Kailua Vacation Rentals

Kailua vacation rentals offer a laid-back, beachy escape on Oahu’s windward coast, known for powdery white sands, turquoise waters, and a local town vibe that’s both relaxed and refined. Just 30 minutes from Honolulu, Kailua feels like a hidden paradise, ideal for travelers seeking peace, beauty, and authentic island living.

Choose from charming beach cottages, modern island homes, and spacious family retreats-all within walking distance to world-famous Kailua Beach and Lanikai. Many rentals include private yards, lanais, outdoor showers, and beach gear, making it easy to live like a local from the moment you arrive.

Spend your days kayaking to the Mokulua Islands, hiking the pillbox trail for panoramic views, or browsing Kailua’s boutiques and farmers markets. With its calm waters, friendly community, and scenic charm, Kailua is perfect for couples, families, and extended stays alike.

Whether you're here to relax, explore, or work remotely, Kailua vacation rentals offer the comfort of home with the beauty of Hawaii just outside your door.

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Modern Kailua Beachside Suite with Mountain Views
Modern Kailua Beachside Suite with Mountain Views
Modern Kailua Beachside Suite with Mountain Views

Modern Kailua Beachside Suite with Mountain Views

Discover this beautifully furnished 600 sq. ft. upstairs suite in Kailua, Oahu, blending modern elegance with beachy flair. Perfect for guests seeking comfort and convenience, it features a spacious bedroom with a plush king-size pillow top bed, dark wood blinds, a 40" TV, and split air conditioning to keep you cool.
Registration Number: 420200410000, TA-071-652-3520-01, GE-071-652-3520-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $212 
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licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage

licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage

Charming beachfront cottage right on Kailua Beach!

licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room.
Registration Number: TA-096-237-9776-01, GE-096-237-9776-01, 430120130000

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $672 
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Hawaii Beachfront Home with Ocean Views in Kailua
Hawaii Beachfront Home with Ocean Views in Kailua
Hawaii Beachfront Home with Ocean Views in Kailua

Hawaii Beachfront Home with Ocean Views in Kailua

The ultimate Hawaii beachside retreat awaits you in our beautifully designed Kailua beachfront home. From tropical Hawaiian furnishings to panoramic ocean views, this home offers an authentic island experience.
Situated directly on Kailua’s renowned white sand beach, our home provides unmatched privacy and stunning scenery.
Registration Number: TA-191-191-0400-01, GE-191-191-0400-01, 430130460000

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,457 
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Luxury Kailua Golf Course View Rental - 30+ Days
Luxury Kailua Golf Course View Rental - 30+ Days
Luxury Kailua Golf Course View Rental - 30+ Days

Luxury Kailua Golf Course View Rental - 30+ Days

Aloha! 5-bath apartment available exclusively for 30+ day rentals. Nestled at the end of a peaceful street, it overlooks the world-famous Mid Pacific Country Club Golf Course, a favorite spot for presidents and golf enthusiasts alike. The open-air design spans 800 square feet, blending old Hawaiiana charm with modern sophistication.
Registration Number: 420480020000, TA-120-590-3360-01, GE-120-590-3360-01

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $259 
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Walker's Lanikai Beach House – Historic Oceanfront Retreat
Walker's Lanikai Beach House – Historic Oceanfront Retreat
Walker's Lanikai Beach House – Historic Oceanfront Retreat

Walker's Lanikai Beach House – Historic Oceanfront Retreat

Welcome to Walker's Lanikai Beach House, a historic and inviting retreat nestled along the pristine sands of Lanikai Beach. Built in 1934 by John Walker, a Scotsman who arrived in Hawaii in the 1870s and became a renowned contractor for Queen Liliuokalani, this home embodies timeless elegance and Hawaiian charm.
Registration Number: 430080930000, TA-043-470-0288-01, GE-043-470-0288-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,976 
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Oceanfront Kailua Beach Vacation Home with Pool
Oceanfront Kailua Beach Vacation Home with Pool
Oceanfront Kailua Beach Vacation Home with Pool

Oceanfront Kailua Beach Vacation Home with Pool

" This spacious and casual retreat features five bedrooms and five and a half bathrooms, making it perfect for family gatherings or a relaxing escape with friends. The expansive outdoor decks are ideal for soaking up the sun, enjoying barbecues, or simply taking in breathtaking views of Kailua Bay's turquoise waters and soft white sands.
Registration Number: GE-060-877-8240-01, 430210250000, TA-060-877-8240-01

  • 5 bedroom
  • 6 bathroom
  • Sleeps 14
Hawaii> Kailua
from $3,887 
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Kailua Beach Ground Floor Retreat with Private Courtyard
Kailua Beach Ground Floor Retreat with Private Courtyard
Kailua Beach Ground Floor Retreat with Private Courtyard

Kailua Beach Ground Floor Retreat with Private Courtyard

Welcome to this turnkey Kailua Beach retreat, perfect for a relaxing getaway. The property features a secure gated entrance leading to a private courtyard with a propane BBQ, water feature, patio table, chairs, and a lighted umbrella, ideal for enjoying the garden day or night.
Registration Number: 143024003000, GE-111-409-1520-01, TA-111-409-1520-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $204 
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Charming Ginger Studio at Hawaii Sheffield House in Kailua
Charming Ginger Studio at Hawaii Sheffield House in Kailua
Charming Ginger Studio at Hawaii Sheffield House in Kailua

Charming Ginger Studio at Hawaii Sheffield House in Kailua

Discover the enchanting Ginger Studio at Hawaii Sheffield House, a charming and legal bed and breakfast in Kailua with over 30 years of hospitality. Located at 131 Kuulei Road, this ground-floor unit offers a private entrance and a lush 'Secret Garden' setting with night lighting and a bubbling fountain in a Chinese steamer pot, creating a magical tropical ambiance.

Registration Number: TA-137-360-9984-01, GE-137-360-9984-01, 430720040000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $336 
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Spacious Kailua Beachside Vacation Home with Pool
Spacious Kailua Beachside Vacation Home with Pool
Spacious Kailua Beachside Vacation Home with Pool

Spacious Kailua Beachside Vacation Home with Pool

Discover this spacious and airy four-bedroom Kailua beachside vacation rental that offers the perfect blend of comfort and tropical Hawaiian charm. Recently remodeled with a modern kitchen and bathrooms, this home provides a luxurious retreat just steps from the pristine sands of Kailua Beach.

Registration Number: 430190530000, GE-126-659-1744-01, TA-126-659-1744-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $996 
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Hale Nani Lanikai: Modern Beach Retreat
Hale Nani Lanikai: Modern Beach Retreat
Hale Nani Lanikai: Modern Beach Retreat

Hale Nani Lanikai: Modern Beach Retreat

Welcome to Hale Nani Lanikai by Gather, a stunning three-bedroom, three-bathroom home nestled in the prestigious Lanikai community of Kailua, Oahu. Built in 2014, this spacious and modern retreat seamlessly combines island charm with contemporary comforts, offering an ideal escape just a three-minute walk from the world-famous Lanikai Beach.
Registration Number: 430050050000, TA-209-884-5696-01, GE-209-884-5696-01

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $836 
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Spacious Kailua Home with Pool and Beach Access
Spacious Kailua Home with Pool and Beach Access
Spacious Kailua Home with Pool and Beach Access

Spacious Kailua Home with Pool and Beach Access

Discover this spacious and private Kailua home, perfect for family vacations or a relaxing getaway. Featuring 3 bedrooms and 2 bathrooms, the house comfortably sleeps up to 6 guests. Two bedrooms are furnished with luxurious King beds, while the third bedroom offers twin beds, ideal for children or additional guests.
Registration Number: TA-143-873-0240-01, 430750280000, GE-143-873-0240-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $434 
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Luxury Beachfront Home with Pool near Kailua Beach
Luxury Beachfront Home with Pool near Kailua Beach
Luxury Beachfront Home with Pool near Kailua Beach

Luxury Beachfront Home with Pool near Kailua Beach

Immerse yourself in the ultimate island getaway at this stunning beachfront home on Kailua Beach. This 4-bedroom, 4-bath residence offers a perfect blend of comfort and tropical charm, designed for a memorable vacation. The property is nestled in a private, tranquil setting, providing direct access to the pristine white sands and gentle waves of Kailua Beach, ideal for walking, jogging, or relaxing by the water.

Registration Number: GE-189-305-8560-01, 1430170750000, TA-189-305-8560-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,180 
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Koi Palms Cottage in Kailua – Island Retreat
Koi Palms Cottage in Kailua – Island Retreat
Koi Palms Cottage in Kailua – Island Retreat

Koi Palms Cottage in Kailua – Island Retreat

Come and experience your own island sanctuary at Koi Palms Cottage, nestled within a secure property in the charming town of Kailua. This delightful 600 square foot one-bedroom cottage offers a cozy yet fully equipped space perfect for relaxing getaways.
Registration Number: 143072028000, GE-058-690-1504-01, TA-058-690-1504-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $341 
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Stunning Oceanfront Beach House in Lanikai with Views
Stunning Oceanfront Beach House in Lanikai with Views
Stunning Oceanfront Beach House in Lanikai with Views

Stunning Oceanfront Beach House in Lanikai with Views

Experience the ultimate Hawaiian getaway at this charming oceanfront duplex in Lanikai, perfectly positioned directly in front of the twin Mokulua Islands. The property offers unobstructed, spectacular views from the yard, living room, dining area, and side deck, creating an idyllic setting for relaxation and adventure.

Registration Number: GE-139-440-7424-01, TA-139-440-7424-01

  • 3 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $482 
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Luxury Kailua Beach Home with Ocean Views
Luxury Kailua Beach Home with Ocean Views
Luxury Kailua Beach Home with Ocean Views

Luxury Kailua Beach Home with Ocean Views

Our stunning Kailua home has been featured in Hawaii Home Magazine and awarded best in class by the Hawaii Builders Association. Located just a 2-minute walk from Kailua Beach Park, the property offers easy access to local attractions like Kalapawai Market and Buzz's Steak House.
Registration Number: GE-030-384-5376-01, TA-030-384-5376-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Kailua
from $720 
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Stunning Oceanfront Villa Near Mokulua Islands
Stunning Oceanfront Villa Near Mokulua Islands
Stunning Oceanfront Villa Near Mokulua Islands

Stunning Oceanfront Villa Near Mokulua Islands

5-bathroom gated oceanfront villa built in 1918 and recently fully remodeled to combine contemporary beach house style with original architectural features. Inside, the open floor plan features beautiful arches, a spacious gourmet kitchen with new appliances, a coffee bar, and wine fridge.
Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

  • 6 bedroom
  • 5 bathroom
  • Sleeps 15
Hawaii> Kailua
from $4,262 
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Charming Kailua Beach Retreat with Mountain Views
Charming Kailua Beach Retreat with Mountain Views
Charming Kailua Beach Retreat with Mountain Views

Charming Kailua Beach Retreat with Mountain Views

Experience the perfect blend of comfort and convenience in this charming Kailua Beach retreat. 5 miles away by bike.
The residence features two spacious bedrooms on the second floor, each furnished with queen beds, nightstands, lamps, dressers, closets, and ceiling fans, providing a restful haven after a day at the beach.
Registration Number: 430180410000, TA-199-189-0944-01, GE-199-189-0944-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $340 
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Seaside Villa in Kailua with Pool and Ocean Views
Seaside Villa in Kailua with Pool and Ocean Views
Seaside Villa in Kailua with Pool and Ocean Views

Seaside Villa in Kailua with Pool and Ocean Views

Escape to this stunning three-bedroom seaside villa in Kailua, a perfect blend of luxury, comfort, and natural beauty. The property offers a private outdoor pool and an oceanside hot tub, ideal for unwinding after a day of adventures. Soak up the sun on the loungers, or take in breathtaking ocean views from the balcony.
Registration Number: 440390160000, GE-097-705-3696-01, TA-097-705-3696-01

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua
from $666 
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Charming Kailua Beachside Vacation Home with Cottage
Charming Kailua Beachside Vacation Home with Cottage
Charming Kailua Beachside Vacation Home with Cottage

Charming Kailua Beachside Vacation Home with Cottage

E komo mai to Hale Makai, your perfect island retreat in Kailua on the windward side of Oahu. Located just three houses from the renowned Kailua Beach, this charming, beachside home offers a serene and authentic Hawaiian experience. Kailua is celebrated for its pristine, protected three-mile beach, frequently ranked among the world's best.
Registration Number: GE-203-074-9696-01, TA-203-074-9696-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $372 
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Charming Kailua Beach House Near White Sand
Charming Kailua Beach House Near White Sand
Charming Kailua Beach House Near White Sand

Charming Kailua Beach House Near White Sand

Experience the ultimate Hawaiian escape at Ohana Beach House, located just a short walk from Kailua's renowned five-mile stretch of white sand beach. This beautifully designed Hawaiian-style home offers a peaceful retreat for your extended family or group.
Registration Number: GE-054-032-3840-01, 430180510000, TA-054-032-3840-01

  • 5 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,213 
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Hale Kainalu Beachfront Cottage in Lanikai
Hale Kainalu Beachfront Cottage in Lanikai
Hale Kainalu Beachfront Cottage in Lanikai

Hale Kainalu Beachfront Cottage in Lanikai

Hale Kainalu offers a charming and private escape at the end of Lanikai, nestled within a gated community with exclusive access to a pristine white sand beach used by only five homes. This beautiful cottage sits directly on the shoreline, providing breathtaking views of crystal-clear blue and green waters.
Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $1,130 
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Beautiful Oceanfront Lanikai Beach Home in Hawaii
Beautiful Oceanfront Lanikai Beach Home in Hawaii
Beautiful Oceanfront Lanikai Beach Home in Hawaii

Beautiful Oceanfront Lanikai Beach Home in Hawaii

Experience the ultimate Hawaiian getaway in this stunning oceanfront home at the start of Oahu's renowned Lanikai Beach. This property features a spacious main house with two bedrooms and one bathroom, along with a separate guest cottage offering two bedrooms and two bathrooms, providing ample space and privacy for your stay.

Registration Number: GE-006-302-3104-01, TA-006-302-3104-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,451 
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Kailua Beachfront Home with Ocean Views and Private Yard
Kailua Beachfront Home with Ocean Views and Private Yard
Kailua Beachfront Home with Ocean Views and Private Yard

Kailua Beachfront Home with Ocean Views and Private Yard

Discover this charming beachfront home nestled in a secure, gated neighborhood in Kailua. The house features island-style rattan furnishings, ceiling fans, cool white tile, and wooden floors, creating a relaxed and inviting atmosphere. The well-equipped kitchen boasts granite counters and beautiful accents, perfect for preparing meals while enjoying the stunning ocean vistas visible from the living room, dining area, kitchen, and master bedroom.
Registration Number: 430180100003, TA-083-865-6000-01, GE-083-865-6000-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $987 
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Lanikai Breeze – Contemporary Comfort Steps from the Shore
Lanikai Breeze – Contemporary Comfort Steps from the Shore
Lanikai Breeze – Contemporary Comfort Steps from the Shore

Lanikai Breeze – Contemporary Comfort Steps from the Shore

Welcome to Lanikai Breeze by Gather, a beautifully designed luxury home just a short stroll from the world-renowned Lanikai Beach. Built in 2017, this contemporary residence offers upgraded appliances and furnishings carefully selected by local designer Lotus Home Staging, creating a perfect blend of casual beach charm and sophisticated luxury.
Registration Number: 430070810000, GE-135-880-0384-01, TA-135-880-0384-01

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,165 
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Naupaka Hale - Lanikai Beach Home & Cottage
Naupaka Hale - Lanikai Beach Home & Cottage
Naupaka Hale - Lanikai Beach Home & Cottage

Naupaka Hale - Lanikai Beach Home & Cottage

Escape to Naupaka Haleta, a charming Hawaiian-style vacation residence nestled on a spacious lot directly in front of a pristine sandy beach. This exquisite property offers breathtaking views of Lanikai Beach, turquoise waters, and the Mokulua Islands, making it an ideal retreat for those seeking tranquility and natural beauty.
Registration Number: TA-151-566-1312-01, GE-151-566-1312-02

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Lanikai
from $1,268 
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Charming Kailua Beachside House Near White Sands
Charming Kailua Beachside House Near White Sands
Charming Kailua Beachside House Near White Sands

Charming Kailua Beachside House Near White Sands

Experience the relaxed island lifestyle at Kailua Beachside, a charming beach house located just steps from the pristine sands of Kailua Beach. Nestled within a large, private garden enclosed by stone walls, this property offers a tropical oasis with palms, banana trees, and vibrant gardens creating a safe and fun environment for families and kids.
Registration Number: 1430150090000, TA-210-792-6016-01, GE-210-792-6016-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua
from $524 
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Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

Hale Lanikai is a beautifully updated Hawaiian-style family vacation rental located on a pristine sandy beach in Lanikai. This property offers a perfect blend of comfort, style, and natural beauty, making it an ideal escape for families and groups seeking a relaxing getaway.

Registration Number: 430050500000, GE-161-257-7280-01, TA-161-257-7280-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $2,781 
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Charming Hawaiian Bungalow Near Kailua Beach
Charming Hawaiian Bungalow Near Kailua Beach
Charming Hawaiian Bungalow Near Kailua Beach

Charming Hawaiian Bungalow Near Kailua Beach

Aloha! This charming Hawaiian bungalow has been thoughtfully renovated to blend old Hawaii charm with modern comforts. Ideal for two easy-going, non-smoking adults aged 25 or older, this retreat offers a peaceful escape in a lush garden oasis. 5 miles of soft white sand and turquoise waters perfect for swimming, kayaking, windsurfing, kiteboarding, snorkeling, and more.

Registration Number: GE-077-835-2640-01, TA-077-835-2640-01, 430110790000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $315 
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Charming Lanikai Cottage with Pool and Ocean Views
Charming Lanikai Cottage with Pool and Ocean Views
Charming Lanikai Cottage with Pool and Ocean Views

Charming Lanikai Cottage with Pool and Ocean Views

Escape to the charming Lanikai Cottage, a delightful property offering two separate dwellings with three bedrooms and two bathrooms, perfect for a relaxing island retreat. The main house features two bedrooms, one bathroom, a fully equipped kitchen, dining area, and a cozy living space that opens to the lush backyard.
Registration Number: TA-111-603-0976-01, GE-111-603-0976-01, 430040320000

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $731 
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Luxury Kailua Beachside Home with Pool & Modern Updates
Luxury Kailua Beachside Home with Pool & Modern Updates
Luxury Kailua Beachside Home with Pool & Modern Updates

Luxury Kailua Beachside Home with Pool & Modern Updates

Welcome to this stunning Kailua beachside home, completely renovated in 2019 with modern touches and luxurious amenities. Located just one block from the renowned Kailua Beach, voted #1 by Dr. Beach in 2019, this property offers the perfect setting for a memorable Hawaiian vacation.

Registration Number: GE-174-185-2672-01, TA-174-185-2672-01, 430190450000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,169 
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Orchid House Lanikai Ocean Views – Elegant 3BR Retreat
Orchid House Lanikai Ocean Views – Elegant 3BR Retreat
Orchid House Lanikai Ocean Views – Elegant 3BR Retreat

Orchid House Lanikai Ocean Views – Elegant 3BR Retreat

Experience the ultimate Hawaiian getaway at Orchid House in Lanikai, a beautifully renovated 3-bedroom, 4-bath retreat offering stunning views of the Mokuluas from most rooms. The home features exquisite exotic hardwood floors, elegant granite countertops, and slate stone flooring, creating a luxurious yet natural ambiance.
Registration Number: GE-087-311-0016-01, TA-087-311-0016-01

  • 3 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Kailua
from $1,014 
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Lanikai Penthouse with Stunning Ocean Views
Lanikai Penthouse with Stunning Ocean Views
Lanikai Penthouse with Stunning Ocean Views

Lanikai Penthouse with Stunning Ocean Views

Welcome to the Lanikai Penthouse, a beloved piece of paradise that's been shared with guests from around the world for over 20 years. This exceptional property offers an authentic Hawaiian lifestyle experience with stunning views and luxurious amenities.
Registration Number: 43005029, W00530010-01, GE-136-047-8208-01, TA-136-047-8208-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $421 
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Charming Kailua Home with Pool and Spa
Charming Kailua Home with Pool and Spa
Charming Kailua Home with Pool and Spa

Charming Kailua Home with Pool and Spa

Welcome to Ka Hale Lai, your perfect Kailua retreat on a spacious 18,000-square-foot lot. This charming home offers a serene setting with a newly tiled swimming pool and spa, ideal for relaxation and fun. Located just five minutes from Kailua Beach and a short drive to Kailua town, it provides an authentic Hawaiian experience with modern comforts.
Registration Number: TA-027-765-7600-01, GE-027-765-7600-01

  • 5 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,853 
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Luxurious Oceanfront Home in Lanikai with Stunning Views
Luxurious Oceanfront Home in Lanikai with Stunning Views
Luxurious Oceanfront Home in Lanikai with Stunning Views

Luxurious Oceanfront Home in Lanikai with Stunning Views

Aloha! Relax and unwind at Kai Hale, a stunning oceanfront home in Lanikai, directly facing the Mokulua Islands. This property offers spectacular views and is ideal for year-round living or a memorable vacation. Whether you're into stand-up paddling, kayaking, boogie boarding, snorkeling, or exploring with children, this location has it all.
Registration Number: TA-013-232-3328-02, 1430040780002, GE-013-232-3328-02

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua
from $884 
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Lokomaikaʻi Kailua Beach Vacation Home
Lokomaikaʻi Kailua Beach Vacation Home
Lokomaikaʻi Kailua Beach Vacation Home

Lokomaikaʻi Kailua Beach Vacation Home

Experience the ultimate island retreat at Lokomaikaʻi Kailua, a beautifully renovated home nestled on Oahu's east side. This spacious rental offers a seamless indoor-outdoor living experience with sliding glass walls that open to tropical gardens and a sparkling pool.
Registration Number: GE-079-127-1936-01, TA-079-127-1936-01, 430830190000

  • 5 bedroom
  • 3 bathroom
  • Sleeps 11
Hawaii> Kailua
from $1,259 
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Hale Ohana Family House with Pool & Ocean Views
Hale Ohana Family House with Pool & Ocean Views
Hale Ohana Family House with Pool & Ocean Views

Hale Ohana Family House with Pool & Ocean Views

Welcome to Hale Ohana, a charming family house nestled on the east side of Oahu. This spacious home features three bedrooms in the main house and an additional bedroom off the game room, making it ideal for families or groups seeking a relaxing island retreat.
Registration Number: 430830350000, TA-139-302-3488-01, GE-139-302-3488-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,057 
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Historic Renovated Kailua Beach Cottage with Pool
Historic Renovated Kailua Beach Cottage with Pool
Historic Renovated Kailua Beach Cottage with Pool

Historic Renovated Kailua Beach Cottage with Pool

Step into a piece of Kailua history with this beautifully renovated 1937 cottage, just one house from the pristine sands of Kailua Beach, ranked as the #1 beach in the world. Nestled between a peaceful park and a rarely used private club, this gated home offers exclusive privacy and tranquility.
Registration Number: GE-045-319-8848-01, TA-045-319-8848-01, 430160220000

  • 5 bedroom
  • 2 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,278 
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Kailua Bliss Beach House with Pool and Ocean Views
Kailua Bliss Beach House with Pool and Ocean Views
Kailua Bliss Beach House with Pool and Ocean Views

Kailua Bliss Beach House with Pool and Ocean Views

Aloha! Welcome to Kailua Bliss Beach House, a relaxed and stylish getaway nestled in the quiet Beachside neighborhood of Kailua. Perfectly situated on a private street just one house away from the pristine sands of Kailua Beach, this home offers easy access to a mile of Dr.
Registration Number: TA-068-883-0976-01, GE-068-883-0976-01, 143018061000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $1,014 
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Luxury Lanikai Beach Guest House Near Kailua
Luxury Lanikai Beach Guest House Near Kailua
Luxury Lanikai Beach Guest House Near Kailua

Luxury Lanikai Beach Guest House Near Kailua

Aloha and welcome to Kolea Landing, your perfect retreat just a short walk (less than 400 steps) from the stunning Lanikai Beach! This beautifully appointed 2,200 sq ft guest house combines island charm with modern comforts, making it an ideal spot for your Hawaii getaway.

Registration Number: 430070230000, GE-082-679-2448-01, TA-082-679-2448-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $644 
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Lanikai Hale: Two Cozy Hawaiian Cottages Near Beach
Lanikai Hale: Two Cozy Hawaiian Cottages Near Beach
Lanikai Hale: Two Cozy Hawaiian Cottages Near Beach

Lanikai Hale: Two Cozy Hawaiian Cottages Near Beach

Welcome to Lanikai Hale, a delightful property featuring two Hawaiian-style cottages that can be rented together or separately. Situated on a spacious, fenced-in lot in the heart of Lanikai, these cottages offer an ideal retreat just 2 miles from Kailua Town on the Windward side of Oahu.
Registration Number: TA-107-927-8080-01, GE-107-927-8080-01

  • 6 bedroom
  • 3 bathroom
  • Sleeps 12
Hawaii> Kailua
from $972 
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Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views
Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views
Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views

Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views

Discover this recently renovated contemporary Kailua home offering stunning ocean views and direct access to Kailua Beach with nearly 100 linear feet of pristine shoreline. 5 bathrooms, all designed with style and comfort in mind. The wraparound outdoor area centers around a sparkling solar-heated pool, perfect for sunbathing and entertaining, while expansive lawns provide ample space for outdoor activities and gatherings.

Registration Number: 1430200510000, GE-176-489-9328-01, TA-176-489-9328-01

  • 6 bedroom
  • 7 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,392 
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Luxury 5-Bedroom Villa in Lanikai with Pool
Luxury 5-Bedroom Villa in Lanikai with Pool
Luxury 5-Bedroom Villa in Lanikai with Pool

Luxury 5-Bedroom Villa in Lanikai with Pool

Discover the allure of Kailua at Villa Hui Hou by Gather! 5-bathroom home offers a perfect blend of beach proximity and luxurious comfort for up to 12 guests. Recently renovated, the property features spacious living areas filled with island charm and modern amenities.
Registration Number: TA-091-214-0288-01, GE-091-214-0288-01, 430030440000

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Kailua
from $1,216 
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Holoholo Hale: Spacious Kailua Beach Retreat on Oahu
Holoholo Hale: Spacious Kailua Beach Retreat on Oahu
Holoholo Hale: Spacious Kailua Beach Retreat on Oahu

Holoholo Hale: Spacious Kailua Beach Retreat on Oahu

Welcome to Holoholo Hale, a stunning two-house estate nestled in the lush surroundings of Kailua on Oahu. This spacious property offers everything needed for an unforgettable Hawaiian vacation, just minutes from renowned beaches like Kailua Beach Park and Lanikai Beach.

Registration Number: 420560420000, GE-141-882-0096-01, TA-141-882-0096-01

  • 7 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Kailua
from $1,144 
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Luxury Pool House in Kailua Near Beaches
Luxury Pool House in Kailua Near Beaches
Luxury Pool House in Kailua Near Beaches

Luxury Pool House in Kailua Near Beaches

The Pool House in Kailua offers 3,200 sq ft of luxurious living space with 6 bedrooms and 4 bathrooms, complemented by an amazing saltwater pool. Nestled in a peaceful, lush neighborhood with views of the Ko'olau Mountain range, this home is within walking distance to Kailua Beach, Lanikai Beach, and Buzz's Steakhouse.
Registration Number: 420540580000, TA-036-329-7280-01, GE-036-329-7280-01

  • 6 bedroom
  • 4 bathroom
  • Sleeps 15
Hawaii> Kailua
from $1,119 
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Luxurious Oceanfront Villa in Kailua with Private Beach
Luxurious Oceanfront Villa in Kailua with Private Beach
Luxurious Oceanfront Villa in Kailua with Private Beach

Luxurious Oceanfront Villa in Kailua with Private Beach

Welcome to this luxurious Kailua beachfront villa where tranquility and elegance blend seamlessly. As you approach through a secure electric remote gate, a sense of calm envelops you, setting the tone for a memorable stay.
Nestled on the pristine shores of Kailua, this estate offers direct access to one of the world's top beaches, renowned for its soft white sands and breathtaking sunrises.
Registration Number: GE-048-077-3632-01, TA-048-077-3632-01, 430190500000

  • 6 bedroom
  • 6 bathroom
  • Sleeps 18
Hawaii> Kailua
from $4,227 
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Hale Lani – Heavenly Lanikai Hillside Luxury
Hale Lani – Heavenly Lanikai Hillside Luxury
Hale Lani – Heavenly Lanikai Hillside Luxury

Hale Lani – Heavenly Lanikai Hillside Luxury

Welcome to Hale Lani, a breathtaking hillside retreat perched atop the lush northeastern coast of Oahu, Hawaii. This luxurious 3-bedroom, 4-bathroom home offers a serene escape with stunning views of Lanikai Beach and the Mokulua Islands. Perfectly situated just outside the charming town of Kailua, Hale Lani combines natural beauty with modern comfort, making it an ideal destination for families, friends, or couples seeking a memorable Hawaiian vacation.

Registration Number: TA-168-604-3136-01, 430060650000, GE-168-604-3136-01

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $3,647 
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La Bella's Bed and Breakfast Hawaii - Luxurious Suites Near Beach
La Bella's Bed and Breakfast Hawaii - Luxurious Suites Near Beach
La Bella's Bed and Breakfast Hawaii - Luxurious Suites Near Beach

La Bella's Bed and Breakfast Hawaii - Luxurious Suites Near Beach

Welcome to La Bella's Bed and Breakfast, where no detail is overlooked in creating a charming and luxurious retreat. Located just a short walk from the pristine beach, our property offers a perfect blend of comfort and natural beauty. Guests can stroll through lush gardens, unwind in well-appointed suites, and enjoy the warm hospitality of our friendly host family.
Registration Number: 440230030000, GE-056-708-4544-01, TA-056-708-4544-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $585 
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Luxury Kailua Beachfront Vacation Home with Pool
Luxury Kailua Beachfront Vacation Home with Pool
Luxury Kailua Beachfront Vacation Home with Pool

Luxury Kailua Beachfront Vacation Home with Pool

Discover this exclusive licensed vacation home on the Windward side of Oahu, offering a luxurious retreat just steps from Kailua Beach. 9 acres, the property boasts a spacious layout, a large swimming pool, and direct access to two miles of pristine white sandy beach, perfect for swimming, bodysurfing, paddling, and kite surfing.
Registration Number: TA-148-509-2864-01, 1430150430000, GE-148-509-2864-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Kailua
from $2,784 
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Charming Lanikai Beach House with Ocean Views
Charming Lanikai Beach House with Ocean Views
Charming Lanikai Beach House with Ocean Views

Charming Lanikai Beach House with Ocean Views

Imagine waking up to the sun rising over the Pacific, with the soothing sounds of tradewinds rustling through palm trees. This charming Lanikai Beach house offers a perfect tropical escape with stunning views of the turquoise ocean and the Mokulua Islands as your backdrop.
Registration Number: TA-102-715-5456-01, GE-102-715-5456-01, 1430050880000

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,854 
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Kailua Beach Villa with Ocean Views and Moonrise
Kailua Beach Villa with Ocean Views and Moonrise
Kailua Beach Villa with Ocean Views and Moonrise

Kailua Beach Villa with Ocean Views and Moonrise

Escape to this charming Kailua beach villa, offering breathtaking views of the Mokulua islands and direct access to one of Hawaii’s most beautiful beaches. Please note a 30-day minimum stay is required, though the calendar may not always reflect this.
Registration Number: TA-212-404-8896-01, GE-212-404-8896-01, 143012022000

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $2,037 
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