Vacation Rentals By Owner In Kailua, HI

THIS PROPERTY IS A LEGAL SHORT TERM RENTALbrCONTACT HOST/RESERVATIONS & DETAILSbrbrThis airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home. Whether you prefer lounging in the sun alongside the very private and enclosed swimming pool, relaxing in the heated spa or watching the sunrise from beautiful Kailua Beach, all are there for your personal enjoyment. This home is located just steps from Kailua Beach on a quiet street. Wonderful restaurants, shops, and water sport rentals are just a few blocks away in Kailua town. br br4 Bedrooms - Two Cal Kings, Queen and two Twin beds. 3 Bathrooms - Master bath includes tub and shower. Spacious living and dining area. AC in living/dining room and 3 bedrooms. Ceiling fans in every room. Driveway and street parking available. Fully fenced and enclosed yard and pool/spa area with outdoor shower for rinsing off sand. Boogie Boards & beach chairs available for use. Beachside with private beach access. 3 minute walk to beach. 30 day rental period.

Beachside Kailua AC - DATES AVAIL incl Christmas! Min Stay 7 Nights-CONTACT HOST

Kailua, Hawaii, United States

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Bath

Sleeps

$253.72

Say aloha to this beautiful vacation rental in east Oahu! This Kailua home features 3 bedrooms, 2 bathrooms, a well-equipped kitchen, and a peaceful yard, making it the perfect home base to explore the island. Whether you're hoping to hike, swim, or learn to hula dance, you won't have to travel far to enjoy your favorite activities! The property is centrally located 12 miles from Honolulu, with so much to discover nearby. Ideal for families or friends, this home has something for everyone!brbr-- THE PROPERTY --brbrTA-045-647-8720-01 | GE-045-647-8720-01 | 430650420000 | Family Friendly | Central LocationbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Living Room: Twin Daybed | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: Dining table, gas grill (propane provided), landscaped yard, beach chairs, boogie boards, cooler, beach towelsbrINDOOR LIVING: Open floor plan, 2 Smart TVs, ceiling fans, dining table, coastal decor, eat-in kitchenbrKITCHEN: Dishwasher, electric stove top, microwave, drip coffee maker, blender, toaster, Crockpot, cooking basicsbrGENERAL: Free WiFi, washer & dryer, mini-split A/C units, keyless entry, linens, towels, complimentary toiletries, hair dryer, high chair, paper products & trash bags (starter supply)brFAQ: Homeowner on-site (main house), 3 external security cameras (facing out), quiet hours (9:00 PM - 8:00 AM)brSUITABILITY: Step-free access, single-story homebrPARKING: Shared driveway (2 vehicles)brbr-- THE LOCATION --brbrOUTDOOR FUN: Kailua Beach (1.0 miles), Kawainui Marsh Wildlife Sanctuary (2.5 miles), Lanikai Beach (2.9 miles), Lanikai Pillbox Hike (3.0 miles), Maunawili Falls (4.1 miles), Waimanalo Bay (6.8 miles)brNEARBY SITES: Ulupō Heiau State Historic Site (2.1 miles), The Byodo-In Temple (7.8 miles), Nu‘uanu Pali Lookout (7.9 miles), Halona Blowhole Lookout (13.1 miles)brHONOLULU HOT SPOTS: Aloha Tower (12.3 miles), Iolani Palace (12.4 miles), Honolulu Zoo (16.2 miles), Lyon Arboretum (16.7 miles), Diamond Head State Monument (18.0 miles)brAIRPORT: Daniel K. Inouye International Airport (16.0 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your staybr- NOTE: Please observe quiet hours from 9:00 PM to 8:00 AMbr- NOTE: The owner provides a starter set of paper supplies, toilet paper, paper towels, soap, and trash bagsbr- NOTE: Your safety matters. This property features 3 exterior security cameras. Cameras 1 and 2 are located on the exterior wall facing the driveway, and there is a Ring doorbell device with an exterior security camera facing the main entry. All cameras are outward facing and do not look into any interior spaces. The cameras record video and sound when activated by motion

Sunny Kailua Home w/ Covered Lanai 1 Mi to Beach!

Kailua, Hawaii, United States

Bed

This memorable Loft in Kailua is the perfect home base for your trip. With a cozy living room featuring 2 queen beds, 2 couches, dedicated workspace with desk and chair, full bath with tub, and full kitchen, this gorgeous property offers a peaceful retreat for guests. Enjoy the convenience of amenities like a washing machine, hair dryer, AC, iron, and WiFi during your stay. Apple TV allows for log in to watch any programs. We are walking distance (12min walk to beach, 12min walk to shopping / restaurants in Kailua Town). Lanikai Beach is close along with multiple golf courses.

Bath

7

Sleeps

Select Dates for Price

Apartment

Charming Loft in peaceful Kailua with WiFi, AC, and Mountain views.

Kailua, Hawaii, United States

Bath

Sleeps

Exceptional(90)

$387.51

OCEANFRONT LUXURY CONDO CLOSEST TO BEACHbr 2br/2ba sleeps (4-6) brbrWhite Sands Village, Kailua-Kona, Kona Coast, Big Island, Hawaii, USA (20 minutes south of airport overlooking White Sands Beach on Alii Drive 3 1/2 miles south of Historic Kona)brbrThis luxury oceanfront condo overlooking White Sands Beach is just steps away from the sand and water. It has spectacular ocean views, with views of sunsets, whales, spinner dolphins, turtles, outrigger canoes and more. You can watch the beach action, boogie boarders, body surfers and surfing from inside your condo or from your private wrap around lanai. You may even see the 'green flash' at sunset. brbrEnjoy spectacular sunsets from your private lanai. Dine inside or on the lanai. This condo has a master bedroom with SMART TV and private bathroom with shower. Washer and dryer is located in master bath too. Guest bedroom has 2 twins, guest bath has tub/shower. Living room has a SMART TV and a couch that converts to a queen size bed. Free wireless internet. All linens are supplied. The full kitchen is equipped with everything you need to cook any meal. The complex has a beautiful pool, with hot tub/Jacuzzi, a game room with pool table, tennis courts and bbqs by the pool area with tables and chairs to dine. No diapers of any kind are allowed in the pool. There is a plastic kiddie pool for children still in diapers. brbrThis well appointed NON-SMOKING condo is only 3 1/2 miles from restaurants and shopping in the Historic Kona village and 1 mile from Kahaluu the best snorkeling beach on the island. Keauhou Shopping Center with quaint shops, KTA grocery, Longs, medical care and Regal Theaters is only 5 minutes away. Local Farmers Markets are close by, so you can pick up fresh local fruits and vegetables, coffee and crafts. Golfing at the Kona Country Club is only 5 minutes away. North Coast golf courses, King Shops and Hapuna Beach are only 40 minutes away. Our central location makes it easy to enjoy all the fun things to see and do on the Big Island. Captain Cook's Bay and Monument, City of Refuge, coffee plantations and tours, Green Sand Beach, Black Sand Beach, Volcanoes National Park, warm ponds, Historic Hilo, waterfalls, botanical gardens, zip lines, Waipio Valley with horseback riding, Parker Ranch, Mauna Kea Observatory, Ancient Hawaiian Fish Ponds and Hawaii Petroglyphs. You can even do snorkel cruises, dinner cruises or Manta Ray dives.brbrNON-SMOKINGbrNO PETSbrNOT HANDICAP ACCESSIBLEbrbrbrbrbrKeywords: Oceanfront Luxury Condo Closest to Beach, Big Island, Kona Coast, Big Island Kona Coast, Kailua-Kona, White Sands Village, Kailua-Kona, White Sands Village Hawaii, Keahou Shopping

Condo

Oceanfront Luxury Condo Closest to Beach

Kailua, Hawaii, United States

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Bath

Sleeps

$431.97

Garage. Recently renovated and beautifully, tastefully furnished. Light & Bright. Full kitchen with high end appliances, Ohia hardwood floors, breathtaking views from every window. No pets firm. Living room, TV room, large kitchen, table, outdoor dining room, wrap around lanai on 3 sides, office, indoor laundry room. 30 day minimum! You won’t want to leave.

Apartment

Heavenly Hale Best monthly Vacation rental - walk to beach!

Kailua, Hawaii, United States

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Bath

Sleeps

$919.0

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private balcony, and full bathroom. Enjoy cool A/C, fast Wi-Fi, and thoughtful touches throughout. Relax, explore, and soak in the best of Lanikai. - Two Separate Private Studios with a small private hallway attaching the two Studios. - 2 Bedrooms | 2 Bathrooms - King sized beds in each studio - Air Conditioning in Every Room - Blazing-Fast Wi-Fi - Parking for 2 cars - Kitchenette in each studio - Dining table in each studio - Sofa in each studio with TV - Two separate outdoor patios A private entrance leads to a staircase where, at the top, you'll find a small hallway with two separate lockable doors—each opening to its own studio. Whole Foods, Target, Shopping, and Dining are just minutes away! There is reserved parking for 2 cars. All bedrooms and bathrooms are stocked with towels, linens, blow dryers, shampoo, conditioner, soap, and toilet paper. Each kitchenette has a mini fridge, microwave, sink, countertop space, utensils, plates, cups, cookware, coffee maker, and toaster. 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

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Kailua, Hawaii, United States

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Bath

Sleeps

$491.7

Just steps from the white sand shoreline of Kailua Beach, Ranch Beach House offers a private, garden-surrounded setting designed for relaxed island living and effortless indoor outdoor flow.brbrSet along one of Kailua’s most desirable residential loops, this single-level home sits behind a gated entrance and fully fenced tropical landscaping. The result is a calm, secluded retreat that feels tucked away while remaining close to cafés, boutiques, and farmers’ markets. Inside, vaulted ceilings, skylights, and an open layout bring in natural light and gentle breezes throughout the day.brbrWhat You’ll Love About Ranch Beach Housebr• Just steps to Kailua Beach across a quiet private lanebr• Fully fenced yard with spacious deck and multiple lanaisbr• Vaulted ceilings with skylights and bright interiorsbr• Private outdoor shower surrounded by lush greenerybr• Ideal monthly rental for couples or small familiesbrbrLiving & DiningbrThe open-concept living area connects seamlessly to both the garden lanai and the main deck, creating an easy flow between indoor and outdoor spaces. Comfortable seating, split air conditioning, and a large Smart TV make this a welcoming place to unwind after beach days. The dining area sits just off the kitchen and opens directly to the outdoor deck for relaxed meals at home.brbrChef-Ready KitchenbrThe kitchen is well equipped for everyday cooking during longer stays, featuring modern appliances, generous counter space, and essential cookware. Whether preparing simple breakfasts or casual dinners, the layout supports easy, functional use.brbrOutdoor OasisbrOutdoor living is central to the Ranch Beach House experience. The main deck features an umbrella dining table and chaise lounges, while a secondary lanai off the living room provides a quieter retreat. A private outdoor shower offers a refreshing rinse after time at the beach, tucked into tropical landscaping for privacy.brbrSleeping Quartersbr• Primary Bedroom: Queen bed, garden view, split A/C, private access to the deck and yardbr• Guest Bedroom: Queen bed, split A/C, ensuite half bathroombrbrA hallway bathroom includes a double vanity, full bathtub, and shower.brbrExtrasbr• High-speed Wi-Fibr• Smart TV with cablebr• Washer and dryerbr• Beach towelsbr• Private entrance with keypad accessbr• One dedicated parking spacebr• Outdoor lighting and in-room safebrbrNearbybrWalk:br• Kailua Beachbr• Local cafés and coffee shopsbr• Boutiques and neighborhood marketsbr• Farmers’ marketsbrbrShort Drive:br• Kailua Town dining and shopping districtbr• Golf coursesbr• Hiking trails and coastal lookoutsbr• Wellness studios and spasbrbrGood to Knowbr• This property is offered as a monthly rental. The monthly rate applies in full regardless of length of stay.br• The home is reserved exclusively for the renter for a full 30-day period.br• Utility fee of $500 per month applies to stays of 21 days or more.br• No pets permitted.br• Smoking is not allowed.br• Free on-site parking for one vehicle.br• Tax ID: TA-129-806-1824-01br• TMK: 430130190000brbrReserve your dates at Ranch Beach House and settle into the rhythm of Kailua life. From morning walks along the shoreline to quiet evenings on the lanai, this private beachside retreat offers a comfortable, well-located home base for an extended island stay.

Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House

Kailua, Hawaii, United States

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Bath

Sleeps

$480.12

**Please note--beginning Sept. 25, 2025 only 90 Day rentals and longer will be accepted.brbrWelcome to paradise! Discover this adorable 4-bedroom gem in Kailua only 4 houses from magnificent Kailua beach. We are on a private lane with path to beach.brbrThis charming house has been completely renovated with new kitchen and bathrooms, hardwood floors throughout main house and all brand new furniture and bedding. Private yard with outside seating and dining. There are 3 bedrooms and one bath in the main house and an attached bedroom with bath and loft area that are accessed from a separate entrance. Fully stocked kitchen. washer/dryer, AC, Smart TV and WiFi. Double Kayak, 3 bikes, snorkels, boogie boards, beach chairs.brPlease Note--Beginning in 2026, there will be an additional bathroom creating a true primary suite--so 3 total.brbrThe house is a 2 min WALK to Kailua beach down a private lane (ignore the VRBO map and stances). Kailua Beach is often rated one of the best beaches in the world. The house is a 15 min. walk or 5 min. drive from Kailua Town. Kailua is a charming town with many delicious restaurants and shopping for everyone including:brIsland Snow, Lanikai Juice, Kalapawai Market, Kailua Beach Adventures, Mahina and so much more! Additionally, there is a Target and Whole Foods in town for your convenience.brbrThe house is close to many great hikes including the Lanikai Pillbox hike--a great way to watch the sunrise! Or you can just walk to the end of our lane and watch the beautiful sunrise over the ocean, then walk down the beach to Kalapawai Market for their amazing Kona coffee--our favorite way to start the day. Come experience the phenomenal comfort and convenience this property has to offer. We look forward to welcoming you to our place.brbrbrThe property will be exclusively available to the renter for a total of 90 days, and no one else may occupy it during that period, even if you leave early. Rates are based on a 90-day rental period. Ask about possible longer-term discounts. Hawaii GET TAT and OTAT are charged. TA-100-709-7344-01 TMK143015028000brbrbrIf the rental period is confusing, please send a message with questions before submitting a booking request. Additionally, we offer a multi-month discount. All bookings are subject to approval.

Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi

Kailua, Hawaii, United States

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Bath

6

Sleeps

$1686.55

Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short drive to the heart of Kailua town. This is a Legal, licensed vacation rentalNUC#90/BB0034. You will feel like you are visiting old Hawaii in this classic home. Enjoy modern conveniences like AC in every room and new kitchen and bathrooms. brWe invite you to experience the beauty of Kailua!!brWe are located in a quiet Kailua neighborhood called Kaimalino—a short walk away from Turtle Beach. We are walking distance from a grocery store and restaurants but away from the busier Kailua town. We are close to the H-3 on ramp which can get you to the airport in 25 minutes. Sand bar and fishing charters available for additional fee if available.brbrThe State of Hawaii is welcoming visitors with negative COVID tests and allowing legal vacation rentals starting this week! We are so excited to welcome you back to Ka Hale Lai!!brSorry no discounts or extended term rates!

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.

Kailua, Hawaii, United States

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Bath

8

Sleeps

Select Dates for Price

This cozy, beachy bungalow is right across from the manicured and security patrolled Kalama beach Park entry onto the world-famous Kailua Beach. Listen to the sounds of the waves at night as you relax after your long work and/or fun-filled beach day. The studio is bright and clean with air conditioning, a full kitchenette, futon or twin bed, clean bathroom, with separate large shower and full bathtub. Garbage disposal in enlarged bath sink, individual lanai, shared outdoor laundry/drier. Carport hosts shared and separate living and parking spaces on the property's private gated entrance. Home has two small breed dogs and a cat now, all very friendly, so pets based on my discretion with additional $500 non-refundable pet-deposit upon move in date. Non-smoking on the property grounds. No tolerance regarding illicit/illegally obtained Rx or non- drugs /paraphernalia/discussion/guests invited or within visibility of the property.brbrThis is our family home, and we are fortunate, with more space than we need. brbrWe are in the perfect location! Why 5–10-minute commute to either MCBH gate in Kaneohe, or bike to PT! Heading the other direction, Kailua attracts millions of people a year and parking is hard to come by! You don’t need to drive to the beach or stores if you don’t want too! We are one street over from the pathway to Kailua Beach! We are within a mile to bike, windsurfing and kayaking rentals. We are also a mile to Whole Foods, cute shopping boutiques and restaurants. We are about a 25-minute drive to Waikiki, 50 minutes to the North Shore but just a few minutes' walk to one of the best beaches in the world without the hassle of parking. The space has a wall unit air conditioner and a ceiling fan. The kitchen has an air fryer, coffee maker, microwave, toaster oven, refrigerator and pots and pans. The studio is attached to our home, and we are a family, but we do our very best to keep quiet. But please keep this in mind if you are looking for super quiet. Free washer and dryer for guests.

Kalama Beach Studio

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$470.71

Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated on a beautifully landscaped property which will lead you to a lusciously landscaped garden with outdoor dining & BBQ. There is a private fenced-in area in the back with relaxed seating to enjoy your morning coffee and to take in the Hawaiian air.brbrNewly and thoughtfully renovated with Hawaiian inspirations and has all your modern day comforts. You have free on-site parking and easy access to our outdoor shower. This spacious 1-bedroom cottage unit is a permitted short term rental which means you can stay for a few nights or as many nights as you would like. Our accommodation is thoughtfully and carefully aid out and has all the modern day comfort features such as mini-split air conditioners, fully equipped full-size kitchen with Keurig coffee machine, drip coffee, toaster, induction stove, microwave, and all the essentials to cook and eat your meal. Super comfortable memory foam king size bed, indoor and outdoor dining area and if you need to bring your work, we have a sit-stand desk with super fast WiFi and CAT 5 network cable. There is a queen size sleeper sofa in the living room and a blue tooth enabled vinyl record player with Hawaiian records. We’ve got many more top notch details throughout. Super comfortable, extremely clean and modern with everything you need for a wonderful stay. You have free use of our beach cruiser bicycles, beach towels, beach tote, coolers. We worked hard to think of all the details so you have a super comfortable and wonderful stay. brbrWe are centrally located in the heart of Kailua. Kailua is best known for having the best beach in the world as well as a charming Kailua town. We are walking distance to Kailua Beach, Kailua Town, boutique shops, cafes, restaurants, bars, breweries. Kailua is a bike friendly town. Make us your home base and you’ll be 15-45 minute drive from many of the main attractions around the island.brQuiet time from 8 PM till 8 AMbrNo events No parties.brNo pets.brNo smoking or vaping on the property or in the units. brNo open flames, candles or incense. No business activities.brbrbrWash off sand and salt water in the outdoor shower before entering the units.brShake off all sand from clothes and towels before using the washer and dryer.brbrFlush ONLY toilet paper down the toilet. Absolutely NO sanitary items, wipes or towelettes down the toilet.

Guest House

Lovely Private Kailua Cottage

Kailua, Hawaii, United States

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Bath

Sleeps

$2824.14

Escape to Hale Aloha by Gather, a serene four-bedroom, two-bathroom waterfront retreat nestled at the end of a peaceful Kailua cul-de-sac. This 1,810-square-foot sanctuary sits on an expansive 12,000-square-foot lot, blending island charm, privacy, and modern comfort with a picturesque pool and lush tropical surroundings.brbrWhat You’ll Love About Hale Aloha by Gatherbr• Waterfront setting with panoramic views of the Mid Pac golf course and Koolau Mountainsbr• Private pool with vibrant blue tiles and spacious pool deckbr• Modern kitchen with stainless steel appliances and granite countertopsbr• Four queen bedrooms, each with split A/C and mountain or garden viewsbr• Peaceful cul-de-sac location, just minutes from Kailua Beachbr• Outdoor BBQ and lanai dining area for relaxed entertainingbrbrLiving & DiningbrHale Aloha welcomes you with an open and airy floor plan that invites natural light throughout. The living room features comfortable furnishings, island-inspired décor, and large sliding doors that connect seamlessly to the lanai and pool area. Enjoy movie nights or unwind with tranquil views of the surrounding tropical landscape.brbrChef-Ready KitchenbrThe spacious kitchen serves as the heart of the home with modern cabinetry, stainless steel appliances, and granite countertops. Fully equipped for all your culinary adventures, this kitchen makes preparing meals a pleasure—whether it’s a quick breakfast before heading to the beach or a family dinner after a day of exploring.brbrOutdoor OasisbrStep outside to your private paradise where lush foliage, a shimmering pool, and sweeping views create the perfect backdrop for relaxation. The pool area is complemented by ample seating, a BBQ grill, and a grassy yard ideal for lounging or dining al fresco. Enjoy morning coffee by the water or an evening cocktail under the stars.brbrSleeping Quartersbr• Primary Bedroom – Queen bed, ensuite bath, garden and mountain views, ceiling fan, split A/C, dresserbr• Guest Bedroom 2 – Queen bed, mountain and garden views, ceiling fan, split A/C, closetbr• Guest Bedroom 3 – Queen bed, mountain and garden views, ceiling fan, split A/C, closetbr• Guest Bedroom 4 – Queen bed, mountain and garden views, ceiling fan, split A/C, closetbr• Additional Sleeping Arrangement – Queen sofa bed in the living areabrbrExtrasbrThis home includes a washer/dryer, Wi-Fi, private parking, and split air-conditioning throughout. Guests will also appreciate an outdoor shower for rinsing off after beach days, along with security cameras located at the front door and garage for added peace of mind.brbrLocation HighlightsbrSet near world-renowned Kailua Beach, Hale Aloha is perfectly positioned for both relaxation and adventure. Spend the day sunbathing, kayaking, or windsurfing, then explore nearby Kailua Town’s charming shops, local boutiques, and dining favorites like Buzz’s Steakhouse and Island Snow. With easy access to hiking trails and water activities, every day brings something new to discover.brbrGood to Knowbr• Monthly rental only (30-day minimum per Oahu ordinance)br• Fixed monthly rate applies regardless of nights stayedbr• No safety fence around pool; children and non-swimmers must be supervised at all timesbr• Exterior security cameras located at front door and garagebr• No screen doors on patio doorsbr• TA-195-940-3520-01brbrLet Hale Aloha by Gather be your gateway to the true essence of island living—where serenity meets sophistication, and every day feels like paradise.

Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach

Kailua, Hawaii, United States

Bed

Bath

8

Sleeps

$772.69

Sprawling oceanfront 5BR/5BA compound, steps to Lanikai beach.brbrShare meals and play games in the oceanside backyard. Walk 5 minutes to gorgeous days on Kailua Beach Park or just steps to iconic Lanikai Beach.brbrFurnished fully-equipped kitchen. Two parking spaces.brThe spacebrLIVING AREASbrHawaiian sunshine showers onto inviting social spaces in the main living area. Spot sea turtles out huge ocean-view windows or watch favorite shows on the 50” TV. Three full-size beds provide additional sleeping space.brbrKITCHEN & DININGbrPrepare delicious meals with island ingredients in the main house kitchen, equipped with ample counter space and a full suite of helpful appliances. Numerous tables provide plenty of dining options.brThe attached apartment is fitted with a convenient kitchenette.brbrBEDROOMS & BATHSbr1BR/1BA attached apartment and 4BR/4BA main house (plus three full-size beds in the living area). Perfect for groups, each bedroom has private yard access.brbrLocated in the main house, the ocean-view master suite features a queen bed and direct access to a private patio. The en-suite bathroom is configured with a walk-in shower.brbrFour more bedrooms each hold two queen beds, while the guest bathroom features a walk-in shower. You’ll also find two convenient half baths alongside two bonus washrooms with walk-in showers.brbrThe attached apartment includes a queen bed and direct access to a private deck. An en-suite bathroom has a walk-in shower.brbrOUTDOOR AREASbrRelax under mature palm trees in your private oceanfront backyard. The lush front yard features a gas grill and another picnic table.brbrEXTRA AMENITIES & MORE DETAILSbrGuest amenities include complimentary Wi-Fi, a washer/dryer, and parking for two cars in the driveway.brAll leases require a minimum 31-day term.brbrGuest accessbrAll areas of the property except the garage with attached guesthouse.brLicense numberbr430080460000, TA-052-469-8624-01

Waterfront Lanikai Beach Compound

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$403.71

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

Bed

Bath

12

Sleeps

$155.39

This fully furnished, turn-key, spacious 1-bedroom, 1-bath, is part of a private, gated, rambling plantation-style property. The 2nd LEVEL apartment catches the ocean breezes and comes with a window A/C in the bedroom, large living area and dining area. Street parking, shared pool, washer/dryer, and poolside bathroom. An outside refrigerator is perfect for keeping drinks cold by the pool while entertaining friends and family.br br The property is 75 yards from LANIKAI Beach access and 1 block away from Lanikai Park. Located 10 minutes from Kailua Town shopping and restaurants. It is 6 miles from Marine Corps Base Hawaii, and 21 miles to Joint base Pearl Harbor Hawaii. Easy access to Pali Highway, Likelike Highway, and H-3.brbr All utilities, cable, and wifi internet access are INCLUDED in the rent. (Sorry, no pets and no smoking.) brbr This property is a legally established dwelling. The City and County Ordinance requires a 30 day rental contract, but does require a minimum amount of days the traveler must stay. As the ordinance is confusing to most, please contact the property manager at (808)354-1436 if you have any questions.

Apartment

LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach

Kailua, Hawaii, United States

Bed

Bath