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.

  • $95/night Special! Air conditioned, WI-FI, 3 miles to beach

    Welcome, We have it all! Air conditioned, ceiling fans, stocked kitchenette, gas BBQ, WIFI, outdoor gazebo, washer/dryer, Beach coolers/beach towels, boogie boards, parking. Only 3 miles away to Kailua Beach and a 30 minute from the Honolulu Inte...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    95 USD - 95 USD

    nightly

    630 USD - 630 USD

    weekly

    2,750 USD - 2,750 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

  • Seastar Studio,walk to Kailua Beach

    Enjoy Kailua in this nicely renovated studio. Studio is attached to our home in an exclusive area of Kailua. Quiet nights and sun filled days will make your Hawaiian vacation just as you imagined. Studio has queen size bed, fully equipped kit...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    125 USD - 125 USD

    nightly

    840 USD - 840 USD

    weekly

    3,450 USD - 3,450 USD

    monthly

  • NEW YEARS SPECIAL $120 p/nt Relax in Luxury & Privacy Kailua on a Gated Property

    Come stay at Hale `Awapuhi the house of red ginger. A luxurious, semi detached from the main home, large one bedroom apartment on the Windward side of Kailua. New for 2015, we just finished construction on a beautiful white fence and gate system s...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    145 USD - 145 USD

    nightly

    1,015 USD - 1,015 USD

    weekly

    3,900 USD - 3,900 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

  • Tradewind Bungalow, in Kailua on Oahu

    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    146 USD - 146 USD

    nightly

    1,022 USD - 1,022 USD

    weekly

  • 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

  • 'Cottage by the Sea' Hawaiian Style Cottage -1/2block to Beach

    The cottage is located half a block from beautiful Kailua Beach on a nice quiet street in one of Kailua`s finest neighbourhoods. Tropical landscaping surrounds the island-style cottage to give a peaceful private setting. Enjoy a BBQ in your priv...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    150 USD - 150 USD

    nightly

    1,100 USD - 1,100 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Best Beach family friendly open March 9th 2017

    Jasmine House is a large attached apartment, with a large separate bedroom with air conditioning. Located in Kailua five minutes walk from world famous Kailua Beach. Enter through a private gated entrance into a private lanai with lots of tropic...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    150 USD - 150 USD

    nightly

    1,050 USD - 1,050 USD

    weekly

    3,900 USD - 3,900 USD

    monthly

  • 5 minute walk to Beach, A/C, WiFi, BEST VALUE! Sunny studio in a great location

    *Calendar is managed off-site. Please inquire about availability and our reasonable monthly rates* Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is de...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    150 USD - 150 USD

    nightly

    980 USD - 980 USD

    weekly

  • Kailua Beachside Studio - Tropical Breeze

    Serene tropical comfort in your own private studio, just steps away from 1 of the top 5 best beaches in the world. Here you can walk for miles on a white, sandy beach or go wind surfing, kite sailing, boogie boarding, kayaking, snorkeling, or swim...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    165 USD - 165 USD

    nightly

    1,155 USD - 1,155 USD

    weekly

  • Perfect Oasis, Steps To The Beach! 100% Solar!

    This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toa...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    179 USD - 179 USD

    nightly

    1,200 USD - 1,200 USD

    weekly

    4,000 USD - 4,000 USD

    monthly

  • Beachside....Kailua at its Best!

    Located in the water sports capital of the world, Beachside, a new single studio unit is perfect for the water enthusiast! Kayaking, snorkeling, windsurfing, kite surfing, and sun bathing are only steps away for the fortunate few vacationing here....

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    195 USD - 195 USD

    nightly

    1,365 USD - 1,365 USD

    weekly

  • Private 1 Bedroom Studio

    Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toa...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    195 USD - 295 USD

    nightly

    2,065 USD - 2,065 USD

    weekly

  • The Beach...Tropical Garden, Koi Pond, Waterfall, Outdoor Shower, Extended Stay

    Long Term Stays Welcome Contact Us for Details and Rates Hawaii Tax ID # W58473390-01 This new garden villa has wall-to-wall carpeting, a 24 'x 12 ' living dining room, 12'x 20' master bedroom area, large hand crafted desk with Wi-Fi. King size...

    0 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    225 USD - 225 USD

    nightly

    3,200 USD - 3,200 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

  • New 2Bd/2Ba, Steps To Beach, Luxury Kitchen,bathroom, Living Room And Pool!

    New beautiful 2 bedroom & 2 bathroom (detached with private entrance) guest house in a tropical and quiet setting. Similar look and feel to a luxurious resort at a much cheaper price and close to the nicest beaches in Hawaii. Indoors: -Newly con...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>kailua

    300 USD - 370 USD

    nightly

    1,890 USD - 2,500 USD

    weekly

    7,000 USD - 8,000 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 - 335 USD

    nightly

    2,345 USD - 2,345 USD

    weekly

  • NOV WEEKLY SPECIALS!!! BEACH FRONT, STEPS TO KAILUA BEACH, OCEAN & MTN VIEWS!!!

    CONTACT FOR NOVEMBER WEEKLY DISCOUNTS AND OTHER SPECIAL PRICING! Our beach house is located on over an acre of land, just steps to the best white sand beach in Hawaii. One of the few properties that is actually a legal vacation rental so you can ...

    3 Bedrooms, 2 Bathrooms, Sleeps 10

    HI>Kailua

    400 USD - 600 USD

    nightly

    2,800 USD - 3,000 USD

    weekly

  • Kailua Beachfront -Charming,Private, Hawaiian Style Home

    Featured in Coastal Living as guest house of the month, this private Kailua beachfront estate is nestled in among almost 50 coconut tress and lush tropical gardens. With over 700 feet of ancient lava rock wall surrounding this original 1930's Haw...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    550 USD - 800 USD

    nightly

    5,425 USD - 5,600 USD

    weekly

  • Beachside home with heated pool

    Enjoy tropical island living in this recently remodelled custom home! This beautiful home is complete with a gourmet kitchen, salt water heated pool, hot tub, tropical garden and three outdoor living spaces, all just steps from world renowned Kail...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    650 USD - 750 USD

    nightly

    13,650 USD - 15,750 USD

    monthly

  • 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

    675 USD - 1,250 USD

    nightly

    4,725 USD - 5,250 USD

    weekly

    20,000 USD - 20,000 USD

    monthly

  • Kakela Kai - Beachfront Home, Kailua, Oahu, Private,Central A/C

    This is a well maintained beachfront home set in a security-gated neighborhood. It is decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile and wooden flooring. There is a gourmet kitchen with beautiful...

    4 Bedrooms, 0 Bathrooms, Sleeps 9

    HI>Kailua

    950 USD - 1,100 USD

    nightly

    25,000 USD - 25,000 USD

    monthly

  • *Special Price $1500 Nightly* Kailua Beachfront Retreat

    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large...

    6 Bedrooms, 5 Bathrooms, Sleeps 12

    HI>Kailua

    1,500 USD - 1,500 USD

    nightly

    30,000 USD - 30,000 USD

    monthly

  • 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

  • Welcome to 'Hale Hibiscus' Your Own Little Piece of Paradise

    This Hawaiian-style vacation rental is far from the hustle and bustle of Waikiki. Located on the Windward side of Oahu, it is just a five minute walk to breathtaking Kailua Beach. Consistently rated one of the best beaches in the world, Kailua off...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • 2 BR House Steps from Kailua Beach available for monthly rentals

    TAX ID: TA-169-296-8960-01; GE-169-296-8960-01 ***FOR MONTHLY RENTALS CONTACT AGENT FOR AVAILABILITY - EXTENSIVE OWNER USAGE - CALENDAR MAINTAINED OFFSITE BY OWNERS*** Duke's Beach Cottage is located on a private lane in a quiet, affluent neigh...

    2 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Kailua

  • The Ginger Hale Beachfront Retreat

    State of Hawaii Transient Accommodations tax ID # W00261024 This terrific, beachfront, Kailua home has three bedrooms, two baths and is ideal for families seeking a comfortable, stylish, yet casual home. The home sits right on world renowned ...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

  • The Ultimate Hawaii Estate

    Hawaii Magazine has rated Kailua Beach on Oahu as the best beach in the state of Hawaii, and you have an oceanfront estate with two houses that are available to rent in paradise. These two magnificent homes both sleep 12 people and are nestled on ...

    6 Bedrooms, 7 Bathrooms, Sleeps 12

    HI>Kailua

  • Perfect Kailua location! 2 blocks to beach! Kitchen, W/D, A/C

    Welcome to our Kailua Beach House! Our gorgeous unit was a long-term rental for 2 years, but is now available again for vacations. We have updated it, repainted it, and it looks beautiful. Large 1-bedroom stand-alone “cottage”: This 600 sq ft ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • BEST LOCATION IN LANIKAI! Directly on the sand, come stay at HALE LANIKAI!

    Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic# TA-176-161-3824-01 Leave your shoes in the suitcase and come enjoy barefoot living on Lanikai Beach! Gr...

    4 Bedrooms, 4 Bathrooms, Sleeps 8

    HI>Kailua

  • Akialoa Getaways: Huge 3 Bedroom, Living, Dining and Kitchen!

    This place is huge! Large 3-bedroom, 2-bath with an amazing outdoor area and full kitchen! Sleeps 6, and it's the best value you can get for $270 a night! Enter into a tropical retreat known as Akialoa Getaways - Island living at its best! With a...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

  • Hawaiian-Style Get-a-Way

    WELCOME to Hawaiian-Style Get-a-Way. The rental is located in a nice quiet neighborhood on the lake. The property is close to the beach/bus/town. There is a good breeze that comes off the lake. From the backyard you can take an energetic k...

    2 Bedrooms, 1 Bathrooms, Sleeps 6

    HI>Kailua

  • 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

  • Luxury Home-Steps to Kailua Beach-Heated Pool-Air Conditioned-Gated Entry

    This beautiful four bedroom, four bath, Hawaiian style home is just a short walk through Kailua Beach Park to pristine Kailua Beach. Newly constructed, this spacious, estate quality home is part of a private, gated community and offers serene Hawa...

    4 Bedrooms, 4 Bathrooms, Sleeps 8

    HI>Kailua

    4,865 USD - 5,565 USD

    weekly

    19,000 USD - 21,000 USD

    monthly

1