Vacation Home Rentals By Owner In Honolulu, HI

Ultimate retreat nestled in a chic oceanfront locale. This private oceanfront residence boasts its very own private staircase that descends to the breathtaking shores of Maunaloa Bay. Conveniently situated in the heart of Portlock, you'll find yourself just a stone's throw away from marina-front dining, boutique shops, a water sports activity center, a fitness facility and grocery stores. Portlock Hale is the perfect haven for ocean enthusiasts and anyone seeking both relaxation and adventure.brbrPortlock Hale welcomes you with a breezy beach-inspired living room, a captivating sitting room offering panoramic ocean vistas, an exquisite kitchen with bar seating, and meticulous custom details throughout. The refreshing ocean breezes naturally cool the entire home, while air conditioning is available in three of the downstairs bedrooms for added comfort. With three king beds, two queen beds, an optional full mattress, and 3.5 bathrooms, Portlock Hale offers a spacious home-away-from-home for your large group.brFor an authentically Hawaiian open-air living experience, the sitting room seamlessly connects with a covered outdoor lounge area. The pool area is the ideal spot to bask in the sun while soaking in the mesmerizing Pacific views during the day, and at night, you can recline under the stars while listening to the soothing ocean waves. Our amenities, including a barbecue grill and beach gear, ensure you have everything you need for memorable excursions.brStrategically located in the coveted Hawaii Kai area of southern Oahu, Portlock Hale provides easy access to renowned beaches like Hanauma Bay (a world-famous snorkeling destination), Waimanalo Beach, and Portlock Beach. A mere 10-minute drive brings you to the Hawaii Kai Golf Course. Plus, within just 15 to 20 minutes, you can explore the trendy Kaimuki Town, Kailua Town, downtown Honolulu, and the historic charm of Waikiki.brFor larger groups (up to 12 persons), we can arrange for an additional full mattress. Our standard house occupancy is set at 10 guests, with additional per-person rates applicable up to a maximum capacity of 12.brbr1. Rates and fees are subject to change. Minimum stay requirements may apply. Inquire about possible discounts.brbr2. Online bookings are subject to manager or owner approval.brbr3. This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX ID # GE-072-291-2768-01 and TA-072-291-2768-01brbr4. Guest is aware that this property has a seawall in the backyard with a drop-off to the water/sand and rocks. Guest accepts all liability and risk in relation to this seawall. Children must be supervised at all times when in the backyard.brbr5. The property will be made exclusively available to the renter for a whole period of 30 days and no one else may occupy the property during that period. Rates are based on a 30-day rental period. Please Inquire.brbr6. A separate rental agreement must be executed for compliance purposes.brbr7. $1000 utilities fee per month will apply to all reservations. it will be charged as Community charge .

Private Oceanfront 5BR! Family Home Hawaii Kai

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$338.96

brThis is your home away from home in an immaculate, spaciously designed guest house built for relaxing in comfort, style & convenience. This an attached 2 bedroom + 2 bath fully-equipped house + sofa bed and a very large stocked kitchen with a separate entrance and foyer for complete privacy. This home has the option of being a one bedroom and one bathroom home should you not require that much space. If that fits your needs better, the cost is reduced by 50.00 dollars per night. brbrEnjoy cool A/C and lots of fresh breezes with 270 degrees panoramic views of Koko Head, Hanauma Bay ridges, and Kuliouou mountain ridges from the living room windows. Features beautiful high vaulted cathedral ceilings, lots of windows and natural light, a large kitchen, hardwood and travertine floors, and an abundance of beautiful luscious vibrant plants. This is a fully stocked 1150 sq ft home with all the amenities ready for our guests to rest, relax and enjoy living in leisure. brbrConveniently located on the beautiful southeast tip of Oahu near the world famous Hanauma Bay and Koko Head, just 8 miles from Waikiki on the left and Waimanalo on the right. This clean, safe neighborhood is in a charming, affluent community near waterfront homes and must-see points of interest found in all the Oahu travel guides.brbrWalking Distance to 1) Hawaii Kai shopping center: Safeway, Costco, Long's Drugs, Walgreens 2) Excellent dining and entertainment: The original Roy's Hawaii Kai, Assagio, Maili's Thai Bistro, Outback Steakhouse, Kona Brewing 3) Consolidated Theatres, ocean marina, beaches, canals, recreation centers & country club.brbrMinutes from 1) world class snorkeling at the famous, breath taking Hanauma Bay. 2) 5 amazing trails - Hanauma Bay, Koko Head, Makapu'u Lighthouse, Kuliouou Ridge, Hawaii Loa Ridge 3) surfing/swimming at Sandy Beach, China Walls, Makapu'u 4) golf nearby at Hawaii Kai Golf Course, Olomana Golf Club, Royal Hawaiian Golf Club.brbrIdeally, you would park your car in the driveway for easy access around the island. Otherwise Uber, Lyft, and bus transportation services are easily accessible.brThis home is decorated with nice artwork and accessories, many of which may not be suitable for small children.brbr快適でスタイリッシュな広々としたゲストハウスで、ご自宅のようにハワイの時間を過ごしていただけます。トロピカル調の内装の1ベッドルーム+ 1バスルームには、ソファベッドからフルキッチン、ダイニング＆リビングルームに、ガラスドアのシャワーなど必要なものが全て揃っています。専用の玄関から出入りでき、リビングルームからは、ココヘッド、ハナウマ湾尾根やクリオウオウ山尾根を眺められます。機能的なキッチンは大型冷蔵庫にコーヒーメーカー、オーブンに電子レンジを完備。長期滞在のお客様に重宝するのが、部屋内にある洗濯機と乾燥機。88平米の部屋は、4名まで宿泊可能。4-5泊より承っております。家は治安の良いハワイカイ地区に位置しており、スノーケリングができるハナウマ湾や、様々なレストランやウォータースポーツが楽しめるココマリーナセンターへは車で5分程という便利さ。美しいビーチ全米Ｎｏ１に選ばれたカイルアにあるラニカイビーチにも車で30分程の距離です。レンタルカーがある場合の駐車場スペースも設けております。チェックインは4ＰＭでチェックアウトは11ＡＭとなります。br

Please contact me for specific dates that you may be interested in.

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

Select Dates for Price

A private porte-cochere leads you to the luxury and grandeur that is Kahala Place. Steps away from Kahala beach, Waialae Country Club, and The Kahala Hotel -- this is a very special estate. All bedrooms with their own en-suite bedrooms. Master with his and her walk-in closets and double private balconies. Grand entry with a circular staircase that leads to the second floor with a private movie/screening room. Elevator. Formal living room. Formal dining room. Family room...

Kahala Estate

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$502.65

This home is perfect for the savvy, discerning traveler who prefers comfort, convenience, cleanliness, spaciousness, and spectacular views. Discover the hidden gems of an affluent neighborhood with gorgeous views, privacy, and lots of aloha.brbrThis renovated, fully equipped, luxury vacation home with breathtaking views of the ocean and a nature preserve right in front of the house. Wake up and watch the sunrise over Hanauma Bay Ridge from your living room and two of the bedrooms in one of the most exclusive neighborhoods in Oahu. brbrThis is your home away from home in an immaculate, spaciously designed modern single story 3 bedroom and 2 bath house that sits right above Kalanianaole Hwy, 2 blocks away from the ocean. A smart A/C system provides relief from the heat with soothing sounds of locals driving around in paradise. The stunning views and fine, coastal lifestyle with walking access to un-crowded sweet spots are both charming and unforgettable. brbrExperience the charming, un-crowded beauty of Hawaii the way locals do in your dream home in the exclusive Kuliouou neighborhood. A short walking distance to secluded, private beaches in Oahu's exclusive premier beach neighborhoods with views and access to the Paiko Lagoon Wildlife Sanctuary and Kanewai Fish Spring. You are 5 minutes to one of the best hiking/jogging trails with a jaw dropping views of Waiamanalo Beach, Hanauma Bay, Diamond Head, etc.brbrAmenities include a gourmet kitchen, beautiful travertine bathrooms, cool A/C with thermostats in all the rooms, and world class sweeping water views from the living room kitchen and both bedrooms. brbrConveniently located on the beautiful southeast tip of Oahu near the world famous Hanauma Bay and Koko Head, just 8 miles from Waikiki on the left and Waimanalo on the right. This clean, safe neighborhood is in a charming, affluent community near waterfront homes and must-see points of interest found in all the Oahu travel guides.brbr5 minutes from 1) Hawaii Kai shopping center: Safeway, Costco, Long's Drugs, Walgreens 2) Excellent dining and entertainment: The original Roy's Hawaii Kai, Heavenly Cafe, Moena Cafe, BeastSide Kitchen, Kona Brewing, 808Tex 3) , ocean marina, beaches, canals, recreation centers & country club.brbrMinutes from 1) world class snorkeling at the famous, breathtaking Hanauma Bay. 2) 5 amazing trails - Hanauma Bay, Koko Head, Makapu'u Lighthouse, Kuliouou Ridge, Hawaii Loa Ridge 3) surfing/swimming at Sandy Beach, China Walls, Makapu'u 4) golf nearby at Hawaii Kai Golf Course, Olomana Golf Club, Royal Hawaiian Golf Club.brbrIdeally, you would park your rental car under the house in the carport. Otherwise Uber, Lyft, and bus transportation services are accessible.brbr* This property only accepts one booking per 30 day period. If a 30 day period is not available, we will not be able to rent the home and will notify you as such. The 30 day block will be determined based on your requested dates to satisfy the minimum 30 day rental period.**

Open and relaxing vacation home with breathtaking panoramic ocean view

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$844.04

Hawaii Kai home is in a Prime Location with circular view of surrounding mountains including Koko Head Mountain. Also includes a view of the Koko Marina from the Lanai. Walking distance to Hanauma Bay (less than a mile), Koko Head Mountain (.5 miles), and Shopping/Restaurants across the street. Remodeled home has 7 bedrooms (5 Queen Beds and 2 Large Bunk Beds for kids) and a huge pool and spa. 2 kitchens, 1 outdoor shower, gas BBQ & outdoors lounge furniture. Home can comfortably sleep up to 16-18 people. Please note that due to the recently passed Bill 89, we will be booking our home once a month to lucky renters. Mahalo. Chrisbrbr

7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$1047.43

Kalani Kai Beach House is a newly renovated, private gated oceanfront home located on one of the Waialae Beach Lots with a beautiful swimming pool nestled next to a sandy beach.brThe upstairs master suite has a king-size bed and panoramic ocean views from a spacious private lanai. The downstairs master suite with its king-size bed opens onto the oceanside pool lanai. The queen bedroom suite is separate just off the great room. For the kids there’s a double-double loft/bunk bed.brKalani Kai Beach House kitchen opens to both the pool lanai and the great room. Cathedral ceilings and tall glass sliders, give the home a grand feeling of space. Each room is air-conditioned with its own zone climate control. There’s a separate cable TV family room and there are also TVs in the larger bedrooms. WIFI is available throughout the house and yard.brBordering the backyard is a sand covered beach where at low tide the Kahala Hotel and its restaurants are a 10 minute walk away. For enjoyment of the many island attractions, it’s only a 10 minute drive to Hanauma Bay and just beyond that there is Sandy Beach and Sea Life Park. While isolated from the hustle and bustle of Waikiki, this private gated retreat is less than a 10 minute drive to the heart of Waikiki. Kahala Mall, Foodland (grocery store), Longs/CVS (drugstore), Costco, local and fine dining are just minutes away. brCreate memories with family and friends around the spectacular sunrises and sunsets, cooking and dining out on the oceanfront backyard pool lanai. Just outside the oceanside gate enjoy fishing, paddleboarding and kayaking. This is the ideal spot for the perfect family Hawaiian vacation!br Small events such as weddings are possible at Kalani Kai Beach House along with an extended stay. Additional charges apply. Please inquire.br br• Waialae/Wailupe Beach Oceanfrontbr• Private gated propertybr• 10 guests maximumbr• Indoor living space of 2,500 square feetbr• 4 bedrooms, 4 bathrooms, 1 half bathbr• Zoned air conditioningbr• Oceanside pool with large surrounding lanaibr• Weber propane grillbr• Ample parking for several vehicles on the propertybr• Monthly Rates:br• Regular monthly rate is $30,000 less 20% = $24,000br• June, July & August monthly rate is $32,000 less 20% = $25,600br• November monthly rate is $35,000 less 20% = $28,000br• December & January monthly rate is $38,000 less 20% = $30,400br• Plus a security deposit of $5,000 (may vary according to length of stay and subject to refundability), cleaning, 3rd party apps/platform reservation fees (if any), excise and accommodation taxesbr• Exit cleaning fee is $850br• GET: GE-141-843-4560-01br• TAT/OTAT: TA-141-843-4560-01br• W39887809-01 br•This property is booked by Kathy Muller Locations, Honolulu, Hawaii and is in full compliance with the State of Hawaii requiring that all rentals periods must be for a 30 day period only. brIn accordance with City and County of Honolulu, this property is a legally established rental accommodation that may not be rented for less than 30 consecutive days. It is compliant with Hawaii State Legislation (HB2078).

Enjoy a Spring Getaway! Oceanfront & Pool Family Hideaway. Ohana Paradise.

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$538.63

True Hawaiiana at its best! Luxury 3 bedroom 2.5 bath waterfront home with pool, spa, tiki bar, boat dock, two 60 inch flat screen TV's /DVD movie surround systems, Bose outdoor music near pool, granite, slate, and many more upgrade too numerous to mention. Located near bus line, shopping, restaurants, cinema's, water sports and white sandy beaches. Step out from the master bedroom on natural stone decking and into the sparkling new fresh water pool. Or relax beside the guest suite in the cool comfort of a private deck and private yard.brbrNear Famous Waikiki, Hanauma Bay, Sandy Beach, and many popular attractions of Honolulu, Hawaii. Many water sports are located near the home, including parasailing, jet skiing, and water jet flying. The golf course is within 2 miles of home.brbrWe welcome inquiries regarding specific dates.brbrbr_____________________________________________________________________________brbrADDITIONAL INFORMATION AND DISCLOSURES:br1. We welcome inquiries regarding specific dates.br2. Online bookings are subject to manager approval. Booking will be confirmed or declined within 24 hoursbr3. This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time regardless of actual occupancy. Please contact the property manager/owner if you have any questions.br4. This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX ID TA-092-645-7856-01, GE-092-645-7856-01; 390570350000brbrKeywords: House

Honolulu Waterfront Oasis

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$834.8

Welcome to Mahina Kai, a serene 5-bedroom, 3-bath retreat in Hawaii Kai offering panoramic views of Koko Crater, the marina, and the deep blue Pacific. This beautifully designed two-level home spans approximately 2,567 sq ft of bright indoor–outdoor living, featuring open-concept gathering spaces, a private heated pool, and room for up to 12 guests. Ideally positioned in a quiet cul-de-sac just minutes from sandy beaches, hiking trails, restaurants, and Koko Marina, Mahina Kai delivers the perfect blend of luxury, comfort, and island adventure.brbrWhat You’ll Love About Mahina Kaibr• Sweeping views of Koko Crater & the surrounding coastlinebr• Private pool, outdoor shower & covered lanai for effortless relaxationbr• Open living & dining spaces with natural light and indoor–outdoor flowbr• Fully equipped kitchen with stainless steel appliances & generous prep spacebr• Fitness room, high-speed internet & thoughtful amenities throughoutbrbrLiving and DiningbrGather in the spacious, light-filled living area where large windows frame dramatic crater and ocean views. Plush seating invites laid-back conversation, family movie nights, or simply enjoying the scenery. The dining area flows seamlessly into the living space, creating an ideal setting for shared meals, celebrations, and easy connection throughout the day.brbrChef-Ready KitchenbrAt the heart of Mahina Kai, the fully equipped kitchen includes stainless steel appliances, ample counter space, a refrigerator, stove, dishwasher, and all the essentials for preparing island-inspired meals. Enjoy breakfast with views of Koko Crater or prep dinner while staying part of the conversation—this open layout is designed for togetherness.brbrOutdoor OasisbrStep onto the covered lanai and unwind poolside as you take in striking views of Koko Crater and the surrounding palms. Lounge in the sun, enjoy alfresco meals, rinse off in the outdoor shower, or let the keiki (kids) play on the grassy lawn. Whether you're relaxing or entertaining, the outdoor spaces offer a soothing, private escape.brbrSleeping Quartersbr• Primary Bedroom (Upper Level) – Cal King bed, ensuite bath, panoramic viewsbr• Guest Bedroom 2 – Two Twin beds, bright & airybr• Guest Bedroom 3 – Queen bed, tranquil ambiancebr• Guest Bedroom 4 – Queen bed, shares bath with Bedroom 2br• Primary Bedroom (Lower Level) – King bed + Sofa Sleeper, ensuite bath, pool access, TVbrbrExtrasbrHigh-speed Wi-Fi • A/C throughout • Washer & dryer • Beach gear (chairs, towels) • Fitness room • Private garage • Streaming-capable TVs • Starter amenities • Optional pool heat (fee applies)brbrMahina Kai Community HighlightsbrSet in one of Oʻahu’s most scenic and convenient neighborhoods, guests enjoy access to outdoor adventures, water activities, shopping, dining, and world-class beaches including Hanauma Bay, Sandy Beach, and Portlock. Hiking, golfing, marina activities, and local boutiques are all nearby—perfect for an active island lifestyle.brbrNearbybrWalk: Parks, hiking paths, local shops & boutiquesbrShort Drive: Koko Marina, beaches, restaurants, markets, watersports, Koko Head Crater TrailbrbrGood to Knowbr• Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts.br• Online bookings are subject to manager or owner approval.br• Standard occupancy for this rental is 10 guests with a max occupancy of 12 guests. There will be an extra fee for additional guests over the standard occupancy.br• Air conditioning notes: AC located in main living room, kitchen, and all bedrooms. br• Pool heating available at additional fee - inquire for detailsbr• Max Included Electric Charge: $400br• Hawaii Tax ID: TA-178-279-8336-01br• TMK 390730320000brbrExclusively offered by Gather, Mahina Kai provides breathtaking views, spacious comfort, and the relaxed ambiance of Hawaii Kai’s premier coastal community. Reserve your stay today and experience an Oʻahu retreat where island beauty and elevated living come together seamlessly.

Mahina Kai: Large Tropical Modern Home w/Pool, Ocean / Koko Head Views, & A/C

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$520.03

This is a truly a local style experience property and the area of Kahala is full of the best of the best of locations on the Island of Oahu with everything close by: City Life , Awesome Beaches , Great Dinning , Tropical Hiking Trails & Views Galore , Look at the Famous Diamond Head Crator From Almost Every room.This property located in a quit serene setting with lots of home privacy. Also this home can offer family members seperated space with upstairs & downstairs living room areas. Just have fun and enjoy the Aloha of this great properties Hawaiian charms.brbrKeywords: On Oahu in Hawaii , this property is in thebr trendy dinning area of Kiamoki and is anbr elegant Hawaiian style home. Enjoy the micro climate environment, which is very close to all local activities and the Waikiki night life is just 5 minutes away and all the areas tropical delights just as close by.The master bath room has a shower that overlooks the Diamond Head crater. There is also a *Jaquzi Spa* bath tub here. The location of the property is very private and quite. Also, another full bathroom on the 2nd floor with plenty of fresh bath towels and beach towels. The Waikiki night life is just minutes away...use the royal Hawaiian Mall parking structure for easy in & out [ you get 2 hours FREE ] here with any purchase in the mall or ABC store there. brbr

Spacious Family Home With Gorgeous Sunset Views of Diamond Head

Honolulu, Hawaii, United States

Bed

Bath

7

Sleeps

Select Dates for Price

kahala home 4,883sf 6 bedrooms 7 bathrooms on 2 levels private gated entry ith video servalliance leading to 10 plus car parking with 3 car garage with pool and poolside kitchen. Gourmet kitchen, upstairs has 4 large bedrooms. Beautiful spacious and convenient getaway for the family.

Family Estate in premier neighborhood close to waikiki

Honolulu, Hawaii, United States

Bed

7

Bath

8

Sleeps

$1921.62

Privately set in one of Oahu’s most prominent residential neighborhoods, Seaside Hideaway 5BR Estate is a discreet Diamond Head retreat offering layered privacy, elevated design, and a rare sense of seclusion just minutes from Waikiki. Comprised of a three-bedroom main house and two separate studio cottage bungalows, this intimate estate blends classic island elegance with modern European finishes and resort-style outdoor living.brbrWhat You’ll Love About Seaside Hideaway 5BR Estatebr• Private Diamond Head estate with main house and two detached studio cottagesbr• Elevated setting with ocean views from the primary suite and select lanaisbr• Secluded pool, Jacuzzi, and outdoor shower tucked below the main lanaibr• High-end interiors featuring Agape Italy bathrooms and SieMatic Germany kitchenbr• Prime location near Waikiki, Kahala, beaches, and Diamond Head landmarksbrbrLiving & DiningbrThe main house offers relaxed island elegance with a modern sensibility. Light-filled interiors, refined furnishings, and thoughtful flow create a welcoming environment for gathering and unwinding. A covered lanai extends the living space outdoors, providing a comfortable perch for lounging while gazing toward Diamond Head’s dramatic coastline.brbrChef-Ready KitchenbrThe kitchen is outfitted with sleek SieMatic cabinetry from Germany and modern appliances, combining function with clean-lined design. Whether preparing casual breakfasts or relaxed dinners at home, the space supports effortless everyday living.brbrSleeping QuartersbrThe estate’s layout offers flexibility and privacy across the main house and detached cottages.brbr• Primary Suite: Located in the main house, featuring ocean views and a private outdoor lanaibr• Additional Bedrooms: Two bedrooms in the main house, styled with comfort and simplicitybr• Studio Cottage Bungalows: Two separate studio suites perched above the main house, each with a private entrance, ensuite bathroom, kitchenette, and sweeping viewsbrbrTogether, the five-bedroom configuration makes the estate well suited for families, extended stays, or groups seeking both togetherness and personal space.brbrOutdoor OasisbrBelow the main lanai, a secluded outdoor area reveals a private pool, Jacuzzi, and outdoor shower, creating a quiet retreat shielded from view. The layered layout of the property enhances privacy throughout, allowing guests to move easily between shared and personal spaces.brbrExtrasbrParking is available for two vehicles on the driveway in front of the garage. The garage itself is not accessible to guests. Please note that from the entry gate at the driveway, the main house and guest cottages are accessed via a steep stairway. Mandatory weekly cleanings are required by the owner at an additional cost.brbrNearbybrThe Diamond Head neighborhood is known for its quiet, upscale residential feel and strong beach community lifestyle. Local beaches, Diamond Head surf breaks, scenic lookouts, and coastal walking routes are within walking distance. Waikiki is approximately a five-minute drive, while Kahala Mall and the Kahala Hotel & Resort are just three minutes away, offering a wide array of dining, shopping, and leisure options.brbrGood to Knowbr• Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts.br• Online bookings are subject to manager or owner approval.br• Mandatory weekly cleanings are required at an additional cost.br• For stays of 21–30 days or longer, a utility fee or utility deposit will be charged.br• For 30-day rentals, the property is made exclusively available to the renter for the full rental period. Rates are based on a 30-day term. Please inquire for details.brbrThis vacation home is registered as a Transient Accommodation with the State of Hawaii.br• Hawaii Tax ID: W20574188-01br• TMK: 310380140000brbrDesigned for privacy, comfort, and flexibility, Seaside Hideaway 5BR Estate offers a refined Diamond Head escape with space to gather and room to retreat. Reserve your stay and experience elevated island living just moments from the energy of Waikiki.

Five-Bedroom Estate Near Diamond Head

Honolulu, Hawaii, United States

5

Bed

Bath

10

Sleeps

$1562.16

Privately tucked off Diamond Head Road, Seaside Hideaway is an intimate three-bedroom retreat perched above Diamond Head’s legendary surf breaks. Discreet, design-forward, and thoughtfully refreshed, this stylish home blends classic island character with modern European finishes, offering a rare sense of privacy and calm in one of Honolulu’s most iconic neighborhoods.brbrWhat You’ll Love About Seaside Hideawaybr• Elevated Diamond Head setting overlooking famed surf breaksbr• Private, discreet location set back from the roadbr• Recently refreshed interiors with high-end European finishesbr• Three-bedroom main house ideal for couples or small familiesbr• Easy access to beaches, coastal walks, and Diamond Head landmarksbrbrLiving & DiningbrThe living spaces strike a balance between relaxed island elegance and contemporary comfort. Clean lines, curated furnishings, and natural light create an inviting atmosphere that feels both polished and livable. Whether gathering after a beach day or enjoying a quiet evening in, the home’s layout encourages easy connection and unhurried living.brbrChef-Ready KitchenbrThe kitchen has been newly updated with sleek SieMatic cabinetry from Germany and modern appliances designed for both function and style. Thoughtful details and refined finishes make it equally suited for casual breakfasts or relaxed dinners at home.brbrSleeping QuartersbrThe three bedrooms are designed as restful retreats, each complemented by split A/C and refined finishes. Newly renovated bathrooms by Agape Italy bring a spa-like sensibility, blending clean design with everyday comfort.brbr• Primary Bedroom: King-size bed, split A/C, refined finishes designed for rest and privacybr• Second Bedroom: King-size bed, split A/C, calm and comfortable layoutbr• Third Bedroom: King-size bed, split A/C, thoughtfully appointed for restful nightsbrbrOutdoor SettingbrSet above the coastline, the home enjoys a peaceful perch with glimpses toward Diamond Head’s surf breaks. Its discreet positioning offers a sense of seclusion while remaining closely connected to the rhythm of the surrounding neighborhood.brbrExtrasbrSplit A/C units are located in the living room and each bedroom. Guests are kindly asked to keep doors and windows closed while A/C is in use. The home is offered as a private, exclusive residence for the duration of each stay.brbrNearbybrLocated in the Diamond Head area, Seaside Hideaway is close to coastal walking paths, beaches, and some of Oahu’s most recognized natural landmarks. Waikiki dining, shopping, and cultural attractions are a short drive away, offering easy access to the best of Honolulu.brbrGood to Knowbr• Rates and fees are subject to change. Minimum stay requirements may apply. Inquire for possible discounts.br• Online bookings are subject to manager or owner approval.br• For stays of 21–30 days or longer, a utility fee or utility deposit will be charged.br• For 30-day rentals, the property is made exclusively available to the renter for the full rental period. Rates are based on a 30-day term. Please inquire for details.brbrThis vacation home is registered as a Transient Accommodation with the State of Hawaii.br• Hawaii Tax ID: W20574188-01br• TA-213-293-6704-01br• TMK: 310380140000brbrQuietly stylish and thoughtfully designed, Seaside Hideaway offers an intimate Diamond Head escape defined by privacy, comfort, and elevated island living. Reserve your stay and settle into one of Honolulu’s most coveted coastal settings.

Private 3BR Home Near Diamond Head

Honolulu, Hawaii, United States

3

Bed

Bath

Sleeps

$5579.44

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.brbrOahu's Newest Luxury EstatebrOcean House is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego based developer Mark Gosselin. This estate is a modern take on Oahu's well-known Banyan House. It captures a similar style of oversized, grand spaces all centered around the stunning ocean view.brbrEvery Room Is A SuitebrWith three ocean view suites, each room affords its own level of comfort and privacy. Each bedroom is spacious with its own ensuite bathroom. The upstairs primary has its own sitting room with a desk and the downstairs primary has an extended split-level room with gym equipment. brbrTrademark Style brThe builder's trademark style was used throughout the home and is quickly apparent with the round-about driveway, floating step entrance and oversized front door. The grand room which is the center of the home, boasts 25-foot ceilings and endless ocean views. Its indoor waterfall only adds to the already relaxing atmosphere.brbrSignature Outdoor LifestylebrDesigned for Hawaii's signature indoor/outdoor lifestyle, the grand room's doors pocket back entirely and open up the home to the outdoor lounge and ocean side yard. The infinity-edge pool and jacuzzi disappear into the horizon and pull the ocean even closer to you.brbrA Hidden Sand TerracebrBeneath the ocean side yard is a hidden sand terrace with two chaise lounges. It is like your own private cove perched above Oahu's most stunning seascape. Just below the same terrace is your private ocean access to the Portlock tide Pools where dipping your toes and searching for hermit crabs, shells and colorful reef fish is only too fun.brbrPortlock, South East Oahu's Luxury NeighborhoodbrLocated in south east Oahu, Portlock is a desirable, affluent neighborhood known for its luxurious estate homes with ocean views. Overlooking Maunalua Bay, Portlock offers a unique perspective facing west where spectacular sunsets over Diamond Head can be enjoyed each evening. Though Portlock itself has no sandy beach, the famous snorkeling paradise, Hanauma Bay, is just around the corner. Also conveniently nearby is Hawaii Kai Town Center and Koko Marina filled with shops, eateries, adventure tour companies and much more! This neighborhood is perfect for a family that wants a little more space, a little more privacy and a more local island experience.brbrPool Heat is optional and can be added to your reservation with an additional charge of $250 + GE Tax per day.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.brbr***Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time.br***This vacation home has been registered as a Transient Accommodation with the State of Hawaii - HAWAII TAX ID TA- TA-199-064-7808-01brTMK 390260010000

15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD

Honolulu, Hawaii, United States

Bed

5

Bath

8

Sleeps

$5838.97

Where timeless Hawaiian charm meets modern sophistication, Kahala Beachside Estate by Gather offers the ultimate oceanfront escape on Oʻahu’s prestigious south shore. Set directly along the sands of Kahala Beach, this magnificent estate spans 7,860 square feet of indoor and outdoor living space, with seven bedrooms and eight bathrooms designed for up to 14 guests. Perfect for families, groups, or extended stays, this home combines the elegance of old Hawaiʻi with world-class modern comforts in a private, fully gated setting.brbrWhat You’ll Love About Kahala Beachside Estatebr• Direct beachfront access to tranquil Kahala Beachbr• Expansive private pool and spa surrounded by palm trees and tiki torchesbr• Seven elegant suites, each with a California King bed and ensuite bathbr• Seamless indoor–outdoor design with disappearing glass wallsbr• Dining space for up to 30 guests, ideal for large gatheringsbr• Separate Carriage House with full kitchen, dining, and living areabrbrLiving & DiningbrFrom the moment you enter, Kahala Beachside Estate envelops you in light and luxury. The open-concept great room showcases soaring ceilings, plush seating, and walls of glass that disappear to reveal breathtaking ocean views. Whether you’re lounging with a book or hosting a sunset dinner, every moment is framed by the natural beauty of Hawaiʻi.brbrThe adjoining dining area invites shared meals in a setting that easily accommodates family-style dinners or festive gatherings. Designed with both comfort and sophistication in mind, this home’s layout encourages connection, conversation, and relaxation.brbrChef-Ready KitchenbrThe gourmet kitchen is a chef’s dream, featuring high-end appliances, extensive counter space, and a generous island for prep or casual dining. Ideal for preparing anything from a fresh island breakfast to a full evening feast, this space blends functionality with elegant design, ensuring every meal feels effortless and enjoyable.brbrOutdoor OasisbrBeyond the glass doors, an oceanfront paradise awaits. The private pool and spa are nestled among tropical palms and tiki torches, with the sandy shoreline just steps away. Multiple lanais and shaded seating areas provide the perfect backdrop for morning coffee, afternoon barbecues, or starlit dinners by the water.brbrAfter a refreshing swim, rinse off in the outdoor shower and relax into the peaceful rhythm of island life.brbrSleeping QuartersbrEach of the estate’s seven suites offers a luxurious retreat, featuring California King beds, air conditioning, ceiling fans, Smart TVs, and ensuite baths with rainfall showerheads. Many include lanais with garden or ocean views.brbr• Bedroom 1 – Seashell Suite (Downstairs, Mauka): Cal King, ensuite bath, garden and ocean views, split A/Cbr• Bedroom 2 – Maile Suite (Downstairs, Makai): Cal King, ensuite bath with clawfoot tub and walk-in shower, private lanai, ocean view, wheelchair-accessible entrybr• Bedroom 3 – Coral Suite (Upstairs, Mauka): Cal King, ensuite bath, private lanai, garden viewbr• Bedroom 4 – Honu Suite (Upstairs, Mauka): Cal King, ensuite bath, mountain and garden viewsbr• Bedroom 5 – Seastar Suite (Upstairs, Makai): Cal King, ensuite bath with jetted tub, ocean and pool viewsbr• Bedroom 6 – Kapa Suite (Primary, Upstairs, Makai): Cal King, ensuite bath with clawfoot tub, ocean and pool views, private lanaibr• Bedroom 7 – Carriage House Suite (Guest House, Upstairs): Cal King, ensuite bath, full kitchen, dining area, living room, and private lanaibrbrExtrasbrEvery detail of Kahala Beachside Estate enhances your comfort:br• Central and split air conditioning throughoutbr• Two sets of washers and dryersbr• High-speed Wi-Fi and Sonos sound systembr• iPod docking station, DVD player, and Smart TVsbr• Printer/scanner/fax for remote workbr• Private parking and gated entrybr• Safe and full home security systembrbrLocation HighlightsbrLocated in one of Honolulu’s most sought-after beachfront neighborhoods, this estate offers easy access to Oʻahu’s best attractions while maintaining total privacy. Spend days lounging on Kahala Beach, shopping at Kahala Mall, or exploring scenic hikes and snorkeling spots nearby.brbr• Walk: Kahala Beach, Kahala Hotel & Resortbr• Short Drive: Waikīkī, Diamond Head, Hanauma Bay, Halona Blowhole, Ala Wai Golf Course, boutique shopping, and fine diningbrbrGood to Knowbr• This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed, as prorated stays are not available.br• This property may not be rented for less than 30 consecutive days.br• Mandatory mid-stay cleaning fee: $519 + tax (for stays of 10 nights or longer)br• Utility fee: $3,500/month for stays of 21 days or morebr• HI Registration: TA-104-487-9872-01br• TMK: 350060190000brbrKahala Beachside Estate by Gather isn’t just a luxury home — it’s a once-in-a-lifetime experience. Here, every sunrise and sunset unfolds over your private stretch of sand, every moment infused with the beauty and spirit of aloha. Whether hosting family, friends, or simply seeking serenity by the sea, this rare gem captures the essence of Hawaiʻi’s finest coastal living.

Kahala Beachside Estate: Luxury Estate w/Pool, Jacuzzi, AC & Spacious Yard

Honolulu, Hawaii, United States

7

Bed

8

Bath

14

Sleeps

$828.38

Welcome to your private rainforest retreat in beautiful Mānoa Valley! This spacious 3-bedroom, 2.5-bath home with a hot tub is perfectly located within walking distance to Manoa Falls, a community pool, tennis & pickleball courts, and wellness classes—all while being just minutes from Waikiki and world-class beaches.brEnjoy the peace of the valley with the convenience of the city: a full shopping center with groceries, restaurants, coffee, and banks is right nearby, and you’ll have quick access to hiking trails, world famous Waikiki, international brands at Ala Moana Shopping Center, downtown Honolulu, military bases, top private and public schools, universities, and major hospitals.brbrSpa-Inspired Bathroomsbr• Primary bath with double vanity and dual shower headsbr• In-suite bathroom with jetted soaking tub shared between the two junior bedroomsbrbrEntertainment & Comfortbr• Living room with wall-mounted Smart TVbr• Bose speaker systembr• PlayStation for gaming nightsbr• Junior bedroom outfitted with a gaming station perfect for teenagersbrbrFull Amenitiesbr• Fully equipped kitchen with gas cooktop, oven, dishwasher, and ice makerbr• Full-size washer & dryerbr• Ultra-fast fiber optic mesh Wi-Fi 7br• Covered outdoor dining areabr• High-speed fans in every room for island comfortbr• Ideal for travel nurses, military families, visiting professors, and relocationsbr• Quiet, safe residential neighborhoodbrbrYou’re perfectly positioned in one of Honolulu’s most desirable neighborhoods:br• Manoa Marketplace: groceries, dining, coffee, and banksbr• Award-winning local restaurantsbr• Weekly farmer’s marketbr• Parks and hiking trailsbr• Easy freeway and bus accessbr• 10–15 minutes to Waikiki Beach, Kalakaua Ave & Ala Moana Shopping Centerbr• Close to military bases, schools, universities, and hospitalsbrbrGuest AccessbrYou’ll have the entire private, free-standing home to yourself—called Rainbow Oasis. Your front door opens to views of the lush Mānoa rainforest and mountains.brThere are a few stairs leading up to the home (a little climb to paradise!), so please note that the property is not wheelchair accessible.brbrInteraction With GuestsbrWe respect your privacy and offer easy self-check-in.brThe property includes two separate homes on the lot (not attached). Each has its own private entrance and amenities. The only shared feature is the hot tub.brWe simply ask guests to follow house rules, quiet hours, and hot tub guidelines so everyone enjoys a peaceful stay.brbrImportant Details (Please Read)brDue to City & County regulations, this property requires a 30-night minimum booking. You are welcome to depart earlier if needed. To comply with local law:br• All reservations must be made for the full 30-day period, even if your stay is shorter.br• We’ve adjusted nightly rates and applied a monthly discount to make this more affordable.br• A strict cancellation policy is required so we can responsibly manage longer-term bookings.

Rainbow Retreat 3bd, Hot Tub, Walk to Waterfalls, close to Waikiki.

Honolulu, Hawaii, United States

3

Bed

Bath

Sleeps

Select Dates for Price

Escape to the quiet community of Paiko Lagoon on Oahu's South Shore. This duplex single story home is the perfect getaway with the right mix of modern and beach. Very private with separate entrance and keypad entry. Enjoy watching the sunrise from your bed over the Lagoon each morning. Beach access is steps away from the front door and a great place for kayaking, snorkeling, fishing, or just lounging in the sun. Full kitchen, queen bed, large bathroom and washer/dryer.

Lagoon Waterfront Retreat

Honolulu, Hawaii, United States

1

Bed

1

Bath

Sleeps

$2794.27

Black Point Ocean Villa rests above the Pacific in Diamond Head’s coveted Black Point enclave, offering rare oceanfront privacy, architectural character, and seamless access to Black Point Pool, a private gated community sea pool carved into the coastline. Elevated over the water with sweeping views toward Koko Head, this historic yet refined residence delivers an authentic sense of island life for extended stays.brbrOriginally built in 1929 and thoughtfully remodeled over time, the home pairs classic craftsmanship with modern comfort. Rich koa wood floors, custom millwork, and vaulted beam ceilings add warmth and depth. Oversized picture windows frame uninterrupted ocean blues from nearly every room. Soft, neutral interiors let the coastline take center stage. This is a holiday home for guests who value space, privacy, and a meaningful connection to the sea.brbrWhat You’ll Love About Black Point Ocean Villabr•Nestled in a private gated peninsula community between Diamond Head and Kahalabr• Gated access to the private oceanfront Black Point Pool with direct water entrybr• Over 200 linear feet of dramatic coastline frontagebr• Elevated Black Point setting with no public beach access belowbr• Two outdoor dining areas for eight, plus indoor dining for gatheringsbr• Vaulted great room with expansive ocean-facing windowsbrbrLiving and DiningbrThe expansive great room anchors the home. Soaring vaulted ceilings with exposed beams and walls of glass draw your gaze straight to the Pacific. A sunken living area wrapped in windows brings you closer to the water, creating a natural space for conversation, reading, or watching the light shift across the horizon.brbrAn indoor dining table sits just off the living area, positioned for ocean views. The layout flows seamlessly to the outdoor garden lanai, making indoor-outdoor living feel effortless. In addition to the indoor dining space, the home offers two distinct outdoor dining areas, each seating eight: one on the oceanfront deck for sunset dinners above the water, and another tucked within the private lava rock garden for more intimate gatherings surrounded by lush greenery.brbrChef-Ready KitchenbrDesigned for extended stays, the kitchen offers generous counter space, quality appliances, and custom wood cabinetry that echoes the home’s original character. Its open connection to the living and dining spaces allows hosting to feel relaxed and unhurried.brbrOutdoor OasisbrOutdoor living defines Black Point Ocean Villa. The spacious oceanfront deck overlooks the gated community’s private sea pool and the coastline beyond, where waves meet lava rock below. Lounge seating invites slow mornings with coffee and long afternoons in the sun. A private pathway winds through dense naupaka to the water’s edge.brbrIn the backyard, a lava rock garden framed by mature tropical landscaping creates a second serene retreat. Shaded seating and an additional eight-person dining table offer flexibility for entertaining, quiet reflection, or simply listening to the rhythm of the ocean.brbrSleeping Quartersbr• Primary Bedroom: King bed, ensuite bathroom, ocean, water, garden, and mountain views, private lanai with outdoor access, central A/C, ceiling fan, blackout drapesbr• Guest Bedroom 2: King bed, ensuite bathroom, partial ocean and garden views, private lanai with outdoor access, central A/C, blackout drapesbr• Guest Bedroom 3: Queen sofa bed, ocean, garden, and mountain views, split A/C, blackout drapesbr• Guest Bedroom 4: King bed, ensuite bathroom, ocean, garden, and mountain views, private lanai with outdoor access, split A/C, blackout drapesbrbrThree bedrooms function as primary-style suites, each with its own lanai and direct outdoor access, allowing guests to step outside to ocean air each morning. Two newly renovated bathrooms feature Toto-style toilets for added modern comfort.brbrExtrasbr• Washer and dryerbr• Central and split air conditioningbr• Ceiling fans throughoutbr• Private garage and additional parkingbr• Smart lock and keypad entrybr• Beach towels providedbrbrNearbybrLocated in Black Point, one of Honolulu’s most private oceanfront neighborhoods, the home offers a peaceful residential setting while remaining a short drive from beaches, dining, and everyday conveniences. Scenic coastal walks, Diamond Head views, and iconic shoreline lookouts are part of daily life here.brbrGood to Knowbr• This property is available exclusively as a 30-day minimum rentalbr• The home is reserved solely for the renter during the rental periodbr• Ideal for families, couples, and digital nomads seeking an extended oceanfront staybr• TAT ID: TA-100-905-7792-01br• TMK / Parcel ID: 1350010070000brbrWhether planning an extended island stay or seeking a refined alternative to a vacation condo, Black Point Ocean Villa offers privacy, space, and a rare oceanfront experience. Inquire to begin your stay at this exceptional short-term rental designed for living well by the sea.

Diamond Head Sea Pool House: Oceanfront Estate w/ Private Sea Pool

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$434.02

Aloha! Welcome to our happy place! brbrbrbr ️ Central Location ️brbrThe location is right on Waikiki Beach. You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more.brbrbrbrAdditionally, our building offers fantastic convenience, with an array of coffee shops, ice cream stores, and restaurants right on-site for easy access to great food and treats any time of day.brbr Sleeping Arrangement brbr2 Queen beds & 1 Sofa Bed (linens are provided for all beds)brbrbrbr Car & Parking brbrThis unit comes with a parking spot in the building.brbrbrbrOr we have a brand new Toyota SUV for rent through Turo. It is around $100 per day, and it comes with free parking inside the building. You can book it using the following link. Insurance options, pick-up and drop-off instructions will be provided when you check out.brbrhttps://turo.com/us/en/drivers...brbrbrbrRenting my car is entirely optional - you can rent a car at any other car rental place.brbrbrbr Self Check-in brbrbrbrYou can self check-in through a code to our smart lock.brbr2 days before your check-in date, we will send you detailed instructions about check-in.brbr Food & Fun brbrCheck out our recommendations on local food and activities on our Food & Fun page.brbrbrbr❓ Frequently Asked Questions (FAQ) ❓brbrYou can get faster answers by reading our FAQ page, where you can find information on:brbrDiscountsbrbrEarly check-in & late check-outbrbrbrbrKitchen essentials & spices providedbrbrBeach gear providedbrbrWasher & dryerbrbrPack-n-play availabilitybrbrDeliver mail, packages, gifts, or groceries to the roombrbrLost itemsbrbrMore...

Oceanview in Waikiki: 2 Queen Beds w/ Parking

Honolulu, Hawaii, United States

Bed

Bath

Sleeps

$304.68

Aloha:br Welcome to your ideal Waikiki Vacation condo Studio Getaway...Ideally located at the start of Waikiki by the Marina, just steps to shops/restaurants and all the fun of Waikiki Beach!brbr Our Condo getaway is tropically appointed in a tropical island decor. Sleeps up to 4 people, and features queen bedding and queen sofa sleeper (2 adults/2 kids or 3 adults total)brbr Prepare your favorite meal in your fully-equipped kitchen, relax in the comfortable sitting area, and enjoy the lovely city/mountain views from the balcony/lanai. Shops & restaurants are just minutes away.brbr An excellent value...perfect for a couples getaway, friends traveling together and smaller families with younger kids.brbr Reserve our Waikiki Studio Vacation Condo today...An Excellent Value and the perfect place to stay in famous Waikiki Beach. Welcome to the islands, aloha. Book today!

Waikiki Studio, Vacation Condo Rental...Steps to Beaches! Sleeps 4.

Honolulu, Hawaii, United States

1

Bath