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Kailua Beach Vacation Rentals

Experience the serene beauty of Oahu's Windward Coast with our curated selection of vacation rentals near Kailua Beach. Whether you're seeking a cozy beachfront cottage, a spacious family home, or a luxurious estate, To-Hawaii.com offers a variety of accommodations to suit your preferences.

Our Kailua Beach rentals provide easy access to the bay's pristine beaches, lush landscapes, and charming town center. Enjoy modern amenities, stunning views, and the tranquil ambiance that makes Kailua Beach a sought-after destination for travelers.

From kayaking and paddleboarding to exploring local shops and eateries, Kailua Beach offers a perfect blend of relaxation and adventure. Browse the listings below to find your ideal vacation rental and start planning your unforgettable Hawaiian escape.

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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.

• 4 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Kailua

from $1,014 

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Hale Aloha by Gather: Waterfront Retreat in Kailua

Escape to Hale Aloha by Gather, a tranquil waterfront retreat nestled just minutes from Kailua's renowned beaches. This elegant 4-bedroom, single-level home spans over 12,000 square feet of lush island landscape, offering a perfect blend of contemporary comfort and Hawaiian charm.

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Kailua

from $859 

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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.

• 6 bedroom
• 6 bathroom
• Sleeps 14

Hawaii> Kailua

from $2,392 

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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.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kailua

from $524 

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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.

• 5 bedroom
• 5 bathroom
• Sleeps 14

Hawaii> Kailua

from $3,887 

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Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores

This exceptional beachfront property in Kailua offers two spacious living areas on the renowned Kailua Beach, known for its pristine white sands and clear waters. The main house features five beautifully renovated bedrooms, each designed with comfort and style, including a luxurious primary suite with a soaking tub and ensuite bath.

• 6 bedroom
• 4 bathroom
• Sleeps 14

Hawaii> Kailua

from $2,769 

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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.

• 5 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Kailua

from $1,213 

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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.

• 3 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Kailua

from $2,784 

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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.

• 3 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kailua

from $340 

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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.

• 4 bedroom
• 2 bathroom
• Sleeps 7

Hawaii> Kailua

from $720 

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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.

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Kailua

from $2,037 

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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.

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Kailua

from $212 

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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.

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Kailua

from $1,180 

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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.

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Kailua

from $341 

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Charming Pink House Near Kailua Beach with Ocean Views

The Pink House offers a charming Hawaiian-style retreat just 100 yards from the pristine sands of Kailua Beach. This spacious home features an open floor plan with a combined living and dining area, complemented by a modern galley kitchen equipped with stainless steel appliances.

• 4 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kailua

from $761 

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Hawaiian Style 4BR Home Near Kailua Beach

Discover this charming Hawaiian-style 4-bedroom, 4-bathroom home just a 3-minute walk from the stunning Kailua Beach on Oahu's Windward Coast. The property offers a perfect blend of indoor comfort and outdoor serenity, featuring a Zen-inspired courtyard and an inviting navy blue mosaic pool in the backyard.

• 4 bedroom
• 4 bathroom
• Sleeps 12

Hawaii> Kailua

from $1,081 

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Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu

Experience island living at its best in this charming Kailua beachfront home located on Oahu's Windward side, just 30 minutes from Honolulu and a mile from Kailua Town. The property offers breathtaking sunrises over Kailua Bay, scenic views of the Ko'olau Mountain Range, and outlying islands, all visible from the spacious front lanai.

• 4 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Kailua

from $2,186 

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Luxury Kailua Beach Residence with Pool and Ocean Access

Experience the ultimate beachfront getaway in this spacious Kailua residence, located just a short stroll from the stunning Kailua Beach. The home boasts a resort-style atmosphere with a private courtyard and solar-heated pool, perfect for relaxing and entertaining.

• 8 bedroom
• 5 bathroom
• Sleeps 20

Hawaii> Kailua

from $1,394 

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Beautiful Private Kailua Hawaii Home with Pool

Experience the ultimate Hawaiian retreat in this beautifully appointed private residence located in the charming Enchanted Lakes area of Kailua. The spacious two-bedroom, two-bath home features elegant Asian-inspired furniture from a designer's eye, creating a serene and luxurious atmosphere.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kailua

from $458 

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Windward Oahu Coconut Corner Vacation Rental

Coconut Corner is a spacious 700 square foot duplex located on the serene Windward side of Oahu in Kailua. It features a comfortable king-size bed, full split A/C units in every room, and Smart TVs in both the bedroom and living area, providing modern comfort and entertainment.

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Kailua

from $259 

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Charming Kailua 30-Day Rental near Beach & Town

Experience the charm of this vintage Kailua home, built in 1949, offering a blend of historic Hawaii character and modern comforts. Located just half a mile from Kailua Beach and within a five-minute walk to Kailua Town, this 30-day rental is ideal for those seeking a relaxed island lifestyle.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kailua

from $310 

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Luxury 8-Bedroom Beach House on Kailua Beach

The luxurious eight-bedroom home offers an exceptional stay right on Kailua Beach, voted America’s number one beach. Perfect for families, reunions, anniversaries, or corporate retreats, this property provides ample space and stunning ocean views.

• 8 bedroom
• 4 bathroom
• Sleeps 14

Hawaii> Kailua

from $2,557 

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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.

• 2 bedroom
• 1 bathroom
• Sleeps 9

Hawaii> Kailua

from $363 

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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.

• 5 bedroom
• 3 bathroom
• Sleeps 12

Hawaii> Kailua

from $470 

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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.

• 5 bedroom
• 5 bathroom
• Sleeps 12

Hawaii> Kailua

from $2,709 

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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.

• 5 bedroom
• 5 bathroom
• Sleeps 10

Hawaii> Kailua

from $2,118 

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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.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kailua

from $625 

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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.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kailua

from $306 

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