Vacation Home Rentals By Owner In Kailua, HI

This beautifully restored one-of-a-kind oceanfront home has all the charm of yesteryear with the added conveniences and sustainability of today. Meticulously appointed and private, the views and location are spectacular. The Guardian newspaper has listed Kona Moana Hale as one of the Top Beach Houses in the World. brbrCompletely renovated, this updated home has hardwood floors, granite countertops, koa cabinets, stainless steel appliances, air conditioning, iHome docking stations, Bose outdoor speakers with Bluetooth receiver (to pair your own devices and play music), iTouch pre-loaded with various Hawaiian music, wireless internet, full size washer/dryer, brand new California king bedroom set, luxurious bedding, hdtv plasma in great room and bedroom, gas bbq, teak lounges, etc etc. All lights are on dimmers so you can create your own environment and mood. There's even an indoor switch to light up the water at night to create a spectacular view!brbrIdeally located overlooking Kahaluu Beach, you are within feet of the best snorkeling and surfing on the island. (If you do surf or stand up paddleboard, you can paddle straight out and be in the break in less than 5 minutes.) Dolphin sightings are quite common. During winter months, whales can be seen daily as they swim by.brbrUniquely situated on a 9000 sq ft oceanfront lot, this home is a one-of-a-kind. You will experience complete privacy with expansive views up and down the coast. (We also own the property next door where you are free to pick papayas, bananas, etc. or just sit and watch the sunset.) While there is so much to do on the Big Island, you will have a difficult time pulling yourself away from your home and the incredible views and sounds of the ocean. You will find this special place to be relaxing, rejuvenating and inspiring.brbrUpon arrival you will be provided with tropical flower arrangements, kona coffee and an assortment of fresh fruit. Playing softly in the background is Hawaiian music accompanied by the gentle sound of the ocean. The setting is nothing short of amazing.

Stunning oceanfront cottage

Kailua, Hawaii, United States

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Bath

Sleeps

$228.91

Contact host for updated calendar. Come and experience life on the lake! This 750 sq ft, second floor one bedroom, one bath with kitchenette, private lanai and private entrance is just what you are looking for. Located in a nice, quiet neighborhood right on Enchanted Lake in Kailua. Wonderful tropical breezes, beautiful views of the lake and mountains. Drop a kayak in the water to cruise around the lake or paddle to Kailua Beach for an adventure! Two miles from Kailua and Lanikai Beach and 1.5 miles to Kailua Town. Parking WiFi, Flat screen TV, Induction hot plate, convection toaster oven, microwave, coffee maker, full size fridge, beach chairs and towels. Please contact owner for availability. TA 064-829-8496-01

Come relax on the lake! Beautiful lake and mountain views. Kayaks included.

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$981.15

Welcome to Holoholo Hale in the beautiful town of Kailua on the island of Oahu. Kailua is the home of two of the best beaches in the world, Kailua Beach Park and Lanikai Beach. The home is a short drive to all the island has to offer including Diamond Head, the pill box hike, the Northshore, and Waikiki. (Contact us for flexible stays)brbrOur Holoholo property has and includes, two houses on beautiful, lush property minutes to the beach and Kailua Town. The main house has 4 bedrooms, 2 bathrooms with a brand-new Chef’s Kitchen, equipped with granite countertops, a 6 burner gas range and oversize refrigerator. The main house is an open concept home, with the kitchen leading into the living and dining room, along with the outdoor spaces. The Ohana house has 3 bedrooms, and 2 additional baths, complete with a 2nd kitchen upstairs. Combined these houses make a perfect setting for larger gatherings of family and friends. The expansive outdoor lanai has several eating areas including a tiki bar, a large table and chairs and comfortable conversational seating. The private pool, set between the houses makes for the perfect center point for your Hawaiian vacation.brbrBoth houses have all the conveniences such as wireless internet, Smart TV's, and A/C units in every room. We have not spared on the details, all of the rooms are comfortably furnished with Hawaiian treasures, top of the line beds, and other luxury furnishings. br brThis property is a legally established dwelling and must be made available for 30 consecutive days. There is no penalty for early departures so you can book for a shorter stay as mutually agreed upon (please contact us for questions). This is in accordance with city and County of Honolulu ordinance section 19-18. brbr br**ALL QUIET HOURS ARE FROM 9PM - 8AM. PLEASE BE RESPECTFUL OF THE NEIGHBORS THEY DO HAVE TO ATTEND WORK/SCHOOL

Large, beautiful, updated home w/pool, AC,mins from beach in Kailua!

Kailua, Hawaii, United States

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Bath

Sleeps

$139.27

Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and convenience, making it the perfect spot for a truly relaxing and authentic Hawaiian vacation.brbrEnjoy a day at Lanikai Beach or Kailua Beach Park, or even get some exercise in with the Lanikai Pillbox hike a few hundred yards up the street.brbrUpon arrival, you’ll be greeted by a private entrance and a securely gated parking area for one car, ensuring your privacy and security throughout your stay. The studio itself has been thoughtfully updated to provide a comfortable and inviting atmosphere. You’ll find all the comforts of home, set against a backdrop of tropical beauty.brbrThis vacation rental is not just about stunning accommodations; it’s also about location. Situated just five minutes from the bustling Kailua Town, you have easy access to a vibrant mix of shopping, dining, and entertainment options. Whether you’re in the mood for a casual dinner, some window shopping, or an evening stroll, everything is conveniently close.brbrThe property itself is expansive, with a private, fenced-in yard with stone patio and grass area for enjoying the sun, a book or a meal. This open space is perfect for enjoying the island’s sunny days and serene nights. The studio was recently remodeled with kitchenette, LG Smart TV, glass shower, and has its own new LG washer and dryer, adding to the convenience, and ensuring that longer stays are as comfortable as possible. If you have an electric car, there is an onsite paid charger available.brbrSocialize and enjoy meals outdoors on the stone patio which is ideal for cooking up a delicious meal while enjoying the company of friends or family, all within the sound of the ocean waves.brbrYour stay at this Lanikai Beach studio ensures not just proximity to one of the top beaches on the island but also a peaceful retreat after a day of adventure or relaxation at the beach. It's more than a place to stay—it's a place to live, breathe, and experience the magic of Hawaii in complete comfort and style. brbr**30 days minimum rental**

Beach Studio with private yard in Lanikai - 30 day Minimum Stay

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$130.76

Tastefully remastered, 1937 cottage + rooftop lanai and BBQ area. The Kailua Beach Hideaway is tucked up on the hillside above the beach park, on a private lane. Ocean, park and Mountain view’s are captured from the rooftop sun deck. brbrThe Set Up:brCozy and efficient floor plan sleeps 2 people MAX with 1 bedroom and a full bathroom + double sinks. Walk-in closet offers ample storage. SOFA-SLEEPER offers guests a separate sleeping option in the living area. brKitchenette, has a full sized fridge and offers a K-Cup coffee maker and electric tea kettle, plus an induction cooktop and convection microwave oven. Smart TV, WIFI, and high speed Internet ready.brbrThis property shares a separate 4 bedroom apartment, w/ private entry and separate meter.brStay in Oahu's most coveted beach town, right next to world-class Lanikai and Kailua Beach. Dine at, local, iconic Buzz's steak house, right down the street. Drive, walk, or bike into Kailua Town to shop at the many boutiques, art galleries and dine at various hip eateries and local brew pubs. Whole Foods, Target, Core Power Yoga, and Barre studios are all near by. Your amazing Hawaii hideaway awaits…brbrNo check-ins allowed on major Holidays: Christmas, New Years Day, Easter, ThanksgivingbrbrHawaii Life Rentals is a locally owned, licensed real estate company with rentals on Kauai, Maui, Oahu, and Hawaii. We offer on-island personal assistance and Concierge services.brbrRates do not include taxes, cleaning and applicable fees.brbrHawaii Life/VRBO bookings: Guests must sign a rental contract within 48 hours of booking to confirm the reservation.brbrTA-126-494-4640-01brbrIn compliance with the Ordinances of the City & County of Honolulu, the Property will be made available to you for your use and occupancy for a minimum period of thirty (30) days.

Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$461.0

ABSOLUTELY FABULOUS very large two bedroom two bath house or more.... if you rent the loft which has another HUGE bedroom bath and kitchenette. .brSparkling pool in a private courtyard in the back yard VERY PRIVATE. brAsian inspired furniture from a designers eye.br brONCE YOU VISIT, YOU WILL NEVER WANT TO LEAVE!brBeautifully appointed two bedroom Hawaiian private residence in quaint Enchanted Lakes. Extremely comfortable house. brWalking distance to schools, theaters. shopping, dining, recreation, entertainment, and fabulous Kailua town. Many restaurants gyms...and of course..everybody loves whole foods.,br From the koi pond at the front entrance to the swimming pool in the back yard area, Home Sweet Home offers the finest in comfort, luxury and convenience. Minutes to Kailua town and Kailua beach , with 2 1/2 miles of white sandy beach. Great early morning and afternoon walks. Its also a three mile walk right around the lake .brPlease note In order to remain compliant with city and county zoning regulations this property is only rented for periods of 30 days or more to one party. This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. Feel free to contact us with any questions.brbrCome and Bar B Q or go out and eat at a new restaurant every night. Also its 1/2 hour over the Pali to downtown Honolulu . Chinatown and World renowned our famous Waikiki Beach ... Home of dukes statue...surfing.. and great restaurants everywhere. Don't let people fool you. Waikiki has been redone, grown up and is a great place place to visit. I promise. brbrThe two bedrooms, one with a king bed and the other with a queen, both with en-suite bathrooms, comfortably sleep four. Both bedrooms have french doors to walk right outside to the courtyard . There are three separate spacious living areas to relax and watch a movie or read a good book....or take a nap. . brbrAntique designer furniture, wonderful stocked kitchen, which includes, dishwasher, refrigerator disposal, microwave, oven, stove, pots, pans, dishes, washer and dryer. There are also, linens, bath towels, and beach towels, for your use. brIt has everything you need. Just bring your clothes...and you dont need many. brbrIdeal location just minutes from Kailua beach, shopping, dining, recreation and entertainment. As i said earlier really..... once you visit you'll never want to leave.brbrCan be combined with an entire, up and downstairs, loft type, 1 bedroom, 1 1/2 bath apartment to sleep another couple. Very PRIVATE VRBO 140949 brWrite me about it. brbrInquiry for Holiday Rates!brbrbr

MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$253.89

Welcome to your dream retreat in Kailua, a sun-drenched haven where tranquility meets convenience. This charming unit is part of a thoughtfully designed duplex, offering a perfect balance of privacy and community. Whether you’re here to relax, explore, or work, this property provides the ideal base to experience the beauty and charm of Oahu’s windward side.brbrKailua is known for its laid-back vibe, stunning beaches, and outdoor adventures, and this home places you in the heart of it all.brbrStep into a bright and airy space filled with natural light and island-inspired decor that sets the tone for a peaceful and rejuvenating stay. With an open floor plan and a seamless flow between the living, dining, and kitchen areas, this home is designed for comfort and connection. Whether you’re traveling solo, as a couple, with family, or even on a work trip, this space adapts to your needs.brbrFully Equipped Kitchen: The kitchen is designed for functionality and convenience, with modern appliances, ample counter space, and all the essentials. Whether you’re preparing a quick breakfast or cooking a full dinner, everything you need is here.brbrCozy Dining Area: Enjoy meals together at the dining table, which comfortably seats your group.brbrWell-Appointed Bedrooms: The bedrooms feature plush beds and high-quality linens ensuring restful nights throughout your stay. Wake up refreshed and ready to enjoy the island’s natural beauty.brbrModern Bathroom: A clean, updated bathroom with a shower/tub combo, fresh towels, and toiletries to get you started.brbrBathroom 1: Full bath with tub and showerbrBathroom 2: Full bath with shower onlybrbrAmenities for a Comfortable Stay:br- Air conditioning to keep you coolbr- High-speed WiFi for work or entertainmentbr- In-unit washer and dryer for added conveniencebr- Starter toiletries and linens providedbrbrThis charming Kailua duplex offers everything you need for a relaxing and enjoyable stay. Whether you’re lounging on the beach, exploring the island, or simply enjoying the cozy comforts of this home, you’ll create unforgettable memories.brbrBook your stay at this Kailua Island Retreat today and experience the perfect balance of comfort, convenience, and aloha spirit!

Tropical Bliss in Kailua

Kailua, Hawaii, United States

Bath

Sleeps

$253.33

Welcome to your island getaway! Nestled in the heart of Kailua, this bright and inviting home is perfectly located just minutes from Kailua Beach, where you can soak up the sun, enjoy crystal-clear waters, or try your hand at paddleboarding.brbrbrbrThis property combines modern comforts with island charm, offering a cozy and stylish space for couples, families, or small groups looking to experience the best of Hawaii.brbrbrbrNote that this is a duplex house.brbrbrbrBright, Cozy InteriorsbrbrStep into an open and airy living space filled with natural light. Thoughtfully designed with island-inspired decor, it creates a relaxing vibe to complement your Hawaiian getaway. The living room is equipped with comfortable seating and a large flat-screen TV for laid-back movie nights.brbrbrbrFully Equipped KitchenbrbrCook with ease in the modern kitchen, which boasts updated appliances, ample counter space, and all the cookware you need. Whether you`re whipping up a quick breakfast before heading to the beach or preparing a dinner with local ingredients, you`ll feel right at home.brbrbrbrComfortable BedroomsbrbrUnwind in cozy, well-appointed 3 bedrooms featuring plush beds, high-quality linens, and storage for your belongings. The neutral tones and inviting ambiance make for the perfect retreat after a day in the sun.brbrbrbrThoughtful Amenities:brbrbrbr- High-speed WiFi to stay connectedbrbr- Air conditioning for ultimate comfortbrbr- In-unit washer and dryer for added conveniencebrbrbrbrPrime Location:brbrLocated on Kalama Street, this home is just a short stroll or quick drive to the iconic Kailua Beach, where you can swim, kayak, or relax on the soft sand. You`ll also be close to Kailua’s charming boutiques, local restaurants, and vibrant farmers’ markets. For outdoor enthusiasts, nearby hiking trails like Lanikai Pillbox offer breathtaking views of the coastline.brbrbrbrWhether you`re a beach lover, foodie, or adventure seeker, this Kailua retreat offers the ideal base to explore the island. With its unbeatable location, modern comforts, and serene ambiance, it’s the perfect place to unwind and embrace the aloha spirit.brbrbrbrBook your stay now and experience the magic of Kailua from the comfort of this stunning property!

Sunlit Island Escape in Kailua

Kailua, Hawaii, United States

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Bath

Sleeps

$1308.74

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.brbrWith front row seats to the ocean and the famous Mokulua Islands of Kailua, Lanikai Oceanside offers the best seats in the house. Newly renovated, this tropical chic and modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea, inhale the fragrant salty air and watch the sun paint magic in the sky as the afternoons turn to evenings. Lanikai Oceanside is sure to make your vacation a memorable and unforgettable one.brbrBuilt in the 1940s, Lanikai Oceanside was once the coveted summer home to Princess Abigail Kawananakoa, a beloved Hawaiian princess who was a politician and ruler in the historic Hawaiian monarchy. Kept within the royal family for years, the home was later sold to a respected prominent family of Hawaii in 1956. The residence embodies a special historic energy, it is no wonder why so many influential individuals have chosen it over and over again.brbrWith beach chic, mid-century modern interiors, this home is a trendy and stylish reimagined classic. Featuring 4 bedrooms, 3 bathrooms, gather with friends and family in one of the two spacious living/dining rooms, depending on if you prefer a more formal or casual setting. Every room is filled with vibrant colors and beachy whites, reminiscent of the island's natural palette. Note: There is a separate 1 bedroom, 1 bathroom Guest House with a kitchen, living and dining area not included in this rental listing, but can be rented together with the main house for an additional fee. Please inquire for more details on this. brbrSitting on over 25,000 sq. ft. of land, Lanikai Oceanside features an expansive yard space with warm tropical landscaping. The oceanfront yard offers a picturesque view of the turquoise blue waters dancing to the melody of the tides. Watch the kayakers go by as they paddle out to the Mokulua Islands daily. brbrBesides being steps to pristine Lanikai Beach, quaint Kailua town is a quick five minute drive for groceries, restaurants, and boutiques. Easy access to the John A. Burns freeway puts downtown Waikiki just 30 minutes away. At Lanikai Oceanside, located in the attractive Lanikai neighborhood of Kailua, Oahu, enjoy the sun drenched beach life Hawaii is known for.brbrThis vacation home has been registered as a Transient Accommodation with the State of Hawaii – HAWAII TAX ID #TA-141-510-3488-01.brbrPlease note, Utility Fee of $1,000 per month will be charged for all stays of 21 days or more.brbrThe property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.brbrTA-141-510-3488-01brTMK: 430030630000

Stunning Oceanfront Beach House w/AC & Mokulua Isle Views at Lanikai Oceanside

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$306.18

This beautiful, cozy cottage in the quiet Coconut Grove neighborhood of Kailua is perfect for your vacation getaway! You'll have your own private, fully-fenced yard, washer and dryer, A/C and ceiling fans in every room and will be close to the beach, downtown and all that Kailua has to offer. 30+ day rentals only, no exceptions: #TA-006-886-2976-01

Coconut Grove Cottage, Walk to Beach and Downtown

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1466.09

Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai overlooks the beautiful beach, Kailua Bay, and Offshore Islands.brbrKailua is a small upscale town with excellent retail stores. Whole Foods is six blocks from home, and three other supermarkets are only a few blocks further. Everything is available and at your fingertips.brbrGreat for Extended Families and Kids. CALL 303-885-6104 with your questions.brbrOur BEACHFRONT home was designed to provide you with a perfect retreat. You will be as close to the beach as a Hawaiian home can be. brbrThe beach of Kailua is renowned for its fine white sand, blue-green waters, and safety. It is not crowded and has a pleasant neighborhood feel.brbrOur four-bed/3.5-bath home gives plenty of space. Upstairs/downstairs and corner bedrooms offer privacy when needed. The 1300 sq ft wrap-around lanai gives everyone a sense of participating in the adventures, whether by watching and yelling encouragement or by showing off newly learned water skills. brOur house has everything you need except groceries. Our casual feeling will make you feel right at home. The Hawaiian-style furnishings and island feel have earned our home a recommendation from some true Hawaiian leaders as the best Hawaiian home available. brbrA garage FULL of BEACH TOYS, YARD TOYS, BBQ, TEAK LOUNGERS, ROCKERS, & TABLES will ensure you never have a dull moment. The Large Yard offers plenty of play and relaxation.br brKailua is a charming town with many delicious restaurants and shopping for everyone. You can get all the essentials and find unique items to take home as mementos of your Hawaiian vacation.brbrGetting to attractions such as PEARL HARBOR, the NORTH SHORE, and HANAUMA BAY is very simple.brbrThe House: Our home has two master bedrooms, one on the ground level and one master of the 3 Upstairs Bedrooms. Total 4 Bedrooms, 3 Bedrooms Upstairs and 1 Bedroom on the Lower Level. brbrThe Upper Primary Suite has a king bed, a full bathroom, and private access to the Lanai. brThe Garden Bedroom has a queen bed and tranquil mountain views.br2 Koa Wood Twin Beds furnish the Koa Bedroom with great views of the beach and yard. brbrA Large Living Room opens onto the Lanai overlooking the ocean and wrapping around three sides of the house, providing views of the beach, the yard, and the mountains. Comfortable couches allow for maximum relaxation while taking in the views of watching a DVD on the flat-screen TV. The dining table is perfect for gathering around for dinner conversation. The Mark Chia, well-respected Oahu artist, chandelier over the dining table provides warm light and is a unique touchbrbrDownstairs is a Semi-Private Suite with a Partial Kitchen, Full Bathroom, and a Private Half Bathroom. brbrThe Lower Living area features a galley-style service kitchen that opens to a dining area, sitting room, and full bath. brbrThe lower common areas lead directly into the large, beautifully landscaped lawn.brbrThe Property: The entire home was designed to be an accurate representation of Hawaii. brbrPlantation-style architecture celebrates Hawaii's heritage of sugar and pineapple plantations; workers and landowners on the plantations would live in homes stylistically similar to ours. brbrThe interior décor of our home reflects this tradition while providing modern convenience and comfort. Our furnishings are made of wood, Koa, Bamboo, and Rattan, all traditionally found on the islands. We strive to keep the feel of Hawaii throughout the house with tastefully chosen accessories.brbrExtras: EVERYTHING for your beach vacation is provided with our home: beach towels, chairs, BBQ grill, loads of beach toys, boogie boards, and an outdoor shower with hot and cold running water. br *The sounds and views of the beach, ocean, and surf are always within range.*brbrRates and fees are subject to change. br The property will be exclusively available to the renter for a total of 30 days, and no one else may occupy it during that period, even if you leave early. Rates are based on a 30-day rental period. Ask about possible longer-term discounts. Hawaii GET TAT, and OTAT are charged. brbrIf the rental period is confusing, please send a message with questions before submitting a booking request. All bookings are subject to approval. Questions Ask Us 303-885-6104

Celebrate America's 250th Birthday & Kailua Fireworks from Beachfront Lanai

Kailua, Hawaii, United States

Bed

Bath

8

Sleeps

Select Dates for Price

This is a newly custom designed and remodeled 4 bdr - 3 bath - 2 kitchens home in one of the best neighborhoods of Oahu and Kailua. I designed this home with lots of love and care with furniture and high quality flooring and materials shipped form the main land and various countries around the world. There is a studio attached to the house, which can be used as a master suite with its own full bathroom and kitchen. The house is spacious & full of light - with beautiful living room, kitchen & dining areas. We also have a movie room with comfortable sofa and relaxing atmosphere. Both kitchens future new appliances. Each room has its own AC & ceiling fans. Wireless internet, 3 TVs and 2 Apple TVs. Beautiful & relaxing yard with outdoor furniture. Desk with a computer screen to connect to your laptop and printer for those that need office space.br3min walk to stunning sunrise beach view. 1min drive to grocery store, restaurants, Starbucks. 10min drive to Whole Foods, restaurants, yoga. 5-10 min drive to Kailua Beach. 10-15min drive to Lanikai Beach. 20-25 min to airport.

Casa Luna - Beautiful & Stylish Remodeled 4bd, 3bath, 2 kitchens Home in Kailua

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$706.42

Kailua Absolutely Oceanfront Deluxe Legal Vacation RentalbrThe closest house to the Ocean in KailuabrLocated in a quiet upscale neighborhood away from the crowdsbrHear the waves breaking just outsidebrGo tide pooling steps awaybr60ft salt-sanitized waterfall lap poolbrDramatic Sunrisesbr16-foot vaulted ceilingsbrWall-mounted Fujitsu air conditioningbrAttached covered outside Oceanview deckbrNo Bedbugs here/Bed Bug Protective Mattress and pillow coversbrbr- This unit looks directly at the oceanbr- Closest Kailua house to the oceanbr- A legal Direct Oceanfront Kailua Vacation Rentalbr- Go tide pooling steps away from your doorbr- Private exterior stairway entrancebr- Located in a quiet upscale Kailua neighborhoodbr- Enjoy the 60-foot, salt lap pool with waterfalls (no red eyes or green hair)br- 1 bathroom with kitchenette/dining/living areabr- 16-foot vaulted ceilings, granite detailing in the kitchen and bathroomsbr- Wall-mounted Fujitsu air conditioning br- wall-mounted smart flat-screen TVbr- Wireless Internetbr- No bed bugs here -Queen bed with encasements br impermeable to mites, br bed bugs, mold, and bacteria. brbrOther details to notebr- City regulations limit the unit to only 2 persons.- Not 2 adults and a child.br- The pool area is restricted to paying guests. This is not a party housebrbr

Absolutely Oceanfront - 60' Waterfall Lap Pool

Kailua, Hawaii, United States

1

Bed

1

Bath

Sleeps

$803.32

Wake up at Kai Nalu to wide ocean views, soft morning light, and the quiet rhythm of Kailua living. This thoughtfully designed 3-bedroom holiday home blends breezy indoor-outdoor spaces with refined coastal style, ideal for families, couples, and digital nomads settling in for an extended island stay.brbrWhat You'll Love About Kai Nalubr• Elevated ocean views from the main living space and lanaibr• Bright, open-concept layout filled with natural lightbr• Stylish kitchen with island seating and seamless flow for gatheringbr• Spacious lanai for outdoor dining and sunset unwindingbr• Split A/C in all bedrooms for personalized comfortbrbrLiving & DiningbrThe heart of the home is open, airy, and effortlessly inviting. Large windows frame the ocean beyond, while soft tones and clean lines create a calm, curated feel. The living area is designed for connection and comfort, whether you're hosting a casual evening or enjoying a quiet night in. Just beside it, the dining space offers a relaxed setting for shared meals or a laptop-friendly workspace with a view.brbrChef-Ready KitchenbrEqual parts functional and beautiful, the kitchen features vibrant cabinetry, generous counter space, and bar seating for casual mornings or evening conversation. Its open design keeps everyone connected, whether you're preparing meals or simply enjoying the space.brbrOutdoor OasisbrThe lanai extends your living space into the open air. Sip coffee as the day begins, dine with ocean breezes, or wind down as the sky shifts at sunset. This private vantage point captures the ease and beauty of island life without leaving home.brbrSleeping Quartersbr• Primary Bedroom: King bed, ensuite bathroom, garden view, split A/C, ceiling fanbr• Guest Bedroom 2: Queen bed, ocean view, split A/C, ceiling fanbr• Guest Bedroom 3: King bed, partial ocean and garden views, split A/C, ceiling fanbrbrExtrasbrDesigned with longer stays in mind, the home offers a flexible layout, multiple A/C zones, and a comfortable balance of shared and private spaces.brbrNearby brLocated in a quiet Kailua neighborhood, you're a short drive from sandy beaches, local cafés, and the town's relaxed mix of shops and dining.brbrGood to Knowbr• This is a 30-day minimum short-term rental; the home is exclusively yours for the full rental periodbr• Rates are based on a 30-day stay, please inquire for detailsbr• TAT ID: TA-168-604-3136-01br• TMK / Parcel ID: 1430060150000brbrSettle into the rhythm of Kailua, where longer stays feel effortless and every day begins with the ocean just beyond your window.

Bright Kai Nalu w/ Ocean Views, Lanai + Open Living

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1279.74

One of the original homes on Kailua Beach, this Renovated 1937 five bedroombrbrCottage is just one house from the middle of Kailua Beach, the #1 Beach in thebrbrworld. Nestled between a park and a rarely used club with only one beachfrontbrbrneighbor, this quiet and serene gated home has private beach access as wellbrbras a salt water pool and hot tub, and giant doors that open the entire centerbrbrof the house to the huge lanai. You'll be greeted every morning with thebrbrsounds of birds chirping, ocean breezes in the palm trees, and the wonderfulbrbrsound of waves crashing at the beach. Enjoy the evenings on the 1,000 squarebrbrfoot lanai listening only to the waves and breezes with your dinner at thebrbrlarge Balinese table, followed by board games with the kids and a glass ofbrbrwine as you relax in the peace, plus a night swim in the warm pool under thebrbrstars.brbrbrbrThis home was renovated in 2019 with all new kitchen, floors, and baths and abrbr20 foot raised central ceiling, all while maintaining the original, historicbrbrcharm of this very unique property. Owned by one family since its purchasebrbrfrom the Queen of Hawaii all the way until 2019, this is an experience inbrbrhistory, beauty and serenity like no other.brbrbrbrThe best boogie boarding in Oahu is directly in front of the home. Walk tobrbrthe left to surf at Castles, walk to the right for parasailing andbrbrkiteboarding. Or just sit still on the beach enjoying one of the greatestbrbrtropical views in the world.brbrbrbrUnder local laws, this property may not be rented for less than 30 consecutivebrbrdays. Rental prices will not be reduced or adjusted based on the number ofbrbrdays the rental is actually used or occupied.brbrbrbrTMK #430160220000brbrbrbrbrbrbrbrHosted by RedAwning Vacation Rentals, over 2,000,000 Guests Served brbr brbrWelcome to RedAwning, a whole new way to travel. We make staying in a uniquebrbrhome or apartment easier than staying at a hotel. By partnering with localbrbrhosts throughout North America, we provide you with the broadest collection ofbrbrhomes in the most destinations. Every stay includes our experienced 24/7brbrcustomer assistance, our free mobile app, and accidental damage protection forbrbryour trip with no security deposits. Wherever you want to go, RedAwning isbrbrhere to make your journey easier! brbr brbrWant your own property to be included here and in the RedAwning Collection brbrJoin Us and we will instantly promote your property everywhere guests shop forbrbrtravel.brbrbrbrTAX ID: GE-045-319-8848-01brbrbrbr

Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

Kailua, Hawaii, United States

5

Bed

Bath

10

Sleeps

$2017.77

LUXURY Lanikai oceanfront home built in 2006, charming board and batten home, concrete floors throughout with the charm of old Hawaii. Beautiful gardens, outside dining and entertainment areas, large pool, big yard spaces, and awesome private outdoor showers that you will love. Extremely private, drive in the garage close the door and your dream home awaits you. Exquisitely furnished, and well appointed, you will never want to leave. Large rooms with private baths and comfortable beds - you will think you are at a 5-star resort.brbr*30-DAY MINIMUM RENTALbr4.712% GET, 10.25% TAT, 3% OTAT

Luxury Lanikai Oceanfront Home!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1806.16

Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new furnishings including all beds and linens and a re-modeled kitchen that includes new stainless steel appliances, new dish ware, and everything needed for those who love to cook. The kitchen includes a center island for food preparation, bar seating for 4 and a thoughtful coffee station to prepare that early morning coffee. Just off the kitchen is a convenient laundry room with double washer and dryer to accommodate the larger family gatherings.brbrThe home is located towards the front entrance to Lanikai, an exclusive enclave of beachfront and beachside homes approximately 2 miles from the center of Kailua Town. The property is on the ocean and just a short walk to Lanikai Beach, a stretch of sugary white sand beach and gentle surf throughout the year. It is also a short walk to Kailua Beach Park which is just to the north with three miles of white sandy beach, and the iconic Buzz's Original Steak House.brbrAs you enter the home, you will be greeted by tropical landscaping, a trickling water fall and heated swimming pool which is the focal point of the home. 5 bedrooms may access the pool directly from sliding windows. The grand master suite and private lanai are located upstairs overlooking the ocean. Also upstairs is a loft/seating area for those looking for a quiet reading area, as well as an additional room that could serve as an office, nursery or extra bedroom if needed. The bedding and bath configuration is as follows:brbrGuest Room 1 - King Bed upstairs primary with ensuite bath. Additional daybed adjacent to master suite.brGuest Room 2 - King Bed - on the lower level with ensuite bathbrGuest Room 3 - Queen Bed - on the lower level with ensuite bathbrGuest Room 4 - 2 Queen Beds on lower level with ensuite bathbrGuest Room 5 - 2 Queen Beds on lower level with ensuite bathbrGuest Room 6 - King Bed on lower level with nearby bath In hallwaybrbrThis home has several gathering areas inside and out, providing guests the option to enjoy an outside barbecue together, watch a movie in the media room or work alongside each other if business calls. The front lanai and grass lawn provide endless hours of ocean enjoyment as paddlers and kite surfers pass nearby. The home has added a high speed wifi system that may be accessed throughout the property to accommodate today's remote workers. Boogie boards, beach chairs, beach towels and quality bath amenities complete this well-equipped home so that you may enjoy your time in paradise.brbrThis Property is professionally managed by Private Homes Hawaii, LLC and is a legally established rental accommodation that is rented for periods of 30 consecutive days or more at any one time. There is an owner paid utility cap of $1500 (electricity) per 30-day period. This home is compliant with Hawaii State Legislation (HB2078) and is available to lease from 1 to 6 monthsbrLic#TA-211-647-0272-01. TMK.

Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!

Kailua, Hawaii, United States

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Sleeps

$1041.45

Experience the ultimate Hawaiian escape at Mokulua Sunrise, a stunning 4-bedroom, 3.5-bath oceanfront villa nestled in the world-famous Lanikai neighborhood of Kailua, Oahu. With sweeping, unobstructed views of the turquoise Pacific and the Mokulua Islands, this exquisite retreat offers an unparalleled blend of luxury, comfort, and island serenity.brbrWhat You’ll Love About Mokulua Sunrise by Gatherbr• Prime oceanfront location with panoramic views of the Mokulua Islandsbr• Newly remodeled interiors by designer Lucky Bennet featuring custom Koa wood finishesbr• Expansive 4,385 sq. ft. open-concept floor planbr• Private oceanside lanai with chaise lounges, hammock, and lush landscapingbr• Spacious gourmet kitchen with stainless steel appliances and granite countertopsbr• Primary suite with ocean-view lanai, jacuzzi tub, and spa-like ensuitebr• Multiple indoor and outdoor gathering areasbr• Central A/C, ceiling fans, and Smart TVs throughoutbr• Gated driveway, 2-car garage, EV charging station, and private courtyard with koi pondbrbrLiving & DiningbrStep through the gated entry into a tranquil courtyard featuring a peaceful koi pond and tropical landscaping. Inside, an expansive open-concept living space welcomes you with floor-to-ceiling windows framing the sparkling ocean. The main living room offers plush seating and a large Smart TV, creating the perfect setting for movie nights or relaxation. A secondary lounge under the open landing invites you to unwind with views of the Pacific.brbrThe formal dining area comfortably seats six, while additional dining spaces allow for easy entertaining. The seamless design connects living, dining, and kitchen spaces, creating a perfect flow for both intimate gatherings and group celebrations.brbrChef-Ready KitchenbrDesigned for the culinary enthusiast, the fully equipped kitchen boasts high-end stainless steel appliances, marble granite countertops, and a central island with breakfast bar seating for eight. With wraparound counters and ample storage, this chef’s kitchen is ideal for preparing family meals or enjoying casual breakfasts before a day at the beach.brbrSleeping QuartersbrUpstairs, four beautifully appointed bedrooms offer privacy and comfort:br• Primary Suite: Olympic Queen bed, Smart TV, ceiling fan, and lanai access with direct ocean views. Ensuite bathroom with dual vanities, jacuzzi tub, walk-in marble shower, and skylight.br• Guest Bedroom 2: Two double beds, mountain views, ensuite with shower, soaking tub, and single vanity.br• Guest Bedroom 3: King bed, Smart TV, and lanai access with ocean views. Shares a Jack-and-Jill bath with Guest Bedroom 4.br• Guest Bedroom 4: King bed, Smart TV, ceiling fan, and access to shared Jack-and-Jill bath with shower/tub combo and vanity.brbrAll bedrooms feature air conditioning and ceiling fans for personalized comfort.brbrOutdoor OasisbrStep outside to the elevated oceanside lanai where sun loungers, hammocks, and lush palms create your private tropical sanctuary. Enjoy morning coffee as the sun rises over the Mokulua Islands or unwind at sunset while gentle waves roll ashore just steps away. The gated driveway and garage provide security and convenience, while the home’s design ensures total privacy.brbrAmenitiesbr• Private oceanfront lanai with hammock and loungesbr• Stainless steel BBQ grillbr• Full laundry room with washer, dryer, and utility sinkbr• 2-car garage with EV charging stationbr• Smart TVs in multiple roomsbr• Central A/C and ceiling fansbr• Complimentary Wi-FibrbrNearby AttractionsbrLocated in Oahu’s prestigious Lanikai neighborhood, Mokulua Sunrise places you minutes from some of Hawaii’s most iconic destinations:br• Lanikai Beach – just steps awaybr• Kailua Town – 5 minutes (shopping, dining, and local cafes)br• Kailua Beach Park – 5 minutesbr• Maunawili Falls Trail – 20 minutesbr• Downtown Honolulu – 30 minutesbr• Honolulu International Airport – 30 minutesbrbrGood to Knowbr• This property is offered as a monthly rental. The monthly rate applies in full regardless of nights stayed (no prorated rates).br• A utility fee of $750 per month applies to stays of 21 days or more.br• The property will be made exclusively available to the renter for a full 30-day period; no other guests may occupy the property during that time.br• Hawaii Tax ID: TA-013-318-7072-01br• TMK: 430040990000brbrEscape to Mokulua Sunrise by Gather, where luxury, natural beauty, and tranquility converge to create an unforgettable island retreat. Whether you’re lounging on the lanai, exploring Lanikai’s pristine beaches, or simply savoring the view, this home is your private piece of Hawaiian paradise.

Superbly Designed Home w/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise

Kailua, Hawaii, United States

Bed

Bath

8

Sleeps

$332.84

TLA Approved! Walk to Kailua Beach • Fenced Yard • Updated 3BR/2BAbrbrEnjoy relaxed island living in this updated, fully furnished 3-bedroom, 2-bath home just a short walk from the soft sands of Kailua and Kalama Beach. Perfect for military families, traveling professionals, or extended stays, this home offers comfort, convenience, and a highly desirable location.brbrThe home features a newly remodeled open-concept kitchen with an island, seating, upgraded farmhouse sink, and stylish floating shelves—ideal for cooking, gathering, or working remotely. Both bathrooms have been recently updated, including a brand-new second bathroom.brbrStep outside to a fully fenced yard and outdoor space, perfect for relaxing, enjoying the trade winds, or spending time with family. A private in-unit laundry adds everyday convenience.brbr⸻brbrPrime Locationbr • Kailua Beach: 0.5 milesbr • Kalama Beach Park: walking distancebr • Kailua Town: 0.9 miles (shops, restaurants, Target, Whole Foods)br • Castle Medical Center: minutes awaybr • MCBH: approx. 10 minutesbr • Easy access to H-3 and major routesbrbr⸻brbrThe Spacebr • Bedroom 1: Queen bed, dedicated workspace, walk-in closetbr • Bedroom 2: Queen bed, large closetbr • Bedroom 3: Queen bed with en-suite bathroombrbr⸻brbrGuest AccessbrbrGuests have full access to the entire 3-bedroom, 2-bath home.brBoth bathrooms have been recently updated for comfort and style.brbrThe left side yard and backyard are fully fenced and available for your use.brbr⸻brbrOther Things to NotebrbrEnjoy true island living with cool trade winds and ceiling fans in every room.brPlease note that the home does not have air conditioning. This is a bottom floor unit in a home. There is one other Ohana unit on the property. All spaces of the unit are private, with the exception of the right side yard, used to access the other unit. Shared driveway.brbrMinimum Stay Requirement:brIn accordance with Hawaii regulations, a 30-day minimum stay is required.brbrSecurity Cameras:brFor your safety and security, exterior security cameras are installed around the outside of the property. There are no cameras inside the home.brbrRegistration Number:br085-276-8256-01

Steps to Kailua Beach • Relaxing 3BR Oasis • Fenced Yard

Kailua, Hawaii, United States

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Bath