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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Stunning Ocean View Master Suite Near Beach

Stunning Ocean View Master Suite Near Beach

The Master Suite in this charming beach house offers breathtaking ocean and mountain views, situated on the third floor for maximum privacy and tranquility. The suite features its own AC, though the soothing sounds of waves and refreshing ocean air typically eliminate the need for it, creating a perfect environment for restful sleep.
Registration Number: GE-032-998-4000-01, 1430200410000, TA-032-998-4000-01

3 bedroom
3 bathroom
Sleeps 9

from $363

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Luxurious five-bedroom modern retreat

This five-bedroom home in
Honolulu offers a blend of modern design and tranquil vibes. The kitchen is modern and functional, with sleek finishes and ample storage. The master suite provides a serene retreat. Outside, a modest zen and peaceful space for relaxation.
Registration Number: TA-005-713-3032-01, GE-005-713-3032-01

5 bedroom
2 bathroom
Sleeps 18

from $1,992

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Charming Kailua Beach Private Studio with Modern Amenities

Charming Kailua Beach Private Studio with Modern Amenities

Welcome to your perfect island retreat in Kailua, Hawaii. This private studio apartment combines comfort, style, and convenience, making it an ideal base to explore the island. The well-designed space features a spacious 550 sq ft layout with bamboo floors, quartz countertops, and a luxurious river rock shower that massages your feet.
Registration Number: TA-155-463-6800-02, GE-155-463-6800-02

1 bedroom
1 bathroom
Sleeps 2

from $176

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Lanikai Beach Oceanfront Vacation Home

Experience the ultimate beachfront retreat at this beautifully updated home on Lanikai Beach, renowned as one of the world's top beaches. The property offers three spacious bedrooms and four bathrooms, all designed with high-end finishes to provide comfort and luxury.
Registration Number: 43003076, GE-164-517-2736-01, TA-164-517-2736-01

3 bedroom
4 bathroom
Sleeps 6

from $2,354

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Spectacular Lanikai Oceanfront Home with Pool

Spectacular Lanikai Oceanfront Home with Pool

Welcome to this stunning six-bedroom oceanfront residence nestled in the exclusive Lanikai enclave, just two miles from Kailua Town. Recently renovated with modern upgrades in 2021, this home offers a perfect blend of luxury and comfort for multi-family or multi-generational groups.
Registration Number: GE-191-501-7728-01, TA-191-501-7728-01

6 bedroom
6 bathroom
Sleeps 18

from $1,441

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Lanikai Hillside Estate – Panoramic Luxury Above the Sea

Lanikai Hillside Estate – Panoramic Luxury Above the Sea

This exquisite property offers a luxurious escape on the remote islands of Lanikai, blending modern elegance with natural beauty. Spanning over 8,400 square feet, this estate features seven spacious bedrooms, each designed for comfort and style, with the primary suite offering panoramic ocean views, a walk-in closet, and a chic Agape bathroom.
Registration Number: 430010090000, GE-053-605-3248-01, TA-053-605-3248-01

7 bedroom
7 bathroom
Sleeps 10

from $4,165

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Luxurious Leaf House in Lanikai with Ocean Views

Luxurious Leaf House in Lanikai with Ocean Views

Welcome to Leaf House by Gather, an exquisite five-bedroom, four-and-a-half-bathroom luxury retreat nestled in the picturesque neighborhood of Lanikai, Kailua, Hawaii. This custom-designed, three-story home offers an unmatched combination of sophistication, privacy, and island charm, making it an ideal destination for families or groups of up to ten guests seeking a memorable Hawaiian escape.

Registration Number: TA-032-430-3360-01, GE-032-430-3360-01, 430020420000

5 bedroom
5 bathroom
Sleeps 10

from $1,163

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Luxury Kailua Beach Estate with Ocean Views

Luxury Kailua Beach Estate with Ocean Views

Welcome to Ranch Beach Estate, a hidden gem just steps from Kailua's pristine white sand beaches. Nestled on a coveted loop, this luxurious home offers easy access to local cafes, boutiques, and farmers' markets. A manicured grass driveway with fragrant plumeria and a salty breeze invites you into a private, fully-fenced tropical oasis.
Registration Number: 430130190000, TA-129-806-1824-01, GE-129-806-1824-01

4 bedroom
4 bathroom
Sleeps 8

from $937

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Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore

Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore

Welcome to Kailua Beach Villa, your ideal luxury Hawaiian retreat on Oahu's eastern shore. This spacious two-level villa features five bedrooms plus an optional sixth, accommodating up to 12 guests comfortably. Designed with a contemporary, open-air style, the home offers stunning views of the sparkling ocean and lush gardens, creating a peaceful tropical sanctuary.

Registration Number: TA-200-559-6160-01, GE-200-559-6160-01, 430160130000

5 bedroom
5 bathroom
Sleeps 12

from $2,709

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Charming Kailua Beachfront Home with Ocean Views

Charming Kailua Beachfront Home with Ocean Views

Welcome to Kai Mele, a charming beachfront retreat nestled on the beautiful shores of Kailua, Oahu. This quaint 3-bedroom, 2-bathroom home offers cozy comfort and stunning views of Kailua Bay, making it an ideal destination for a relaxing island escape.

Registration Number: 430130320000, TA-160-294-7072-01, GE-160-294-7072-01

3 bedroom
2 bathroom
Sleeps 6

from $890

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Beachfront Kailua Villa with Ocean Views

Beachfront Kailua Villa with Ocean Views

Escape to the tranquil shores of Kailua at Kailua Hale Kahakai, a spacious beachfront villa nestled on one of the most beautiful stretches of Kailua Beach. This serene property sits on a quiet flag lot, surrounded by lush palm trees and tropical flora, offering a peaceful retreat with direct access to pristine sands and sparkling blue waters of Oahu's eastern coast.

Registration Number: 430130020000, GE-039-143-1168-01, TA-039-143-1168-01

6 bedroom
5 bathroom
Sleeps 12

from $1,288

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Seahorse Beach House in Kailua with Ocean Views

Seahorse Beach House in Kailua with Ocean Views

Seahorse Beach House is a hidden gem on Oahu’s east coast, offering a luxurious and peaceful retreat just steps from Kailua’s pristine white sand beaches. Located on one of Kailua’s most desirable loops, this home provides easy access to local cafes, boutiques, and farmers’ markets, making it an ideal base for exploring the vibrant town and surrounding natural beauty.

Registration Number: 430130190000, TA-129-806-1824-01, GE-129-806-1824-01

2 bedroom
2 bathroom
Sleeps 4

from $625

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Charming 1-Bedroom Home Near Kailua Beach Park

Charming 1-Bedroom Home Near Kailua Beach Park

Live the beach lifestyle in this charming ground-floor 1-bedroom, 1-bath home located just across the street from Kailua Beach Park. The property offers a perfect blend of sandy shores, lush grassy areas, tall ironwood trees, and turquoise waters.
Registration Number: TA-164-136-7040-01, GE-164-136-7040-01, 430090180000

1 bedroom
2 bathroom
Sleeps 4

from $306

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Luxury 4BR Retreat Near Lanikai Beach

Welcome to Lanikai Hideaway, a stunning four-bedroom, three-bathroom private residence nestled in the charming town of Kailua, Hawaii. This property, renovated in 2021, offers a perfect blend of comfort, style, and luxury, making it an ideal destination for up to nine guests seeking a memorable Hawaiian escape.
Registration Number: GE-093-106-8416-01, TA-093-106-8416-01, 430030430000

5 bedroom
3 bathroom
Sleeps 9

from $834

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Luxury Oceanfront Villa Near Kailua Beach

Luxury Oceanfront Villa Near Kailua Beach

Discover the ultimate luxury experience at Hale 'Oli 'Oli, a stunning oceanfront villa situated just steps from the pristine sands of Kailua Beach. This exquisite property offers a seamless open-concept layout, a chef�s dream gourmet kitchen, and six spacious bedrooms designed for comfort and style.
Registration Number: TA-048-077-3632-01, GE-048-077-3632-01, 430190500000

6 bedroom
6 bathroom
Sleeps 12

from $7,732

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Charming Kailua Home with Pool Near Beaches

Charming Kailua Home with Pool Near Beaches

Escape to this charming Kailua home nestled in a quiet neighborhood, just a mile from Kailua town's shopping and dining options. The property is ideally located within biking distance to the world-famous Kailua and Lanikai Beaches, offering stunning views of the Ko'olau Mountains and refreshing breezes from Kailua Bay.
Registration Number: 43067102, TA-143-675-2896-01, GE-143-675-2896-01

3 bedroom
2 bathroom
Sleeps 7

from $193

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Kailua Beach Villa - Luxury Hawaiian Beachfront Home

Kailua Beach Villa - Luxury Hawaiian Beachfront Home

Welcome to Kailua Beach Villa, your ultimate Hawaiian getaway. This luxurious two-level beachfront home offers five bedrooms, four bathrooms, and space for up to 11 guests, making it ideal for families or groups seeking comfort and privacy. Every detail of this property is designed to provide a relaxing tropical retreat, with breathtaking ocean views and direct access to the renowned Kailua Beach.
Registration Number: TA-123-605-1968-01, 430180070002, GE-123-605-1968-01

6 bedroom
5 bathroom
Sleeps 11

from $2,387

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Lanikai Ola Nani Beachfront Retreat with Modern Comforts

Lanikai Ola Nani Beachfront Retreat with Modern Comforts

This stunning property offers a luxurious, modern 4-bedroom, 4-bathroom retreat just steps from the calm waters of Lanikai Beach. Designed for comfort and privacy, it comfortably accommodates up to 8 guests seeking tranquility in one of Hawaii’s most exclusive neighborhoods.

Registration Number: 430060440000, GE-053-385-4720-01, TA-053-385-4720-01

4 bedroom
4 bathroom
Sleeps 8

from $758

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Mokulua Seaside Luxury Beach Retreat in Kailua

Mokulua Seaside Luxury Beach Retreat in Kailua

Welcome to Mokulua Seaside by Gather, a luxurious retreat nestled just one house away from Kailua's pristine beaches on the tranquil east end of Mokulua Drive. This stunning four-bedroom, four-bathroom home comfortably accommodates up to ten guests, making it perfect for families or groups seeking a peaceful escape surrounded by natural beauty.

Registration Number: TA-013-318-7072-01, GE-013-318-7072-01, 430040990000

4 bedroom
4 bathroom
Sleeps 10

from $951

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Kailua Beachside Luxury Villa with Pool and Ocean Views

Kailua Beachside Luxury Villa with Pool and Ocean Views

Kailua Beachside by Gather offers a stunning five-bedroom, five-bathroom villa perfect for up to ten guests, located directly on the pristine Kailua Beach. This modern, architect-designed home combines luxury and comfort with breathtaking ocean views and seamless indoor-outdoor living.
Registration Number: 430200630000, GE-028-490-7520-02, TA-028-490-7520-01

5 bedroom
5 bathroom
Sleeps 10

from $2,118

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Charming 4-Bed Kailua Beach Retreat

Welcome to your dream Hawaiian escape! This charming 4-bedroom home is located just four houses from the stunning Kailua Beach, offering the perfect blend of comfort, convenience, and natural beauty.
Nestled on a private lane with a direct path to the beach, this fully renovated house boasts a modern kitchen and bathrooms, hardwood floors throughout the main living areas, and brand-new furniture and bedding for a cozy, stylish stay.

Registration Number: GE-100-709-7344-01, TA-100-709-7344-01, 143015028000

4 bedroom
2 bathroom
Sleeps 6

from $488

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Hawaii Minivan Camper in Kailua - Ocean & Mountain Views

Hawaii Minivan Camper in Kailua - Ocean & Mountain Views

Immerse yourself in the natural beauty of Hawaii with our custom minivan camper located in Kailua. Perfect for solo travelers or couples, this mobile retreat offers the comfort of home amidst stunning island scenery. The van features a plush 8-inch memory foam mattress with fresh linens, ensuring restful sleep after days filled with adventure.
Registration Number: TA-304-451-9023-02, GE-223-011-9008-16, 99981440

1 bedroom
1 bathroom
Sleeps 2

from $333

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Hale Alapi'i Lanikai Getaway - Monthly Rental

Hale Alapi'i Lanikai Getaway - Monthly Rental

Welcome to Hale Alapi'i Lanikai Getaway by Gather, a beautifully renovated four-bedroom, three-bathroom home nestled in the heart of Kailua's iconic Lanikai neighborhood. This serene property offers a perfect blend of island charm and modern comfort, making it an ideal retreat for families or groups seeking to immerse themselves in Hawaii's natural beauty.

Registration Number: 430030350000, GE-150-218-4960-01, TA-150-218-4960-01

4 bedroom
3 bathroom
Sleeps 6

from $666

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Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance

Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance

Discover this exquisite luxury oceanfront home in Lanikai, built in 2006 with charming board and batten architecture. The concrete floors add a touch of Old Hawaii charm, complemented by lush gardens and inviting outdoor entertainment areas. The expansive outdoor spaces feature a large pool, perfect for relaxing under the Hawaiian sun, along with spacious yard areas for outdoor activities.
Registration Number: TA-127-965-6960-01, GE-127-965-6960-01, 1430010120001

4 bedroom
4 bathroom
Sleeps 6

from $2,009

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Spacious Kailua Beach Retreat with Private Studio

Spacious Kailua Beach Retreat with Private Studio

Experience the ultimate Hawaiian escape just four homes from the pristine sands of Kailua Beach. This spacious property combines a stunning 4-bedroom main house with a separate private studio cottage, offering ample space and privacy for families or groups of friends.
Registration Number: GE-161-351-8336-01, TA-161-351-8336-01, 430270250000

5 bedroom
3 bathroom
Sleeps 12

from $470

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Luxury Lanikai Beachside Retreat with Tropical Fruit Trees

Luxury Lanikai Beachside Retreat with Tropical Fruit Trees

Nohie Lanikai by Gather offers a charming beachside retreat just a block from the renowned Lanikai Beach. This beautifully remodeled four-bedroom, three-bath home offers 2,002 sq. ft. of interior living space on a lush 7,516 sq. ft. landscaped lot filled with avocado, mango, and Hawaiian orange trees.
Registration Number: 430060920000, TA-139-353-0368-01, GE-139-353-0368-01

4 bedroom
3 bathroom
Sleeps 8

from $595

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Charming Aloha Suite in Kailua, Hawaii - Cozy & Eco-Friendly

Charming Aloha Suite in Kailua, Hawaii - Cozy & Eco-Friendly

Welcome to our charming Aloha Suite nestled in Kailua, Hawaii. With over 30 years of hosting experience, we offer a comfortable, eco-conscious retreat designed for a memorable stay. The suite, approximately 350 square feet, features a cozy Queen Bed, a fully stocked kitchenette with utensils, pots, pans, microwave, refrigerator, and coffee maker.
Registration Number: 420200220000, TA-188-004-1472-01, 90/BB-0102, GE-188-004-1472-01

1 bedroom
1 bathroom
Sleeps 2

from $185

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Charming Kailua Bed & Breakfast for Relaxing Stays

Charming Kailua Bed & Breakfast for Relaxing Stays

This inviting Kailua bed & breakfast features a comfortable bedroom and a spacious living room with a cozy sofa bed, offering extra space for relaxation. The peaceful surroundings create an ideal setting for a restful retreat. Amenities include WiFi, air conditioning, and a washing machine, making it suitable for both short and extended stays.
Registration Number: TA-185-831-1680-01, 1430520420000, GE-185-831-1680-01

1 bedroom
1 bathroom
Sleeps 4

from $166

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Charming 3-Bedroom Home in Kailua with Pool

Charming 3-Bedroom Home in Kailua with Pool

This charming 3-bedroom house in Kailua offers a perfect retreat for your Hawaiian vacation. Located in a peaceful neighborhood, it features two queen beds and two twin beds, ensuring restful nights for all guests. Modern amenities include air conditioning, high-speed WiFi, a refreshing pool, and a washing machine for your convenience.
Registration Number: 44013049, TA-173-947-0848-01, GE-173-947-0848-01

3 bedroom
2 bathroom
Sleeps 8

from $490

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Lanikai Paradise across the street from the beach with AC and Parking!

Lanikai Paradise across the street from the beach with AC and Parking!

Welcome to your tropical escape in the heart of Lanikai, across the street from one of the most breathtaking beaches in all of world. This licensed short-term rental offers comfort, style, and space. Additional bedrooms are available to sleep up to 16 guests!

Registration Number: TA-015-067-6992-01, 1990/NUC-1752, GE-015-067-6992-01, 430080300000

4 bedroom
3 bathroom
Sleeps 10

from $1,820

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