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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Luxurious Mokulua Sunrise Ocean Villa in Lanikai
Luxurious Mokulua Sunrise Ocean Villa in Lanikai
Luxurious Mokulua Sunrise Ocean Villa in Lanikai

Luxurious Mokulua Sunrise Ocean Villa in Lanikai

This exquisite property offers a luxurious monthly rental experience on the eastern shores of Oahu in the renowned neighborhood of Lanikai. Set in a tranquil, private location, the Mokulua Sunrise ocean villa provides breathtaking unobstructed views of the Mokulua Islands and direct access to the world-famous Lanikai Beach, known for its soft sands and turquoise waters.

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

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,075 
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Charming Villa Frangipani Near Kailua Beach
Charming Villa Frangipani Near Kailua Beach
Charming Villa Frangipani Near Kailua Beach

Charming Villa Frangipani Near Kailua Beach

Welcome to Villa Frangipani, a beautiful Hawaiian retreat nestled within a fully gated property surrounded by lush tropical gardens and palms. The highlight is a tranquil lagoon-style pool, perfect for relaxing after a day exploring the nearby white sands of Kailua Beach, just a two-minute barefoot walk along a private lane.
Registration Number: 430150140000, TA-172-544-1024-01, GE-172-544-1024-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $609 
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Remodeled 2-Bedroom Condo Near Kailua Beach
Remodeled 2-Bedroom Condo Near Kailua Beach
Remodeled 2-Bedroom Condo Near Kailua Beach

Remodeled 2-Bedroom Condo Near Kailua Beach

Welcome to this beautifully remodeled 2-bedroom, 2-bath townhouse located in the desirable Akahi Gardens community in Kailua. This inviting condo offers a perfect retreat for families or couples seeking a relaxing Hawaii getaway.
The spacious living area features modern updates and a comfortable atmosphere, while the kitchen opens onto a private lanai with a barbecue grill—ideal for outdoor dining and enjoying island breezes.

Registration Number: TA-141-705-0624-01, GE-141-705-0624-01, 44011082

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Kailua
from $381 
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Luxury Kailua Beach Rental with Stunning Ocean Views
Luxury Kailua Beach Rental with Stunning Ocean Views
Luxury Kailua Beach Rental with Stunning Ocean Views

Luxury Kailua Beach Rental with Stunning Ocean Views

Experience the best of beachside living in this beautifully renovated luxury rental overlooking Kailua Beach and Kailua Beach Park. The home features stunning views of the turquoise ocean, soft sandy shores, lush grassy areas, and tall ironwood trees, creating a perfect tropical retreat.

Registration Number: GE-164-136-7040-01, TA-164-136-7040-01, 430090180000

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $583 
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Charming Renovated 1-Bedroom Cottage in Kailua
Charming Renovated 1-Bedroom Cottage in Kailua
Charming Renovated 1-Bedroom Cottage in Kailua

Charming Renovated 1-Bedroom Cottage in Kailua

Welcome to our newly renovated, spacious 1-bedroom cottage in the heart of Kailua. Nestled on a beautifully landscaped property, this private retreat offers a lush garden with outdoor dining and BBQ, perfect for relaxing or entertaining. The fenced-in backyard features comfortable seating, ideal for morning coffee or enjoying the Hawaiian air.
Registration Number: GE-121-728-3584-01, 43071011, TA-121-728-3584-01, 143071110000

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $425 
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Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores

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.
Registration Number: 430130010000, TA-137-826-1504-01, GE-137-826-1504-01

  • 6 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,769 
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Charming Beachside Home in Lanikai Kailua
Charming Beachside Home in Lanikai Kailua
Charming Beachside Home in Lanikai Kailua

Charming Beachside Home in Lanikai Kailua

Discover this charming beachside residence in the heart of Lanikai, Kailua, offering over 1400 square feet of relaxed Hawaiian living. The upper half of a main house, this fully furnished home features a thoughtfully decorated interior with a natural, inviting ambiance.
Registration Number: TA-136-919-6544-01, GE-136-919-6544-01

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $261 
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Luxury Lanikai Hilltop Bungalow with Ocean Views
Luxury Lanikai Hilltop Bungalow with Ocean Views
Luxury Lanikai Hilltop Bungalow with Ocean Views

Luxury Lanikai Hilltop Bungalow with Ocean Views

Escape to this exquisite two-bedroom, two-bath private residence perched at the top of Lanikai, offering breathtaking panoramic views of the Kailua coastline and the deep blue Pacific. Nestled just beneath the popular Lanikai Pillboxes hiking trail, Koʻohoʻo provides unobstructed vistas of the Mokulua Islands, making it a truly unique hilltop retreat.
Registration Number: N/A, GE-073-725-6960-01, 1430050430000, TA-073-725-6960-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $379 
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Hale Aloha by Gather: Waterfront Retreat in Kailua
Hale Aloha by Gather: Waterfront Retreat in Kailua
Hale Aloha by Gather: Waterfront Retreat in Kailua

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.
Registration Number: TA-195-940-3520-01, GE-195-940-3520-01, 420180550000

  • 5 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $859 
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Luxury Kailua Beach House with Pool & Ocean Access
Luxury Kailua Beach House with Pool & Ocean Access
Luxury Kailua Beach House with Pool & Ocean Access

Luxury Kailua Beach House with Pool & Ocean Access

Indulge in an unforgettable stay at our brand-new luxury beach house nestled in the heart of Kailua Beach, renowned for its pristine sands and crystal-clear waters. This contemporary retreat seamlessly combines upscale comfort with the breathtaking natural beauty of Hawaii, offering a perfect sanctuary for relaxation and rejuvenation.

Registration Number: TA-060-008-4480-01, GE-060-008-4480-02, 430150540000

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $396 
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Charming Lanikai Beachside Studio with Modern Updates
Charming Lanikai Beachside Studio with Modern Updates
Charming Lanikai Beachside Studio with Modern Updates

Charming Lanikai Beachside Studio with Modern Updates

Escape to your perfect Hawaiian retreat with this charming, recently renovated studio located just a block from the stunning sands of Lanikai Beach. Designed as a cozy yet stylish home away from home, this property offers a unique combination of privacy and convenience, making it ideal for a relaxing and authentic Hawaiian experience.

Registration Number: TA-200-243-0464-01, GE-200-243-0464-01, 430080730000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $157 
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Charming Lanikai Cottage with Private Garden & Beach Access
Charming Lanikai Cottage with Private Garden & Beach Access
Charming Lanikai Cottage with Private Garden & Beach Access

Charming Lanikai Cottage with Private Garden & Beach Access

Discover the perfect escape at the Lanikai Bungalow, a private cozy cottage nestled in a lush tropical setting just steps from the beautiful ocean. This charming one-bedroom retreat offers a relaxing living space with a king-sized bed adorned with soft linens, a full kitchen, and a bathroom for your convenience.
Registration Number: 430040010000, GE-123-128-4224-01, TA-123-128-4224-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $112 
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Charming 1-Bedroom Apartment Near Kailua Beach
Charming 1-Bedroom Apartment Near Kailua Beach
Charming 1-Bedroom Apartment Near Kailua Beach

Charming 1-Bedroom Apartment Near Kailua Beach

Enjoy a peaceful escape in this charming one-bedroom apartment located just 700 yards from the beautiful Kailua Beach. Designed with comfort and convenience in mind, the unit features a spacious bedroom with a King bed, a wall-mounted flat-screen TV, split AC, and glass sliding doors that open onto a large covered lanai overlooking a lush grassy yard.
Registration Number: TA-143-873-0240-01, GE-143-873-0240-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $167 
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Spacious Ocean View Home in Lanikai Kailua
Spacious Ocean View Home in Lanikai Kailua
Spacious Ocean View Home in Lanikai Kailua

Spacious Ocean View Home in Lanikai Kailua

5-bath ocean view home in the beautiful Lanikai Kailua area on Oahu's NE shore. With 2,200 sq ft of living space, this tranquil retreat offers breathtaking sunrise to sunset ocean vistas from nearly every room. The gourmet kitchen features a large cooking island and modern appliances, perfect for preparing family meals.
Registration Number: TA-052-598-3744-01, GE-052-598-3744-01, 430030030000

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $750 
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Hawaiian Style 4BR Home Near Kailua Beach
Hawaiian Style 4BR Home Near Kailua Beach
Hawaiian Style 4BR Home Near Kailua Beach

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.
Registration Number: 430180300000, GE-096-373-7600-01, TA-096-373-7600-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 12
Hawaii> Kailua
from $1,081 
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Charming Old Hawaii Beach House in Lanikai
Charming Old Hawaii Beach House in Lanikai
Charming Old Hawaii Beach House in Lanikai

Charming Old Hawaii Beach House in Lanikai

Immerse yourself in the timeless charm of Old Hawaii at the Old Hawaii Beach House and Guest Cottage in Lanikai. This historic 1931 cottage, nestled on a lush 12,000 square foot lot on prestigious Mokulua Drive, offers an authentic Hawaiian experience blending nostalgia with modern comforts.

Registration Number: TA-179-651-4304-01, GE-179-651-4304-01, 430040100000

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $296 
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Charming Ground Floor 2BR Near Kailua Beach
Charming Ground Floor 2BR Near Kailua Beach
Charming Ground Floor 2BR Near Kailua Beach

Charming Ground Floor 2BR Near Kailua Beach

Discover this attractive ground-floor two-bedroom unit located on the beautiful island of Oahu. Perfectly situated just a 6-8 minute walk from the renowned Kailua Beach, this condo offers a comfortable and relaxing retreat for your Hawaii vacation.
Registration Number: TA-086-379-5200-01, GE-086-379-5200-01

  • 3 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> Kailua
from $185 
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Kailua Beach Studio with Private Access and Ocean View
Kailua Beach Studio with Private Access and Ocean View
Kailua Beach Studio with Private Access and Ocean View

Kailua Beach Studio with Private Access and Ocean View

Enjoy a serene Hawaiian escape just a two-minute walk (75 yards) from the stunning Kailua Beach with exclusive private access. This charming 700 sq ft studio offers a perfect blend of comfort and island charm. Inside, vaulted ceilings and beautiful wood flooring create an airy, inviting atmosphere, complemented by a large tiled bathroom and a cozy kitchen.
Registration Number: GE-192-192-7168-01, TA-192-192-7168-01, 430190620000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $277 
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Charming Kailua Beach Studio Near Ocean & Town
Charming Kailua Beach Studio Near Ocean & Town
Charming Kailua Beach Studio Near Ocean & Town

Charming Kailua Beach Studio Near Ocean & Town

Start your Hawaiian holiday with a stroll along one of the world's most beautiful beaches. Wake up to stunning sunrises in Kailua, where your adventure begins. Kailua Beach offers a perfect escape from everyday life—swim, boogie board, surf, kayak, sail, or windsurf in the warm, inviting waters.
Registration Number: TA-014-134-8864-01, 430260540000, GE-014-134-8864-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $296 
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Charming Kailua Beach Family Retreat with Pool
Charming Kailua Beach Family Retreat with Pool
Charming Kailua Beach Family Retreat with Pool

Charming Kailua Beach Family Retreat with Pool

Located just steps from the most beautiful part of Kailua Beach, this charming family retreat offers the perfect Hawaiian getaway. A short walk through Kailua Beach Park takes you to wide sandy shores with gentle waves, shaded by plenty of trees—ideal for relaxing, picnicking, or playing with kids all day long.

Registration Number: TA-079-018-3936-01, GE-079-018-3936-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $661 
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Hale Kolea Oceanview Family Retreat in Lanikai
Hale Kolea Oceanview Family Retreat in Lanikai
Hale Kolea Oceanview Family Retreat in Lanikai

Hale Kolea Oceanview Family Retreat in Lanikai

Experience the ultimate Hawaiian escape at Hale Kolea, a stunning three-story home nestled at the end of Lanikai with access to an exclusive secluded beach. This beautiful hillside residence offers breathtaking panoramic views of the sparkling blue and green waters, creating a serene backdrop for your vacation.
Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

  • 6 bedroom
  • 9 bathroom
  • Sleeps 12
Hawaii> Kailua
from $2,460 
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Charming Lanikai Beachside Cottage with Pool and Garden
Charming Lanikai Beachside Cottage with Pool and Garden
Charming Lanikai Beachside Cottage with Pool and Garden

Charming Lanikai Beachside Cottage with Pool and Garden

This charming Lanikai beachside cottage offers a perfect blend of traditional Hawaiian style and modern comfort. Nestled in an upscale neighborhood, the property features a lush tropical yard and a stunning lagoon-style pool, creating a private resort atmosphere just a short walk from the soft sands of Lanikai Beach.
Registration Number: 44005080, GE-124-185-8048-01, TA-124-185-8048-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua
from $1,037 
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Hale Pulelehua: Spacious Kailua Hawaii Retreat
Hale Pulelehua: Spacious Kailua Hawaii Retreat
Hale Pulelehua: Spacious Kailua Hawaii Retreat

Hale Pulelehua: Spacious Kailua Hawaii Retreat

Stay in comfort at Hale Pulelehua, or "The Butterfly House," a spacious Kailua retreat with open design and Hawaiian charm. Inside, large rooms feature sliding door walls and windows that invite the refreshing trade winds and fill the space with the sweet scent of Hawaiian flowers.
Registration Number: TA-049-642-4960-01, GE-049-642-4960-01

  • 5 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $397 
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Charming Private Guesthouse Near Kailua Beach
Charming Private Guesthouse Near Kailua Beach
Charming Private Guesthouse Near Kailua Beach

Charming Private Guesthouse Near Kailua Beach

Discover this charming private guesthouse located in a peaceful neighborhood just a short stroll from Kailua's beautiful beaches. The detached unit offers a peaceful retreat with its own entrance, ensuring privacy during your stay.
Inside, you'll find a thoughtfully decorated 'L' shaped living space featuring a well-equipped kitchen, a cozy queen-size bed, and a separate bedroom with two twin beds.
Registration Number: 113012040000, GE-131-660-8000-01, TA-131-660-8000-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $258 
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Kailana Beachside Vacation Home in Kailua, Oahu
Kailana Beachside Vacation Home in Kailua, Oahu
Kailana Beachside Vacation Home in Kailua, Oahu

Kailana Beachside Vacation Home in Kailua, Oahu

Our Kailana home offers a recently renovated, stylish tropical retreat in the charming beachside neighborhood of Kailua, Oahu. It’s just a short walk to the pristine beach, making it perfect for relaxing days by the water. The property is spacious, private, and peaceful, with lush tropical plants surrounding the yard, creating a serene oasis.

Registration Number: 430260120000, GE-012-164-3008-01, TA-012-164-3008-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $423 
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Kailua Beach Cottage with Private Pool and Lanai
Kailua Beach Cottage with Private Pool and Lanai
Kailua Beach Cottage with Private Pool and Lanai

Kailua Beach Cottage with Private Pool and Lanai

Discover this tranquil 400-square-foot cottage nestled just minutes from the renowned Kailua Beach. The detached studio offers a restful retreat with a private entrance, parking, and access to a serene pool area. Inside, you'll find a full bath and a kitchenette equipped with a full-sized refrigerator, microwave, and toaster oven, ideal for extended stays of 30 days or more due to local zoning laws.
Registration Number: 430190420000, GE-166-476-8000-01, TA-166-476-8000-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $182 
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Charming Pink House Near Kailua Beach with Ocean Views
Charming Pink House Near Kailua Beach with Ocean Views
Charming Pink House Near Kailua Beach with Ocean Views

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.
Registration Number: TA-065-234-5344-01, GE-065-234-5344-01

  • 4 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $761 
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Hale Alapi'i: Lanikai Vacation Home Near Beach
Hale Alapi'i: Lanikai Vacation Home Near Beach
Hale Alapi'i: Lanikai Vacation Home Near Beach

Hale Alapi'i: Lanikai Vacation Home Near Beach

Welcome to Hale Alapi'i, your charming home in the stunning neighborhood of Lanikai on Oahu. This beautifully renovated 3-bedroom, 2-bathroom main house offers approximately 1,400 sq. ft. of comfortable living space, perfect for families or small groups seeking a relaxing Hawaiian getaway.
Registration Number: 430030350000, TA-150-218-4960-01, GE-150-218-4960-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua
from $385 
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Charming 1-Bedroom Apartment Near Kailua Beach
Charming 1-Bedroom Apartment Near Kailua Beach
Charming 1-Bedroom Apartment Near Kailua Beach

Charming 1-Bedroom Apartment Near Kailua Beach

Welcome to our beautifully renovated 1-bedroom apartment in Kailua, Oahu, offering a cozy and family-friendly atmosphere that makes you feel right at home. This ground-floor suite spans approximately 800 square feet and comfortably accommodates up to four guests.
Registration Number: TA-065-136-8448-01, 430240120000, GE-065-136-8448-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $169 
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Spacious Studio with Pool and Canal Views Near Beach
Spacious Studio with Pool and Canal Views Near Beach
Spacious Studio with Pool and Canal Views Near Beach

Spacious Studio with Pool and Canal Views Near Beach

Experience a spacious studio with a large bathroom nestled beside a tranquil home. Step onto your private patio to enjoy coffee while overlooking the pool and the canal. Perfect for kayaking or paddleboarding to the beach, this quiet and clean space offers a peaceful retreat.
Registration Number: 420470480000, TA-007-640-8832-01, GE-007-640-8832-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $334 
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Luxury Kailua Villa Near Beach with Lagoon Pool
Luxury Kailua Villa Near Beach with Lagoon Pool
Luxury Kailua Villa Near Beach with Lagoon Pool

Luxury Kailua Villa Near Beach with Lagoon Pool

A lush tropical paradise awaits you at this gated estate just steps from Kailua Beach, offering a luxurious mini resort experience. 5M upgrade, Palione Papalani (Hawaiian for "Heavenly Sands") is an impressive 6-bedroom estate set amid exotic gardens and a serene lagoon-style pool with a hot tub.
Registration Number: 1990/NUC-1787, 430170580000, TA-206-682-7264-01, GE-206-682-7264-01

  • 6 bedroom
  • 6 bathroom
  • Sleeps 16
Hawaii> Kailua
from $3,089 
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Luxury Kailua Beach Residence with Pool and Ocean Access
Luxury Kailua Beach Residence with Pool and Ocean Access
Luxury Kailua Beach Residence with Pool and Ocean Access

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.
Registration Number: 430180600000, GE-017-575-5264-01, TA-017-575-5264-01

  • 8 bedroom
  • 5 bathroom
  • Sleeps 20
Hawaii> Kailua
from $1,394 
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Charming Kailua Guest House with Pool & Gardens
Charming Kailua Guest House with Pool & Gardens
Charming Kailua Guest House with Pool & Gardens

Charming Kailua Guest House with Pool & Gardens

Come enjoy the tranquil breezes of the windward side at the Kailua Palms Estate Guest House, a charming and spacious two-bedroom, two-bath vacation retreat located in the peaceful Kailua Town near the renowned Kailua Beach. The two bedrooms offer comfortable and airy accommodations, perfect for a relaxing getaway.
Registration Number: GE-007-808-6144-01, 440230180000, TA-007-808-6144-01

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $515 
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Charming Lanikai Cottage with Pool and Beach Access
Charming Lanikai Cottage with Pool and Beach Access
Charming Lanikai Cottage with Pool and Beach Access

Charming Lanikai Cottage with Pool and Beach Access

Discover this charming cottage in the beautiful neighborhood of Lanikai, completely renovated in 2021 with modern furnishings and amenities. The cozy interior offers a fully equipped efficient kitchen, a washer and dryer for convenience, and a spacious lanai perfect for outdoor dining and relaxing.
Registration Number: 430040610000, GE-006-174-7200-01, TA-006-174-7200-01

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $677 
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Windward Oahu Coconut Corner Vacation Rental
Windward Oahu Coconut Corner Vacation Rental
Windward Oahu Coconut Corner Vacation Rental

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.

Registration Number: GE-048-719-5648-01, TA-048-719-5648-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $259 
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Charming 2BR Beachside Apartment Near Kailua Beach
Charming 2BR Beachside Apartment Near Kailua Beach
Charming 2BR Beachside Apartment Near Kailua Beach

Charming 2BR Beachside Apartment Near Kailua Beach

Escape to paradise with this beautifully maintained beach-style apartment located just a short stroll from Kailua Beach Park. Nestled under a fragrant plumeria tree, this private 2-bedroom, 1-bathroom unit offers a perfect retreat for families or small groups seeking comfort and convenience.
Registration Number: TA-030-384-5376-01, GE-030-383-5376-02

  • 2 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> kailua
from $265 
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Charming Ocean View Cottage Near Kailua Beach
Charming Ocean View Cottage Near Kailua Beach
Charming Ocean View Cottage Near Kailua Beach

Charming Ocean View Cottage Near Kailua Beach

Escape to this charming two-bedroom, one-bath ocean view cottage located just a few steps from the renowned Kailua Beach, voted the number one beach in America. The cottage offers a comfortable, home-away-from-home atmosphere with a private entrance, ensuring your privacy during your stay.
Registration Number: 430180570000, GE-149-231-0528-01, TA-149-231-0528-01

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kailua
from $686 
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Beautiful Private Kailua Hawaii Home with Pool
Beautiful Private Kailua Hawaii Home with Pool
Beautiful Private Kailua Hawaii Home with Pool

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.
Registration Number: TA-047-591-0144-01, GE-047-591-0144-01, 420410950000

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua
from $458 
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Charming Kailua 30-Day Rental near Beach & Town
Charming Kailua 30-Day Rental near Beach & Town
Charming Kailua 30-Day Rental near Beach & Town

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.

Registration Number: 420200540000, GE-014-499-8400-01, TA-014-499-8400-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua
from $310 
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Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu

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.
Registration Number: TA-179-906-2528-01, GE-179-906-2528-01, 1430150100005

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua
from $2,186 
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Luxury Lanikai Beach Home with Rooftop Deck
Luxury Lanikai Beach Home with Rooftop Deck
Luxury Lanikai Beach Home with Rooftop Deck

Luxury Lanikai Beach Home with Rooftop Deck

Guests will find our well-appointed, multi-story residence nestled in a quiet, sought-after beach community. Tucked away down a private lane, the property sits on a large tropical lot just 400 feet from the world-famous Lanikai Beach, offering both privacy and easy access to pristine sands.

Registration Number: TA-185-301-6064-01, GE-185-301-6064-01, 430080750000

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua
from $1,250 
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Oceanfront Deluxe Kailua Vacation Rental with Pool
Oceanfront Deluxe Kailua Vacation Rental with Pool
Oceanfront Deluxe Kailua Vacation Rental with Pool

Oceanfront Deluxe Kailua Vacation Rental with Pool

The Kailua Absolutely Oceanfront Deluxe Legal Vacation Rental offers an unparalleled escape in one of Hawaii's most sought-after neighborhoods. Located just steps from the ocean, this property provides breathtaking ocean views and the soothing sounds of waves breaking outside your window.
Registration Number: GE-077-897-3184-01, TA-077-897-3184-01, 1330220850000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kailua
from $702 
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Luxury 8-Bedroom Beach House on Kailua Beach
Luxury 8-Bedroom Beach House on Kailua Beach
Luxury 8-Bedroom Beach House on Kailua Beach

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.

Registration Number: GE-149-231-0528-01, 430180590000, TA-149-231-0528-01

  • 8 bedroom
  • 5 bathroom
  • Sleeps 14
Hawaii> Kailua
from $2,557 
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Luxury Kailua Beachfront Villa with Pool & Jacuzzi
Luxury Kailua Beachfront Villa with Pool & Jacuzzi
Luxury Kailua Beachfront Villa with Pool & Jacuzzi

Luxury Kailua Beachfront Villa with Pool & Jacuzzi

Escape to this stunning Kailua beachfront villa that offers direct access to the renowned Kailua Beach, perfect for a luxurious and relaxing vacation. The property features five spacious bedrooms, each equipped with private split-system A/C units, ensuring comfort during your stay.
Registration Number: TA-112-883-7120-01, GE-112-883-7120-01, 430170600000

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua
from $2,992 
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Hawaii's Hidden Hideaway Award-Winning Bed & Breakfast
Hawaii's Hidden Hideaway Award-Winning Bed & Breakfast
Hawaii's Hidden Hideaway Award-Winning Bed & Breakfast

Hawaii's Hidden Hideaway Award-Winning Bed & Breakfast

Hawaii's Hidden Hideaway is an award-winning bed and breakfast renowned for its romantic ambiance and exceptional guest experience. Recognized for two consecutive years with the Most Romantic Hideaway Award, as voted by visitors, our charming property has been featured in Travel Magazine and other international publications.
Registration Number: TA-213-164-6464-01, GE-213-164-6464-01, 430040470000

  • 4 bedroom
  • 2 bathroom
  • Sleeps 3
Hawaii> Kailua
from $382 
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Kailua Beachside Hawaii Vacation Home with Pool
Kailua Beachside Hawaii Vacation Home with Pool
Kailua Beachside Hawaii Vacation Home with Pool

Kailua Beachside Hawaii Vacation Home with Pool

Discover the 'Star of Hawaii' Hale, a stunning private beachside retreat nestled on a tranquil lane in Kailua. Surrounded by lava rock walls, the home offers exclusive privacy with lush gardens and a inviting pool, just a few steps from the pristine sands of Kailua Beach, renowned for its gentle waves and breathtaking scenery.

Registration Number: 430150080000, GE-061-116-6208-01, TA-061-116-6208-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 12
Hawaii> Kailua
from $743 
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Luxury Lanikai Beach House with Private Pool
Luxury Lanikai Beach House with Private Pool
Luxury Lanikai Beach House with Private Pool

Luxury Lanikai Beach House with Private Pool

Experience the ultimate Hawaiian retreat at this luxurious Lanikai beach house, available for minimum 30-day stays. Surrounded by lush tropical landscaping, palm trees, and vibrant flowers, this property offers a serene oasis just steps from the sands of Lanikai Beach.
Registration Number: TA-019-850-2400-01, GE-019-850-2400-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua
from $595 
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Hawaiian Beach Estate with Ocean & Mountain Views
Hawaiian Beach Estate with Ocean & Mountain Views
Hawaiian Beach Estate with Ocean & Mountain Views

Hawaiian Beach Estate with Ocean & Mountain Views

Experience ultimate relaxation at our beautiful Hawaiian beach estate located on over an acre of lush land in Kailua. Just a 30-second walk down a sandy beach path leads you to one of Hawaii's top ten beaches, renowned for its pristine white sands and tranquility.
Registration Number: GE-076-336-5376-01, TA-076-336-5367-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua
from $909 
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Private Tropical Home Near Lanikai and Kailua Beaches
Private Tropical Home Near Lanikai and Kailua Beaches
Private Tropical Home Near Lanikai and Kailua Beaches

Private Tropical Home Near Lanikai and Kailua Beaches

Experience a tranquil escape in this beautifully designed private home nestled amidst lush tropical gardens. Crafted by renowned architect Vladimir Ossipoff, the residence features open-plan layouts that capitalize on refreshing trade winds and stunning views of the Koolau mountains.

Registration Number: GE-119-399-0144-01, TA-119-399-0144-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua
from $372 
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Luxury Maluhia Beachfront Villa in Kailua
Luxury Maluhia Beachfront Villa in Kailua
Luxury Maluhia Beachfront Villa in Kailua

Luxury Maluhia Beachfront Villa in Kailua

Escape to the serene beauty of Maluhia, a luxurious beachfront villa nestled in the desirable east Oahu area of Kailua. This expansive 5,000 sq. ft. home is a favorite among celebrities and families seeking a tranquil island retreat. As you step through the front door, you're welcomed into a grand living space featuring soaring vaulted ceilings, elegant travertine and wood flooring, and a stylish stone fireplace, creating an ambiance of refined comfort.
Registration Number: TA-129-612-3904-01, GE-129-612-3904-01, 430830170000

  • 4 bedroom
  • 4 bathroom
  • Sleeps 9
Hawaii> Kailua
from $1,317 
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