Vacation Home Rentals By Owner In Honolulu, HI

Welcome to Kahala Grand Splendor, a 5,002-sq-ft luxury retreat in Honolulu, HI, where sophisticated design meets the tranquility of island living. With five beautifully appointed bedrooms and seamless indoor–outdoor flow, this expansive estate comfortably accommodates up to 10 guests. Lush tropical landscaping, a large private pool, and elegant gathering spaces make it an exceptional home for families and groups seeking comfort, privacy, and refined Hawaiian style.brbrWhat You’ll Love About Kahala Grand Splendorbr• Grand living areas with soaring ceilings and abundant natural lightbr• Elegant dining space for eight, perfect for shared meals and entertainingbr• Private pool framed by tropical gardens for serene days in the sunbr• Chef-ready kitchen with high-end appliances and a concealed pop-up TVbr• Expansive yard with outdoor kitchen ideal for grilling and al fresco diningbrbrLiving and DiningbrDesigned for connection and relaxation, the spacious great room features large windows that frame views of the pool and vibrant gardens. Disappearing glass doors invite indoor–outdoor living, creating a breezy, open atmosphere. The adjacent dining area seats eight comfortably, offering an elegant setting for meals with family and friends.brbrChef-Ready KitchenbrThe gourmet kitchen is fully equipped with modern appliances—including a stove, oven, and dishwasher—plus a generous island with bar seating. Garden and pool views create a relaxing backdrop for cooking, while the hidden pop-up television adds a touch of high-tech luxury.brbrOutdoor OasisbrStep outside into your private tropical sanctuary, where a sparkling pool and plush lounge seating invite full days of sun and relaxation. The outdoor kitchen—with built-in grill and countertop space—sets the stage for unforgettable evenings under the stars.brbrSleeping Quartersbr• Primary Bedroom – Upstairs: California King bed, ensuite bath, lanai accessbr• Guest Bedroom – Upstairs Queen: Queen bedbr• Guest Bedroom – Upstairs Office Trundle Room: Twin trundle bedbr• Guest Bedroom – Downstairs King: King bed, ensuite bathbr• Guest Bedroom – Downstairs California King: California King bed, ensuite bathbrbrExtrasbrCentral air conditioning • High-speed Wi-Fi • Full laundry room • Beach gear (towels, chairs, cooler) • Smart TVs • Starter amenities (dish soap, shampoo, paper goods)brbrKahala Grand Splendor Community HighlightsbrLocated in one of Honolulu’s most prestigious neighborhoods, guests enjoy effortless access to upscale shopping and dining, world-class golfing, water activities, and family attractions such as the Honolulu Zoo and Waikiki Aquarium. Diamond Head, sandy beaches, and scenic coastal strolls are just minutes away.brbrNearbybrWalk: Local cafés, boutique shopping, and dining optionsbrShort Drive: Beaches, Honolulu Zoo, Waikiki, hiking trails, cultural sitesbrbrGood to Knowbr• The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.br• Hawaii Tax ID: TA-117-388-6464-01br• TMK 350130320000brbrExclusively offered as a 30-day luxury rental, Kahala Grand Splendor delivers elevated comfort, resort-style amenities, and the serene elegance of Kahala living. Reserve your stay today and experience an unforgettable Hawaiian retreat designed for relaxation, connection, and pure island luxury.

Luxurious Kahala Grand Splendor: Private Home w/Pool, Spa, AC & Lush Landscaping

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$641.45

*please read property description thoroughly*brbrCome stay at my large, private, extra-comfortable, 4 bedrooms 3000 sqft house in a located in beautiful East Honolulu - one of the premier neighborhoods on Oahu. Located at only a 20 minutes drive from Waikiki, East Honolulu is known for its convenience, safety, top rated school districts, and easy access to some of the best hikes/beaches/attractions on the island. The location is close enough to the best dining and shopping options in the city, but far enough to be in your own peaceful world in Honolulu. The house is surrounded by a yard accessible by guests for BBQing. The home is located very close to the best beaches in East Oahu including Hanauma Bay, Makapuu, Waimanalo Beach, Bellows Beach and Sherwood's Beach, as well as some of the best hikes on the island, including Koko Head Stairs, Kuliouou Ridge Trail, Hawaii Loa Ridge Trail, and Mariner's Ridge trail.brThe rental includes:br-Living roombr-Fully equipped kitchenbr-Master Bedroom (king size bed)br-Bedroom 2 (king size bed)br-Bedroom 3 (king size bed)br-Bedroom 4 (two full size beds)br-AC in all bedrooms as well as in the living room (Living room, master bedrooms, and bedroom 4 have new ACs installed in 2023)br-Living roombr-Washer/dryer usage for free (before 9pm)br-ParkingbrbrWe also have everything to make you feel like this is your home away from home, including:br-New 60 4K TV w/ Netflix, and other streaming servicesbr-High speed internet and WiFibr-Cookware, dishware, cutlerybr-Clean sheets, bedding, towelsbrbrbrThe location of the house is in one of the best neighborhoods in East Honolulu. The following are driving times from the house:br-3 minutes to a shopping center that includes a gourmet supermarket (w/ a deli, great wine selection, and delicious poke), Starbucks, McDonald's, Subway, local restaurants, Uncle Clay's shave ice (#1 dessert place ranked on Tripadvisor), a post office, a gym, a yoga studio, and a librarybr-8 minutes to the famous Kahala Mall shopping center, which includes Whole Foods, movie theaters, Macy's and various restaurantsbr-8 minutes to Costcobr-10 minutes to Koko Head Crater Hikebr-15 minutes to Hanauma Bay (the best snorkeling on the island)br-18 minutes to Makapuu Lighthouse Trailbr-20 minutes to Sea Life Parkbr-15 minutes to The Kahala Hotel/restaurantsbr-15-20 minutes to Waikikibr-15-20 minutes to Ala Moana Shopping Centerbr-30 minutes to Waimanalo Beach, Bellows Beach, and Sherwoods Beachbrbrbr***Please note: one side of the home--completely isolated from the main house for rent--is occupied by the owner and two golden doodles. You will have your own private entrance so you will have lots of privacy, but you must observe the house rules, respect your neighbors, and keep the noise level to a minimum after 9pm. Absolutely no parties or gatherings and only registered guests will be allowed.***brbr*** Please also note we've added a white recliner sofa in the living room ***brbr*** Due to rising electricity costs and to discourage wasting electricity, we will provide $300 of electricity credits per month for your stay. Any usage in excess of this amount will be charged separately. ***brbrbrbrbrbrThis property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.brbrReservation requests for fewer than 30 days will not be approved.brbrPlease contact us for last minute, long-term, and seasonal discounts.brbrAloha and safe travels!

Convenient to Waikiki Large 3000 sqft 4br 2ba house in East Honolulu

Honolulu, Hawaii, United States

4

Bed

Bath

8

Sleeps

$377.71

. Wailupe is on mountain side , 5 blocks facing ocean. enjoy tennis, bball/park across street, great views. brbr Convenient location to town, Waikiki 4 miles away. Two bedrooms in large great room. Main bedroom has a queen size bed, sons room has a twin, and living room has a sleeping futon.WiFi , no TV, So if 2 couples or children can sleep in each bedroom and one, or two on living room for futon, can sleep 5br

Live Local Redwood Pole house panaramic Ocean views quiet convienent nbrhood

Honolulu, Hawaii, United States

Bed

1

Bath

5

Sleeps

$857.18

Private Lagoonfront Villa | Courtyard Pool | Designer Living | Luxe Island RetreatbrbrExperience refined island living in this architecturally unique, resort-style villa—tucked along one of Honolulu’s most discreet and scenic coastlines. Designed for privacy, elegance, and effortless comfort, this secluded 4-bedroom, 4.5-bath residence accommodates up to 10 guests across detached suite-style bedrooms, all encircling a tranquil lagoon-view courtyard and private pool.brBlending the best of boutique resort ambiance and residential serenity, this home is ideal for multigenerational families, couples, executives, or remote professionals seeking peace and privacy within minutes of Kahala’s luxury shopping and Waikīkī’s vibrant culture.brbrWhat Sets This Property Apartbr*Detached bedroom suites for ultimate guest privacybr*Sunset-facing pool courtyard overlooking calm lagoon watersbr*Expansive indoor-outdoor great room with 15’+ ceilings & pocket doorsbr*Designer chef’s kitchen with kitchen island & bar seatingbr*Situated in an exclusive beachfront enclave—10 minutes to Kahala, 15 minutes to Waikīkībr*Perfect for extended stays, celebrations, or intimate retreatsbrbrElevated Interiors – Seamless Indoor/Outdoor FlowbrThe main great room is an architectural showpiece: vaulted ceilings, natural textures, and disappearing glass walls create a fluid connection between indoor living and the open-air pool courtyard. Lounge on a designer sectional, dine under woven pendant lights, or slide open the doors to let in the ocean breeze and golden light of sunset.brbrGourmet Kitchen – Entertaining ReadybrThe kitchen is thoughtfully equipped for chefs and hosts alike, featuring:br*Polished granite countersbr*Oversized island with 3 bar stoolsbr*Premium stainless appliances and full cookware suitebrPerfect for everything from casual breakfasts to elegant in-villa dining experiences with a private chef.brbrLagoon Courtyard & Outdoor LivingbrAt the heart of the villa lies a private, lagoon-facing courtyard anchored by a sparkling pool. Relax on padded loungers, fire up the built-in gas grill, or unwind beneath the palms as the sun sets over Diamond Head.br*Lagoon and mountain viewsbr*Alfresco dining and shaded seating areasbr*Private and peaceful, ideal for wellness routines or sunset cocktailsbrbrFour Private Bedroom Suites – Peace, Comfort & DesignbrEach suite offers its own private entry, spa-style bath, A/C, blackout drapes, and serene views. Designer bedding, custom textiles, and thoughtful amenities complete the experience.br*Primary Suite: King bed, lagoonfront views, lanai access, split A/C, spa-style ensuite with deep soaking tub, crib space availablebr*Suite 2: King bed, water & garden views, ensuite, window A/Cbr*Suite 3: Two twin beds that can convert to a King on request, water & garden views, ensuite, window A/Cbr*Suite 4 (Guest House): Two queen beds + twin sofa bed, panoramic views (ocean, mountain & garden), split A/C, ensuite (located above garage; garage not accessible)brbrLuxury Amenities Include:br*High-speed Wi-Fi throughoutbr*Smart TV with streaming appsbr*Luxury linens, beach & bath towels, robesbr*Washer/dryer, iron, and laundry essentialsbr*Fully stocked kitchen + local welcome amenitiesbr*Optional concierge services (chef, massage, provisioning) upon requestbrbrThis stunning lagoonfront villa offers a rare opportunity to live like a local while enjoying the amenities, privacy, and elegance of a five-star retreat. Whether you're here for a long-awaited family gathering, a work-from-paradise stay, or an unforgettable special occasion—this is your home base for barefoot luxury and island elegance.brbrExclusively offered through the LXRE Collection, Honolulu Lagoonfront Estate is part of a carefully curated portfolio of luxury homes designed for elevated island living. Each property is professionally prepared and supported by a local hospitality team dedicated to creating a seamless, personalized experience. From private chefs and in-home spa treatments to activity planning and grocery delivery, concierge services are available to help tailor your stay. Our team remains available throughout your visit to ensure a relaxed and memorable experience from arrival to departure.brbrPlease note that the lagoon is a protected nature preserve, home to native birds and fish. Guests are welcome to enjoy its serene beauty from the shore, but swimming is not permitted to protect its delicate ecosystem.brbrThe property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.brbrTAT: TA-026-818-7136-01brTMK: 380010560000

Honolulu Lagoonfront Villa by Gather | Private Pool Villa Near Waikiki & Diamond

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$961.37

Nestled at the base of Diamond Head in Honolulu’s storied Gold Coast, Hale Mahie is a rare 1926 Spanish Colonial Revival residence that blends historic character with refined contemporary comfort. Just a short walk from Waikiki Beach and steps from the beloved south shore surf break known as Tongs, this 3,795 sq. ft. home offers elegant island living across three thoughtfully curated levels. Restored with modern luxuries while honoring architect Carl William Winstedt’s original vision, Hale Mahie provides a serene long-stay retreat with rich architectural detail, bright gathering spaces, and a collection of inviting outdoor nooks.brbrWhat You’ll Love About Hale Mahiebr• Historic 1926 Spanish Colonial Revival design with timeless charmbr• Third-floor primary suite with peek-a-boo ocean views and Diamond Head scenerybr• Chef’s kitchen with marble counters, custom cabinetry, and top-tier appliancesbr• Steps from Tongs surf break and a 10-minute walk to Waikiki Beachbr• Multiple living and relaxation zones including a media room, office, and reading nookbrbrLiving & DiningbrWarm light fills the main living areas, highlighting curved archways, plaster walls, and coastal hues that complement the home’s classic architecture. The cozy living room invites relaxed mornings, while the adjacent reading nook provides a tucked-away spot for books, quiet conversation, or afternoon tea. Spend evenings gathered in the dining area beneath a vibrant chandelier, where garden views and Waikiki breezes flow through open windows. Downstairs, a dedicated media room offers a comfortable, cinema-style ambiance, perfect for movie nights after beach days.brbrChef-Ready KitchenbrThe expansive kitchen is designed for culinary ease, featuring marble countertops, a large island, commercial-grade appliances, and custom cabinets. Whether preparing fresh island seafood or hosting friends for dinner, the layout supports both everyday cooking and elevated entertaining. A secondary half kitchen on the lower level includes a sink, microwave, and mini fridge, ideal for extended stays or added guest convenience.brbrOutdoor OasisbrHale Mahie’s Spanish Revival facade opens to a charming front lanai shaded by arches and terracotta accents. Here, morning coffee pairs beautifully with soft ocean air. A garden path leads to peaceful outdoor seating areas, where you can unwind after exploring the nearby shoreline. With Waikiki Beach, Kapiolani Park, and scenic coastal viewpoints just minutes away, your daytime adventures remain effortlessly close.brbrSleeping Quartersbr• Primary Suite – King bed, ensuite bath, walk-in closet, free-standing soaking tub, rain-style shower, lanai access, partial ocean and mountain views, central AC, TVbr• Guest Bedroom 2 – Queen bed, main level, ensuite bath with tub (shared with office), central AC, ceiling fan, TVbr• Guest Bedroom 3 – King bed, lower level, shared bath, smart TV, standing fanbr• Guest Bedroom 4 – Queen bed, lower level, shared bath, split AC, TVbrbrExtrasbr• Dedicated office for remote workbr• Media room with oversized seatingbr• Reading nook with classic architectural detailingbr• Beach chairs, towels, and coolerbr• Washer and dryerbr• Smart TVs, DVD player, Wi-Fibr• Fully stocked kitchen with blender, rice cooker, coffee maker, and morebrbrNearbybr• Walk: Waikiki Beach, Waikiki Aquarium, Honolulu Zoo, Tongs surf break, Kapiolani Park, Diamond Head hiking trails, Waikiki shopping and dining, public tennis courtsbr• Short Drive: Museums, additional Waikiki restaurants, Oahu golf courses, scenic coastal lookoutsbrbrGood to Knowbr• This is a monthly rental. Full monthly rate applies regardless of nights stayed.br• Standard occupancy is 6; maximum occupancy is 8; extra guest fees apply.br• Online bookings are subject to manager or owner approval.br• AC notes: Central AC in main living area, split AC in primary, bedroom 2, bedroom 4, and TV room.br• A $500 electric security deposit is required. Includes up to $350 electricity usage. Refundable if within limits.br• Property must be exclusively occupied by renter for entire 30-day period.br• Tax ID: TA-044-602-3680-01br• TMK: 310330200000brbrReserve Your StaybrHale Mahie offers a rare blend of architectural history and modern island living in one of Honolulu’s most iconic neighborhoods. Reserve your dates now and experience the timeless beauty of this Diamond Head treasure.

Hale Mahie by Gather: Spanish Colonial Historic Home w/ Ocean Views & AC

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$345.28

Hawaii Kai Dream - 30-Night MinimumbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbr brPrepare to be wowed by unforgettable views at this 4BR/3BA home, ideally situated in Honolulu’s beautiful Hawaii Kai.brbrOverlooking Maunalua Bay, Koko Marina, and Hawaii Kai, enjoy sweeping ocean and Koko Head vistas from almost every room as well as on two private lanais.brbrAmple living and dining space provide plenty of room for entertaining, while an upstairs master and a large downstairs suite offer added privacy.brbrWithin minutes of Oahu’s famous beaches and a plethora of attractions, this conveniently located home puts you close to famed snorkeling at Hanauma Bay, body surfing at Sandy Beach, amazing views from Makapu’u lighthouse, and family fun at Waimanalo beaches.brbrDrive 2 minutes to an array of restaurants, theaters, and shops at Koko Marina and Hawaii Kai town centers.brbrABOUT THE HOMEbrbrPerched on Mariner’s Ridge overlooking beautiful Maunalua Bay and Koko Marina, this three-story home offers the best views with absolutely no obstructions. You’ll also be at a level that’s easy to access the town center via a short 15-minute walk.brbrThe main living area has soaring ceilings, ample natural light, and stunning 270-degree vistas of the ocean and mountains. Relax on the sofas and armchair to watch the 65” TV.brbrTwo expansive decks offer shimmering ocean views. Dine alfresco on the upper deck, or unwind on a sprawling lower deck furnished with wicker chairs.brbrThe well-equipped kitchen has granite countertops and stainless steel appliances. Serve meals at the breakfast bar for four or the six-person dining table.brbrThe inviting master suite offers a king bed, two large closets, and private access to the deck. An en-suite bathroom has a walk-in shower and double vanity.brbrThe second and third bedrooms each have a queen bed and ample closet space. The adjacent bathroom features a tub/shower combination.brbrDownstairs, find a large 500 square foot suite with a queen bed, a living area with a love seat and 57” TV, a separate space for yoga, as well as access to the backyard. The en-suite bathroom is configured with a walk-in shower.brbrEXTRA AMENITIES & MORE DETAILSbrbrThe house is fully set up as a work-from-home paradise. Recent upgrades include:brbr-Two height-adjustable desks with built-in wireless phone chargers and large monitors.br-Enterprise-grade wireless system, 3 routers, solid Wi-Fi coverage throughout the home. br-High speed Internet: 200 Mbps download and 12 Mbps upload.brbrParking is available for one in the garage and two in the driveway. brbrThis rental does not have air-conditioning. A washer/dryer is available.brbrAll leases require a minimum 31-day term.brbrTHE LOCATIONbrbrExplore uncommercialized gems at nearby beaches such as Portlock, Sandy, Makapu'u, and Waimanalo. brbrHead to Makapu'u Lighthouse for a leisurely hike, whale watching, and one of the best views on the island.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: There are video cameras installed above the garage door, outside the deck, and on the front porch. All cameras are pointed away from the property to ensure guest privacy and are solely used for monitoring purposes.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Hawaii Kai Dream with large lanai, ocean views, & a home office - near beaches

Honolulu, Hawaii, United States

4

Bed

3

Bath

8

Sleeps

$2776.44

At Nanea Kai Villa, ocean breezes, Diamond Head views, and beachfront living come together in a spacious four-bedroom retreat. This two-story estate offers 4,700 sq. ft. of refined island living, complete with a heated saltwater pool, spa, and private beachfront access just beyond the lawn. With sweeping Pacific panoramas and quick access to Honolulu’s best dining and conveniences, this luxurious coastal home invites you to experience Oʻahu at its finest.brbrWhat You’ll Love About Nanea Kai Villabr• True beachfront setting with panoramic ocean and Diamond Head viewsbr• Heated saltwater pool with waterfall overflow and adjacent hot tubbr• Expansive indoor-outdoor living with multiple covered lanaisbr• Home theater, modern kitchen, and elegant dining space for tenbr• Stand-up paddleboards, kayaks, and direct access to the sandbr• Convenient location close to Honolulu restaurants, Costco, and HNL AirportbrbrLiving & DiningbrSunlight pours through floor-to-ceiling windows, illuminating the spacious living room with uninterrupted ocean views. Plush sectional seating creates a comfortable gathering place after long beach days, while the home theater system elevates movie nights. The dining area offers seating for ten and opens seamlessly to the lanai through sliding glass doors.brbrChef-Ready KitchenbrThe fully equipped kitchen includes stainless steel appliances, a center island, wraparound counters, a breakfast nook, and ocean views that make cooking feel like part of the vacation experience.brbrOutdoor OasisbrYour private resort atmosphere awaits. The heated saltwater pool features a gentle waterfall overflow and sits beside a relaxing hot tub. A fire pit lounge provides a front-row seat to breathtaking sunsets. Lush lawns lead all the way to the beachfront, where paddleboards and kayaks invite spontaneous ocean adventures. Multiple shaded dining and lounging areas offer the perfect setting for quiet mornings or lively gatherings.brbrSleeping Quartersbr• Primary Suite: King bed, ensuite bath, ocean views, lanai access, split ACbr• Guest Suite 2: Queen bed, ensuite bath, ocean views, split ACbr• Guest Suite 3: Queen bed, garden views, Jack-and-Jill ensuite, split ACbr• Guest Suite 4: Two queen beds, Jack-and-Jill ensuite, split ACbrbrExtrasbrThe villa includes a home theater, smart TVs, children’s toys, laptop-friendly workspaces, multiple lanais, full laundry, and free parking.brbrNearbybr• Walk: Beachfront just steps away; Kapiʻolani Park and Diamond Head trails nearbybr• Short Drive: Costco, Honolulu restaurants, Ala Moana Center, Waikiki nightlife, Daniel K. Inouye International Airport (HNL)brbrGood to Knowbr• This property is offered as a monthly rental; the full-month rate applies regardless of nights stayedbr• Rates and fees are subject to change; minimum stay requirements may applybr• Online bookings are subject to manager or owner approvalbr• Split AC in main living areas and bedroomsbr• Max included electric charge: $500br• This property requires an Electric Security Deposit of $1,000 (fully refundable after check-out if usage remains within allowable limits)br• Please note that this property has an on-site caretaker who helps maintain the grounds and provide support as needed. The caretaker respects guests’ privacy at all times and will not enter the home or guest areas without prior notice, except in the event of an emergency or required maintenance. By booking this property, you acknowledge and agree to the presence of the caretaker on the premises.br• Exclusive 30-day occupancy per reservation periodbr• Hawaii Tax ID: TA-048-406-5280-01br• TMK: 390020080000brbrReserve your dates now and experience Honolulu’s blend of luxury, comfort, and coastal beauty at Nanea Kai Villa.

201 Portlock Rd by Gather: 4BR Beachfront Villa w/ Pool, Oceanviews & Hot Tub

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$1162.22

Discover Aloha Nalu, meaning “warm, welcoming sea,” a luxurious hillside retreat in Honolulu’s prestigious Portlock neighborhood. Perched along Koko Crater with sweeping views of the Pacific Ocean and Diamond Head, this four-bedroom villa offers 3,387 square feet of elegant living space for up to ten guests. Designed for families and groups, Aloha Nalu blends modern sophistication with the warmth of Hawaiian hospitality.brbrWhat You’ll Love About Aloha Nalubr• Elevated position with panoramic ocean and Diamond Head viewsbr• Private pool terrace with lounge seating and BBQ grillbr• Expansive second-level primary suite with spa-like bath and sitting areasbr• Modern chef’s kitchen with bar, drink fridge, and high-end finishesbr• Prestigious Portlock location near beaches, dining, and shoppingbrbrLiving & DiningbrFrom the moment you step inside, the open floor plan frames mesmerizing ocean views through floor-to-ceiling windows. Two comfortable living areas invite conversation or cozy movie nights, with Smart TVs in the living room and three bedrooms. Elegant finishes—polished stone floors, wood accents, and white quartz countertops—create a serene, contemporary ambiance. The dining area, seating ten, flows seamlessly to the outdoor terrace, where ocean breezes complement every meal.brbrChef-Ready KitchenbrCulinary enthusiasts will appreciate the chef’s kitchen, equipped with high-end appliances, quartz countertops, and a dedicated wine fridge and bar. Prepare island-inspired dishes or tropical cocktails while enjoying the ocean views that define this stunning home.brbrOutdoor OasisbrStep outside to your private pool terrace, where two shaded lounge areas and sunbeds overlook the ocean and Diamond Head. Fire up the BBQ grill for alfresco dining, relax under the Hawaiian sky, or take a refreshing dip in the pool surrounded by lush greenery.brbrSleeping Quartersbr• Primary Suite (Upper Level) – California King bed, ensuite bath with steam shower and soaking tub, sitting area, desk, walk-in closet, and panoramic ocean viewsbr• Primary Bedroom 2 – King bed, ensuite bath, garden viewsbr• Guest Bedroom 3 – Queen bed, Smart TV, shared bath accessbr• Guest Bedroom 4 – Two Twin beds (convertible to King upon request)brbrExtrasbrEnjoy air conditioning throughout the main living areas and bedrooms, Smart TVs, Wi-Fi, washer and dryer, and a collection of games. Beach-ready gear—including boogie boards, towels, chairs, and a rolling ice chest—is provided for guest use. Optional concierge services, private chef experiences, and guided tours are available upon request.brbrResort / Community HighlightsbrLocated in Honolulu’s exclusive Portlock area, Aloha Nalu offers convenient access to the best of O‘ahu’s south shore. Nearby attractions include Hanauma Bay (world-class snorkeling), Waimanalo Beach, Portlock Beach, and the Hawaii Kai Golf Course. Within a 15–20 minute drive, explore dining and shopping in Waikiki, Kailua, and downtown Honolulu, or enjoy restaurants and water sports just minutes away in Hawaii Kai.brbrNearbybr• Walk to: Local beaches and marina-front dining in Hawaii Kaibr• Short drive to: Hanauma Bay, Waimanalo Beach, Kaimuki Town, Waikiki, and Ala Moana CenterbrbrGood to Knowbr• Standard occupancy is 8 guests; maximum occupancy is 10 (extra guest fee applies)br• This property is available for a 30-day rental period; monthly rates are fixed regardless of stay lengthbr• Max included electric charge: $500br• TA-019-941-5808-01br• TMK 390130060000brbrExperience the beauty, comfort, and refined aloha spirit of Aloha Nalu—where ocean views, privacy, and modern luxury meet. Reserve your stay today.

Aloha Nalu: Luxury Home w/ Diamond Head Views, AC & Private Pool

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$875.29

Tucked within the prestigious Kahala neighborhood, Ho‘okipa Villa by Gather blends vintage Hawaiian charm with modern comfort for the ultimate island retreat. Originally built in 1938 and lovingly restored, this five-bedroom, four-bathroom estate spans over 3,000 sq. ft. and accommodates up to 14 guests. With a private pool, lush outdoor spaces, and a separate guest cottage, this residence offers a perfect balance of space, style, and serenity just minutes from Kahala Beach and Waikiki.brbrWhat You’ll Love About Ho‘okipa Villa by Gatherbr• Classic Hawaiian architecture beautifully updated with modern finishesbr• Expansive outdoor living with pool, BBQ, and covered lanai for alfresco diningbr• Main home with four bedrooms and three baths, plus a private guest cottage with full kitchenbr• Gourmet kitchen and two bright living areas for gathering and relaxationbr• Prime location near Kahala Beach, the Kahala Hotel & Resort, and Waikiki attractionsbrbrLiving & DiningbrStep into this bright and inviting home where vintage details meet contemporary design. The open layout connects the living areas with the kitchen and dining room, creating a seamless flow for entertaining and everyday comfort. The spacious living rooms feature cozy seating, flat-screen TVs, and large windows that fill the interiors with natural light.brbrThe newly remodeled kitchen is fully equipped with modern appliances, stone countertops, and a breakfast bar for casual meals. The adjacent dining area features a long farmhouse-style table perfect for family dinners or festive celebrations.brbrOutdoor OasisbrOutside, a sparkling private pool and lush gardens invite you to unwind under the Hawaiian sun. Lounge by the water, enjoy a backyard BBQ under the covered lanai, or cool off with an outdoor shower after a day at the beach. The setting provides both privacy and tranquility, with plenty of space for dining, sunbathing, and connecting with loved ones.brbrSleeping Quartersbr• Primary Suite – King bed, split A/C, ensuite bathroom with shower/tub combo and single vanity.br• Bedroom 2 – Queen bed, central A/C, direct backyard access, adjacent full bath.br• Bedroom 3 – Two Twin beds, split A/C, shares full ensuite with Bedroom 4.br• Bedroom 4 – Two Twin beds, split A/C, connected to Bedroom 3 via shared full bath.br• Bedroom 5 (Guest Cottage) – Queen bed, split A/C, ensuite bath, full kitchen, and private living area with sofa bed.brbrEach bedroom offers a unique layout and charm, ensuring both comfort and privacy for guests.brbrGuest CottagebrPerfect for extended families or guests seeking added privacy, the separate cottage includes its own living room, dining nook, kitchen, and full bath. The cottage suite features a Queen bed and private access to the pool area.brbrExtrasbrThis home is equipped with split and window A/C units throughout, high-speed Wi-Fi, smart TVs, laundry facilities, and gated entry. The thoughtful layout and multiple gathering spaces make it ideal for families or groups traveling together.brbrLocationbrNestled in exclusive Kahala, Ho‘okipa Villa places you close to the island’s most beautiful beaches and attractions. Walk or drive a few minutes to Kahala Beach for swimming and sunbathing, or visit the nearby Kahala Hotel & Resort to dine oceanside and see the resident dolphins. Waikiki’s world-class shopping, dining, and nightlife are less than a 10-minute drive away.brbrGood to Knowbr• Monthly rental only; full-month rate applies regardless of stay lengthbr• Standard occupancy 10 guests; maximum occupancy 14 guests (extra guest fee applies)br• Electric security deposit: $500; includes up to $400 usage allowancebr• Split and window A/C units throughoutbr• TA-088-184-4224-01br• TMK: 350100100000brbrYour Island Story AwaitsbrFrom leisurely poolside mornings to sunset strolls along Kahala Beach, Ho‘okipa Villa by Gather offers a timeless Hawaiian experience where comfort, history, and aloha come together in perfect harmony.

Ho'okipa Villa: Historic Home+Guest Cottage in Kahala near the Beach w/Pool & AC

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$407.07

Kahala Cottage – A Tranquil Retreat in HonolulubrWelcome to Kahala Cottage by Gather, your home-away-from-home in the exclusive Kahala neighborhood on O‘ahu’s south shore. Offered as a monthly rental, this two-bedroom, two-bath island retreat blends laid-back Hawaiian charm with modern comfort, providing a serene escape for families or small groups of up to eight guests.brbrWhat You’ll Love About Kahala Cottagebr • Sunny pool area with BBQ grill and outdoor diningbr • Spacious open floor plan with two inviting living areasbr• Split A/C in both bedrooms and main living room for consistent comfort throughoutbr • Fully equipped chef’s kitchen with ample counter spacebr • Prime location near Kahala Beach, Kahala Mall, and world-class golfbrbrLiving & DiningbrStep into a bright, open layout designed to capture natural light and island breezes. Two comfortable living areas offer plenty of seating for everyone to unwind after a day of exploring. Enjoy family movie nights on the flat-screen TV with DVD player or gather around the dining table for eight to share island-inspired meals. Large sliding doors open to the pool area, allowing seamless indoor-outdoor living.brbrChef-Ready KitchenbrThe fully equipped kitchen makes at-home dining a pleasure. Outfitted with stainless steel appliances, generous counter space, and every essential for meal prep, it’s ideal for everything from breakfast pancakes to sunset dinners. The main living area is equipped with split air conditioning, offering a cool and comfortable retreat at any time of day.brbrOutdoor OasisbrSpend sunny days lounging by your private pool surrounded by lush tropical greenery. Fire up the BBQ grill for al fresco dining or sip cool drinks under the lanai as gentle tradewinds move through the palms. This outdoor sanctuary offers the perfect mix of relaxation and island living.brbrSleeping Quartersbr • Primary Bedroom – King bed, sitting area, split A/C, private access to pool, ensuite bathbr • Guest Bedroom – Two Twin beds, split A/C, bright and airy with sliders to lanaibr • Additional sleeping options available upon request to accommodate up to eight guestsbrbrExtrasbrKahala Cottage includes split air conditioning in both bedrooms and the main living room, high-speed Wi-Fi, two living areas with TVs and DVD players, and an in-home washer and dryer. Beach-ready gear—chairs, towels, and coolers—is also provided to make days by the ocean effortless.brbrResort / Community HighlightsbrLocated just minutes from Kahala Beach and Kahala Mall, you’ll find an array of shopping, dining, and entertainment options close to home. Nearby championship golf courses, Waikiki, and Diamond Head offer the perfect blend of recreation and relaxation within easy reach.brbrNearbybr• Walk to: Kahala Beach, Kahala Mall, local shops and restaurantsbr• Short drive to: Waikiki, Diamond Head, Honolulu Zoo, golf coursesbrbrGood to Knowbr• This property is offered as a monthly rental; rates are based on a 30-day period and remain fixed regardless of length of staybr• Standard occupancy for this home is 4 guests; maximum occupancy is 8 (extra fees apply beyond standard occupancy)br• Split air conditioning in both bedrooms and main living room, with ceiling fans throughoutbr • Electric Security Deposit: $400 (refundable if usage within limits)br• Maximum included electric charge: $250br• Parking provided for guestsbr• TA-038-170-4192-01 br• TMK 350150260000brbrReserve your stay at Kahala Cottage by Gather and experience authentic island living where comfort, privacy, and Hawaiian elegance come together.

Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$307.26

Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to Hanauma Bay, the North Shore, Pearl Harbor or a beach on the Windward Side of the island. Drive 5 minutes to the expressway and be anywhere on the island in short order. The trip from the airport is 20 minutes. Come back home and relax while discussing the day’s adventures before heading for dinner in one of the restaurants in Kaimuki - 5 minutes away - or Waikiki – 2.5 miles away. Or prepare dinner in the large, well-appointed kitchen and dine on the expansive lanai while appreciating a gorgeous sunset. Before retiring, spread out in the roomy living room, watch the wide screen TV in the den, or play board games around the dining room table. There are two bedrooms – one with a king bed and one with a queen bed. The couch in the den also converts to a queen bed. There’s an easy parking spot plus plenty of off-street parking and free WiFi. A washer and dryer with detergent are available on the first floor, as well as an outside shower to wash off the beach sand. The house has lovely large side and back yards with mango, lychee and citrus trees and numerous flowering tropical plants. It’s situated on a steep street (hence the great views) and in a neighborhood where local residents go to work in the morning and come home in the evening – so there is street noise at those times. The rental unit is the entire second floor (22 steps up from the parking area) of a 2-story vintage Hawaiian home. There is a long term tenant on the ground floor who has a completely separate entrance. The manager lives right across the street and has received rave reviews for her advice and attention to tenants needs. brReserve your tickets, pack your bags and vacation in Paradise with all the comforts of home.

Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$526.69

Flexible 1-12 Month Lease TermbrFor 1-3 months at $12,000/month + taxes all utilities are includedbrFor 4 months or more at $11,000/month + taxes utilities are charged by usagebrCall/ sms direct 4152519696 for 30-days minimum stay per the Ordinance brbrWelcome to your private Diamond Head hideaway — a tranquil, tropical retreat tucked into one of Honolulu’s most iconic neighborhoods. brbrThe home sits on terraced grounds with a private entrance and steps walkway descending through lush landscaping, flowering plants, and mature trees. This rare estate‑style setting offers complete privacy while still being walkable to Waikiki’s beaches, dining, and attractions.brbrInside, the home features a well‑equipped gourmet kitchen with slate countertops, a gas stove, and full appliances. Outdoor living is a highlight here: shaded lanais, stone patios, hideaway terrace, teak furniture, and soft evening lighting create the perfect atmosphere for morning coffee, relaxed BBQs, or romantic outdoor dining.brbrYou’ll be surrounded by tropical greenery and the sounds of island birds throughout the day — a peaceful, inspiring environment that past guests have loved for writing, creative work, and quiet relaxation.brbrMain Levelbr- Two air‑conditioned bedrooms with king and queen bedsbr- Balcony with outdoor seatingbr- Large open stone patio, deck and hideaway terrace br- Full kitchen, living area, and outdoor dining spacesbrbrLower Level - Accessed via exterior stairsbr- One air‑conditioned bedroom with queen bedbr- Samsung Bespoke AI laundry combo with sitting areabr- Full screen-in bathroom with rain shower brbrA caretaker lives on‑site in a separate dwelling for added convenience and property care.brbrSetting & ViewsbrThe property backs directly onto Diamond Head’s conservation land, offering panoramic views of the crater, tropical foliage, and gentle ocean breezes. The environment is quiet, shaded, and filled with birds — a true island sanctuary.

Hidden Diamond Head Paradise Retreat • Lush, Secluded, Walk to Beach and Waikiki

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$1494.58

Set on the slopes of Koko Kai, this spacious, two-story, family-style home offers panoramic ocean views and breathtaking sunset over Diamond Head. Decorated with a touch of island decor, this villa is perfect for indoor/outdoor living. The large full kitchen, two living room areas, and large lanais provide plenty of room for families and friends to relax.brEnjoy a swim in the private, solar-heated swimming pool after a day at the beach. Watch all the water activities at Maunalua Bay. And if you're lucky, you may spot a few whales during their season.brThe magical night lights which grace the nearby hillside, with the moon and stars, totally change Hale Ohana's ambiance.brNearby beaches include Portlock (five minutes away), and Hanauma Bay and Sandy Beach (both about five to eight minutes away). Hale Ohana offers the best of both worlds: privacy, great family accommodations -- and, of course, convenience with Waikiki only 20 minutes away. Hawaii Kai offers great entertainment and dining, lots of shopping, close by beaches.brbr 90/TVU-0258 TMK 350060160000 Local Contact - Paradise Hideawaysbr 7 night minimum over any major holiday and 12 night over Christmas. Our home has several stairs: Front Driveway Approx. 9 stairs up to first landing, than another 4 stairs to front door. brAll 3+ bedroom rooms are located upstairs, Approx. 4 stairs to first landing, than another 4 stairs to 2nd landing, than another 4 stairs to top level. We do have a double futon bed downstairs in the living room area.

Hale Ohana, Private, Oceanview home w/pool, Licensed TAT home

Honolulu, Hawaii, United States

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Bath

Sleeps

$151.3

Open floor plan, over 1500 sq. ft., filled w/ imported Chinese furniture, beautiful ocean, other islands, mountain views, full size decks - master bedroom & dining room, full size kitchen w/ appliances, house sits back from the road - private, peaceful and secure

Very Private, Peaceful,& Prestigious - Beautiful Ocean, Other Islands &Mtn Views

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$265.3

Your personal tropical paradise awaits at Hawaii's Only Waterfall Villa in Honolulu on the island of Oahu. Enjoy the Hawaiian Rainforest that surrounds you and relax to the sounds of waterfalls, streams and tropical birds. This is Modern Hawaii living at its finest in the prestigious Dowsett area off the historic Old Pali Road. This place is truly a one-of-a-kind retreat away from busy Waikiki, but still minutes from the beach, restaurants, shopping, downtown, airport, and freeway.

Hawaii's best waterfall retention in Honolulu

Honolulu, Hawaii, United States

Bed

Bath

7

Sleeps

$337.95

***Location and Getting Around***brCentrally located in Hawaii Kai! Short walk to Maunalua Bay Beach Park and less than a mile to Safeway, Costco and a handful of restaurants! Less than a ten minute drive in either direction to a number of activities and attractions. Just eights miles from Waikiki, Diamond Head, The Honolulu Zoo and The Waikiki Aquarium. Heading east you'll find Hanauma Bay, Makapu'u Light House and some of the best beaches the island has to offer in Waimanalo. brbr***Three Bedrooms***brBedroom 1: Queen Bed brBedroom 2: Queen BedbrBedroom 3: Twin BedbrBonus sleeping - queen size pullout couch in living room brbr***Two Bathrooms***brBathroom 1: Walk in shower with separate jacuzzi tubbrBathroom 2: Walk in showerbrbr***Exclusive Amenities***brNewly updated kitchen and bathroomsbrPrivate poolbrSingle level home - no stairs on propertybrOutdoor showerbrAccess to marina launch for kayaks and paddle boards (not included), exclusive to six homes on the streetbrWasher and dryerbrDriveway parking for two vehicles (owner's car is kept in the garage)

Charming home w/ private pool & marina access

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$322.98

Welcome to Villa Laule'a~~Hawaiian for peaceful happiness. This beautifully furnished & well equipped 4 bedroom townhouse is ready for your luxury vacation. Fine sheets and towels, fabulous kitchen. You'll enjoy the waterfront lagoon and close access to the ocean. You'll be in the charming town of Hawaii Kai, which is surrounded by the warm lagoon waters that flow into the ocean. All the amenities are close by: Costco, Safeway, banks, drug stores, movie theater, wonderful restaurants.brbrThis house is located in The Moorings, a beautifully maintained townhouse community. You can use the swimming pool, you can book the recreation center for a private party, there is parking for you and a guest, plus additional street parking just outside the entrance.brbrRecreation is all around: rent a kayak for the lagoon, jet ski at the beach park, Hanauma Bay for world class snorkeling just up the road, famous beaches are a walk or short drive from this house, and the sun sets over Diamond Head.brbrWe are just a phone call away, and we have a team of wonderful people on the island to help you with any needs you may have.brbrCome to rejuvenate and enjoy the beauty of Hawaii in a unique island home with all the amenities!

Waterfront home of peaceful joy: Villa Laule'a

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$540.21

This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. brbrSpectacular 4 bed 2 bath home with private pool and breathtaking ocean and mountain views. Situated on the ridge in the highly desired area of Hawaii Kai. brbrThe main level includes a large open kitchen and dining area with plenty of space for a large family to congregate in. There is also a living area, the master bedroom and bathroom along with an additional half bathroom off the hallway. In addition, a large balcony which is the perfect location to start your morning with a cup of coffee while enjoying a beautiful sunrise or to end your day of fun with a sunset in the evening. Down the stairs to the second level you will find three bedrooms, one bathroom and an additional living area that opens up out to the enclosed yard and private pool. The home includes smart TV's so the children can have quiet time while the parents kick back or the whole family can relax and watch a movie after a long day out exploring! brbrThe home is just a few miles to Sandy Beach and the well known nature preserve at Hanauma Bay, as well as fifteen minutes to Waimanalo Beach, one of the best beaches on the Island! Safeway, Costco, many restaurants, movie theaters and all kinds of Water Sports activities are all within a mile. Maunalua Bay is the home base for competition paddlers, amateur fishermen, and everything in between. Just the perfect home away from home for your stay!brbrbr TA 011-442-5856-01 brLocal Contact: Hawaiian Vacation Rentals

Ocean views and Private pool - Mariners Ridge Home

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$239.73

Enjoy gorgeous unobstructed ocean, marina & mountain views from our beautiful guest house. Located on the ridge, in a safe, quiet and upscale neighborhood in Hawaii Kai, East Honolulu, just around the corner from famous Hanauma Bay, Halona Blow Hole, spectacular Sandy Beach and more! Sea Life Park, Makapuu Beach and Waimanalo Beach are all about 10 minutes away. brbrThis beautifully appointed open concept residence, is light, airy, pleasant, peaceful and immaculate! A private entrance takes you through a cozy garden, down a few steps, to a welcoming deck and your front door. As soon as you come in, you can enjoy the fantastic view that you can admire from almost every room! With a complete kitchen with gas stove and oven, a full size refrigerator, and long granite counter-tops; you can cook as much or as little as you like. We have a tall dining table set where you can sit and marvel at the view while you enjoy your meals. In front of a big window, you will find a nice area that you could use as a desk. The breezy open concept living room area includes a sleeper sofa, coffee table, armchairs and TV.brbrThe main bedroom has gorgeous views as well! You can watch the sunrise as well as the moonrise from your comfortable queen size bed. Although there is always a nice breeze, there is a ceiling fan for your comfort as well as an air conditioner unit. This bedroom is separated from the main living area by a half wall to maximize view and airflow. br brThe second bedroom also has a comfortable queen size bed and an air conditioner unit. This bedroom is perfect for those who prefer to sleep in a darker room, its window doesn't offer a view but lets in the fresh air, and this room offers more privacy with a door that separates it from the main living area. brbrHigh quality, white, 100% cotton linens are used for all beds. brbrThe bathroom is super clean, large and convenient. The shower has great water pressure and hot water. A clean set of 100% cotton towels is also supplied for every guest.brbrAn efficient washer and dryer unit for your own use is also inside the guest house.brbrThis vacation retreat is equipped with high quality 100% cotton linens, towels, cookware, china, silverware, and more. Even boogie boards, snorkel sets, beach umbrella, beach towels and beach chairs! We have even installed a hotel style safe for your peace of mind. brbrFree WiFi! Fast and reliable wireless internet, digital cable TV service with DVR allows you to record, pause, and play your favorite movies and shows, and a pivoting 47' smart TV that lets you watch from the living area and bedroom.brbrFree street parking is available right in the front of the house.brHawaii Kai has something for everyone: beaches, parks, lots of ocean activities, fun hikes of different levels, a great variety of restaurants, movie theaters and shopping. Farmer's markets, supermarkets, beauty salons, gyms, various services, and even Costco are all within 5 minutes. You can be in the hustle and bustle of Waikiki in 20 minutes and at the airport in 40 minutes.brbrYou will love staying at our guest house! It is peaceful, private, immaculate, and just beautiful! My husband, daughter and I live in the main house.brbrIn accordance with Ordinance 22-7 of the City and County of Honolulu, “this property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.”

Wonderful retreat, Fantastic View, Immaculate, Beautiful, Private and Peaceful!

Honolulu, Hawaii, United States