148 USD - 160 USD

    nightly

    999 USD - 1,120 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Spacious, Upscale Kailua Garden Studio, Ideal Location, Best Value

    This thoughtfully crafted tropical oasis, is perfectly located between beach and town, providing easy walking access to all Kailua has to offer. Intended for owner occupation, this large, airy studio, has been carefully designed for privacy and ...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    149 USD - 149 USD

    nightly

    900 USD - 900 USD

    weekly

    3,000 USD - 3,000 USD

    monthly

  • 2 Blocks From Beautiful Kailua Beach

    Come and enjoy our island home with us. We are tucked away on a private lane off the main street. The cottage has all the comforts of home. You will enjoy this spending your time here with its own private entrance to a 500 square foot 1 bedroom 1 ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    180 USD - 180 USD

    nightly

    1,200 USD - 1,200 USD

    weekly

    5,000 USD - 5,000 USD

    monthly

  • New-custom built, near the beach, perfect for couples, very private.

    Ginger Hale, is a brand new, professionally designed, custom built, very private high-end, one bedroom upstairs apartment. You have your own private motorized entrance gate that leads to your off-street parking and apartment entrance. Ginger Hale...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    190 USD - 190 USD

    nightly

    4,200 USD - 4,200 USD

    monthly

  • 'Koi Palms Luxury Cottage' Short Walk to Kailua Beach

    Come and enjoy our island home with us. Koi Palms Cottage is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua. The owners live on the property in the main house. The cottage is a 600 square foot 1 bedro...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    195 USD - 195 USD

    nightly

    1,225 USD - 1,225 USD

    weekly

    4,800 USD - 4,800 USD

    monthly

  • Special!! $199/night, Wifi, Air-conditioned, 3 miles to Kailua Beach

    Welcome. This is it! This is the one you've been looking for...your home-away-from-home. My on-line calendar is up to date and you can scroll all the way down to see all the bigger pictures. Convenient location in Kailua, clean and breezy, Air co...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    199 USD - 199 USD

    nightly

    1,365 USD - 1,365 USD

    weekly

    5,700 USD - 5,700 USD

    monthly

  • Kailua- 350 Steps to Beach- Tropical & Spacious Beach

    Kailua, a relaxed lifestyle, and a Hawaiian home to relax and vacation with your family and friends. NO BOOKING FEES WHEN YOU CONTACT OWNER DIRECTLY. The beauty of Judys' Beachside Corner is that you can have one bedroom upstairs, and one downsta...

    2 Bedrooms, 1 Bathrooms, Sleeps 6

    HI>Kailua

    285 USD - 315 USD

    nightly

    1,995 USD - 2,205 USD

    weekly

    6,500 USD - 6,500 USD

    monthly

  • Entire, Spacious, Airy Family House - Minutes to Beach

    All the comforts of home await you at this perfect Hawaii getaway. The aroma of plumeria blossoms welcomes you. Designed by the dean of Hawaii residential architects, Vladimir Ossipoff, this large, open-plan home with a big, private back yard is a...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

    296 USD - 444 USD

    nightly

    1,851 USD - 3,047 USD

    weekly

  • Beautiful Kailua Home - Walk to Beach

    Relax in a very comfortable Island home located within walking distance (5-6 blocks), to beautiful Kailua Beach or a 3 minute drive. Enjoy the privacy of a spacious yard, under the canopy of two Mangoe trees, perfect for sunbathing on a lawn chai...

    3 Bedrooms, 2 Bathrooms, Sleeps 7

    HI>Kailua

    298 USD - 359 USD

    nightly

    2,275 USD - 2,275 USD

    weekly

    5,375 USD - 5,375 USD

    monthly

  • Beautiful Hawaiian Home on Cul de Sac with Gorgeous Kitchen, Bike to Beach

    E komo mai, welcome to our home in paradise. Our well equipped tropical home is located in the beach town of Kailua, world famous for it's white sandy beaches and bay. It's new on the market and is conveniently located less than a mile from bot...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    335 USD - 395 USD

    nightly

    2,345 USD - 2,765 USD

    weekly

  • Serenity Beachfront Cottage

    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto K...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    350 USD - 550 USD

    nightly

    3,850 USD - 3,850 USD

    weekly

  • Happy Kailua Beachside Home 1/2 Block from Kalama Beach Park

    The Happy Kailua Beach House is located 1/2 block down from Kalama Beach Park a small, clean local beach park which has showers, restrooms, and a nice grassy area with picnic benches. The waves at the beach are as gentle as the soothing tradewind...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    375 USD - 425 USD

    nightly

    2,975 USD - 2,975 USD

    weekly

  • This House Has It All - Location, Pool, Renovated, Steps From Kailua Beach

    Spend your vacation in our Hawaiian-style 4 bedroom 4 bath home just steps from the sands of beautiful Kailua Beach - pristine beach, magic waters, and the definition of the word paradise! Relax and splash around the pool or walk over to the beach...

    4 Bedrooms, 4 Bathrooms, Sleeps 12

    HI>Kailua

    595 USD - 1,250 USD

    nightly

    4,725 USD - 5,250 USD

    weekly

    15,000 USD - 20,000 USD

    monthly

  • Pikake Hale - EMAIL for Availabilty

    Beautiful, private Hawaiian home Located less than 100 yards down a sandy path (no shoes required) to world-class Kailua Beach. Enjoy beautiful sunrises and the soothing sounds of the ocean. Tasteful furnishings create a gracious, tranquil Hawa...

    5 Bedrooms, 4 Bathrooms, Sleeps 13

    HI>Kailua

    650 USD - 1,050 USD

    nightly

    4,550 USD - 5,425 USD

    weekly

  • 9BR/5BA W/Pool-2.5Blocks 2 Beach Last Minute Specials as low as $695/nt

    Paradise Found Retreat Property Description: Our resort style home is the ideal spot for large gatherings and family reunions. The free flowing floor plan makes it perfect for entertaining. The main house has 5 bedrooms, and three bathro...

    8 Bedrooms, 5 Bathrooms, Sleeps 22

    HI>Kailua

    975 USD - 1,200 USD

    nightly

    6,825 USD - 8,400 USD

    weekly

    12,000 USD - 15,000 USD

    monthly

  • Majestic Island Home with new pool, perfect for families and close to beach

    Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spaciou...

    9 Bedrooms, 5 Bathrooms, Sleeps 22

    HI>Kailua

    1,135 USD - 1,685 USD

    nightly

    7,945 USD - 7,945 USD

    weekly

  • Royal Kailua Estate - Upscale Private Beachfront Resort with Stunning Courtyard

    Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahus northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination. The grounds are c...

    8 Bedrooms, 8 Bathrooms, Sleeps 16

    HI>Kailua

    49,000 USD - 87,500 USD

    weekly

    196,000 USD - 350,000 USD

    monthly

    7,000 USD - 12,500 USD

    nightly

  • LAST MINUTE DISCOUNT- 10% OFF OR MORE- Ke'aloha Spectacular Beach-Side Getaway

    Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means "love," is certainly appropriate for this cottage. From the momen...

    4 Bedrooms, 2 Bathrooms, Sleeps 11

    HI>Kailua

  • A Month in Paradise! - 250 Steps to the Beach

    E komo mai to The Cottage at Hale Makai - our piece of island paradise in Kailua. Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu. Kailua Beach is routinely voted one of the bes...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach

    Just steps from one of the most beautiful tourist-free beaches on the island of Oahu, this Hawaiian style home is a perfect peaceful getaway for your extended family. Listen to the waves crashing as you relax on the lanai, or barbeque for your gr...

    5 Bedrooms, 3 Bathrooms, Sleeps 12

    HI>Kailua

    4,550 USD - 5,250 USD

    weekly

    9,000 USD - 9,000 USD

    monthly

  • Premier Beachfront Getaway

    Theres a reason why Kailua is consistently voted as one of the top beach destinations in the world: its spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzzs Steak House and the qu...

    6 Bedrooms, 5 Bathrooms, Sleeps 12

    HI>Kailua

  • Kailua Kalama Plantation Home 1 Block to Beach, Newly Built, Very Quiet, Kids!!

    Our quiet home is 1 block and a walk through Kalama park to the beach. Our beach is much less crowded that Kailua or Lanikai and much better to just relax on. * 3 bedroom/2.5 bath. * 1 King Bed | 1 queen pull out | 1 double and 2 singles(childre...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

  • Private Executive Estate Waterfront W/ Pool in Kailua

    Welcome to Kailua Waterfront Estate (KWE). This private and gated executive home is perfect for your Hawaii vacation. Located in Kailua, Oahu, this clean, impeccably maintained home sits on an awesome corner lot with waterfront, golf course, and m...

    3 Bedrooms, 4 Bathrooms, Sleeps 6

    HI>Kailua

    2,975 USD - 4,550 USD

    weekly

    10,600 USD - 12,000 USD

    monthly

  • Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night

    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and kitchenettes. These are deluxe rooms ...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Super Cute 4 Bedroom Ohana Beach House in Kailua 1 Block to Kalama Beach Park.

    Aloha! Our house is perfect for one or even two families traveling together. Every bedroom has a slider that gives access to the enormous backyard. Each bedroom also has a ceiling fan. The house has been recently completely renovated and newly fur...

    4 Bedrooms, 3 Bathrooms, Sleeps 10

    HI>Kailua

    2,333 USD - 4,000 USD

    weekly

    10,000 USD - 10,000 USD

    monthly

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