Kailua Vacation Rentals

Kailua is one of the most popular 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. Browse through this fine selection of Kailua vacation rentals below and find your perfect home away from home.

  • Unique Oceanfront Home in Gated Community

    Kona Onenalo is a ONE-OF-A-KIND property on the beautiful Kona Coast. There are 12 identical and individual homes in this quiet, gated community. The complex sits on a point of land adjoining La Aloa Bay, and is just a 3 minute walk to Magic Sands Beach. You'll love the sunsets! The House is two stories, with two bedrooms upstairs, complete with king-size beds and private baths. The master bedroom has spectacular ocean views with only the sound of the waves to lull you to sleep. The living room features huge sliding doors which open to the covered lanai to create true island living. While sitting on the lanai, be sure to keep an eye open for spinner dolphins, and, in the winter, humpback whales! The pool, spa and grounds are expertly maintained. Within minutes of your arrival, you will feel like you have your own piece of paradise. Hawaii license number W91686388-01 Keywords: Oceanfront, Gated Community, Gorgeous Sunsets, Pool, Spa

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Kailua
    5 night min stay39  reviews
    $385 per night
  • Newly- Renovated Designer Studio - Minutes From Kailua Beach

    Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just minutes away from the beach by foot or bike. Located in the world famous beach community of Lanikai, in the town of Kailua, on the island of Oahu, Hawaii, there are two highly rated beaches within minutes. Kailua Beach Park is a 4 minute bike ride (bikes provided during stay!), 14 minute walk, and 2 minute drive by car. Lanikai beach is 5 minute bike ride, 17 minute walk, 3 minute drive. Lanikai's is noted as the best sunrise in Hawaii and most scenic beach in America. The Mokulua Islands off shore from Lanikai have been included in numerous advertisements and movies. You can kayak out to them and explore the island on the left. Between these natural attractions and the comfort of the Studio, we promise you will enjoy your stay. The bedroom has a comfortable queen-size bed, and the living room is fully furnished including a stylish sitting area all recently remodeled and decorated in 2014. For your entertainment we provide a flat screen TV with WirelessTV. High-speed internet access is included. The Kitchen has all the amenities including a full size refrigerator, microwave/convection oven, coffee maker. Many stay for a month or longer. TAT W00802860-001

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua
    5 night min stay9  reviews
    $175 per night
  • Ocean View Condo

    Enjoy your Hawaiian vacation in one of Kona's most popular complexes. Casa is very well maintained with beautiful gardens and an awesome ocean-front salt water pool. We are steps from the ocean and have a wonderful sunset view from the lanai. Unit 201 is easily accessible with parking close by. The unit is open, clean, and comfortable. There's tile floors through out and new appliances and furnishings. A full size washer and dryer are in the unit, saving you time and money doing laundry on your vacation. The private, extra large lanai offers a dining area as well as sun bathing. We sleep 3 adults or up to 4, including children. Keywords: Condominium

    • 2 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Kailua
    3 night min stay4  reviews
    $99 per night
  • Lanikai Villa by the Sea

    This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches within, expanded the gourmet kitchen with all new appliances, a coffee bar and wine fridge. Saltilo tile and wood flooring bring a Mediterranean feel. Every bedroom has a view of the picturesque ocean and world renowned Mokulua islands. The open living space, and an expansive front entry and back yard are perfect for families and large groups.The dining room is located on the lanai overlooking the ocean for indoor/outdoor entertaining at its best. The home is decorated in vibrant color themes complimenting the natural surroundings. Local art throughout the home add a special island feel. The back yard has an outdoor bar, bbq, hot tub, shower, and lounge area. In addition an adorable 1 bedroom, 2 bathroom cottage with pull out sofa is included that sleeps up to 4. Just a few steps away is access to a beautiful, secluded white sand beach. Enjoy your days kayaking and snorkeling or just relax on the beach and enjoy the view of the islands. Don't be surprised if you see giant sea turtles swim by or whales jumping out in the distance during the winter months. Fall asleep to the sound of gentle ocean wave and wake up each morning to the most breathtaking sunrises right outside your bedroom. This unique property is truly paradise. We are a family owned and operated property, please feel free to call me at 808-286-1264 Aloha, Gina

    • 8 bedroom
    • 7 bathroom
    • Sleeps 15
    HI> Kailua
    5 night min stay13  reviews
    $3,000 per night
  • Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!

    This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor plan offers a serene Hawaiian ambiance. stone floors, granite counters, top of the line finishes and appliances throughout, this private estate leaves nothing to the imagination. Wake up to a feeling of old Hawaii, stroll down to Kailua Beach or Castle Point and watch the sunrise, take a short drive to Buzz's for lunch or dinner, Island Snow for a shave ice, Kailua town for shopping or watch the windsurfers and kayaks from Lanikai Point. Everything is at your doorstep!

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    HI> Kailua
    1 night min stay2  reviews
    $599 per night
  • Reduced Rate! Only $395/night on new reservations for stays thru June 30th

    Hale Malahini is located just steps to beautiful Kailua Beach Park, Buzz's Steakhouse and Kalapawai Market and Deli. This 3 bedroom home is perfect for families and couples. Recently remodeled, the home sleeps up to 8 with 2 double beds, one queen and a pull out sofa bed. The kitchen is fully appointed with all new appliances including a double oven, microwave and fridge with filtered water and ice.There is also an in house washer and dryer. AC units are in the bedrooms as well as living room to keep the home cool and comfortable. The living room and master bedroom both have cable TV. Everything in the home is brand new and decorated tastefully with bright cheerful furnishings and local art. Outside is a warm shower, gas bbq and seating areas. Relax on the deck and take in the gorgeous Koolau mountain and water views. A short walk away is Kailua Beach park, known for its soft white sand, clear blue waters and breathtaking sunrises. Kayaking, stand up padddle boarding, windsurfing and kiteboarding are all popular water activities and rentals can be easily arranged for your stay. Kailua town offers an array of family friendly restaurants, specialty boutiques, and grocery stores including Whole Foods, Safeway and Foodland. The farmers markets are also a must for locally grown produce, delicious plate lunches and products. Once you get here, it's hard to leave Kailua but if you wish to adventure out to the north shore, Waikiki or Pearl Harbour for a day trip it's easy to travel around the island from the east side.

    • 4 bedroom
    • 1 bathroom
    • Sleeps 8
    HI> Kailua
    4 night min stay3  reviews
    $460 per night
  • Newly renovated three bedroom apartment near stunning Kailua and Lanikai beaches

    Get away from it all in this spacious 2nd floor 1500 sq. ft. apartment with additional private lanai off the master bedroom. The property is only 100 yards to the lush Kailua Beach Park, with world class Lanikai Beach right around the corner. Perfectly located for the best possible Hawaiian getaway. Start your day out on the lanai with a cup of coffee and watch the birds flutter about in the trees. Ahh, the simple pleasures! After a hot day of sightseeing, come back and cool off in air conditioned comfort! And rest assured - this is a green building with solar photovoltaic panels. The Shore Shack is the second floor of a three story house. While The Shore Shack is perfect for larger groups, we also have two other listings at this property. The Suite Spot (#1012761) is great for groups to be together in an open plan studio layout, and The Secluded Hideaway (#1012725) is perfect for smaller groups in a more cozy and intimate setting! Please note that you may hear occasional movement from the units above during your stay at The Shore Shack. Keywords: Studio, vacation rental, close to beach, condo, apartment

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Kailua
    2 night min stay1  reviews
    $325 per night
  • Star of Hawaii Beachside home with pool & jacuzzi that sleeps up to 12

    You have found The Star of Hawaii in beautiful Kailua, Oahu, Hawaii. This walled and private residence is on a charming beachside lane in a great Kailua Beach location. The setting offers relaxation from a hurried world. The gardens, pool and spa are encircled with lava rock walls. Relax around the pool or walk barefoot to the beach. Be our guests and let worries melt away as you take sunrise swims and sunset walks along this soft white sand beach. Surrounded by tall palms and flowering plants, Hawaii embraces you. A few steps down the lane takes you to a peaceful and secluded stretch of world-famous Kailua Beach. You will have the amenities for a perfect vacation when you walk through the garden gate. This 4B/3B home offers an opportunity for separate entertainment and sleeping areas. The main level has 3B/2B with 2 Queens and a set of twins in the bedrooms. The living room has a sofa sleeper for 2. Upstairs is a large 580sf guest suite with a King Bed, another sofa sleeper for 2, bath, kitchenette and sitting area for TV, reading or games. This design offers couples and families privacy and flexibility. The house has a fully equipped gourmet kitchen and family sized dining room. Living spaces open to pool and gardens. The house has that "Hawaiiana" feeling of bringing the outside in. The grounds of this elegant home will leave you dreaming of your next visit. We have provided a lei making basket complete with easy instructions and supplies; you are encouraged to pick flowers and string your own Hawaiian leis. Welcome to the islands and our home.

    • 4 bedroom
    • 3 bathroom
    • Sleeps 12
    HI> Kailua
    7 night min stay38  reviews
    $875 per night
  • LANIKAI, OCEAN VIEW EXEC SUITE: HAWAII TAX ACCOUNT 441-H01185583F-01

    Lanikai hillside location on a quiet cul de sac. Large, modern and private. Upscale 2 bedroom suite, part of an executive estate. Each room has private outside access separate from the main house. Ensuite furo style marble tile bathroom plus large separate tiled shower stall. Off-street guest parking. Includes large supply of beach and bath towels, cable TV, free Wi-Fi Internet access, air-con, ceiling fans, wood floors, skylights, sliding glass doors, hair dryer. Kitchenette with fridge, microwave oven, toaster oven, hotplate, sink. Iron and Ironing Board. Outdoor charcoal BBQ. Walk to Lanikai Beach. Enjoy magnificent ocean view of Mokulua Islands and sunrise over the beach. Glass table and chairs on private deck for ocean view al fresco dining. 2 miles from Kailua Town, 35 minutes to Honolulu International Airport (Via Interstate H-3) and 12 miles to Waikiki (via the Pali Highway).

    • 2 bedroom
    • 1 bathroom
    • Sleeps 5
    HI> Kailua
    4 night min stay19  reviews
    $169 per night
  • LANIKAI PRIVATE 4 Bedroom 4 Bath OCEANFRONT HOME AIR CON & POOL

    This delightful oceanfront home sets the backdrop for the perfect family retreat. The large, tropical living areas open onto the oceanfront lanai. Hear the waves lapping against the seawall; launch a kayak from your private lawn; watch the turtles play just in front of the home . . . This home brings turquoise waters right into your living room. Each of the 4 bedrooms are air conditioned. The kitchen (with awesome ocean views!) and also view of the yard and pool. Enjoy coffee watching the sun rise from your oceanfront deck or lanai by the pool then settle in on the back lawn to watch the sun set behind the mountains just in front of you. This is paradise!

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Kailua
    7 night min stay5  reviews
    $950 per night
  • Ocean View Lanikai - Renovated, Private, Exclusive - sleeps up to 10!

    Enjoy peace and tranquility from this beautifully remodeled home while soaking in the endless, unobstructed views of the Pacific Ocean and Mokulua Islands. This 4 bedroom, 4 bath home with separate cottage is located on a gently sloping hillside just a few minutes walk to the white sand beaches of Lanikai. The home was beautifully designed to take full advantage of the view and gentle trade-winds by mid-century architect Vladimir Ossipoff. Ossipoff's ability to "bring the outside in" has been a signature at the many luxury homes and prominent buildings he has designed throughout the Hawaiian Islands. The home features a tastefully renovated kitchen that is well stocked for entertaining, hardwood flooring, built-in niches and cabinetry throughout. Each bedroom has an ocean view while a comfortable, open floor plan overlooks the ocean on one side and tranquil water feature on the other. Expansive covered lanai allows guests to embrace the open-air, Island lifestyle with gas grille, outdoor dining and inviting seating areas. The bedrooms enjoy a private, en-suite bath - modernized for maximum comfort. Additional bedding is available for extended family/friends, making this home comfortable for up to 10 guests: Master Bedroom - King Bed w/en suite bath Master Office/Sitting Room - Queen Sleeper Sofa (shared bath with Master) Guest Bedroom 1 downstairs - Queen Bed w/en suite bath Guest Bedroom 2 downstairs - King Bed w/en suite bath Guest Room 3 (Separate Guest Cottage) - Queen Bed (full bath inside main house) The home is just 10 minutes drive to the center of quaint Kailua Town where guests can enjoy many restaurants, shops, grocery, farmers' markets and convenience stores. Activity centers provide kayaks, paddle boarding, snorkel equipment, bikes and more - also delivered to your door, if preferred. This property is a professionally-managed, 30 day rental property, and is compliant with Hawaii State Legislation (HB2078) for rental accommodations: #TA-178-839-9616-01.

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    HI> Kailua
    7 night min stay2  reviews
    $900 per night
  • Why Spend All Your Money On Accommodations?

    Our wonderfully clean and spacious house is our primary home so it is well cared for. This summer rental is perfect for families traveling with younger children or extended family. With two living areas, front and back porches (lanais), a new BBQ, it is easy to find a place to relax. Located in a residential area you get the peacefulness of a suburb with easy access to public transportation and major streets. The house comes with many beach toys: two man kayak, life jackets, foam surfboard, beach chairs, beach towels, snorkeling gear, boogie boards, etc. Famous Kailua town is just 1/2 mile down the hill where you can enjoy a variety shops, supermarkets, restaurants, and perhaps a shave ice! And Kailua Beach is just 1 and 1/3 mile down the hill! Please contact me for more information and photographs!

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Kailua
    5 night min stay1  reviews
    $320 per night
  • Fantastic Views from Direct Oceanfront Penthouse Condo in Kona with A/C

    Visit our beautifully furnished direct oceanfront/beachfront penthouse condo situated on Alii Drive in the quiet desirable town of Kailua-Kona. Our lanai is only 25 feet from the ocean and you will find there is no better place to relax on our lanai in the comfortable teak lounge chairs or having a nice relaxing dinner at the teak dining table watching the wonderful sunsets. Looking down below in the ocean you will have fun watching the surfers, spinner dolphins, turtles and even whales breaching! Note: There is not a road between this condo and the surf. Only a strip of lawn, palm trees, new sea wall and the ocean!!! This spacious and comfortable two bedroom and two bath direct oceanfront penthouse condo is on the fourth floor (top floor). It has been just been totally renovated with a brand new kitchen (inclduing new cabinets, granite counter tops and applicances), both bathrooms completly redone (with new showers, cabinets, and countertops), new tile floors (kitchen, hallways, living room, dining room, bathrooms and lanai), new bamboo floors in the bedrooms and comes with all new furnishings, appliances and accessories. It sleeps up to six adults, is very nicely decorated and includes a large comfortable California king size bed, two twin beds, queen size sofa sleeper, two full bathrooms - both with walk in showers. We also have a new crib that is available for use in the condo. It is fully stocked with all the comforts of home plus many items you have never even thought about. The condo comes with a full size washer, dryer, air conditioning, dishwasher, iron, ironing board, hair dryer and a full suite of kitchen appliances such as microwave, coffee grinder, water purifier, blender, coffee pot, rice cooker, etc. Plenty of dishes, plates, glasses, pots, pans, silverware, utensils, and cooking spices. Plus, lots of cotton sheets, towels, linens, beach towels, beach chairs, etc. The condo also comes with 32 inch big screen cable TV, DVD player, stereo, CD player, plenty of videos, DVD’s, lots of mystery novels, Hawaiian books, games and puzzles for the kids. Ceiling fans in all the rooms and a large 18,000 BTU air conditioner in the living room. Non-smoking unit. Free Broadband and secure wireless internet in the condo. Free telephone calling to the mainland, including Canada. Condo has everything you need with all the comforts of home to make for a very relaxing and enjoyable vacation or long-term stay. The condo is located at the beautiful Oceanfront Kona Bali Kai Property. The condo complex has a nice heated swimming pool and Jacuzzi, oceanfront gas BBQ's and picnic areas, very nice tropical landscaping and a sandy beach area for sunbathing and wading in the tide pools. Lounge chairs are available to all condo guests at the beach front area. There are also some shady spots if you wish to take a break from the sun. There is a an elevator to take you to the condo, no need to walk up stairs at this condo! A surf shop/snorkel rental shop is on the grounds of this condo complex as well as a small sandwich shop/sushi bar and a Doctors office. A convenience store is located across the street. The sandy swim beach is located one mile south, the snorkel beach is one and half miles south and the Kona Country Club golf course (36 holes for public use)is 3 miles south. This is a truly a condo you will want to return to year after year (as you will see many repeat guests in the condo guest books). Warning: The Big Island has so much to offer and after one trip and you will be hooked!! :) Please call the owner direct to make a reservation at 310 940 9101. Be sure to check out the YouTube video in the Link and Video section. Mahalo and hope to see you soon at our condo. Keywords: Condominium, Direct Ocean Front penthouse condo, total privacy and seclusion, outstanding views and tranquility, fully furnished and outstanding value. Book now for summer, fall and winter of 2016/2017.

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Kailua
    3 night min stay18  reviews
    $159 per night
  • Kailua Beach Aloha Cottage 10 minute walk to Famous Kailua Beach!

    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. The Space This is an attached "Ohana" or cottage that was just renovated. You can cook using the microwave or enjoy a cup of coffee with the coffee maker. There is a full double door refrigerator and freezer. We provide a lovely space for your trip along with beach chairs, cooler and snorkel gear to help you explore everything that Kailua has to offer. Guest Access Guests have access to the attached cottage along with beach chairs and snorkel gear. Interaction with Guests We live in the home nextdoor with our three dogs. You can enjoy your privacy and please feel free to say Aloha when you see us. The Neighborhood We live in Coconut Grove, a great beach community. 10 minute walk to Kailua Beach and there is a Whole Foods and Target just down the road ( 1 mile) Getting Around We would recommend a car however Oahu is known for its amazing bus system with stops that can take you all over the island just a few hundred feet away. Other Things to Note We offer a space for street parking in front on the house. Also we have 3 great dogs, Kona, Ule and Lip!

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Kailua
    2 night min stay1  reviews
    $159 per night
  • Great Oceanfront Home for Large Groups of Family & Friends

    The charming and expansive "Ocean House" is literally located on the shore of Lanikai Beach. Voted the most beautiful beach in the United States, waves gently lapping can be heard from every room in this truly unique oceanfront home. A perfect gathering place for large families, reunions, and group retreats of all sorts, "Ocean House" offers a warm atmosphere and the ambiance reminiscent of old time family weekend getaways. You'll enjoy the casual comfort of the Great Room with its unbelievable view of the Mokulua Islands and daily sightings of sea turtles swimming just offshore.

    • 5 bedroom
    • 5 bathroom
    • Sleeps 22
    HI> Kailua
    7 night min stay13  reviews
    $1,295 per night
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