Vacation Rentals By Owner In Kailua, HI

State of Hawaii Transient Accommodation Registration: TA-046-155-5712-01brbrIn compliance with the revised ordinances of the City and County of Honolulu, the minimum rental period for this property is 30 days. This property, a legally established dwelling, will be available for your occupancy for a minimum of 30 days. Schedule your stay for as long or as short as you like. Feel free to reach out with any questions regarding the length of stay and availability.brbrYour fully furnished cottage with On-site parking, equipped with A/C, W/D, Integrated sound system to a smart phone, walk in shower for two, smart TV, Cable and free Wi-Fi is just a short five minute walk to beautiful Kailua Beach, a two mile stretch of sparkling white sand and turquoises waters. Adjoining Lanikai beach is just a couple more minutes walk away. Both have been rated among the best beaches in the USA.brSome of Oahu's best hiking trails are also in close proximity to our location. brbrbrbrbrbrbrbrbrbrbrbrbrSwim with the green sea turtles. Kayak or sail to one of the secluded offshore islands to enjoy the best Hawaii has to offer.brbrLocated only a few houses from beautiful Kailua Beach Park. This tastefully decorated and fully furnished studio, king sized bed, provides the perfect vacation spot in paradise.brbrWith more than 50 years of Kailua residency, your hosts will gladly suggest sights and adventures to help you have the very best vacation possible.brbrKeywords: Cottage - Attached

Cottage

Footsteps to Hawaii's Best Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$4253.84

As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.brThis luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises and step onto the beach from your very private and modest oceanfront estate. This Beachside Villa is the perfect estate whether you are a small family wanting total privacy while having an intimate vacation or a larger group looking for a large and open space with full suite sleeping quarters. brThis property captures the calmness of Beachside in Kailua along with the outdoor beauty as there are tons of large windows and doors creating endless ocean and mountain views. This amazing spacious luxury villa is surrounded by the beauty of the Pacific Ocean and white sandy beaches where Kailua Beach has year after year been named one of the top beaches in the world.brThis one-of-a-kind elegant beachfront villa is complemented by a lovely interior designed grand entertaining room with full A/C and huge windows with large sliding glass doors that lend to the indoor-outdoor living. Your private chef will create the perfect meal for you and your family and friends in this gourmet kitchen outfitted with subzero and wolf appliances.brEvery Bedroom has full en-suite bathrooms along with luxurious mattresses for that perfect night’s sleep. Each room affords its very own level of comfort and privacy with amazing views throughout. The upstairs primary room has vaulted ceilings, 2 lanais, and a spa-like bathroom with floor-to-ceiling windows overlooking the ocean and Mokes with a vessel tub and a very expansive walk-in shower. brThe palatial villa offers a total of 6 bedrooms, 5.5 Bathrooms with the capability to sleep 18 people. This home comes with luxurious linens, bathing towels, and a starter set of toiletries including lotions, shampoo, and conditioner. This kitchen has more than anything you or your private chef could want. All you need to bring is your swimsuit and toothbrush. For your daily fun at the beach, we have included Beach Chairs, Umbrellas, Beach Towels, Boogey Boards, SUP Boards, and Kayaks.brThe monthly rent includes water/sewage, gas, internet w/ WIFI, monthly gardening service, jacuzzi, and weekly maid service. To see the video go to 25 Wilikoki dot com.brNot included in rent are any electric bills over $450/month, GET and TAT (Taxes) charges along with required renters insurance which we can help you acquire if needed. There is also a vehicle available for rent if needed. Any utilities over $450/mo. will be taken out of the security deposit and proof of expenses will be provided.br90 -Day Rentalbrbr***This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX ID TA- TA- TA-048-077-3632-01

Luxury beachfront villa on a world class beach in Kailua, HI

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$339.32

Large Studio with roomy bathroom beside a quiet home. Enjoy your coffee on your own patio near the pool overlooking the canal where you can kayak or paddle board to beautiful Kailua Beach. Quiet, private and clean. We supple you with a start of necessities. Walk to market and excellent restaurants all nearby. This town has many Farmers/Craft markets weekly. You will love everything we have to offer for a perfect vacation.

Peaceful Hawaii Paradise three minutes from Beautiful Beach in a quaint Town

Kailua, Hawaii, United States

1

Bed

1

Bath

2

Sleeps

$365.55

Yes, we are a legal, licensed bed and breakfast. We are available and legal for stays of less than 30 days. We are not effected by the recent controversy which effect unlicensed bnbs in Honolulu. See license numbers below.brbr Walk to beach from Hawaii Sheffield House. Located just 10 houses from Kailua Beach the Garden Suite has a queen bed and single bed sized day bed/with trundle and a delightful window seat which is also the size of a single bed. It has a private entrance and a private bath. brbrThe Garden Suite is a ground floor unit and has a one step entrance. There are ceiling fans in all of the rooms as well as quiet split system air conditioning. Yes, we are in the tropics. Yes, there are geckos , anoles and chameleons and insects. Yes, we use pesticides.brbrSheffield House is located in a neighborhood only a short walk (10 houses) from secluded Kailua Beach - one of the best beaches on Oahu. Sunbathe or swim in the cool water or just walk on the white sandy beach. On breezy days watch the windsurfers, or look for sea turtles between Flat Island and Kailua Beach Park. brbrTake advantage of waking up early from the time zone change and walk down to the beach to watch the sun rise out of the ocean over the Mokulua Islands. Or once a month check out the full moon rise out of the ocean. Bird watching is superior over the canal at Kailua Beach park or in Kawainui Marsh. See stilts, herons, or iwa birds. br. br A parking space for this unit is in the driveway just steps from the entry to this unit.brbr It rents from $259-$325 per night for a party of two. A $30 extra per person charge. At this time we are not taking children under the age of 3 in this unit . We only take small children when 30018 is rented together with VRBO 572484 as a two bedroom two bath unit..brbrIt has Mexican tile floors and Hawaiian quilts on the beds.brbrThe kitchenette in the Garden Suite has kitchen cabinets with granite counter tops, a half size refrigerator, hot plate, toaster, microwave, electric frying pay, and coffeemaker. It has an outdoor garden area with umbrella, table and 4 chairs . Towels, beach towels and paper towels are provided. Yes, we provide a hair dryer. A charcoal grill is provided upon request for your use in the garden area.brbr We offer internet and high definition cable TV.brbrIt has off street parking, phone, tv, and wifi. A complimentary breakfast or snacks of: Hawaiian juice, fruit and coffee or tea, is provided for your first morning. Upon arrival or while you are here you will meet Paul or Rachel Sheffield. Yes, we need to know your arrival timebrbrCheck in is 3 p.m. and check out is at 10 a.m. There is a $30 per person extra person charge. No refunds will be given . Due to our residential area we have a quiet time between 10 p.m. and 6:30 a.m. Also note that there is a community pool only 13 houses up the street. Also, there are 2 coin operated laundromats 1/3 of a mile away.brNote we are a non smoking property and this a NON SMOKING UNIT. br br We love sharing our corner of paradise with our guests.brbrWe have offered hospitality for over 30 years in Kailua, HawaiibrYes, we have a minimum night stay. However, always inquire to Hawaii Sheffield House as we will take shorter stays if it is between longer stays or last minute if the room is available! Hawaii Sheffield Housebrhas been in business over 25 years. ( Yes, we have been in business so long we are older than the internet! We are still listed in guidebooks such as the Lonely Planet , Frommers, and Foders. We have been listed in the magazine Coastal Living and the Los Angeles Times ! ) brbrWe have recently become interested in astronomy. Ask about upcoming events at the Windward Community College observatory.brbrbrHawaii Sheffield HousebrKailua , Oahu Hawaii 96734brbrHawaii License Number - HI TA137-360-9984-01brCity and County of Honolulu -License No. 90/BB-0077brbrThe Ginger Studio VRBO 572484 also has a queen bed. Rented together both can sleep a total of 4 people in beds, plus 1 on the single daybed (with trundle) couch or a small child in the single bed sized window seat.brbr:Kailua, Vacation Rental, Suite , Studio, Walk to Beach, Walk to Kailua town. Bed and Breakfast, Kailua Hotel, Kailua Motel, Oahu Motel, Oahu Hotel, Kailua Home, Kailua House, Hawaii Near Beach, Convenient to Kailua Whole Foods. Can Sleep 5 when rented with adjoining VRBO 572484.brVideo here:brhttps://tours.360aaa.net/public/vtour/display/906421#!/

Available and legal for stays less than 30 days

Kailua, Hawaii, United States

Bed

Bath

Sleeps

Select Dates for Price

Relax in the beautiful three-bedroom seaside villa in Kailua, where soothing sea waves and soft breezes carry you off. Indulge in the outdoor pool, where you can soak up the sun and relax and end a day of hiking or golf with a massage in the oceanside hot tub. Stay connected with the high-speed WiFi, and enjoy the convenience of the in-unit washer and dryer. Curl up on the couch and stream your favorite shows on the smart TV. In the cool evenings, there's a firepit on the ocean deck to relax at the end of a day while listening to the sounds of the ocean waves. The deck has cafe lights to provide just the right amount of light to enjoy the evenings. brbrVenture out and explore the top nearby attractions, including the vibrant Honolulu Harbor, the bustling Ala Moana Center, and the lively Waikiki Beach Walk, all within a short drive. Back at the property, you'll find a fully stocked kitchen, perfect for whipping up delicious meals. Savor your culinary creations at the dining table, or step outside and fire up the grill for an al fresco dining experience. brbrUnwind in the comfortable bedrooms, each with its own bathroom, and enjoy the luxurious amenities, including air conditioning, linens, and a hair dryer. Venture out to the balcony and soak in the breathtaking ocean views, or relax on the beach loungers with a good book. With games, a stereo, and toys for the kids, there's something for everyone to enjoy at this enchanting beachfront retreat.brbrThis house has never been listed on Craigslist. Any listing besides VRBO is a scam and should be avoided. The owner will not honor any rental from Craigslist.

Kailua Oceanfront Villa with Heated Pool & Spa

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1026.97

From the moment you arrive at Hale Wailele (Waterfall House), tropical scenes take your breath away. Perched above the Kona Coast, this spectacular home invites you to unwind in complete comfort. Enjoy expansive ocean views, indoor-outdoor living, and evenings spent watching the sky melt into the sea. This spacious home with floor to ceiling windows in the great room looking out onto fountains in the pool with an incredible ocean view beyond the palm trees and torches connects you to the ocean, to nature, and to each other. The architecture of the home highlights open spaces, cooling breezes and peaceful privacy. Hale Wailele surrounds you with beautiful architecture and artistic touches such as arches, niches, cathedral ceilings, gorgeous paintings, music and sculptures throughout.brbrOur home is in a quiet neighborhood where most people live with open windows. Therefore, we do not offer it for weddings, meetings, or parties. The use and enjoyment of the house, pool, etc. is limited to the individuals listed on the rental agreement. We will only confirm reservations that give details about the group, purpose of the trip, and reassurances about being respectful and keeping noise at normal conversation levels. Disruptive behavior and excessive noise are not permitted.brbrThe primary bedroom is furnished with a king bed, TV, garden tub with separate shower, Toto bidet commode, and infra-red sauna. brbrBedroom two has a king and a queen bed, and full guest bath. brbrBedroom three has a king bed, and sitting area and full guest bathbrbrThe den has a TV, recliner, and a pullout sofa. It opens to a side yard perfect for game of croquet or bocce. The den and bedroom three share the full guest bath.brbrThe loft looks over the great room, has a computer desk, foosball table, 2 queen futons and 1 double futon.br The gourmet kitchen features stainless appliances and two adjoining dining areas with ocean views. There are also two bar areas- all focused on the gorgeous view and pool area.brbrIf you prefer to cook and dine on the lanai, we have a large stainless gas grill, and an Evo grill. There is plenty of seating at two lanai tables.brbrTropical gardens surround the home on the spacious one acre lot. Outdoor enthusiasts will love the orchid garden, herb garden and extensive assortment of flowers and fruit trees including, papaya, lemon, lime. apple-banana, avocado, fig, and mango. brbrThere are 3 smart-home features installed. 2 Nest doorbells, one at the front door and one at the side door (both facing parking areas); and a smart lock, that will be programmed with a code to unlock the door, for your convenience. brbrAlso a quick note about our animal friends :)brbrGeckos: Because of the tropical climate and vegetation in Hawaii you are likely to see our friends the geckos. They are a beautiful bright green with a few magenta spots. They have no teeth, are harmless, and considered good luck on the islands because they eat harmful insects. They are most easily spotted outside by lights waiting for dinner, but can fit through the smallest openings and are sometimes seen inside as well. If you see one inside and prefer not to have its company, please just toss a hand towel over it and release it into the gardens. brbrBirds: There are many birds around the house and throughout the neighborhood including Brazilian cardinals, finches, doves, exotic pheasants, chickens, and others. While they are fabulous to watch and a favorite part of the tropics, they can also be noisy for light sleepers. We recommend adding a sleep app to any smart phone or bringing earplugs if you think you might be bothered. brbrPlease include the correct number of guests, information about your group, and purpose of your trip with your inquiry. Mahalo!

Breathtaking Kona Estate. Panoramic Ocean Views, Waterfalls, Pool and Spa.

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1002.11

Set along Kailuana Loop on Oahu’s beautiful windward coastline, Hale Ohana by Gather offers a spacious, family-friendly retreat designed for easy island living. With nearly 3,000 square feet of indoor-outdoor space, a private pool and hot tub, and a dedicated guest wing and game room, this home brings comfort, fun, and connection together in one inviting place.brbrWhat You’ll Love About Hale Ohanabr• Private pool, hot tub, upper deck BBQ, and rooftop deck with peekaboo ocean viewsbr• Game room with ping pong and classic Spider-Man pinballbr• Spacious floor plan with seamless indoor-outdoor livingbr• Gourmet kitchen with premium appliances and two islandsbr• Split A/C throughout, plus ceiling fans in all bedroomsbr• Multiple indoor and outdoor lounge areas designed for families and groupsbrbrLiving & DiningbrLarge sliding doors open the main living areas to the outdoors, creating a bright and welcoming place to gather. Relax in the comfortable seating areas or enjoy meals in the spacious dining room overlooking the garden. With several lounges throughout the home, everyone can find space to unwind.brbrChef-Ready KitchenbrWith two islands, top-tier appliances, warm wood cabinetry, and generous prep space, the renovated kitchen is ideal for everything from casual breakfasts to full family dinners. Steps away, the upper deck offers a built-in BBQ with pool and treetop views.brbrOutdoor OasisbrDays move easily between the covered lanai, sun patio, and private pool. A tranquil waterfall feature sets a relaxing tone while the hot tub invites evening soaks. The rooftop deck is the perfect place to enjoy soft trade winds and peekaboo ocean views. Outdoor seating and dining spaces make al fresco living effortless.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath with shower and double sink, garden and pool views, split A/C, ceiling fanbr• Guest Bedroom 2 – Queen bed, garden view, split A/C, ceiling fan, loveseat, shared bathbr• Guest Bedroom 3 – Double bed, split A/C, ceiling fan, shared bathbr• Guest Bedroom 4 (Guest Wing) – Queen bed, split A/C, ceiling fan, located beside the game room; full bath nearby with exterior accessbrbrExtrasbr• Game room with Spider-Man pinball, ping pong table, and lounge spacebr• High-speed Wi-Fibr• Split A/C throughoutbr• Washer and dryerbr• Beach gear including chairs and umbrellasbr• Multiple lanais and outdoor seating areasbrbrCommunity HighlightsbrExplore the nearby coastline with ease. Public beach access is a short walk from the home, while iconic spots such as Waimanalo Beach, Makapu’u Point Lighthouse, and the Pali Lookout are just minutes away. Kailua’s dining, shopping, and golf courses are close by, and Nico’s restaurant is within walking distance.brbrNearbybrNearby – Walk:br• Public beach access (5–7 minutes)br• Nico’s restaurantbr• Local shops and cafésbrbrNearby – Short Drive:br• Kailua Town dining and shoppingbr• Hiking at Makapu’u Lighthouse and Pillbox trailsbr• Waimanalo Beach and water activitiesbrbrGood to Knowbr• This home is offered as a monthly rental; the full monthly rate applies regardless of nights stayedbr• The property will be made exclusively available to the renter for a full period of 30 days, and no one else may occupy the home during that timebr• Rates based on a 30-day rental period; rates and fees are subject to change, and minimum stay requirements may applybr• Inquire for possible discountsbr• Standard occupancy is 8; maximum occupancy is 10 with additional guest feesbr• Max included electricity usage is 350 dollars; excess usage is subject to additional chargesbr• This property requires a 500-dollar Electric Security Deposit, refunded after checkout if usage remains within the allowable limit and no additional charges applybr• Split A/C throughoutbr• Online bookings are subject to manager or owner approvalbr• Neighborhood beach access is available only for stays of six months or longer; all other guests may use the nearby public beach access point (5–7 minute walk)br• TA-139-302-3488-01br• TMK 430830350000brbrLet Hale Ohana by Gather be your home base for slow mornings, relaxed afternoons, and unforgettable days on Oahu’s beautiful windward shore.

Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$274.02

Nestled in the beachside residential community of Lanikai in Kailua, this home is well appointed with all the creature comforts of a home away from home. It is a separate and distinct 2 bedroom, 1.5 bath cottage. Upstairs is a full kitchen and a living/dining area as well as a convenient half bath. Downstairs are two bedrooms: the master with a queen-sized bed and the second one with two twins. Both share a jack and jill full bathroom. The home is fully furnished, including a TV, books, games, toys as well as beach towels, linens, and an initial supply of paper products and soaps including dish soap, laundry soap and body soap.brbrThe front porch opens out to a very large monkey pod tree, spanning two properties and home to songbirds (manu mele) - our morning serenade!! brbrIt is only a five to seven minute walk to the world famous Lanikai beach, the best swimming beach in all of Hawai’i. The town of Kailua is a seven minute drive, making us close to shopping, some great restaurants and the Kailua Beach Center that rents kayaks and other ocean toys. The property is managed by a long-term resident of Hawaii. brbrPlease contact owner for availability and pricing.brbrPLEASE EMAIL US FROM THIS WEB SITE - CLICK ON THE EMAIL BUTTON BELOW. brbr brbr brbrbr brbrKeywords: separate single family home

Cottage

Little Yellow Cottage: Steps to Lanikai Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$592.57

brWe offer a solar-heated Pool, AC , WIFI, Kayaks, and up to 50% Discounts on monthly rentals. This property is a 2 1/2 to 3 min walk from the sandy beach of Lanikai (the property marker shows the property location incorrectly).brWalk through the entry gate, and find yourself in the middle of your own personal resort. A lush tropical yard greets you as you walk to the front door of this unique traditional beach-side cottage in the up-scale Lanikai neighborhood. The professionally landscaped property creates a welcoming and cool setting even on hot summer days. You just might have trouble pulling yourself (and the kids) away from our beach-entry pool to get over to Lanikai beach with its powder-soft sand, 200 meters away. The pool is always a great hit with young and old with its lagoon feeling. This combined with this property's beach-side location, makes enjoying the unique feel of Lanikai a highlight. brWe are looking forward to sharing our little piece of paradise with you!brbrWindward beaches with their powdery soft sand and gentle protected waters are among the best swimming beaches in the world. The Mokulua Islands off shore have been included in numerous advertisements and movies. brThis home is one of the last few remaining Hawaiian-style beach cottages offering its renters an exceptional tropical setting and truly unique Hawaiian experience. The house has an open floor-plan with an extensive patio deck, which is ideal for island-style indoor-outdoor living and delights with a casual elegance. It even boasts a rare fireplace (for Hawaii). brIt is updated to today's standards, and tastefully decorated, while maintaining its traditional charm. There are two master bedroom suites and one bedroom with an adjoining bathroom off the hallway. All of the bedrooms have wall-unit air conditioning. The 'great room' containing the kitchen, living room, den, and dining area has central air conditioning. The kitchen has marble counters and modern appliances. Hardwood floors throughout are easy on your barefoot feet. brWe welcome families with children. Our typical group is 4 adults plus 2 children. Our max. is 6 adults at any time. We welcome children two-yrs and above. If you have other needs, please inquire.brbrADDITIONAL INFORMATION:brbr1. The rental will be exclusively reserved for one rental party for 30 consecutive days, even if the rental party occupies late or vacates early, and only uses a portion of the time booked. We require a 30-day rental contract.brbr2. Rates and fees are subject to seasonal change, special discounts, how many bedrooms are rented, and if shared property use is available or requested. We give up to 50% discounts. Please inquire. brbr3. If you are unsure about your guest list, or your guest list changes, please contact the owner before making final arrangements with your guests. Occupancy is limited to the maximum number of occupants on the rental contract for each 30-day consecutive booking period. Guest names and ages must be the same as on the rental contract. We require the main renter, who signs the rental contract, to be physically present throughout the rental period. The house rules listed in the rental contract forms part of the VRBO accepted house rules signed by renter. brbr4. Your safety matters. This property features an exterior security camera which provides a driveway view and a street-side view of the front gate. The camera does not look into the yard or any interior spaces. brbr5. We strive to provide guests with prompt attention when issues arise. Therefore we have engaged an owner representative to help us out in addition to our caretaker services. brPlease see the glowing reviews of previous guests about our representative/caretaker services. brThe owner representative will maintain guests privacy at all times and not enter the main property unless invited or needed. You are on a holiday... we (owner and service providers) are here to make your stay perfect! To accommodate this, we have a fenced-off, detached, and completely separate functioning caretaker house with its own entrance and amenities privately situated on the other end from the main house of our 16'000 sqft property.

Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat

Kailua, Hawaii, United States

Bed

Bath

6

Sleeps

Select Dates for Price

Kailua is a much-coveted beachside town with award winning beaches and the most beautiful tepid waters.brExperience a taste of paradise with laid back island vibes and activities to suit all types of personalities and moods.brAdventures from the mountains to the oceans awaits, with the convenience of modern day living at your fingertips; this space is close to it all. brWake up to birds chirping and a serene atmosphere that inspires you to breathe, reflect and do something healthy and uplifting!brbrbrTHE SPACE:brWe live on a quiet and safe street near the end of a cul-de-sac. brOur neighborhood is spacious with decent sized lots. A lot of privacy between us and our neighbors (unlike many places in Kailua!)brbrINDOOR:brYour unit is a separate suite that is attached to the main house (private walkway and entrance). brThere is a queen bed and a twin day bed. Sleeps total of 3.brRight beside your unit is the entrance to your private kitchen/ laundry area. brThe total indoor living space is approximately 400 square feet. brThe space is fully equipped to make you feel like home. brbrbrOUTDOOR:brYour living space overlooks a large 20x10 foot covered patio with a 6-seater dining set and outdoor lights for a beautiful evening ambiance. brA massive backyard (2,500 square feet) has tropical foliage, plumeria flower trees and breadfruit if you forget to shop and hungry! :PbrIf you are too lazy to drive 5 minutes to the beach you can opt to catch some tan in the yard with the trees to keep your head cool. brAlmost everything is brand new as of July 2023.brThe unit has split AC and high ceilings, making it extra airy and bright. There are blackout curtains throughout on the days or mornings you prefer it dark though :) brYou'll have your own parking spot on street directly in front of the house.brbrPRIVATE KITCHEN/ LAUNDRY: FULLY EQUIPPEDbr• Large capacity washer and dryer br• Full fridge br• Microwavebr• Double burner br• Toasterbr• Large Convection oven (can fit 12” pizza)br• coffee maker br• Blender br• Electric kettle br• Crock potbr• Rice cooker br• Brita water filter br• Pots/ pans/chopping board/ spatulas etc.br• Plates/bowls/ cutlery etc.br• Food storage containersbr• Kitchen towels/ potholders etc.brbrGUEST ACCESS:brbrYou have your own high-speed router set up.brHost may use the back yard from time to time when we are home. brBesides that, all the areas described above is for your use only. brThere is a hose in front, side and back of the house. brI have stand up paddle boards, surfboards, a beach cruiser, and ocean gear like snorkels that you are welcome to borrow.brbrWHATS CLOSE BY:br• Beaches/ ocean- 5 min br• UFC gym (and other exercise facilities) – 4 minbr• Kailua town center (Target, whole foods, restaurant, boutiques etc)- 4 minbr• Enchanted lakes shopping center – 2 min br• Hospital- 5 min br• Hikes (some w/waterfall)- 10-20 minbr• Skate Park -2 minbr• Bus stop- 5 min walkbrbrThe only thing I drive to town for is Costco!brbrGETTING AROUND:br• You can bike everywhere in Kailua easily and quickly. Everything is so close. Super fun way to get around- I have a cruiser you can most likely borrow. br• Bus stop is 5 min walk awaybr• Car is great option if you want to explore the island ( I could have one for rent. Just ask!)brbrMY IDEAL TENANTbr• Single occupancy but open to double.br• Professional, responsible, respectful, and considerate. br• Minimum 3 months (open to 6 month) with option to extend. Will consider 1 month so just ask! br• No smoking on propertybr• Visiting family/ guests allowed for short stays but please inform me ahead of time so I know who and for how long.brbrbrbrABOUT ME br• Sometimes I’m around and sometimes not.br• People describe me as personable, easy going with great vibes and always helpful. br• I am not fussy nor super particular. I only ask you respect my house rules and have open honest communications.br• Let me know if I can help recommend activities to make your stay more enjoyable!br

LARGE KAILUA STUDIO

Kailua, Hawaii, United States

1

Bath

Sleeps

$468.91

RESERVATIONS: 2 NIGHT MINIMUM ... 8 NIGHT MAXIMUM . . br brBOOKINGS OF 8 Nt's OR MORE REQUIRE THE HOST'S CONSENTbrMID-STAY CLEANING; $90, REQUIRED FOR 10 Nt's OR MOREbr2 PERSON ACCOMODATION ONLYbrbrOur Hawaiian Style Vacation Rental apartment is Legally Operated and sits on Kailua Beach, one of Hawaii's most beautiful white sand beaches, and rated among one of the USA's best. brbrThe apartment is in the BACK portion of a beachfront home with it's own private entrance. This spacious room has no view of ocean, but is just steps away from the ocean shore line and large front lawn where you can relax to soak in the panoramic view of the bay. There is convenient FREE parking on driveway just outside the rental unit. The bedroom has one king-size bed and two over head ceiling fans, an 2 table fans for extra ventilation an comfort.. There is a connecting private bathroom and shower supplied with bath towels sets an beach towels. The sitting room includes a couch and lounge chair with leg rest. There are 4 floor to ceiling louver windows for cool breeze flow an additional ventilation. There is NO AC.brbrThe unit also has a large study desk / table, TV with cable, and unit is computer “WIFI” wireless ready. The kitchenette provides a microwave, large sink, Kreuig coffeemaker with 4 complimentary k-coffee cups to start tenants off, Malita coffee drip cup w/ filters, electric hot water decanter, refrigerator with freezer, toaster, dishes & drinking cups/glasses, and utensils. Tenants are responsible for their own food an beverages, and all personal soaps an toiletries and laundry. There is NO Washer/Dryer. Laundromats are 5 min away.brbrRental has direct side walk private access to front lawn sitting area where tenants can relax an enjoy the spectacular panoramic view of Kailua Bay and Mokulua Twin Islands with steps just at the yards corner to beach. Lounge & beach chairs and boogie boards are included for use at rental beach premise only. There are out side hose's and faucets for rinsing off sand after going to beach and swimming. There are convenient clothes lines right outside rental door for drying suits, towels, an clothes.brbrbrRates are based on 1-2 adults and all reservations are made through instant booking on a 'first come' basis.brWe accept tenants 21 years an older . . . We do not accept children, or infants.brAll credit fees of 3% included in rental rates.brbrALL CANCELLATIONS MUST BE MADE:br- 30 DAYS PRIOR TO ARRIVAL FOR FULL REFUND.br- 15 - 29 DAYS PRIOR TO ARRIVAL, HALF REFUNDbr- 14 OR LESS PRIOR PRIOR TO ARRIVAL, NO REFUNDbrbrPRIOR TO ARRIVAL, WE REMIND TENANTS TO PLEASE 'REVIEW AND VERIFY' OURbr br HOUSE POLICIES :brbr* RENTAL FACILITY IS FOR TENANTS USE ONLYbrbr* NO OVERNIGHT GUESTSbrbr* NO MORE THAN 2 GUESTS VISITING AT A TIMEbrbr* VISITING WITH GUESTS MUST BE OUTSIDE ON FRONT br LAWN OR BEACH ONLYbrbr* TENANTS GUESTS MUST PARK ON STREET SIDE BEYOND br CAL-DE-SACbrbr* MICROWAVE COOKING ONLYbrbr* ONE BED UNIT - PLEASE LEAVE COUCH IN UPRIGHT br POSITIONbrbr* NO WASHER & DRYERbrbr* NO PARTIES OR ENTERTAINING IN RENTAL, OR br ON PREMISESbrbr* NO CHILDRENbrbr* SURFBOARDS, BIKES, & LARGE EQUIP MUST BEbr KEPT OUTSIDE ON WALL LEDGE OFF SIDEWALKbrbr* PLEASE TURN OFF ANY LIGHTS, ELECTRICAL APPLIANCES, br AND FANS WHEN NOT IN USE, OR LEAVING RENTALbrbr* PLEASE RINSE SAND/DIRT OFF FEET & BEACH CHAIRSbrbr* PLEASE SHAKE SAND OFF BEACH TOWELS, ETC.. PRIOR br TO ENTERING RENTALbrbr* NO ANIMALS OR SERVICE ANIMALSbrbr* NO SMOKINGbrbrNOTE** WE KINDLY ASK TENANTS TO LEAVE RENTAL STRAIGHTENED IN CONDITION IT WAS IN WHEN ARRIVEDbr br THANK YOU VERY MUCH FOR ADHERING!brbr** This is a licensed rental unit. br~ Hawaii Tax Certificate NUC-90/BB-0029br~ GE/TA tax: 168-049-0496brbrbrbrbrbrbrbrbrbrbrbrKeywords: Apartment

Private Beachfront Rental

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1412.63

Wake up to panoramic views of the Mokulua Islands at Lanikai Oceanside 5 Bedroom, a rare oceanfront retreat blending historic charm with modern coastal design. Once the summer home of Princess Abigail Kawānanakoa, this expansive estate offers direct access to world-famous Lanikai Beach, tropical gardens across more than half an acre, and bright interiors designed for gathering with family and friends.brbrWhat You’ll Love About Lanikai Oceanside 5 Bedroom br* Oceanfront location with sweeping views of Lanikai Beach and Mokulua Islandsbr* Direct beach access just steps from your back lawnbr* 4BR/3BA main house + detached 1BR guest house with full kitchenbr* Historic significance as the former summer home of Princess Kawānanakoabr* Recently renovated with mid-century modern coastal designbr* Expansive yard and gardens with postcard-worthy oceanfront seatingbrbrLiving & DiningbrInside, vaulted ceilings, walls of glass, and tropical-chic accents create a breezy setting that flows seamlessly to the outdoors. Two living areas offer space to gather: one more formal, one casual and cozy for movie nights. The dining space is designed for long, relaxed meals with ocean views just beyond the windows.brbrChef-Ready KitchenbrThe sleek, updated kitchen features ocean-view counters, stainless appliances, and everything you need to prepare island-inspired meals. A separate full kitchen in the guest house ensures added convenience for multi-family groups.brbrOutdoor OasisbrSettle into a lounge chair on the oceanfront lawn as kayakers paddle toward the Mokuluas. Expansive gardens, swaying palms, and multiple lanais offer both sunny and shaded escapes. A large backyard with direct beach access means the sand and sea are always just steps away.brbrSleeping Quartersbr* Primary Suite – Cal King bed, ensuite full bath with dual vanities, lanai, split A/C, ocean viewsbr* Guest Bedroom 2 – Cal King bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest Bedroom 3 – Queen bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest Bedroom 4 – Queen bed, shared full bath, lanai, split A/C, ocean viewsbr* Guest House Suite – Queen bed, ensuite full bath, private lanai, split A/C, full kitchen and living areabrbrExtrasbr* High-speed Wi-Fi and multiple smart TVsbr* Washer/dryer, beach gear, and parkingbr* Expansive property on 25,000+ sq. ft. lotbr* Historic mid-century design details and tropical art throughoutbrbrNearbybr* Walk: Pristine Lanikai Beach and the Lanikai Pillbox Trail for iconic sunrise viewsbr* Short Drive: Kailua town (5 minutes) for cafés, boutiques, and local markets; Waikiki (30 minutes) for shopping, dining, and nightlifebrbrGood to Knowbr* Minimum 30-day rental; full exclusive use of the propertybr* Utility fee of $1,000/month applies to stays of 21 days or longerbr* Standard occupancy is 10 guests (max occupancy 10)br* Pets not allowed; no smoking permittedbr* Hawaii Tax ID: TA-141-510-3488-01br* TMK: 430030630000brbrReserve your stay at Lanikai Oceanside 5 Bedroom and experience oceanfront living with a sense of place, history, and effortless island style.

Gorgeous Oceanfront Home w/Mokulua Isle Views, Yard & AC: Lanikai Oceanside

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$342.28

Only steps to beach through private street gate, and a short 1.5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok. brbrMonthly rentals only - TLA ApprovedbrbrFull kitchen, large deck with grill looking out over the Koolau mountains. brbr2 large bedrooms have queen beds, nightstands, lamps, dresser, closet and ceiling fans; small bedroom has a double bed, and closet. The two baths both have large showers and 1 with a deep soaking tub. brbrWe have bikes, surf & body boards, beach chairs, towels and plenty of snorkel gear for guests to use at Kailua Beach. Great trade winds blowing off the ocean keep the home nice and cool year round. Located between Kalama Beach park and the canal, far enough away from Kailua Beach Park to avoid the crowds. brbrIt is a quiet residential neighborhood so discretion is required and no loud parties. We kindly ask our tenants to keep their guests and visiting to a “minimum Request that guests observe quiet hours from 9:00 pm to 8:00AM. brbrThe world famous Kailua beach (voted the #1 American beach by Conde Naste). Many wonderful local restaurants and shops, along with any water-sport or adventure activity you can think of. Great nearby golf courses, hikes, and other activities to keep you active if desired. brbrThere is 'NO Smoking' permitted in rental premise. brbrKeywords: Retreat, Kailua Beach, vacation Rental, Beach, Home, Casa, Vacation Home, Retreat Home,

Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

Kailua, Hawaii, United States

Bed

2

Bath

4

Sleeps

$991.01

Recent Updates: Newly constructed upstairs deck, Brand new window ac unit in master bedroom, new patio furniture, new sectional couch in living room. brbrOur beach estate is located on over an acre of land, just one house back (a quick 30 second walk down a sandy beach path) to one of the best white sand beaches in Hawaii. This is the only beach in Hawaii to consistently show up as one of the top ten beaches in the world lists. Unlike most beaches in Hawaii our beach is mostly free of tourists so you can actually have space and relax. On weekdays you will virtually have the entire beach to yourself!brbrOur 2200 sq foot home neighbors some of the finest properties on Oahu, just doors down from where the Obama family stays when they come to Hawaii. One of the very few properties that is actually a LEGAL vacation rental and has been since the early 90's, so you can be assured that your rental will be available when you arrive! brbrOur property offers the utmost relaxation and tranquility. Feel the white sand between your toes, bask in the warm Hawaiian sun, dive into the crystal clear aqua waters, and be glad you've made the best choice for your Hawaiian vacation! brbrOur two story house offers Ocean and Mountain Views, one house back from Kailua beach, 30 second walk down a sandy beach path. We are also just about a 5 mine drive to the famous Lanikai Beach. Escape to Kailua, a small beach town located just 20 minutes from Honolulu and Waikiki, truly away from it all! brbrOur home features high speed wireless internet, two flat screen tvs, Hawaiian koa wood cabinets, marble, and crown molding, modeled after the historic residence next door. There is a NEW window A/C unit in the master bedroom (it's the only bedroom that has ac as it doesn't face the ocean) and screens on all windows and fans throughout the house. brbrThere are two large lanais one upstairs (with ocean and mountain views) and one downstairs. Brand new deck as of October 2024. The house is situated on an acre of land with lush landscaping, allowing ample room to lay out in the Hawaiian sun or let the kids play. The yard has beautiful plumeria trees, red hibiscus bushes, orchids, and of course, a coconut grove. brbrThe house has one King bed, two queen beds and two twin beds. We also provide a pack n play if needed. It has two full bathrooms, one with a tub/shower combo the other with a walk in shower. The master bedroom (king bed and a twin) and one full bathroom are located upstairs where the kitchen, dining room and living room are. The other two bedrooms and second bathroom are located on the first floor. The second bedroom has a queen bed and the third bedroom has a queen and a twin. brbrThe kitchen is stocked with everything you need to cook. It has a full sized oven, four burner cooktop, refrigerator/freezer, microwave, dishwasher, toaster and coffee maker. The kitchen has four barstools, perfect for hanging out while meals are prepared or for casual breakfasts. The dining room table seats six and there is also an outdoor patio set complete with tables and chairs with an ocean view. New sectional couch in living room. brbrA full sized washer and dryer are located inside the house for your convenience as well.brbrWe have one security camera located outside to the left of the front door that monitors the driveway to ensure guest and property safety. brbr1990/NUC -1795brTax Map Key No. 430180450002brbrKeywords: House, Kailua, Lanikai, Beach, Watersports, View, Private, Ocean, Hawaii, Relax, Mountain, legal, sand, vacation, estate

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$4288.97

This gorgeous 5 bedroom, 4.5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches within, expanded the gourmet kitchen with all new appliances, a coffee bar and wine fridge. Saltilo tile and wood flooring bring a Mediterranean feel. Every bedroom has a view of the picturesque ocean and world renowned Mokulua islands. The open living space, and an expansive front entry and back yard are perfect for families and large groups.The dining room is located on the lanai overlooking the ocean for indoor/outdoor entertaining at its best. The home is decorated in vibrant color themes complimenting the natural surroundings. Local art throughout the home add a special island feel. The back yard has an outdoor bar, bbq, hot tub, shower, and lounge area. br Just a few steps away is access to a beautiful, secluded white sand beach. Enjoy your days kayaking and snorkeling or just relax on the beach and enjoy the view of the islands. Don't be surprised if you see giant sea turtles swim by or whales jumping out in the distance during the winter months. Fall asleep to the sound of gentle ocean wave and wake up each morning to the most breathtaking sunrises right outside your bedroom. This unique property is truly paradise. br30 day minimum rentalbrTAT Lic. #TA-180-925-6448-01brbrWe are a family owned and operated property. Please check out our other rental homes:brListing#'s 421527, 422462, 422463, 925923, 436336brbrbrbrbrbr

Villa

Gorgeous Lankai Villa with Access to Secluded White Sand Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$833.36

Just steps from the turquoise shoreline of Lanikai Beach, Lanikai Cottage by Gather is a beach-chic 3-bedroom, 2-bath retreat with two separate dwellings on one property and a brand-new private pool. Ideal for families or couples traveling together, this island holiday home blends coastal charm with modern comforts in one of Oahu’s most beloved neighborhoods.brbrWhat You’ll Love About Lanikai Cottage by Gatherbr• Two private dwellings: main house with 2 bedrooms and 1 bath, plus guest studio with bath, kitchenette, and lanaibr• New pool & fenced backyard with sun loungers, covered seating, BBQ, and outdoor diningbr• Two-minute stroll to Lanikai Beach via Pokele Beach Accessbr• Adventure gear included: two kayaks, stand-up paddleboard, bikes, snorkel sets, and boogie boardsbr• Split A/C and high-speed Wi-Fi for easy, comfortable livingbrbrLiving & DiningbrThe main house welcomes you with bright, breezy interiors that open to the front lanai and the backyard. A comfortable lounge anchors the space for relaxed movie nights and post-beach downtime, while the adjacent dining area seats the crew for family meals or game night.brbrChef-Ready KitchenbrCook with ease in the well-equipped main-house kitchen featuring stainless appliances, ample counter space, and convenient flow to indoor dining and the outdoor grill. In the guest studio, a handy kitchenette supports light bites and morning coffee on the lanai.brbrOutdoor OasisbrLinger in the private, fenced backyard where the new in-ground pool glimmers beside swaying palms. Settle into loungers for lazy afternoons, gather beneath the covered seating area, and fire up the BBQ for al fresco dinners. Rinse, repeat, and wander back to the beach for sunrise or a golden-hour stroll.brbrSleeping Quartersbr• Primary Bedroom (Main House) – King bed, Split A/C, ceiling fan, shared bathbr• Guest Bedroom 2 (Main House) – Two twin beds, Split A/C, ceiling fan, shared bathbr• Guest Studio – King bed and sofa bed (sleeps 2 adults + 2 children or 3 adults), ensuite bath with tub/shower combo, kitchenette, living area with TV, Split A/C, ceiling fan, balcony with partial ocean viewbrbrExtrasbr1,469 sq ft of interior living across both dwellings, washer and dryer, flat-screen TVs, high-speed Wi-Fi, and complimentary adventure gear make this vacation rental as practical as it is inviting. It’s an effortless base for families, couples, and digital nomads alike.brbrNearbybrReach Lanikai Beach in minutes via Pokele Beach Access, or launch kayaks to the Mokulua Islets when conditions allow. Kailua Town is a short drive for cafés, boutiques, and Whole Foods. HNL is the nearest major airport for easy arrivals.brbrGood to Knowbr• This property is offered as a monthly rentalbr• The monthly rate applies in full regardless of number of nights stayedbr• Minimum 30-day booking period requiredbr• Standard occupancy 6 guests; max 8 with prior approval and additional feesbr• Online bookings subject to owner or manager approvalbr• Electric Security Deposit: $1,000; refundable after checkout if usage is within limitsbr• Electric allowance: $300 includedbr• Split A/C in main-house bedrooms and guest studiobr• Rates and fees are subject to change; minimum stay requirements may applybr• TAT ID: TA-111-603-0976-01br• TMK: 430040320000brbrReserve your dates at Lanikai Cottage by Gather and enjoy effortless days between the pool, the sand, and the laid-back charm of Kailua.

Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach

Kailua, Hawaii, United States

Bed

2

Bath

6

Sleeps

$724.14

Large 3 BR, 2.5 Bath on quiet family friendly beachside street, steps to private street access to beautiful Kailua Beach! Bamboo floor throughout, new kitchen and baths.brbrSplit AC in all bedrooms.brbrLarge covered lanai, pool, and hot tub. Open floor plan allows for fourth bedroom to be used for office, playroom or bedroom (with air mattress).brbrBasic Cable, Wifi and lawn and pool service included. Private Laundry.br2 car off street parking.brbrJust minutes from Kailua town, MCBH, and H3 accessbrbrMinimum 30 day stay - TLA Approved

Pilipu Palms 2

Kailua, Hawaii, United States

Bed

Bath

5

Sleeps

$1670.33

VIP Luxury Villas welcomes you to Leaf House, a serene three-story sanctuary set above Lanikai’s turquoise shoreline. Sophisticated architecture, panoramic Mokulua Island and mountain views, and over 7,000 combined square feet of indoor and outdoor living create an unforgettable island retreat designed for wellness, connection, and quiet luxury.brbrWhat You’ll Love About Leaf Housebr• Private gated entry leading to a thoughtfully crafted Hawaiian residence on an oversized hillside lotbr• A tranquil pool oasis with waterfall, cabana, outdoor kitchen, fire table, tiki torches, and twinkling evening lightingbr• Sweeping ocean, Mokulua Islands, and Ko‘olau mountain vistas from nearly every levelbr• An expansive veranda shaded by a mature mango tree, perfect for slow mornings or twilight gatheringsbr• Wellness-inspired amenities including an outdoor yoga room, steam shower, whole-home sound system, and private movie theaterbrbrLiving & DiningbrInside, coastal elegance meets artisanal craftsmanship. Jerusalem stone floors flow through the main living level, complemented by hand-woven Balinese-style ceilings and rich Hawaiian Koa wood. A wall of windows frames Mokulua views while inviting natural light into the open-concept living and dining spaces. Host memorable meals around the formal dining table for eight or unwind with ocean breezes on the adjacent lanai, where a fire table sets the tone for relaxed evenings.brbrChef-Ready KitchenbrThe gourmet kitchen is designed for ease and inspiration. Enjoy a gas cooktop, large refrigerator, multiple wine fridges, espresso machine, and abundant prep space. Breakfast at the bar becomes a moment of calm as morning light rises over the Mokuluas.brbrOutdoor OasisbrLeaf House’s outdoor sanctuary feels completely private. Lounge by the pool beside sea-inspired sculptures, read under the cabana’s soft shade, or dine al fresco in the outdoor kitchen. At twilight, string lights and tiki torches transform the setting into a peaceful haven. The upper-level veranda invites afternoon tea, journaling, or family time beneath the mango tree.brbrSleeping Quartersbr• Primary Suite – King bed, ensuite bath with soaking tub and walk-in shower, ocean views, private lanai, split A/C, ceiling fanbr• Guest Bedroom 2 – King bed, partial ocean view, split A/C, ceiling fan, downstairs with reclaimed oak driftwood aestheticbr• Guest Bedroom 3 – King bed, garden view, lanai access, split A/C, ceiling fan, downstairsbr• Guest Bedroom 4 – Two twin beds, partial ocean view, split A/C, ceiling fan, downstairsbr• Guest Bedroom 5 – Queen bed, ocean views, split A/C, located upstairs near the kitchenbrbrExtrasbr• Private movie theaterbr• Steam showerbr• Outdoor yoga roombr• Beach chairs, boogie boards, coolersbr• Basketball, football, and soccer ballbr• Board gamesbr• High-speed Wi-Fi and dedicated workspacebrbrNearbybr• Walk: Lanikai Beach, beach access paths, neighborhood strollsbr• Short Drive: Kailua Town dining and boutiques, Lanikai Pillbox Trail, watersports, golf, hiking, marketsbrbrGood to Knowbr• Monthly rental; full 30-day rate applies regardless of nights stayedbr• No prorated rates; property is exclusively yours for the full rental periodbr• Telescope and massage chair are not available for guest usebr• Construction next door may cause noise or partial view obstruction through 2026–2027br• Tax ID: TA-212-540-3648-01br• TMK: 430020420000brbrReserve your dates now and experience the quiet elegance, comfort, and restorative beauty of Leaf House.

Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1229.51