Vacation Home Rentals By Owner In Kailua, HI

Indulge in an Unforgettable 30+ Night Stay at Our NEW Luxury Beach House at Kailua BeachbrbrImportant Compliance Notice: This home is available only for stays of 30 nights or longer, in full compliance with Kailua’s strict short-term rental regulations. We appreciate your understanding as we adhere to local laws.brbrEscape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed to blend upscale comfort with the breathtaking beauty of Hawaii. With high-end finishes and state-of-the-art appliances, every detail has been thoughtfully curated to offer you a lavish experience like no other.brbrWake up to the soothing sound of waves and start your day with a peaceful stroll along the pristine sands of Kailua Beach, picking up your morning coffee at the charming Kalapawai Market. Relish in serene outdoor dining on the lanai, breathing in the fresh ocean breeze, or take a dip in the private pool, surrounded by lush tropical landscaping that will leave you enchanted. Whether you’re here to work remotely, recharge, or simply unwind, this home is crafted to make you feel right at home while enjoying a serene island getaway.brbrNote: Our other property in Napa boasts a 100% 5-star rating on VRBO!brbrNo guests under the age of 13 are permitted on the property.brbrKey Features:brbr•Two Spacious Bedrooms: Each with an en-suite bathroom, ideal for couples or small groups.brbr•Air Conditioning & Dedicated Parking: Full climate control and a reserved parking spot.brbr•Modern Appliances: Stainless steel kitchen with dishwasher, oven, refrigerator, washer, and dryer.brbr•Direct Beach Access: Step right onto Kailua Beach from your front door.brbr•Private Pool and Spa: A serene backyard oasis for relaxation.brbr•Newly Built Luxury: Sleek, fully equipped living spaces with seamless indoor-outdoor flow.brbr•Outdoor Dining & Remote Work Area: Functional lanai for meals, sunsets, or working remotely.brbr•Impeccably Clean: Meticulously maintained and sanitized for your comfort.br•Extended Stay Focus: Minimum 30-night stay to fully embrace island living.brbrElectricity & Propane Usage Policy:brGiven Hawaii’s high energy costs, we include a $700 monthly allowance for electricity and propane in your rental. Usage beyond this amount will be deducted from your security deposit. We encourage mindful energy practices such as using natural ventilation and conserving resources to support sustainability and keep stays affordable.brbrThank you for helping us promote a greener, more responsible travel experience!

Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$306.58

This adorable pup-friendly, 3 bedroom, 1 bath vacation rental is ideally located, walking/biking distance to both the quaint shops and eateries of Kailua Town and renowned Kailua Beach! Fill your days with walks on the beach, surfing, SUP or kayak to the islands in Kailua Bay, waterfall hikes, biking, wandering through nearby neighborhoods, window shopping in Kailua Town, and finish with dining at one of our local treasures. The possibilities are endless! We have a secure, fenced yard for your pet and would love to host your stay!

Coconut Grove Kailua Vacation Home

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$2250.0

Welcome to your tropical escape in the heart of Lanikai, across the street from one of the most breathtaking beaches in the world. This licensed short-term rental offers comfort, style, and space. Additional bedrooms are available to sleep up to 16 guests (additional reservation required). - 4 Bedrooms | 3 Bathrooms - A second living room with a sofa bed - Air Conditioning - Blazing-Fast Wi-Fi - Washer & Dryer - Parking for 3 cars - Minutes from the beach - Other rental available on property Whole Foods, Target, Shopping, and Dining are just minutes away! The house sleeps 10 with 4 bedrooms and 3 bathrooms. There are extra bedrooms and bathrooms available if you needed more space to sleep up to 16 people. Please inquire to see if those spaces are available. There is reserved parking for 3 cars. If you know anything about Lanikai, you know that this is extremely rare. On the first floor, there are 3 private bedrooms and 2 bathrooms. The bedrooms have 3 queen beds. On the second floor is the master bedroom with a king bed and the master bathroom. There is also a second living area on the second floor pull-out sofa and TV. The backyard is massive and has a seating area, tiki bar, picnic table, and lots of grass to run around in! All bedrooms and bathrooms are stocked with towels, linens, blow dryers, shampoo, conditioner, soap, and toilet paper. The kitchen is fully stocked with a stove, oven, dishwasher, utensils, plates, cups, coffee maker, pots, pans, and just about everything else you might need! There is a property manager who lives on property in a private section with her own entrance. The property manager is meant to assist with emergencies and to help with any questions. You will not know that the property manager exists because she does not share any common areas with you and she has her own private entrance separate from the house entrance. If you need anything additional, please don't hesitate to ask! TMK: 4-3-008:030 License Number: 1990/NUC-1752 General Excise: GE-015-067-6992-01 Transient Accommodations: TA-015-067-6992-01

Lanikai Paradise across the street from the beach!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$979.74

Wake up to ocean breezes, tropical gardens, and the quiet magic of Lanikai. This authentic Hawaii home--rich with soul and character-- is located steps from ocean access, directly facing the iconic Mokulua Islands, and a short walk to world-famous Lanikai Beach brbrDesigned to fully embrace indoor-outdoor island living, the home is immersed in nature. Ocean breezes flow through the new jalousie windows, sunlight filters through lush gardens, and nearly every space opens to greenery and sky. The result is a calm, grounded and aesthetic living experience.brbrThoughtfully designed and beautifully maintained, the home reflects a sense of quiet luxury rooted in place and purpose. Designed by renowned Hawaii architect John McAuliffe, partner of IM Pei & Partners, the architecture blends tropical modern principles with warmth and livability--prioritizing light, airflow, and a seamless connection to the landscape. The craftsmanship and intentional design give the home an unmistakable sense of authenticity that is immediately felt.brbrThe main house features three bedrooms and two and a half baths, a fully equipped kitchen, and spacious living areas filled with natural light and peaceful garden views. A separate Ohana guest studio offers additional privacy with a king bed, full bath, kitchenette, fold-out couch, and its own indoor and outdoor seating areas--ideal for extended family, private workspace, or a quiet retreatbrbrWith king and queen beds plus sleeper sofas in over 2,500 square feet of living space, the home can accommodate up to 12 guests. brbrThe home is fully fenced and private, surrounded by mature tropical landscaping including mango, banana, citrus, lime, and starfruit trees. Expansive lanais invite relaxed gathering, and the outdoor shower is a favorite after beach days.brbrCeiling fans and split air conditioning ensure year-round comfort. nearby, enjoy scenic hiking and biking trails, or spend your days swimming, snorkeling, and paddling in the calm turquoise waters of Lanikai Beach. A home meant to be enjoyed, experienced and remembered. brbrPlease feel free to reach out with questions, availaitily or to see if this home is the right fit. brbrThis is a special place--ideal for families and groups seeking beauty, privacy and an authentic connection to one of Hawaiis most beloved neighborhoods.

Stunning Lanikai Home just steps to the Ocean-Authentic Hawaiian Tropical Charm

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$934.94

Lanikai Seashore is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your backyard. This luxurious 2,100 square-foot retreat artfully blends comfort and style, featuring exquisite ocean views that immerse you in the essence of island life.brbrWhat You’ll Love About Lanikai Seashorebr• Secluded access to Lanikai Beach right off your private yardbr• Four bedrooms, each with a king bed, accommodating up to 12 guestsbr• Fully equipped chef's kitchen with state-of-the-art appliancesbr• Outdoor dining space with a gas BBQ, perfect for sunset mealsbr• Air conditioning and ceiling fans throughout for your comfortbrbrLiving & DiningbrThe spacious living area welcomes natural light through large windows framing aquamarine ocean views and the iconic Mokulua Islands. Ample seating creates the perfect place to gather, unwind, and share memorable moments.brbrChef-Ready KitchenbrModern appliances—including a refrigerator, microwave, and dishwasher—make it easy to prepare your favorite meals. With two dining areas, you can enjoy both intimate dinners and larger family gatherings with ease.brbrOutdoor OasisbrStep into your private yard lined with lush gardens and a cozy gazebo framed by Royal Palms. Gentle breezes enhance the charm of the outdoor dining area, while a short path leads you directly to the soft sands of Lanikai Beach.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath, beachfront viewsbr• Guest Bedroom 2 – King bedbr• Guest Bedroom 3 – King bedbr• Guest Bedroom 4 – King bedbrbrExtrasbrEnjoy conveniences like high-speed Wi-Fi, a washer and dryer, complimentary beach gear (chairs, umbrellas), and 24-hour self-check-in for a seamless arrival.brbrResort / Community HighlightsbrExplore nearby hiking trails, enjoy watersports, or embark on horseback riding and fishing excursions. The Kailua community offers a warm, welcoming ambiance perfect for exploration and relaxation.brbrNearbybrYou can walk straight to Lanikai Beach for sun-soaked days by the water, while a short drive brings you to local dining, boutique shopping, and cultural sites throughout Kailua and beyond.brbrGood to Knowbr• Tax ID: TA–151-764-5824-01br• TMK 430050620000br• This luxury Lanikai Beach rental home will be made exclusively available to the renter for a full 30-day period and no one else will occupy the unit during that period. Rates are based on a 30-day rental period. Please inquire.brbrReady to immerse yourself in the tranquil luxury of Lanikai Seashore Reserve your dates now while your preferred week is still available.

Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush Yard

Kailua, Hawaii, United States

4

Bed

Bath

12

Sleeps

$2401.94

Prices start at $36,000/month and will not be pro-rated based on the length of stay. Please inquire for an accurate quote.brbrWelcome to Kailua Beach Villa. This luxury beachfront home is perfect for your next Hawaiian vacation. This spacious 2 level home has 5 bedrooms (1 additional optional bed/bath), 4 bathrooms and sleeps up to 11 guests. Every detail of this home was designed with comfort and relaxation in mind. Breathtaking views and the world renowned Kailua Beach just steps away make this home the perfect place to unwind in tropical paradise. The beachfront location of this home provides direct access to Kailua Beach, while it's gated and enclosed grounds afford privacy and seclusion.brbrThe large chef's kitchen fully equipped with top of the line appliances and great room provide the perfect space for family and friend gatherings. The large sliding glass doors allow people to flow seamlessly to the lanai, pool, and expansive gardens. A variety of lounge chairs and tables provide numerous poolside areas to soak up the sun or enjoy the colorful Hawaiian sunsets. brbrThere are two oceanside Primary Suites, beautifully designed spacious baths, and comfortable guest rooms offer ample space for privacy. Two of the bedrooms have air conditioning for optimal temperature comfort. brbrOver 3500 square feet of indoor living area. Award-winning Great Room opens onto lanai & pool deck. Gourmet kitchen and dining area for ten. TVs, VCR, DVD and stereo. Ceiling fans in every room. Full laundry facilities. Outdoor Living. Exclusive privacy. Gated and full enclosed grounds. Large, covered wrap-around lanai and enclosed courtyard. Spacious pool. Gas BBQ grill. Outdoor shower. Boogie Boards & beach chairs available for use.brbrADDITIONAL INFORMATION AND DISCLOSURESbr1. Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts.br2. Online bookings are subject to manager and owner approval. br3. This vacation home has been registered as a Transient Accommodation with the State of Hawaii Lic# TA-123-605-1968-01.brbrThe property will be made exclusively available to the renter for a full 30-day period and no one else may occupy the property during that period.

Kailua Luxury Beachfront House

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$266.14

brAt Old Hawaii Beach House and Guest Cottage in Lanikai, we extend to all our guests the old-fashioned Hawaiian Hospitality, and the famous Spirit of Aloha. brbrStep back in time to the romance, the charm, that is truly 'Old Hawaii.' brbrTropical plants and flowers (seasonal) in the 12,000 square foot lot. Ceiling fans add to the aura of Old Hawaii. This treasure is available for you to enjoy.brbrYou can relax on this heavenly tropical beach, or on the lanai overlooking the expansive grassy lawn. Listen to the soft music of the trade winds in the coconut palms. Enjoy nostalgic Lanikai, as it was since time immemorial before the rest of the world discovered it. brbrThis beach hale was built by our family in 1931. It is an authentic cottage home, located on prestigious Mokulua Drive, offering the comfort and ambiance of Old Hawaii, but with all the modern conveniences, including air conditioning in the bedrooms and living room, and WiFi for your Internet connection. brbrThere are two bedrooms in the main hale and a full bathroom. The detached cottage has air conditioning, a half bathroom and a private outdoor garden shower with hot and cold water, which is a favorite, included in the rental. There are two outdoor dining areas.brbrThere is a stove, a refrigerator/freezer, a microwave oven, and a washer and dryer. brbrThis is a family-friendly, kid-friendly home. brbrYou will be located a short walk from beautiful Lanikai beach, named the best beach in the world by the Travel TV Channel.brbrThis property is 30 day /monthly rental. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. brbrPLEASE NOTE: Our hale is located in a residential neighborhood. Quiet hours from 9 PM to 8 AM are strictly enforced. Please be considerate. Absolutely no parties or large gatherings allowed. Only 6 people maximum are allowed by the contract and VRBO. No additional overnight guests are allowed. No camping or tents in the yard, no exceptions. Please be sure this is the right fit before booking. Mahalo for your understanding.br

Sweet Vintage Hawaiian Cottage and Guest House! Great deal in beautiful Lanikai!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1067.55

Inquire about short stays, we accommodate them where possible. Spend your vacation in our Hawaiian style 4 bedroom, 4 bathroom home a 3 minute walk from Kailua Beach. Our home features a balance of indoor and outdoor living. There is a Zen like courtyard and inviting navy blue mosaic swimming pool in the backyard. Each bedroom has its own private full bathroom and AC unit. The living room also has AC.brbrThere is a property manager that is available to do check in, check out and if there is any troubleshooting needed.brbrThis home is located on Kalaheo Avenue, just a 2 minute walk from beautiful Kailua Beach, located on the Windward Coast with 2 miles of soft sand, turquoise water, and gentle breezes. Kailua Beach is also a hub for water sports such as surfing, windsurfing, body boarding, kayaking, paddle boarding and parasailing.brbrIf you are up to a challenging hiking trail, Ehukai Pillbox is only 2.4 miles away. It’s a 30 minute hike up to two old military bunkers that overlook the North Shore coastline. The views are breathtaking!brbrTry the breakfast at Cinnamons in downtown Kailua.brbrWalk to Kalapawai Market for sandwiches or burgers before heading to the beach.brbrCraving Asian food You can choose between Champa Thai, Saigon Noodle, or Tokoname Sushi.brbrThinking about Italian or Mexican Maybe you can look into Assaggio, Buone Era or Cactus.brbrWhy not try some fresh poke at Foodland or Wholefoods brbrAfter a beautiful sunset by the beach, try the freshly caught seafood at Buzz's Lanikai by the canal.brbrThe floor plan enables every room to have a view of water and lush greens, and also enables tropical breeze to free flow through the property. The 4th suite also has a separate entrance. The spacious kitchen, dining room and living room are in between the courtyard and backyard so it has the privilege of both pool and pond views and ample lights. Perfect for family vacation, family reunion, and other special family event celebration.brbrThe home has been newly renovated with a fully equipped kitchen, modern floors, and island decor. To make working and learning remotely from paradise more efficient, we have upgraded our internet service to ultra-package throughout the property, and stored additional computer desks in case multiple working stations are needed.brbrOffering a truly Hawaiian experience, it is a great place to relax away from the crowds but still close enough for trips to Waikiki and North Shore. Walk to the Kalapawai Market for morning coffee. Wind surf or kite board from the best spot on the island, rent a kayak or paddle board, head to the Moku islands, or have shaved ice at Island Snow later in the day.brbrBEDROOMS AND BATHROOMS: There are 4 bedrooms with en-suite bathrooms. The expansive master suite has a king bed and spacious walking closet. Two others each have a queen bed. The 4th suite has 2 twin beds that you can put together for a King bed, if you need. You can also use the queen size air mattress in the living room or the master bedroom.brbrKITCHEN: The fully stocked gourmet kitchen has everything you could possible need to from wine glasses to pots & pans, and a rice cooker. The kitchen with a bar opens into dining area beyond which you can step into the lanai/courtyard. We also have an outdoor grill by the pool and under the coconut tree for your use.brbrLIVING ROOM: There is spacious and bright living room with large sliding doors that open into zen themed courtyard on one side and swimming pool/backyard on the other.brbrCleaning Policy:brYour health and safety are our top priority. We are now following a thoroughly enhanced cleaning policy. This home has been thoroughly cleaned using SafeStay standards, an EPA approved, hospital-grade disinfectant that has been found to kill 99.9% of detectable pathogens. The front door is then sealed with a tag and no one is allowed to enter till you do so with your access code. We want you to assure you that cleaning and disinfection is being done to the highest of standards.brbr*This property is a legally established dwelling that is rented for periods of 30 consecutive day minimum. There is no penalty for early departures so you can book for a shorter stay as agreed upon on the site. This is in accordance with city and County of Honolulu ordinance section 19-18. A 30 rental agreement to be included.*brbrRegistration Number: GE-096-373-7600-01, TA-096-373-7600-01brbrIt is best to rent a car. Parking is available at the property and on the street.

Zen Home with AC, Pool, Near Kailua Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1008.84

ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1 house from the white sands of Kailua beach (Private beach gate is located adjacent to our property and the house is less than 350 feet to the beach). Our central Kailua Beach location allows access to a mile of Dr. Beach's No. 1 US-rated beach in each direction. brbrWith 4 bedrooms and 4 baths, plus a family/game room, this remodeled 'beach-chic' family-friendly property has a large swimming pool and game room providing a fun play area for kids of all ages. Extensive remodel, inside and out, was completed including new furniture, high speed wireless internet, flat screen HDTVs, hardwood and natural stone flooring, air conditioned bedrooms, modern kitchen, laundry, and bathrooms.brbrThere are 2 large furnished patios, one upstairs with a beautiful mauka (mountain) view perfect for breakfasts and star gazing at night and one downstairs outside the game room/family room, and one deck upstairs with makai (ocean) views to enjoy the cool ocean breeze.brbrIt's equipped with many extra amenities such as:brbr-Air conditioning in all bedrooms and downstairs TV/Game room: Quiet ductless A/C brbr-TV/GAME ROOM: with air hockey, video games, and large variety of board and card games. Convenient wet bar for easy access to hot popcorn and snacksbrbr-BABY READY: Pack-n-Play with mattress and linens, bed rails, baby gate system, booster chair, high chair, infant bath tub, baby monitor.brbr-Modern open kitchen with Viking dual fuel (gas top and electric oven) range and quartz countersbrbr-Kitchen is fully-equipped with coffee makers (drip, Keurig, and pour-over) & coffee grinder, rice cooker, pots and pans, Vitamix blender, electric griddler for pancakes, electric waffle maker, and so much more!brbr-Ample supply of dishes and utensils (30 sets of each) for large groupsbrbr-Beach gear including beach chairs, cooler, boogie boards, kids’ sand toys, and a beach wagon to carry all the gear down to the beach. Pool toys and electric air pump for inflatables.brbr-Flatscreen HDTVs in each bedroom, living room, and family room with Netflix and 150+ cable channelsbrbr-iPod/iPhone docking station/alarm clock in each bedroombrbr-Portable splash-proof bluetooth speakerbrbr-In-room safes in each bedroombrbr-Variety of books, board games, cards, puzzles, and toddler toysbrbr-Large pool with chaise lounges. Mesh pool safety fencing will be installed if there are young children in your group.brbrPlease be aware that the Kailua Bliss Beach House sits on a sand dune above the street, so in addition to it being a 2-story house with stairs, there are also 10 steps to get to the main house from the street or garage. Bedroom #4 is a private suite and while it is attached to the main house, it can ONLY be accessed through an exterior breezeway entrance which may not be ideal for younger children.brbrBedding arrangement:brbrUpstairs:brbrBedroom 1: King bed with en suite bathroom with shower; air conditioningbrbrBedroom 2: Queen bed with en suite bathroom with shower (this bathroom has an additional entry door for guest use); air conditioningbrbrDownstairs:brbrBedroom 3: King bed or can be configured as 2 twin beds with en suite bathroom with tub/shower; air conditioningbrbrBedroom 4 (Downstairs Stand Alone Suite with Exterior Entry ONLY - cannot enter this suite from inside the house): King bed or can be configured as 2 twin beds with en suite bathroom with shower; air conditioningbrbrGame Room/Family Room: Twin bed (this bed is located in the game room and is not private)brbrDiscover Kailua, a small beach town located 20 minutes from Honolulu and Waikiki, where flip flops, sand between your toes, and surf attire are commonplace. Less than 3 minutes away is a 24-hour Safeway grocery store, Starbucks, and a few restaurants. The main retail center of Kailua is located under 2 miles away from Amazing Kailua Beach House, where you will find a variety of shops (Target, Whole Foods), coffee, and dining options, as well as twice weekly farmers markets (Thursday nights and Sunday mornings), public tennis courts, basketball courts, and bicycle and surfboard rentals. Lanikai Beach and the beautiful Mokulua Islands are less than 3 miles away.brbr*** IMPORTANT PROPERTY DISCLOSURES*** brRental Agreement/Guest Registration Form will be emailed after booking and is required to be filled out and electronically signed within 3 days of receipt to confirm the reservation (this is the same agreement that has to be viewed and approved during the VRBO booking process)brbr-Bedroom #4 is a private suite and while it is attached to the main house, it can ONLY be accessed through an exterior breezeway entrance.brbr-Garage and garage gym are reserved for owners use. Guest parking is in the driveway. brbr-Living area over the garage is reserved for owners personal use and this wing is locked off from the rest of the house (guests have exclusive use of the property during their stay so no one else will be using the area over the garage during a guest stay).brbr-Maximum occupancy is 8 adult guests, or up to 10 guests total if the 9th and 10th guests are children under 18. $50/person/per night extra guest fee for all groups of more than 8 people. Please review bedding arrangements described above.brbr-The Kailua Bliss Beach House is a casual and relaxed beach house, not to be confused with or compared to a luxury home, and we would never represent it as such. It is clean, quiet, tastefully furnished, and well-equipped. brbr-The Kailua Bliss Beach House is located at the end of a narrow private road and there is no on-street parking allowed. All guest vehicles must park on-property only. There is space for up to 3 vehicles to park on-property, 2 vehicles in in the driveway and a 3rd on the grass off the driveway. The garage is locked and reserved for owners' use.brbr-QUIET HOURS ARE FROM 9PM-8AM: The Kailua Bliss Beach House is located in a residential neighborhood and guests must be aware and respectful of neighboring properties at all times. Noise carries at night and although the Amazing Kailua Beach House guests are on vacation, our neighbors are not, therefore ALL outdoor activities, including outdoor conversations, must be brought inside the home by 9pm. Please be sure that ALL the members of your group are aware of the quiet hours and will be able to comply BEFORE booking this property. brbr-NO SMOKING: Please be aware that smoking, including e-cigarettes, is not allowed anywhere on the Kailua Bliss Beach House property.brbr-GROUP GATHERING RESTRICTIONS: Are you part of a larger group all visiting Oahu at the same time Have friends and/or family living or staying on Oahu Visiting Oahu for a wedding or reunion Please consider another property or be sure to make other arrangements for activities and gatherings at locations elsewhere. The use of this property is restricted to registered guests only. Non-registered guests are NOT allowed on property at any time.brbr-14.962% Hawaii State Taxes + 3% Oahu Transient Tax + 3% processing fee, $975 cleaning fee (cleaning fee includes full checkout cleaning and one mid-stay partial cleaning)brbr-3% processing fee (shown on VRBO quote as Administrative Fee applies to all reservations and will be added before a reservation can be confirmed.brbr- Absolutely NO SMOKING, including e-cigarettes, inside the house or anywhere on the property.brbr*Please note that you are not required to stay for 30 days but in compliance with the City and County of Honolulu Land Use Ordinances including Ordinance 22-7, this property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.

★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1380.62

Inquire about short stays, we accommodate them where possible. Spacious, resort-style residence located within 100 yards of Kailua Beach. Featuring a private courtyard and pool, this indoor/outdoor floor plan is ideal for family gatherings. The extensive renovation features an expansive master suite, a workout area, renovated bathrooms, an open bistro-style chef's kitchen, and a distinct laundry room in addition to a solar-heated pool. An oasis of genuine luxury awaits you in paradise.brbrThe property manager lives a few minutes away from this home and is available to help, even on weekends and after hours.brbrThis house is located in the beachside community of Kailua. There are many restaurants within a couple miles as well as a Whole Foods Market for your grocery needs.brbrThe entire house can be used by the guests. The only exceptions are the garage and one of the two closets in the master bedroom.brbrBathrooms and bedroomsbrThere are five restrooms and eight aesthetically pleasing bedrooms. Five rooms, each, feature a queen bed. Both rooms feature a king-size bed. And one room with a twin trundle bed and a full bed.brbrThe kitchen brThe kitchen is exceptionally well-appointed with every conceivable item, including wine glasses and dishes and cookware. The kitchen is exposed to the indoor/outdoor dining area and features counter seating. In addition, two refrigerators have been added per a guest's recommendation.brbrWhile diningbrLarge sliding doors in the dining area lead to the outdoor covered lanai, which provides additional seating for eight. Five bar stools are located atop the kitchen island.brbrLOUNGE ROOMbrAn additional set of sizable sliding doors in the expansive living room provide access to the lanai.brbrEXTRAS:brCable television; expedient WiFi throughout the residence; a laundry room with an extra-large washer and dryer.br-Dishwasher -Air conditioning in the living room and all bedroomsbr-Snorkels, beach chairs, and beach towels -An outdoor showerbrPlay Pac-n-PlaybrbrATTRACTIONS and LOCATION: brThis residence is situated a mere five houses from the shoreline and a two-minute stroll from Kailua shoreline, one of the most picturesque beaches globally. There are numerous restaurants and a Whole Foods Market within a couple of miles for your grocery requirements.brbrAC:brAir conditioning is provided in the living room and all bedrooms. Although the kitchen and dining room lack air conditioning, substantial sliding doors allow for the ingress of chilly trade breezes.brbrLegally recognized as a residence, this property is rented for a minimum of thirty consecutive days. Early departures do not incur any penalty, so you may reserve a lesser stay as specified on the website. This is in compliance with sections 19-18 of the ordinances of the city and county of Honolulu. A thirty-day rental agreement is required.brbrbrIt is best to rent a car. Parking is provided at the home. If you are interested in renting our van at the property, please let us know.

Huge House, Heated Pool, AC, Steps to Kailua Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1354.55

This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!brbrEach room has an individually controlled AC system. The primary bedroom has bath ensuite. The poolside king room and queen room share a bath. The twin room and king room share another bath. The poolhouse has an outdoor shower and 1/2 bath. brbrSmart TV's can be found in the living room and pool house. The pool house has a large refrigerator and a wine refrigerator. brbrThe home is one block from world-famous, 2 .5 mile long Kailua Beach (Voted #1 by Dr. Beach in 2019) There are no roads to cross to access the beach making this home ideal for your family beach vacation!brbrBy law this home can only be rented once in a 30 day period. Price is negotiable depending on number of occupants and length of stay. Longer stays rewarded with discount!brbrCome be our guests and experience the magic of this Kailua beachside location and the island of Oahu!brbrThis property has one active security camera on the driveway.brbrGET & TAT tax #174-185-2672-01brTMK 430190450000brbr

Beachside Family, vacation home with pool NO CLEANING FEE!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$219.89

(Not suitable for folks with mobility limitations due to steep walk.)brExperience Windward Hawaii at this beautiful 1 bedroom in the heart of Lanikai. You'll be within a short walking distance of one of the best beaches on the island and close to Kailua town with many unique shops and restaurants. You'll enjoy beautiful views of the sunrise and the full moonrise over the Mokulua islands from the beach, splash into protected snorkeling between purple coral heads, sunbathe to the envy of every instagram follower, cool off in the air conditioning or the breezy lanai under coconut palms and upload your day's adventures thanks to the free WiFi. Dine alfresco with grilled steaks under the palms for a romantic night in. Stretch out in a king size bed and wake up refreshed in a separate bedroom from the living space.brWhat's nearby:brYou are just a few blocks away from Lanikai beach where you can spend the day lounging, swimming, snorkeling and sunning or go for an evening walk or early morning sunrise. You are 3 miles from Kailua town with grocery stores, restaurants, galleries and fun shops. A great lunch or dinner spot even closer than Kailua town is Buzz's Original Steakhouse and Kalapawai market, steps from Kailua beach. For the adventure hiker, you are a few blocks from the Lanikai PillBox trail for great views. Of course, no trip to Hawaii is complete without driving around the island and seeing the North Shore and going for a fun night out in Waikiki.brThings to Know:brFree WiFibrBeach towels brBeach chairs brKayaks available with waiverbrSnorkeling fins available for use, but bring your own snorkel/maskbrFull kitchen with counter convection oven and no dishwasherbrWasher/dryer brPrivate outdoor lanai with dining and grillbrParking on site or streetbrPrivate entrance brShared property and shared walls in residential neighborhoodbrNot suitable for pets or animals brSuitable for respectful visitors who enjoys a quiet environmentbrNot suitable for folks with mobility issues

1 bedroom steps to white sand beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1243.99

Welcome to Hale Mokulua; an exclusive, quiet and private home adjacent to the spectacular blue waters of Lanikai Beach. With 3 separate living spaces, this remodeled Lanikai home accommodates up to 14 guests. The main house of consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful, covered lanai for lounging, dining and enjoying the warm Kailua evenings. The large loft on the 2nd floor includes a king bed and queen sofa pull-out, private ocean-view lanai and ensuite bath. Two spacious guest rooms on the main level also have ensuite bath. A large yard with a heated, tiled swimming pool and hot tub separates the main house from a one bedroom cottage (sleeps up to 4) and separate refurbished studio (sleeps 2) making this an ideal place for multi-family or large multi-generational gatherings. The white sands of Lanikai Beach are just steps away from this gated and private home. Each bedroom has its own air conditioning making this home cool and comfortable throughout the year.brbrWhat You'll Love:br*top to bottom renovations, updating the property with upscale furnishings and tropical designbr*steps from Lanikai Beachbr*Completely air-conditioned throughoutbr*Located on the quiet-side of the Lanikai loopbr*Separate living spaces with extra kitchens, private entriesbr*Lush, tropical gardens surrounding heated pool, spa and covered lanaibrbrBedroom Configurations are as follows:brMain House - 1st Level:brBedroom 1 - Primary bedroom - King Bed, en suite bathroom, shower & soaking tub, split a/c, TVbrBedroom 2 - King Bed, en suite bathroom, shower, split a/c split, smart TVbrbrMain House - 2nd level:brBedroom 3 - 2nd Primary Bedroom - King Bed & Queen Sofa Bed (shared room), en suite bathroom, shower, split a/c. Private outside lanai w/ocean view, smart TVbrbrOne Bedroom Cottage (separate entry, detached from main house):brBedroom 4 - King Bed & Queen Sofa Bed in living area w/bathroom in between, shower, split a/c, smart TV in living area brbrStudio Cottage (separate entry, detached from main house):brBedroom 5 - Queen Bed, bathroom with shower, split a/c, smart TVbrbrOffered as monthly rental (30 day minimum) - fixed monthly rate applies regardless of length of stay. This Property is professionally managed by Private Homes Hawaii, LLC and is a legally established rental accommodation compliant with Hawaii State Legislation (HB2078). It is available to lease from 1 to 6 months Lic#TA-005-853-7984-01. TMK.

Hale Mokulua - Lanikai, Oahu / pools, spa, beach!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1020.92

ORCHID HOUSEbrTA # 087-311-0016-01brbrWith magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone flooring, gourmet kitchen and appliances, skylights, AC in every room for those rare Kona days, and much more.brbrEnjoy outdoor dining on your tree-shaded lanai to extend the living space of this single level retreat. The inviting tropical pool with waterfall, cabana, and additional pool bath complete the picture of the perfect Hawaiian lifestyle with a large sunny ocean view pool deck. brbrWith an unbeatable location on a quiet street just a short 8 minute stroll to the white sands of Lanikai you will never want to leave.brbrMain House- 3 Bedrooms, 4 BathbrMaster Bedroom - King, full bath with dual vanities and large walk in shower with Ocean Views, split A/C, TV.brGuest Bedroom 2 - Queen, split A/C, full bathroom in adjacent hallway with shower/tub combination.brGuest Bedroom 3 - Queen, day bed, full bath with large walk in shower, split A/Cbrbr4th Bathroom is in pool area with a shower.brbr**Please note; currently waterfall feature is on from 9:30am to 10am and 4:30pm to 5pm. brPool stairs into 2 foot shallow end slopes to 12 feet in deep end. Kids should always have adult supervision!brbrMid-Stay cleans are mandatory for stays 31 days and longer;brEvery 30 day period, 1 mid-stay clean with no linens $275 + GET/TAT/HTAT = $324.40 or with linen changes $350 + GET/TAT = $412.87 brbr1.The 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. The 30-day rental period will be communicated to guest upon booking.br2. Online bookings are subject to manager or owner approval.br3. All children must be supervised by adult. Pool can be cooler in Winter months. POOL HEAT OPTIONAL AND AVAILABLE AT $150/DAY PRE ORDERED. $175/DAY UPON ARRIVAL OR $3500/PER MONTH.br5. Christmas & New Year are subject to a premium.

Orchid House - Pool and Endless Ocean views!

Kailua, Hawaii, United States

Bed

4

Bath

7

Sleeps

$4536.81

Perched above the crystalline waters of Lanikai Beach, Lanikai Hillside Estate by Gather is a newly designed 5-bedroom, 5.5-bath luxury retreat with 6,295 sq ft of interior living plus expansive lanai spaces. Floor-to-ceiling glass, an infinity-edge pool, and panoramic ocean and mountain views create a seamless indoor–outdoor experience in one of Oahu’s most coveted enclaves.brbrWhat You’ll Love About Lanikai Hillside Estate by Gatherbr• Unparalleled ocean vistas from nearly every room and the infinity-edge poolbr• Private rooftop retreat with jacuzzi, fire pit, and lounge seating for sunrise, sunset & stargazingbr• Resort-style amenities including media room/home theater, gym, sauna, office, and multiple lanaisbr• Exclusive shoreline access for effortless days on Lanikai’s soft white sandbr• Central A/C and a refined modern aesthetic that frames the natural beauty outsidebrbrLiving & DiningbrOn the main level, expansive living and dining areas open wide to the lanai and infinity pool where the horizon meets the sea. Clean-lined furnishings, warm textures, and artful lighting set a tranquil yet elevated tone. The indoor dining area flows easily to the outdoor pavilion, making relaxed family dinners and celebratory feasts equally effortless.brbrChef-Ready KitchenbrA contemporary, fully equipped kitchen anchors the home’s social heart with generous island prep space, sleek cabinetry, and ocean views that turn cooking into a pleasure. Whether you’re preparing a casual brunch or collaborating with a private chef, the layout supports easy entertaining.brbrOutdoor OasisbrThe estate’s grounds are designed for unhurried island days. Lounge beside the infinity pool as it visually blends into the turquoise bay. Multiple lanais offer both sun and shade, while a BBQ zone and dining pavilion invite al fresco gatherings. Ascend to the rooftop deck to soak in the jacuzzi, cozy up by the fire pit, and take in moonrise over the Mokulua Islets.brbrSleeping Quartersbr• Primary Suite – King Bed, Upstairs, Expansive Lanai, Panoramic Ocean View, Spa-like Agape Ensuite, Walk-in Closetbr• Guest Bedroom 2 – King Bed, Upstairs, Ocean View, Ensuite Bathbr• Guest Bedroom 3 – King Bed, Doubles as an Office/Study Space, Upstairs, Expansive Ocean Viewsbr• Guest Bedroom 4 – Twin Bed, Twin Trundle Bed, and Lofted Double Bed, Perfect for the Kids, Upstairs br• Guest Bedroom 5 – Cal King Bed, Main Level, Private Sitting Area, Kitchenette, Lanai Access, Separate Entrance, Ensuite BathbrbrEach bedroom offers calming finishes, floor-to-ceiling glass, and thoughtful privacy so every guest wakes to a stunning natural backdrop.brbrExtrasbrCentral A/C, high-speed Wi-Fi, washer & dryer, private office, media room/home theater, smart TVs with satellite/cable, speaker system, printer/scanner/fax, home gym, sauna, exclusive shoreline access path, and a private gated community setting for added peace of mind.brbrResort / Community HighlightsbrPrivate gated community in Lanikai with direct access to one of the world’s most celebrated beaches.brbrNearbybrKailua Town is minutes away for cafés, boutiques, and farm-to-table dining. Launch kayaks to the Mokulua Islands, snorkel calm turquoise waters, or hike the Lanikai Pillbox Trail for sweeping coastal views. HNL is the nearest major airport for convenient arrivals.brbrGood to Knowbr• This property is offered as a monthly rentalbr• The monthly rate applies in full regardless of the number of nights stayedbr• Minimum 30-day booking period requiredbr• Utility fee: 3,500 USD per month for stays of 21+ daysbr• Exclusive use for the duration of the rental periodbr• TAT ID: TA-053-605-3248-01br• TMK: 430010090000brbrReserve your time at Lanikai Hillside Estate by Gather and experience elevated island living above one of Oahu’s most iconic beaches.

Lavish Lanikai Hillside Estate: Oceanview w/Pool/Spa, AC & Mokulua Isle Views

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$3712.19

This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#TA-148-509-2864-01. TMK.brbrWelcome to Gigi's Retreat, one of the few Licensed Short-Term Vacation Rentals on the Windward side of Oahu. This three bedroom, three bath home with large swimming pool sits on .9 acres of Kailua Beachfront. The home has been recently refurbished with new furnishings, fixtures, appliances, linen and accessories making it clean, comfortable and refreshed. A beautiful, ocean front lawn separates the home from the ocean, offering quiet and privacy. Two miles of white sandy beach front the home - an ideal spot for swimming, bodysurfing, paddling and kite surfing.brbrThe spacious rooms offer a flexible bedding arrangement that will appeal to groups of various sizes and makeup.brbrThe Bedroom configurations are as follows:brBedroom 1- (Primary) King Bed and Queen Sleeper Sofa split a/c, en-suite bathroom with walk in shower (Sleeps 2-4)brbrBedroom 2 - Queen bed, split a/c, en-suite bathroom, shower (Sleeps 2)brbrBedroom 3 - Two Queen Beds and Twin sized Bunk Beds, split a/c, en-suite bathroom, shower (Sleeps 4-6)brbrThis classic Kailua beachfront home is located on the Windward side of Oahu, 30 minutes from Honolulu and approximately 1 mile from the center of Kailua Town where guests will enjoy a variety of family-friendly restaurants, grocery and boutique shops. Cool, ocean breezes keep the home comfortable throughout the year. Newly installed air conditioning split systems have been added to all the bedrooms for extra evening comfort on those hot summer nights.brbrNote; this property is for quiet residential vacation accommodations only. Parties, weddings, receptions, Luaus, events and gatherings of any kind are prohibited.

Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783

Kailua, Hawaii, United States

Bed

Bath

10

Sleeps

$613.35

Steps to the beach! Stylish 3BR/2BA home on a private lane with an attached 1 BR/1BA guest suite. Newly renovated kitchen, huge island, brand new Cafe and Samsung smart appliances, and sliding doors to a backyard oasis with two large lanais, perfect for cooking, dining, lounging and entertaining. Fully-enclosed, shaded backyard area with pet-friendly faux grass for ease of maintanance Spacious upstairs primary with private rooftop lanai and ocean views. Split AC, ceiling fans, parking for 3-4 cars, and storage for surfboards and kayaks. Walk to Buzz's Steak House, Kalapawai Market & top-ranked Ka'ohao Charter School!

Spacious 4BR/3BA home w/ WiFi, AC - walk to beaches, parks, shops & restaurants!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$339.53

Two story home in Quiet Kailua neighborhood. Master bedroom is overlooking a beautiful pool and spa with views over the town of Kailua and the ocean. Upper family room has a pool table and also a fantastic view of Kailua town & ocean. Entire home was built in 2008 and has all new appliances. All counter tops are granite. Ground floor has large ceramic tile. Upper floor is Bamboo wood floors. Travertine floors and showers in upper bathrooms. Master has a king sized bed, second and third bedrooms have queen beds.

Kailua Home Pool & Spa with amazing views

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$755.25

In order to assist you in with your booking, regardless of your travel dates, it is really best to send us a brief message. As such, we apologize in advance and want to be clear that we will not accept any bookings prior to communicating with travelers about your dates of travel, etc. Please understand that we list our home in other places as well and need to check to be sure there are no conflicts with booking dates. Also, please view the Hawaii Travel Restrictions website at https://www.hawaii-guide.com/hawaii-travel-restrictions in order to understand the current requirements when traveling to Hawaii. brbrNewly renovated and upgraded home that is arguably in the best vacation location in all of Hawaii (rated the number beach in the world). If you are looking for a clean (electrostatic disinfecting sprayer used with each cleaning), safe, and quiet tranquil tropical place to stay for yourself and family, this would be the place to be. As we advertise our property on other platforms, we ask that prior to requesting a booking you communicate with us and provide us with the following; Phone number, number of guests in your group, their ages, and your relationship with them (i.e. Including myself, we have a total 8 people in our group to include my husband (34), my parents (65 and 67), and my 3 kids (3, 7, and 10), along with the dates of travel. We will then call you as soon as we can (we normally will call you immediately upon receiving your inquiry). Once again, we appreciate you not booking any dates until you have communicated with us over the phone and we advise you that the dates are available. brbrCentral Air Conditioning* Ocean View Near Beachside Home*, *Spacious 2,200 SF 3 BR, 2 1/2 BA Home - Full Service Gourmet Kitchen* Huge Master Bedroom* Indoor Laundry* Barbecue Gas Grill* 85 Samsung TV & WIFI* Parking* 2-Mile Walking Loop* Golf * Hiking Trails* Playground * Park. Sleeps 8- Mst. Bedroom (King Size), Old Mst. Bedroom (Queen size), Middle Bedroom (2 twins), Upstairs (2 pullout couches), 2 Futons also available. brbrSpectacular ocean views captivate you from sunrise to sunset from this home. There are 3 bedrooms and 2.5 baths that comfortably sleeps up to 8 (partially renovated with new floors and new shower). The home boasts a spacious ocean view gourmet kitchen with large cooking island. The great room and dining area is large and open to the kitchen with vaulted open beam ceilings and walls of glass to take in spectacular ocean views. The large area gives plenty of room to gather and play cards, or have great conversation with all the family about the events of the day. The open character allows guests to simply relax with each other and experience the essence of Hawaii. Living area is serviced by a unique half bath with custom painted wall mural. Game room also enjoys similar hand painted tropical wall art. Enjoy great vacation conversations, games, and memorable meals with family and friends, always mesmerized by the perfect blend aloha spirit and tropical ocean views. The private and spacious master suite includes a separate sitting area, full bath, and walk-in closet. The remaining two bedrooms share a second full bath. An indoor laundry room is conveniently located near the bedrooms. Enjoy the outside lanai where you can barbecue, sunbath, or have lunch with the family on the table overlooking the ocean. Ocean views simply abound from this home.brbrFor those with toddlers we have a pack and play, high chair, stroller, inflatable baby tub, and car chair for your use. brbrThis Hawaii ocean view home is uniquely located in Lanikai-Kailua on the cooler, tropical, NE shores of Oahu. This area is best known for its miles of white sandy beaches, gentle turquoise ocean surf, and trade wind breezes. Lanikai is tucked in along the beach next to the popular town of Kailua. brbrEscape from your everyday life to this private beachside Hawaiian style home. Relax on the lanai with your favorite cool tropical drink. Absorb stunning ocean views with the Moke's (Mokulua Islands) just offshore, listening to the crashing surf. Stroll over to the white sand beach and work on your tan, take a dip in the inviting surf, launch a kayak, or paddle board. You'll be thrilled watching the pros kite surf, and canoe teams practice and race each other. Come experience why Lanikai Beach is consistently rated among the 10 top beaches in the world. brbrThe neighborhood is exceptionally quiet and peaceful surrounded with lots of tropical vegetations. Many of the visitors especially appreciate the sounds of the birds in the morning or the ocean at night. brbrThis property is a legally established dwelling. In compliance with ordinance 19-18 (bill 89) this property is available for 30 days or more rentals. For available dates, pricing, discounts, and other questions feel free to contact us with your questions . Mahalo

Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps

Kailua, Hawaii, United States