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.

  • Covered Lanai.3 Blks To Beach, Kailua Town. Air Cond. Free WiFi,Parking,Bike Use

    Studio unit in a private home . Private entrance and private bathroom . This is a family, monogamous home and prefer similar guests. No single's parties or guests. Meal prep area small appliances, dishes, pots and pants, utensils . There is fre...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    85 USD - 90 USD

    nightly

    565 USD - 600 USD

    weekly

    2,155 USD - 2,280 USD

    monthly

  • $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

  • 100 yards from the Beach! Private, peaceful and cold Air conditioner

    We really are 100 YARDS from travel magazines top beach. KAILUA!!! Relax and enjoy your morning coffee in your own peaceful, PRIVATE GARDEN ! or walk 100 yards to the beach and watch the sunrise. Come home from enjoying the beautiful Hawaiian Isla...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    115 USD - 115 USD

    nightly

    2,750 USD - 2,750 USD

    monthly

  • 5 minute walk to Beach, A/C, WiFi, BEST VALUE!

    *Calendar is managed off-site. Please inquire about availability and our 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 designed for ...

    0 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

    150 USD - 150 USD

    nightly

    980 USD - 980 USD

    weekly

  • Beautiful High Ceiling Studo With A Comfortable Hawaiian Feel. Gated parking

    The high ceiling studio has a island feel to it with natural colors to sooth and comfort you after a long day of adventuring. Many arched windows provide nice lighting to the studio. the room has Air conditioning and a small kitchenette. a back y...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    150 USD - 150 USD

    nightly

    1,000 USD - 1,000 USD

    weekly

    5,000 USD - 5,000 USD

    monthly

  • THEY ELOPED !!! SEPT CANCELLATION SPECIAL 20% OFF, NOW $170/NT SLEEPS 4

    Exquisite one bedroom, 1.5 Bath, treetop location overlooking the world famous Mid Pacific Country Club Golf Course. Where Presidents play. This lovely apartment provides old Hawaiiana charm with modern design features. The unit provides 800 squ...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    170 USD - 240 USD

    nightly

    1,325 USD - 1,325 USD

    weekly

    5,250 USD - 5,250 USD

    monthly

  • The Windsurfer Cottage Hawaii - Kaimakani - 'The Sea Wind'

    The cottage is located 100 yards from beautiful Kailua Beach on the windward side of Oahu. It is landscaped in true Hawaiiana-style. Palm trees and bamboo trees surround cottage, lanai, and yard giving a peaceful private setting. Just renovated, ...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    175 USD - 250 USD

    nightly

    1,400 USD - 1,750 USD

    weekly

  • Kailua Tropical Garden Cottage, Sleeps 3-4

    Welcome to our beautiful Island cottage, nestled among lush tropical foliage. A separate cottage to relax and escape life's rigors, with your feet touching the sands of our world famous Kailua beach, a 10 minute walk, from your front door. Head in...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

    180 USD - 200 USD

    nightly

    1,200 USD - 1,200 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • Very Close To Kailua Town And Beach!

    The Maipele Hale is located on a Ohana (family) style property. The unit is on a second floor of the main home. This is a family friendly environment and we may even let your travel pet stay too! This 2 bedroom, 1 bathroom unit has everything...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    180 USD - 225 USD

    nightly

    1,575 USD - 1,575 USD

    weekly

  • Experience the Seabreeze in Kailua

    Enjoy a quiet, romantic, tropical vacation at 'The Seabreeze' located one block from award winning Kailua Beach. Our tropical Hawaiian estate is the ideal place to relax and get away from it all. We are situated on one half acre heavily landscap...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

    185 USD - 185 USD

    nightly

    1,295 USD - 1,295 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$220 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

    220 USD - 220 USD

    nightly

    1,540 USD - 1,540 USD

    weekly

    6,000 USD - 6,000 USD

    monthly

  • Blue Ginger Cottage/Mele Hale

    Blue Ginger Cottage/Mele Hale - 'Happy Home' is situated in the wonderful town of Kailua on the windward side of Oahu. We are the owners living on the property, next to the attached cottage. We are available at your request to answer your questio...

    1 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    225 USD - 225 USD

    nightly

    1,575 USD - 1,575 USD

    weekly

    4,500 USD - 4,500 USD

    monthly

  • AC, Mountain Views, Wi-fi, 5 Minutes to Kailua Beach

    We welcome you to stay at this lovely 3 bedroom 2 bath home located in a lush peaceful setting, which offers gorgeous mountain views, updated kitchen appliances, with granite countertops. Kiana's Place is just minutes away from World Famous Kailu...

    3 Bedrooms, 2 Bathrooms, Sleeps 7

    HI>Kailua

    250 USD - 425 USD

    nightly

    1,750 USD - 2,975 USD

    weekly

    7,500 USD - 7,500 USD

    monthly

  • Beach Cottage, sleeps 5, with AC, WIFi, beach bikes, 240 steps to Kailua beach

    The Kalaheo Beach House is a spacious 2 bedroom, 1 1/2 bath traditional plantation home offering an authentic Hawaiian living experience in a private, serene, garden setting, only steps away from world famous Kailua Beach on Oahu's windward side. ...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    259 USD - 259 USD

    nightly

    7,700 USD - 7,700 USD

    monthly

  • Beautiful Apartment at Prime Beach Location

    We have a beautiful, spacious, architect designed 2 bedroom, 1.5 bath apartment with private access to Kailua Beach. Our home is only one lot off the beach and has a private access to the beach. It is in a gated community of three homes. Our ap...

    2 Bedrooms, 1 Bathrooms, Sleeps 5

    HI>Kailua

    290 USD - 290 USD

    nightly

    1,950 USD - 1,950 USD

    weekly

    7,900 USD - 7,900 USD

    monthly

  • Kailua Beach Cottage Home Rental with a/c, large yard & walk to beach.

    Kailua, Oahu Beach Cottage Home *Perfect for the seasoned Hawaiian vacationer or those looking for relaxation & lots of comfort away from crowds. *Home is spacious with large yard & ample parking. A large patio/lanai with palms, plumeria with ...

    3 Bedrooms, 1 Bathrooms, Sleeps 7

    HI>Kailua

    290 USD - 350 USD

    nightly

    1,950 USD - 2,400 USD

    weekly

    5,250 USD - 6,300 USD

    monthly

  • Steps to Paradise - Kailua Beachside - Daily or Special Monthly Rates

    E komo mai to Hale Makai, our piece of island paradise in Kailua. Whether you rent for 10 days or a month, you're gonna love it here! Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

    425 USD - 425 USD

    nightly

    8,200 USD - 8,200 USD

    monthly

  • Family friendly, steps to beach, sleeps up to 10, AC, pool, yard, private

    Recently remodeled and refurnished from the ground up. Everything is fresh, new, clean, and modern. This beautifully designed, spacious Kailua home has 3 bedrooms and 2 bathrooms, with a 1 bedroom, 1 bathroom apt. (that can be rented in addition t...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua

    470 USD - 470 USD

    nightly

    12,000 USD - 12,000 USD

    monthly

  • Spectacular views views of Kaneohe Bay, the ocean and the Ko'olau Mtns.

    This wonderful home is located in one of the best kept secret areas of Oahu. The privacy of the home in a quiet, safe neighborhood, the breathtaking views of the ocean, the picturesque Kaneohe Bay and the majestic Ko'olau mountain view, the open f...

    4 Bedrooms, 2 Bathrooms, Sleeps 10

    HI>Kaneohe

    475 USD - 675 USD

    nightly

    3,675 USD - 4,725 USD

    weekly

    10,600 USD - 14,000 USD

    monthly

  • 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

    1,085 USD - 1,225 USD

    weekly

    2,500 USD - 2,500 USD

    monthly

  • Footsteps to Hawaii's Best Beach

    State of Hawaii Transient Accommodation Registration: W40799764-01. Your fully furnished cottage, equipped with A/C, W/D, and On-Site parking is just a short walk to beautiful Kailua Beach, a two mile stretch of sparkling white sand and turquoise...

    0 Bedrooms, 1 Bathrooms, Sleeps 4

    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

    9,990 USD - 12,000 USD

    monthly

  • The Kailua Lifestyle at it's Best

    Luxurious, private, secure, and energy efficient unit with over 1,000 square feet of living space, second story, attached apartment, built in 2014, has all the creature comforts of home while you are on vacation in Paradise. Kailua Dreams incor...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach

    Pacheco's Hale is a beautiful two-bedroom, second-floor unit - nice and breezy with a private entrance. This clean, quiet unit is completely furnished. The two lanais have views of palm trees, lush green tree tops, Mount Olomana and the Koolau Mo...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • Kailua, Oahu Beachfront

    Be prepared for absolute seclusion, with an electronic gate that opens and closes upon your arrival. Once inside the property, all you will hear are the birds, the sound of the surf pounding, and the rustle of the palm fronds from the many coconut...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua

  • Kailua Executive Estate Resort Living

    It is your home away from home. 4 bedrooms/ 4 baths/ Full Kitchen/ Living Room with 2 sitting rooms. Private Tennis Court and Swimming Pool. Beautiful landscaping on 2 and half acres. Views of Ocean and Mountains from most rooms. A bonus, a large...

    4 Bedrooms, 4 Bathrooms, Sleeps 10

    HI>Kailua

    8,365 USD - 9,765 USD

    weekly

    24,995 USD - 24,995 USD

    monthly

  • The Beach, Tropical Setting, Hawaiian Style Home, Pool, Yard, Monthly Stays

    Long Term Stays Welcome Contact Us for Details and Rates Hawaii Tax ID # W58473390-01 Hale Pulelehua “The Butterfly House' has a spacious open feeling inside and out. The large windows front and back allow the trade winds to carry the sweet scen...

    4 Bedrooms, 2 Bathrooms, Sleeps 10

    HI>Kailua

    4,200 USD - 5,250 USD

    weekly

    8,550 USD - 9,750 USD

    monthly

  • Usually Solidly Booked, Unique Opportunity to Rent in July, September or October

    Our BEACHFRONT home is designed to provide you with a perfect vacation retreat. You will be as close to the beach as a house can be built. The beach of Kailua is renown for its fine white sand, blue green waters and safety. This is not a crow...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua

    8,750 USD - 9,450 USD

    weekly

    25,000 USD - 40,500 USD

    monthly

  • Beautiful Island Getaway ~ Kuu Home Uluwehi

    KU’U HOME ULUWEHI, 'My Verdant Home', Ku’u (To release, let go and welcome relaxation). Uluwehi (Verdant, green, lush and beautiful. A place where beautiful plants and guests thrive). This spacious home is a place of peace within a garden. Lo...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

  • Truly A Beach House - Beachfront Estate

    Charming beach house with the old kamaaina feel! This 3 bedroom, 3 bath house is one of the last around. This amazing property has it all. It is one of the few lots which offers the old hawaiian feel and sits on probably the most uncrowded white s...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Kailua

    4,865 USD - 6,965 USD

    weekly

    12,000 USD - 12,000 USD

    monthly

  • Ginger Studio OPEN:9/29-10/3,10/15-26,10/27-30,11/8-17, 11/30-12/10,12/15-24,1/2

    The Ginger Studio with a 'Secret Garden. It has a private entrance and is on the ground floor with windows opening to a tropical bank of Areca palms. The Ginger Studio has a private entrance and a private bath that has a huge walk-in shower . A...

    1 Bedrooms, 1 Bathrooms, Sleeps 3

    HI>Kailua

  • Kailua Beach Guest House

    Lovely Guest House with lots of upgrades. Large Bathroom with paintings of Lanikai Beach California King Bed with 60inch Flat-Screen TV Fast High Speed Internet up to 60MB/s with WiFi Access Full Kitchen with Top of the line appliances. Washe...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua

  • Ocean View Guest Cottage

    A two-bedroom, one-bath, ocean view cottage located a few steps from Kailua Beach... Voted Number One in America for three years! Magnificent ocean view from your second-story, home-away-from-home. This charming, fully furnished apartment has...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Kailua

  • 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 10

    HI>Kailua

    5,250 USD - 5,950 USD

    weekly

    15,000 USD - 20,000 USD

    monthly

  • JUST NOW AVAILABLE FOR CHRISTMAS/NEW YEAR! Fabulous Luxury Kailua Beachfront

    Six bedrooms of beach-front paradise in Kailua. Swimming pool, Jacuzzi, game and TV room make this property an ideal vacation recreation destination. Three-quarter acre gated estate on Kailua Beach with pool, spa, beach vollyball and unobstructe...

    6 Bedrooms, 4 Bathrooms, Sleeps 12

    HI>Kailua

    17,500 USD - 17,500 USD

    weekly

    50,000 USD - 50,000 USD

    monthly

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