Vacation Rentals By Owner In Kailua, HI

Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of sand. Blending timeless coastal architecture with luxurious modern amenities, this 5,902-square-foot residence offers the ultimate beachfront lifestyle — steps from turquoise waters, framed by swaying palms, and infused with island light.brbrWhat You’ll Love About Kailua Beachfront Estatebr • Direct access to world-famous Kailua Beach with panoramic ocean viewsbr • Heated pool and spa surrounded by lush tropical landscapingbr • Main residence plus detached guest house and carriage suitebr • Vaulted ceilings, natural wood accents, and elegant modern finishesbr • Private, gated setting within Kailua’s coveted Beachside enclavebrbrLiving & DiningbrFrom the moment you enter, the sound of the surf and the sight of the Pacific fill the home with tranquility. The open-concept great room features grand windows, designer lighting, and seamless flow to the lanai and pool terrace. Indoors, a graceful blend of whitewashed walls and natural textures creates a bright, refined backdrop for entertaining or family gatherings.brbrChef-Ready KitchenbrA gourmet kitchen with dual islands, premium appliances, and ocean-view dining space anchors the home. Marble surfaces and custom cabinetry complement its breezy sophistication, whether you’re enjoying a casual breakfast or hosting a private chef’s dinner.brbrOutdoor OasisbrDesigned for relaxation and connection, the courtyard pool and spa serve as the heart of the property. Enjoy sunrise swims, afternoon lounging, and sunset dining on covered lanais. Beyond the landscaped dunes, your private path opens directly to Kailua Beach — one of the world’s most celebrated stretches of soft white sand and crystalline water.brbrSleeping Quartersbr• Primary Suite – King bed, ensuite bathroom, ocean view, split AC, ceiling fanbr• Guest Suite 2 – King bed, ensuite bathbr• Guest Suite 3 – Queen bed, ensuite bathbr• Guest Suite 4 – Queen bed, ensuite bathbr• Guest Suite 5 – Queen bed, ensuite bathbr• Guest Suite 6 – Queen bed, ensuite bathbr• Carriage House Loft – Flexible layout, full bath, kitchenette, and ocean proximitybrbrExtrasbrHigh ceilings, central AC, full laundry room, media space, and abundant parking — including a two-car garage and a sports-car bay. The estate also includes a detached guest home and pool house, each designed with privacy and elegance in mind.brbrNearbybr • Walk – Kailua Beach and Lanikai Beach for kayaking, paddleboarding, and morning swimsbr • Short Drive – Kailua Town boutiques, cafés, and fine dining; Mid-Pacific Country Club; Lanikai Pillbox HikebrbrGood to KnowbrTAT ID: TA-056-254-2592-02brTMK: 1430190360000brbrExperience the serene beauty, privacy, and prestige of beachfront living at Kailua Beachfront Estate — your private gateway to Hawaii’s coastal elegance.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.

Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House

Kailua, Hawaii, United States

7

Bed

6

Bath

14

Sleeps

$1352.48

Welcome to Kailua Hale Kahakai, a serene beachfront estate set along one of the most breathtaking stretches of Kailua Beach. With six bedrooms, five bathrooms, and over 4,300 sq. ft. of breezy living space, this expansive retreat blends open-air island design, panoramic ocean views, and peaceful privacy on a quiet flag lot surrounded by swaying palms. Ideal for family gatherings, reunions, group travel, and extended stays, this home delivers a true Hawaiian beachfront experience.brbrWhat You’ll Love About Kailua Hale Kahakaibr• Direct beachfront access to Kailua Beachbr• Four ocean-view bedrooms on the upper levelbr• Expansive shaded lanai and lush oceanfront backyardbr• Large chef-ready kitchen with stainless appliances and center islandbr• Two living rooms, formal dining room, and multiple indoor/outdoor gathering spacesbr• Natural tradewinds and ceiling fans throughout (home is not air-conditioned)brbrLiving & DiningbrDesigned for families and groups, the spacious living areas invite relaxation with coastal décor, sliding glass doors, and sweeping views of the turquoise shoreline. The formal living room overlooks Kailua Beach, while the adjacent TV room features a Smart TV for movie nights or quiet downtime. The bright, window-wrapped dining room seats your group comfortably and opens to the oceanfront backyard.brbrChef-Ready KitchenbrThe fully equipped kitchen includes stainless-steel appliances, a large center island, microwave, mixer, blender, toaster oven, coffee maker, grinder, and ample cookware. Whether preparing meals or crafting island cocktails, this kitchen is ready for every occasion.brbrOutdoor OasisbrStep onto the shaded lanai overlooking a private, palm-framed lawn that stretches toward the shoreline. Enjoy covered outdoor lounging and dining, oceanview seating areas, and a direct pathway to Kailua’s soft sandy beach. It’s the perfect setting for sunrise coffee, sunbathing, or sunset unwinding.brbrSleeping Quartersbr• Main Bedroom Suite (Upper Level) – King bed, balcony with ocean and bay views, ensuite with soaking tub and dual vanitiesbr• Guest Bedroom 2 (Upper Level) – King bed, ocean view, shared full bath with tubbr• Guest Bedroom 3 (Upper Level) – King bed, garden view, shared full bath with tubbr• Guest Bedroom 4 (Upper Level) – King bed, ocean view, shared full bath with shower/tub combobr• Guest Bedroom 5 (Upper Level) – Queen bed, ocean view, shared full bath with shower/tub combobr• Guest Bedroom 6 (Main Level) – King bed, garden view, private ensuite bath with walk-in showerbrAdditional full bath on the ground level.brbrExtrasbr• Beach chairs, mats, umbrella, boogie boards, coolersbr• Insulated cooler bag and beach bagbr• Full-size washer/dryerbr• Additional beddingbr• On-site parkingbr• Smart TVs and cablebr• Ceiling fans and natural breezesbr• Secure smartlock entrybrbrNearbybr• Walk: Kailua Beach, Kalama Beach, Kailua Beach Park, Kailua Town shops and restaurants, Island Snow, Lanikai Bike Pathbr• Short Drive: Lanikai Beach, Lanikai Pillbox Hike, Downtown Honolulu, Ala Moana Center, Kahala Mall, Koʻolau Golf Course, Maunawili Falls Trail, Whole Foods Kailua, Target KailuabrbrGood to Knowbr• Monthly rental; full monthly rate applies regardless of number of nights stayedbr• Home does not have air conditioning; cooled by trade winds and ceiling fansbr• Exclusive to renter for the full 30-day periodbr• Tax ID: TA-039-143-1168-01br• TMK: 430130020000brbrReserve your dates now and experience the beauty, privacy, and beachfront serenity of Kailua Hale Kahakai.

Villa

Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions

Kailua, Hawaii, United States

6

Bed

5

Bath

12

Sleeps

$5,900

This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1802 It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#TA-060-877-8240-01. TMK0.brbrPlace in Paradise* - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted Best Beach in the United States by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit. Large outdoor deck spaces provide the perfect place to relax in the sun or enjoy a barbecue while taking in the breathtaking views of the Bay. Kailua Beach offers 3 miles of fine, soft white sand along a crescent shaped bay bordered by clear turquoise waters which have a consistent year round temperature of about 75 degrees F (25 C). The steady off shore trade winds, water temperature and protective reef make this bay a popular area for all sorts of water sports including Kayaking, Stand-Up Paddling, Surfing, Boogie Boarding, Swimming and Kite Surfing. The home includes a fully equipped kitchen with granite counter tops and up-to-date appliances. A large living area features picture windows facing the sea in addition to a comfortable media room for entertainment.brBeach chairs, boogie boards, and beach towels, are a few of the amenities included.brbrThe Bedroom Configurations Are As Follows:brUpstairs:brBedroom 1 - (Primary Bedroom) King Bed, ocean front with private lanai, split a/c, Smart TV, and ensuite bathroombrBedroom 2 - King Bed, ocean front with private lanai window a/c, and ensuite bathroom.brbrDownstairs;brBedroom 3 - Two Queen Beds, window a/c, smart TV, and ensuite bathroombrBedroom 4 - Two Queen beds, split a/c, smart TV, and ensuite bathroombrBedroom 5 - King bed with view of ocean across the courtyard, split a/c, Smart TV, and ensuite bathroombrbrSmart TV in media roombrbrThe main living space, dining and kitchen areas are not air conditioned but as we are on the ocean, the home enjoys tradewinds year 'round.brbrWith periodic restrictions for maintenance, guests may also enjoy the facilities of the Hale Kai Surf and Racquet Club with a swimming pool, tennis court, paddle tennis court (also used for pickleball) and clubhouse (generally available after 12noon to rental guests), located just steps away. This is a great, casual retreat at any time of the year. brbr* Place in Paradise is a registered trademark of RLK Kalaheo LLC and may not be used without the expressed written consent of the owner.brbrSPECIAL NOTICE TO GUESTS: This home is for quiet residential vacation accommodations only. Parties, weddings, receptions, events or gatherings of any kind are strictly prohibited. Private chefs, caterers, photographers and other commercial vendors are not permitted.brPARKING: Guests are provided a garage to accommodate 1 large or 2 small vehicles. In addition, 2 cars may be parked on the driveway surface only. No street parking is permitted in this area.

Place in Paradise-Summer Available -Short term Lic#1990/NUC-1802

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$1013.86

This stylish, designer decorated, 4 bed, 4 Bath home is just across the street from Kailua Beach. We call her Coastal Soul. Lounge in the beach chic living room, cook in the gourmet, fully equipped kitchen, or swim in the heated lagoon pool. With a gazebo, the private yard is like a mini resort. And best of all, NO CLEANING FEE on 30 day bookings!brJust across the street is Kailua beach park with award-winning 3 mile long, white sand, Kailua Beach. brWalk just down the street to the iconic Buzzs Steakhouse for lunch or dinner. brCome see what Coastal Soul has to offer. Amenities include central air conditioning, Subzero fridge, Wolf range, wine fridge, gas barbecue, two bikes, lots of beach toys and off-street parking in a gated, private community. brThe heart of Kailua town is just 1.5 miles away. There you will find boutique shopping, trendy, restaurants, a Whole Foods Market and Target for those things you might've forgotten :-)brThis 3025 sq. ft. home is professionally managed and sparkling clean. brThis 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.

Steps from Kailua Beach, heated pool, gazebo, AC, NO CLEANING FEE!

Kailua, Hawaii, United States

Bed

Bath

8

Sleeps

$371.96

Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the breeze off of Kailua Bay this quiet home is the perfect place to relax and unwindbrbrEnjoy island living at its best in this fully furnished bright and breezy home with in ground pool and spacious Lanai. Lounging by the pool or under the lanai can be as relaxing as it is a great enviornment to work while away from home. This house is located only one block from the gorgeous Kawainui Marsh Wildlife Sanctuary and Kaha Park, allowing for a great walking, running, or simply enjoying nature and the Ko'olau Mountain views.brbrThe interior of this home is spacious, open, and bright, with ample room for spening quality time together. The Mauka facing lanai is a wonderfully relaxing spot in the morning or early evening. Perfect for sipping coffee or a cocktail while appreciating the view of the mountains and the sunsets.brbrThe Ko'Olau Room has a queen size bed with soft bamboo sheets. A full wall of windows opens up to a deck that overlooks the pool and lounge area. At night you have a view of the beautiful mountain sunsets. The room also has a large dresser with a matching mirror and a comfy corner chair. The flooring is Brazilian cherry.brbrThe Plumeria Room also has a queen size bed with sot bamboo sheets. The cool ocean breeze flows through the double windows allowing for a comfortable sleep. The room has a deep closet, night stand with lamp, ceiling fan and air conditioning. The flooring is wall to wall carpet.brbrThe Mango Suite (master suite) has a comfy king sized bed with soft cotton sheets. The room has vaulted ceilings with a ceiling fan and air conditioner. There are oversized deep double closets as well as a linen closet, a large dresser with matching mirror and night stand with a lamp. This room also has double windows facing the north. Attached is an open room with french doors allowing it to be a flexible space that can be used for an office, quiet tv or entertainment center or even a nursery. This room has wall to wall windows that lead to the back deck and outside stairs with views of the Ko'Olau Mountains and pool. This room has a new TV, a couch, and large ottoman that coverts into a small bed if needed. The master bath has a large vanity with lots of storage and a separate pocket door for the shower and toilet area. A full tub and glass shower enclosure.brbrThe kitchen and formal dining area has granite countertops, an electric range, microwave oven, a Bosh dishwasher and GE refrigerator. The kitchen is fully stocked with pots, pans, glass wear, cooking utensils, food processor, rice cooker, waffle maker, Instant Pot, Keurig Coffee maker, baking wear, a Kitchen Aid mixer and lots of baking supplies as well. There is a breakfast table for 4 or a larger table next to the wall to wall windows that can seat 8. The kitchen has vaulted ceilings with multiple lighting options. The flooring is Brazilian Cherry.brbrThe living/family room has a love seat and couch. This also has vaulted ceilings with a large ceiling fan, an entrance table with lamp and a large Bali Boo book case. This room gets incredible breezes day and night from the ocean. This room does share an air conditioner with the dining and kitchen area. This room is the entry to this welcoming living space. The exterior also has outside decking along the front. brbrThere is a completely seperate unit below with two quiet tenants. One of the tenats takes care of the property and is available to help if, for example, sometheing needs to be fixed or any other issues that may arise.

Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool

Kailua, Hawaii, United States

3

Bed

2

Bath

7

Sleeps

$651.73

Experience relaxed coastal living at Seahorse Beach House by Gather, a serene monthly rental perched just steps from the soft white sands of Kailua Beach. Nestled along one of Kailua’s most sought-after beachside loops, this elevated 2-bedroom, 2-bath retreat blends privacy, comfort, and island elegance—perfect for extended stays on Oahu’s stunning windward coast.brbrWhat You’ll Love About Seahorse Beach Housebr• Just steps to Kailua Beach—one of Oahu’s most iconic shorelinesbr• Spacious wrap-around deck with multiple seating areas and partial ocean viewsbr• Open-concept living, dining, and kitchen design for effortless flowbr• Large primary suite with private deck access, workspace, and spa-style ensuitebr• Fully fenced yard with gated entry for privacy and peacebrbrLiving & DiningbrAn elevated floor plan captures cooling breezes and island views throughout the home. The living and dining areas enjoy beautiful partial ocean views through floor-to-ceiling windows, creating a bright, airy space for gatherings, meals, and relaxation. Sliding doors open seamlessly to the expansive deck, offering a true indoor-outdoor lifestyle.brbrChef-Ready KitchenbrThe kitchen’s clean, modern design features generous counter space, quality appliances, and all the essentials you’ll need for long-term stays. Whether preparing simple breakfasts or hosting dinner outdoors, this space makes cooking a pleasure.brbrOutdoor OasisbrThe spacious wrap-around deck offers shaded seating areas, chaise lounges, and a bar-height dining table with umbrella—perfect for morning coffee, evening cocktails, or dining under the stars. The fully fenced, tropical yard provides privacy and a peaceful setting surrounded by lush greenery and ocean breezes.brbrSleeping Quartersbr• Primary Bedroom – King bed, ensuite bath with stand-alone tub, shower, walk-in closet; split A/C; workspace; private deck access; partial ocean viewbr• Guest Bedroom – Queen bed, split A/C, workspace, floor-to-ceiling windows with deck views; access to shared full bath across the hallbrbrExtrasbr• Split A/C throughoutbr• High-speed Wi-Fibr• Washer and dryerbr• Beach gear and towels providedbr• Dedicated workspaces in both bedroomsbr• Fully fenced yard and gated entrybrbrNearbybr• Nearby – Walk: Kailua Beach, local cafés, boutiques, farmers’ marketsbr• Nearby – Short Drive: Lanikai Beach, Pillbox Hike, shops and dining in Kailua TownbrbrGood to Knowbr• This property is offered as a monthly rental. Full-month rate applies regardless of nights stayed.br• A utility fee of $500/month applies to stays of 21+ days.br• This property may not be rented for less than 30 consecutive days.br• Tax ID: TA-129-806-1824-01br• TMK: 430130190000brbrSeahorse Beach House by Gather offers an exceptional blend of beachside tranquility and modern comfort—an ideal retreat for anyone seeking an extended stay immersed in Kailua’s sun-lit, ocean-kissed lifestyle.

Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$678.64

brTHIS PROPERTY IS A LEGAL SHORT TERM RENTAL brDAYS NOT SHADED (See Online/Inactive Calendar) ARE AVAILABLEbrCONTACT HOST/RESERVATIONS & DETAILSbrbrThis beautiful four bedroom, four full bath air conditioned Hawaiian style home is just a short walk to pristine Kailua Beach. Consisting of two luxury master suites, a junior suite and one guest bedroom with adjoining full bath.brbrThis spacious, estate quality home offers serene Hawaiian ambiance with maximum security. Heated pool, Travertine stone floors, granite counters, top of the line finishes and appliances throughout.brbrStroll to Kalapawai Market for a latte and watch the sunrise. Walk to Buzz's for lunch or dinner, Island Snow for a shave ice treat or watch the windsurfers and kayaks from Lanikai Point. Everything is at your doorstep! br30 day rental period discount.brbrKeywords: House

Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST

Kailua, Hawaii, United States

Bed

Bath

8

Sleeps

$3411.76

This property is professionally-managed by Private Homes Hawaii, LLC and is a licensed short-term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1774 for the main house and 1990/NUC-1775 for the guest cottage. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, License#TA-187-952-4352-01. TMK.brbrKailuana Beachfront Estate - Fully-remodeled Kailua home sits on nearly an acre of prime Kailua beachfront. brThe two homes sleep 8-12 guests in a main house and detached guest cottage. This enchanting Kailua Estate is located in the premier part of the bay where the sand is at its widest and the turquoise-blue waters are most inviting. An expansive ocean front lawn provides ample privacy and is ideal for relaxing and recreation where the worries of the world are left behind. Following recent renovations, the home contains just the right blend of modern comforts in its updated kitchen and baths, with elements of charm carefully preserved from a richly felt past. brbrThe main home offers 3 bedrooms and 2 baths overlooking the large grass lawn with the beach and ocean beyond. Two sun-decks offer space for casual dining and/or informal gatherings overlooking the ocean. The two bedroom one bath guest cottage sits adjacent to the main house, with private entrance, living area and a modernized kitchen of its own.brFully air-conditioned, with modernized amenities, both homes are comfortable year round and ideal for extended family stays.brbrBedding Arrangements are as follows:brMain House; brGuest Room 1 - KingbrGuest Room 2 - QueenbrGuest Room 3 - Queen with ensuite bathbrNote: Guest Rooms 1 and 2 share a large bathroom between the 2 bedrooms with tub, shower, double sink and commode.brbrCottage:brGuest Room 4 - KingbrGuest Room 5 - 2 QueensbrbrNote; this property is for quiet residential vacation accommodations only. Parties, weddings, receptions, Luaus, events and gatherings of any kind are prohibited. Please inquire further with our agents.brbrLocated on a quiet drive just minutes from the center of Kailua Town guests can stroll down Kailua Beach to the famed Kalapawai Market, or enjoy a local favorite; shaved-ice at popular Island Snow Hawaii, or, dine at Buzz's Original Steak House in Lanikai, just minutes away. Kayak and paddle board rentals are just a few minutes walk at Kailua Beach Adventures - providing all the water toys needed for your days on the water. The steady off shore trade winds, water temperature and protective reef make this bay a popular area for all sorts of water sports including Kayaking, Stand-Up Paddling, Surfing, Boogie Boarding, Swimming and Kite Surfing. The setting is magnificent and awaits your next Hawaii vacation.

Center of Kailua Bay! Licensed Beach Front Rental #1990/NUC-1774,1775

Kailua, Hawaii, United States

5

Bed

3

Bath

12

Sleeps

$3923.01

This property is professionally-managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1757. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, Lic#TA-043-470-0288-01. TMK.brbrWelcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). brbrMr. Walker's inviting presence is felt in the structure of this, his favorite hideaway on Lanikai Beach. Built in 1934, this enchanting environment transports you back to an era of graceful living, where the worries of the world are lost in the luxury of sea, sand and restful surroundings. Following recent renovations, the house contains just the right combination of added comforts in its updated kitchen, guest quarters and “boat house”, with elements of charm carefully preserved from a richly felt past. brbrOne of the first homes to take advantage of Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, John Walker’s Beach House set the standard by which the surrounding community grew…a standard which has been nurtured by his family through the years for you to enjoy. Although only with us in spirit, John Walker’s love of Lanikai is preserved by one of his most revered places in the world.brbrThe main house features 3 bedrooms, kitchen and large great room with spacious guest rooms. Steps away is the white soft sands of Lanikai Beach with access to the water provided from the front lawn. With a separate entry, the 'guest cottage' located off the entry courtyard features a queen-bedded room and a small parlor with kitchenette (sleeps up to 4). Another private entry boathouse sits above the garage - complete with its own living room, kitchen, bathroom and lanai. The boathouse also has a loft area with double bed that may be suitable for young children (sleeps 2-4). This is the classic Lanikai Beach House - for those looking for a casual, relaxing getaway on the shores of one of the worlds' best beaches!brbrBedroom configurations:brMain House Primary - King Bed, ensuite bathroom with shower, split a/c, smart TVbrMain House Guest Room (Ocean) - Queen Bed, shared bathroom in hall with shower & bathtub, split a/cbrMain House Guest Room (Courtyard) - Queen Bed, shared bathroom in hall with shower & bathtub, split a/cbrbrCottage Guest Room One - Queen Bed, ensuite bathroom with shower, split a/c, Smart TVbrCottage Guest Room Two - Full Bed brbrBoat House Lanai - Queen Bed, shared bathroom with shower, split a/cbrBoat House Loft - Full Bed, shared bathroom with showerbrbrNote; this property is for quiet residential vacation accommodations only. Parties, weddings, receptions, Luaus, events and gatherings of any kind are prohibited. Please inquire further with our agents. Note: Limit of 3 vehicles.

Walker Beach House - Lanikai Ocean Front Lic.#1990/NUC-1757

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$3204.04

Enjoy everything Hawaii has to offer in a very private three-acre estate on the shore of historic Keauhou Bay, six miles south of Kailua Kona on the Big Island of Hawaii. Called “Hale Kai” (house by the sea), you will be surrounded by lawns and lush tropical gardens with old-growth trees. The home was designed by noted architect Vladimir Ossipoff, and built in 1955 for State Sen. “Doc” Hill.br brThe main residence includes a spacious open air living room, a fully equipped kitchen, office and a generous master suite. An outside lanai dining area seats 10 to 12 people. 30 coconut palms line the bay front. A private dock allows easy access into the warm bay waters with tropical fish and occasional turtles. A separate building (pool house”), fronts a beautiful tile swimming pool and contains a king-size bed and bath. An additional building in the garden area contains two separate bedrooms and baths, each with a queen-size bed and a single. 10 guests can be accommodated in the bedrooms. Each bedroom has air conditioning. The office also has two single beds, but no air conditioning. There are beds for 12 people in total.br brA private tennis court is a primary attraction, along with a swimming pool. Paddle boards and kayaks can be arranged and launched directly from our dock. The 18-hole Kona Country Club golf course is open to the public and is a five minute drive away. Keauhou Bay is noted for the population of manta rays at its mouth. Dive boats pass our dock every evening taking people out to watch these beautiful creatures. br brThere is a full-time caretaker couple who live in home at the entrance to the property. They provide daily landscape pickup, safety and security. They have lived in Hawaii for many years and provide assistance for our guests. We have owned the property for 14 years and our family visits about 150 days a year, leaving 200 days available for guests. Most of our guests repeat their visits every year or two. There is an excellent grocery store, restaurants and shops about a half-mile away. If you want privacy, seclusion and a beautiful setting Hale Kai is a great solution. Most frequently our guests are multigenerational families.br brOur property is not available for weddings or events. No commercial filming or photography allowed. brbrHawaii State Transient Accommodation ID # TA-126-531-7888-01brGeneral Excise Tax ID # GE-126-531-7888-01brShort-Term Vacation Rental (STVR) # 19-353909brNUC Number: N/A - Property is a Permitted STVRbr Permitted STVR

OCEAN FRONT PRIVATE RESIDENCE AT KEAUHOU BAY WITH POOL & PRIVATE DOCK

Kailua, Hawaii, United States

Bed

Bath

10

Sleeps

$249.26

New Listing Special!brbrWelcome to this charming 2-bed, 1.5-bath condo in a prime downtown Kailua location, just a short stroll from world-famous Kailua Beach. This updated home features a fully equipped and stocked kitchen, 2 comfortable queen beds, and modern amenities for a relaxing stay. Located near local shops, restaurants, and outdoor activities like hiking, kayaking, and biking, you`ll enjoy the perfect balance of relaxation and adventure. Your Hawaiian stay at Koolau Vista starts here!brbrHighlights:br-Sleeps up to 4 people with a Queen bed in both bedroomsbr-Assigned parking space on the ground level below the unitbr-Fully stocked and equipped kitchen (With Dishwasher)br-Dedicated workspace with desk, office chair, 300 Mbps WiFibr-In unit Washer and Dryerbr-Contactless entry to condo unit with lockboxbr- 2 stories and 800 sq ft of living space; bedrooms, full bath, and laundry upstairsbr-100 feet to Target and Safewaybr-1.8 miles (6 min drive) to Castle Medical Centerbr-Less than a mile to Kailua BeachbrbrKitchen:br-Large appliances: dishwasher, electric stove/oven, microwave, refrigerator br-Small appliances: toaster oven, blender, rice cooker, Keurigbr-Plates, bowls, cups, mugs, tupperware, wine glassesbr-Fully stocked for your cooking needs with pots, pans, cooking utensils, baking dishes, measuring cups, cutting boards, oils and spices, etc.br-Kitchen bar seating brbrLiving room:br-Large and cozy couch with chaisebr-55` LG smart TV with cable (personal account required for steaming apps)br-Standing desk with 27` HD computer monitorbr-Wagon and Yeti cooler for guest usebr-Books and board gamesbr-Window AC Unit for the living room and kitchenbrbrBedroom 1:br-Queen Bedbr-Blackout curtainsbr-Ceiling light and fanbr-Large dresserbr-Large closet spacebr-Window AC unitbrbrBedroom 2:br-Queen Bedbr-Blackout curtainsbr-Ceiling light and fanbr-Large closet spacebr-Portable AC unitbrbrBathrooms:br-Downstairs half bathbr-Upstairs full bath with tub/shower combobrbrBuilding Complex:br-Playground, BBQ grills and picnic tablesbr-Locked and secure back gate that takes you to the Target and Safeway shopping centerbr-Onsite assigned parking space below the unit br-Elevator and stairs to get from parking to third floor unitbrbrCheck in time: 4pmbrCheck out time: 10ambrbrThe entire space is included in this rental. Please, make yourself at home. You will also have access to all of the complex common areas.brbrWe are here for you during your stay, but our level of interaction is up to you. We`re only a phone call/message away. You will be able to check yourself in upon arrival.brbrWe will do everything we can to ensure you have the most enjoyable, relaxing, productive, or adventurous time on Oahu as possible. Please don`t hesitate to send us a message!brbrPlease remember that you are staying in a privately owned condo unit. Please treat the space with respect. If any problems arise, we will do our best to take action ASAP, but we are not on site 24/7.brHouse Rules:brbr-No smoking in the unit, in the elevators or any covered common areabr-No pets are allowed in the unitbr-No parties or events on the premisesbr-Please observe quiet hours of:brSun-Thurs 9pm-7ambrFriday 10pm-7ambrSaturday 10pm-9ambr-Please do not remove or rearrange any items, any damages or missing items will be charged to the guest. br-Additional guests not listed on the reservation are not allowed.br-A mail key is not included in this listing, please have any mail or packages delivered to the nearest post officebr-Please keep the door closed when you are not present in the unit.br-No items can be stored or left outside the unit, or hung off of any of the railingsbr-Guest must register with the resident manager within 7 days of arrivalbr-Please leave the Condo keys (3) in the lockbox when you check out. A fine of $200 will be passed on to the guest per lost key.br-A fee of $50 plus shipping will be charged for the return of any items left behind.brbrPlease treat the home and its furnishings with care.A $25 charge will apply for stains on items.A $50 charge will apply for handling and shipping of lost & found items.These policies help us maintain the property in excellent condition and ensure smooth service for all guests. Mahalo for your understanding!brbrABSOLUTELY NO SMOKING OR VAPING INSIDE THE UNIT or on the unit property unless explicitly designated by a sign designating an area for smoking. Additionally if the smell of smoking Tobacco, Hemp, Clove, Marijuana or any other organic or inorganic substances is observed inside the unit upon your departure there will be a $500 charge. Additionally, any evidence of illegal substances (Marijuana or other illegal substances) left behind by guests will be reported to authorities. We want you to enjoy your time with us, but we have ZERO TOLERANCE for Drug use and our properties are SMOKE FREE.

Downtown Kailua Steps to shops W/D Parking

Kailua, Hawaii, United States

2

Bath

Sleeps

$285.97

This 2-bed/2-bath home with central air conditioning offers two queen beds (one ensuite), a work desk, and ample street parking next to the driveway.brbrThis is an ideal spot for travelers because it’s incredibly close to everything you need. The Enchanted Lake Shopping Center is just down the hill (2 minutes away), featuring Safeway, local dining spots, and coffee. Close to Kailua & Lanikai beach.brbr*There are other tenants with friendly dogs living on property.brThe spacebrPrime Kailua Location: Serenity Meets ConveniencebrEnjoy a peaceful neighborhood setting with unparalleled access to everything Kailua offers:brbrWorld-Class Beaches: Just a 5-10 minute drive to the pristine sands of Kailua Beach and Lanikai Beach.brbrDining & Shopping: A quick 5-minute drive to the heart of Kailua Town, and only a 10-minute walk to the nearby Enchanted Lakes Shopping Center for groceries and essentials.brbrHome Amenities & FeaturesbrThis house provides essential comfort and modern convenience:brbrClimate Control: Stay cool with Central Air Conditioning throughout the entire home, plus a ceiling fan in each bedroom.brbrFull Kitchen: Complete with a fridge, stove & oven, microwave, and dishwasher, making meal prep simple.brbrIncluded: Spacious Living Room and washer/dryer in unit.brbrSleeping AccommodationsbrComfortable arrangements for up to four guests:brbrBedroom 1: Features a Queen Bed, a dedicated desk/chair workspace, and an ensuite private bathroom.brbrBedroom 2: Features a Queen Bed.brbrParking: Street parking is conveniently available near the property's driveway.brbrGuest accessbrGuests are welcome to utilize and enjoy the front yard area.brbrOther things to notebrThere are other tenants living on the property; however, all spaces are fully separate and private, including entrances and living areas. We also live on the property with our two very friendly chocolate Labradors.brbr**Minimum stay: 30 days (system requires 28 days but booking less than 30 days will be declined)**

Keolu Hills Haven: Renovated 2/2 & Easy Parking

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$559.73

Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and tropical flowers. The spacious yard is perfect for sun bathing, barbecuing or enjoying your favorite cocktail after a dip in the pool. Prefer the white sands and turquoise waters of Lanikai Beach The property is conveniently located just a few steps from Lanikai's beach access. brbrThe main house includes a primary bedroom with king bed, TV and bathroom en suite. The guest bedroom has a queen bed and separate bathroom. The living room space is cozy and comfortable with warm, natural light, bamboo flooring and views of the pool and landscape. And for your ultimate comfort, the home is fully air conditioned!brbrThe updated kitchen is fully equipped and includes a glass-top range and oven, dishwasher, microwave and all the kitchenware needed to whip up your favorite meal. brbrA one bedroom, one bath cottage has a private entry and features a charming open-floor plan, bedroom with king-sized bed, and separate bath, and an extra twin bed in the living room space for sleeping or catching a quick nap.brbrThe Bedroom configurations are as follows:brMain House :brGuest Room 1 (Primary) - King Bed, ensuite bathroom, Smart TV, ACbrGuest Room 2 - Queen Bed, Smart TV, ACbrbrCottage :brGuest Room 3 - King Bed, Smart TV, ACbrLiving Room - Twin Bed, ACbrbrThe home is located in the middle of Kailua's popular Lanikai loop - convenient to the beaches, hiking trails and a short drive to the center of Kailua Town.brbrThis Property is professionally managed by Private Homes Hawaii, LLC and is a legally established rental accommodation that is rented for periods of 30 consecutive days or more at any one time. It is compliant with Hawaii State Legislation (HB2078) and is available to lease from 1 to 6 months Lic# TA-019-850-2400-01. TMK0.

Steps to beach, tropical garden and private pool

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$547.79

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family and close to amenities. brbrOur luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation.brbrWe have two suites available:brbrHonu (Turtle) Suite:br-Queen size bed with luxury beddingbr-Private entrance br-Kitchenette br-Private bathroombr-ACbr-TVbr-Microwave br-Coffeemaker with k-cupsbr-Free Parking (one space per room)brbrNai’a (Dolphin) Suite: inquire with us about our second suite. br-King size bed with luxury beddingbr-Private entrance br-Kitchenette br-Private bathroombr-ACbr-TVbr-Microwave br-Coffeemaker with k-cups. br-Free Parking (one space per room). Note: We do our best to offer all things listed and shown in pictures at La Bella’s. If items are not available or need replaced we will try and match listing photos and detailed descriptions as close as possible. However, if somethings are different or not available this does not constitute a refund or discount. If you have any questions about anything before you arrive at La Bella’s we are happy to address your questions or concerns. Thank you for understanding. Owner and kids live onsite.

Bed & Breakfast

La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

Kailua, Hawaii, United States

1

Bed

1

Bath

Sleeps

$462.98

Relax in this Modern vacation retreat located right across the street from Kailua beach park. Just steps from the white sand beaches of Lanikai/Kailua and minutes from local dining, shopping, and outdoor adventures. This is a 3 bedroom 1 1/2 bath with a beautiful outdoor shower. This thoughtfully designed home blends sleek contemporary style with relaxed island living, featuring open-concept interiors, high-end finishes, and expansive windows that invite in the tropical breeze. This home is your perfect base for experiencing the best of the Windward side.

The Modern Kailua Beach House

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$164.22

Welcome to this marvelous apartment in Kailua. This cozy space features 1 bedroom with a comfortable queen bed with mountain views, plus a separate office room for computer business, privacy glass throughout, perfect for a couple or solo travelers. The bathroom is equipped with a shower, bidet, and hair dryer for your convenience. Enjoy the modern amenities such as WiFi, a washer/dryer, smart TV's and AC during your stay. Book now and enjoy everything this apartment has to offer.

Charming 1.5 bedroom cottage, fully furnished in a great location!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$542.68

Licensed Vacation Rental: NUC #: 1990/NUC-1738 for Tax Map Key: 43005018brbrIndulge in the tranquility of Lanikai Beach, just a stone's throw away, and let the allure of this coastal paradise wash over you. With the studio's inviting comforts and the endless ocean possibilities at your disposal, your stay promises to be an extraordinary journey of relaxation and exploration.brbrExperience the ultimate paradise steps away from the breathtaking Lanikai Beach! Nestled conveniently across the street, this idyllic studio offers the perfect blend of comfort and tropical bliss. As you step through the private gated garden entry, a world of calm tranquility awaits you, courtesy of refreshing air-conditioning that soothes your senses after a sun-drenched day on the beach.brbrLANIKAI GARDEN STUDIO DETAILSbrInside, you'll find a meticulously furnished space thoughtfully designed to provide all the comforts of home. An efficient kitchen stands ready to cater to your culinary desires, while a luxurious king-size bed beckons you to unwind and indulge in restful slumber. Sink into the embrace of two plush armchairs, perfectly positioned for relaxation, and take in the exquisite teak furnishings that enhance the space. Adorning the walls are captivating works of art by local talents, adding a touch of cultural richness to your surroundings.brbrOccupancy Maximum: Two (2) GuestsbrOur rental can accommodate a maximum of two guests. brThis includes:br * One or Two adults ORbr * One adult and one child, regardless of the child's agebrbrLATE DEPARTURE: Lanikai Tree House | Lanikai Garden StudiobrCheck-Out Time: 10:00 AM or earlierbrWe do not pre-sell a late check-out. Late check-out inquiries may be made 24 – 48 hours before the confirmed departure (check-out) date.brbrExtended Stay Fee Schedule (If Available, Pre-Arranged & Approved in writing):brUp to 3 Hours: $50 per hour br3 to 5 Hours: Charged at a half-day ratebr5+ Hours: Charged at a full-day rate (may not extend beyond 11:59 PM of the day of confirmed departure) brSame-Day Transitions: On days when we have both a departure and an arrival guest, check-out must be by 10:00 AM; no exceptions. brGuaranteed Late Check-Out: Guests can purchase the additional night when booking to ensure a late check-out. brbrStay connected to the outside world with complimentary Wi-Fi, allowing you to share your magical moments with loved ones. Rest easy knowing that convenient on-site parking is available, ensuring a hassle-free experience from arrival.brbrDon't miss out on this incredible opportunity to immerse yourself in the wonders of Lanikai Beach. With its prime location and abundant amenities, this studio promises an unforgettable stay in paradise.brbrImmerse yourself in the serene beauty of Lanikai Beach, just a mere 100 yards away from this enchanting studio. Step inside and be greeted by a thoughtfully furnished space adorned with exquisite teak furnishings and adorned walls displaying captivating works of art masterfully created by local artists. Sink into the embrace of two comfortable armchairs, inviting you to relax and soak in the tropical ambiance.brbrConvenience is at your fingertips, as on-site parking is included, ensuring a seamless experience from the moment you arrive. And if you're craving some ocean adventures, look no further than Kailua Town, where many outfitters await, ready to provide you with all the necessary equipment for an unforgettable experience on crystal-clear waters.brbrDiscover the perfect blend of convenience and coastal charm in this home, a mere 2.5 miles from the vibrant Kailua Town. Prepare to embark on an adventure-filled experience as you explore the myriad of outfitters available to cater to all your ocean activity equipment needs. Whether it's snorkeling gear, paddleboards, or kayaks, you'll find everything you desire to make your beach outings unforgettable.brbrKailua Town has even more to offer beyond ocean adventures. Hop on a bicycle, available for rent in Kailua Town, and cruise through the picturesque streets, allowing the warm breeze to guide you to the town's hidden gems. Indulge in a culinary journey at the town's exceptional restaurants, savoring the diverse flavors that delight each dining experience.brbrTake your time strolling through the local boutiques and gift shops to find unique treasures and souvenirs to commemorate your visit. For the freshest local produce and handmade crafts, immerse yourself in the vibrant atmosphere of the farmer's market, where the community gathers to celebrate local artisans and culinary delights.brbrWhen you return to your home away from home, you'll appreciate its serenity, allowing you to unwind and recharge for the next day's adventures. Bask in the satisfaction of knowing that you can easily access all the amenities and attractions Kailua Town offers while also enjoying the tranquility of your private oasis.brbrPrepare for an unforgettable experience where coastal wonders meet the vibrant energy of Kailua Town. With its proximity to outfitters, bicycle rentals, various shops, and a delectable dining scene, this home offers the perfect balance between relaxation and exploration, ensuring that your stay is nothing short of extraordinary.brbrEnsure a trouble-free stay by staying in our licensed short-term rental. The City and County of Honolulu have imposed strict enforcement on vacation rentals that do not possess a Nonconforming Use Certificate (NUC). Our NUC allows us to rent nightly, versus the minimum ninety (30 - 90) nights; without this certificate, the minimum rental occupancy must be ninety (30 - 90) nights or more. brThe last issuance of NUC Certificates was in 1989. brbr * NUC #: 1990/NUC-1738 for Tax Map Key: 43005018br * Transient Accommodations Tax (TAT) ID: TA-095-917-0560-01br * General Excise License (GET) ID: GE-095-917-0560-01 br * Compliant with Hawaii State Legislation (HB2078) br____________________________________________________________________________brbrApplicable Hawaii general excise tax a GET (currently 4.166%), applicable transient accommodations tax TAT (currently 10.25%), Honolulu Surcharge Tax (.5%), and Oahu transient accommodations tax OTAT (currently 3.0%) will be added to the Daily Rental Rate, Cleaning Fees, and all other charges payable by Principal Guest(s) to Agent under this Rental Agreement. Should the State of Hawaii raise either the transient accommodations tax (TAT), general excise tax (GET), or Oahu transient accommodations tax OTAT, we will amend all applicable reservations and collect the additional tax(s) from Guests before check-in. brbrFor stays of 10 - 19 Nights, we collect an additional $150.00 for a mid-stay cleaning fee, plus applicable taxes.

Since 1985 Legal Lanikai Garden Studio AC, across the street from Lanikai Beach!

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$670.52

To comply with Honolulu vacation rental rules, we only rent once in a 30-day period. You may inquire about a shorter stay if our calendar is open for a full 30 days.brPlease request dates that you would like to book, and we will reply.brbrWarmest Aloha ........You have found the 'Star of Hawaii' Hale on a private beachside lane. The home, gardens, & pool, are private surrounded by lava rock walls. Just a few steps down the lane, with no streets to cross, is the world-famous Kailua Beach. brbrThis 4B/3B home offers separate entertainment and sleeping areas. The main level has 3B/2B with 2 queens and a set of twins in the bedrooms plus one sleeper sofa. Upstairs is a large 600 sf private suite. King bed, bath, kitchenette, and living area. This design offers couples and families privacy and flexibility. The house has a fully equipped kitchen and family-sized dining room. You have ocean kayaks, boogie boards, beach and pool toys, beach chairs, ice chest, stroller, a pac-n-play, highchair, and other amenities for a perfect vacation.brbrLiving spaces are open to the pool and gardens. The house has that 'Hawaiian' feeling of bringing the outside in - welcoming you to the islands.brbrKailua town for shops, restaurants, and groceries is a 10-minute walk. Honolulu, Waikiki, and the Airport are a 25-minute drive. Kailua Beach Park with para-sailing and windsurfing rentals is just down the beach. Walk along the beach to the Kalapawai (Green Market) for morning coffee and a little something.brbrWe will provide details on accessing the house once your booking is complete. Check-in time is 3 p.m. & check-out is 10 a.m. Rates are higher for Holiday periods.

'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families

Kailua, Hawaii, United States

Bed

Bath

Sleeps

$213.74