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Discover Charming Cottage Vacation Rentals Across Hawaii

Escape to the serene beauty of Hawaii with our selection of cottage vacation rentals. These cozy accommodations offer a perfect blend of comfort and authenticity, providing an ideal retreat for couples, families, and solo travelers alike. Nestled in lush landscapes or steps away from pristine beaches, each cottage invites you to experience the islands at your own pace.

Enjoy the unique charm of Hawaiian living with features like private lanais, tropical gardens, and ocean views. Whether you're seeking a romantic hideaway or a family-friendly abode, our curated listings ensure a memorable stay. Immerse yourself in local culture, explore nearby attractions, or simply relax in your peaceful haven.

Ready to find your perfect island retreat? Browse our listings below to discover the cottage that best suits your Hawaiian adventure.

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Charming Kauai Country Cottage with Goat Yoga and Farm Fresh Fruits

Experience the authentic charm of this beautifully renovated Kauai country cottage, nestled in a native Hawaiian farm homestead. Guests are invited to pick ripe fruits like avocados, mangoes, passion fruit, and coconuts directly from the farm, adding a fresh touch to your stay.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Anahola

from $601 

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Charming Private Guest Cottage on Avocado Farm

Your own private guest cottage sits on a scenic 3-acre working avocado farm, offering a peaceful escape away from Kona's hustle and bustle. Situated at approximately 1,200 feet elevation, this charming retreat provides a cool, comfortable environment while still being just 12 minutes from major grocery stores and restaurants.

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Kailua-Kona

from $319 

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Kukuiula Makai Cottage #12 By Parrish Kauai

Kukuiula Makai Cottage #12 is a charming cottage nestled in the heart of Poipu’s highly sought-after Kukuiula neighborhood. This single-story plantation-style retreat blends vintage Hawaiian charm with upscale modern comforts. Featuring two bedroom suites, this cottage offers a private and peaceful escape—perfect for a romantic getaway or a small family retreat.

• 2 bedroom
• 3 bathroom
• Sleeps 4

Hawaii> Koloa

from $1,303 

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Charming Ocean View Kukuiula Beach Cottage in Poipu

Welcome to Kukuiula Vacation Home #2, a delightful ocean view beach cottage nestled in the heart of Poipu's sought-after Kukuiula neighborhood. This single-story plantation-style residence beautifully blends vintage Hawaiian charm with modern luxury, creating a memorable retreat for your island getaway.

• 3 bedroom
• 2 bathroom
• Sleeps 7

Hawaii> Koloa

from $1,133 

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Luxury Hualalai Coffee Farm Villa with Ocean Views

Welcome to this exquisite 3-acre luxury estate nestled on the slopes of Hualalai, offering spectacular views overlooking Kailua-Kona and the Pacific Ocean. This unique property includes a spacious Vista Suite and a charming one-bedroom Cottage, perfect for families or groups seeking privacy and comfort.

• 3 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Holualoa

from $1,311 

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Charming 4-Bedroom Cottage with AC, Smart TVs, and WiFi in Lower Kula

Escape to this wonderful cottage in picturesque Kula. This cozy retreat features 4 king bedrooms, 2 bathrooms with showers, and 2 additional living spaces with queen beds. Guests can enjoy the convenience of amenities like AC, WiFi, Smart TVs, Washer and Dryer, etc.

• 4 bedroom
• 2 bathroom
• Sleeps 12

Hawaii> Makawao

from $1,078 

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Princeville Makai Golf Course Cottages - Hawaii

Escape to the serene beauty of Princeville with a stay in these spacious suites at Club Wyndham Makai Club Cottages. Nestled along the first fairway of the renowned Makai Golf Course designed by Trent Jones, the cottages offer breathtaking views and a peaceful atmosphere.

• 4 bedroom
• 4 bathroom
• Sleeps 12

Hawaii> Princeville

from $468 

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Charming Princeville Island Home with Lanai and Pool View

Welcome to our charming island retreat in the heart of Princeville. This beautifully decorated home offers a cozy and inviting atmosphere, perfect for relaxing after exploring the stunning Hawaiian surroundings. Located centrally, you'll be just minutes from gorgeous beaches, delicious restaurants, shopping, and local attractions.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Princeville

from $516 

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Maui North Shore Cottage with Oceanfront Pool

Discover your perfect Maui escape at our charming 2-bedroom cottage overlooking the breathtaking North Shore. This inviting retreat features a sparkling pool surrounded by stunning oceanfront scenery, offering a serene setting for relaxation and adventure.

• 2 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Paia

from $917 

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Charming Laie Cottage Near Beach and Parks

Consider this charming cottage your home away from home while visiting Laie, Hawaii. This spacious property features 4 bedrooms, including a king bed, two bunk beds, a queen bed, and a cozy futon, providing ample sleeping options for your group.

• 4 bedroom
• 4 bathroom
• Sleeps 11

Hawaii> Laie

from $720 

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Moloa'a Bay Beachfront Cottage with Ocean Views

Moloa'a Bay Cottage offers an idyllic escape on the north shore of Kauai, nestled just steps from a pristine white sand beach. This charming property features a separate 994 sq ft air-conditioned guest house with one bedroom, a den, a loft, and a full bathroom, providing ample space and privacy for guests.

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Kilauea

from $762 

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Luxury Beachfront Villa at Moloa'a Bay Kaua'i

Welcome to your dream getaway at Moloa'a Bay, located on the northeast coast of Kaua'i. This expansive, private property offers nearly half a mile of pristine white sand beach, ideal for coastal activities such as snorkeling, surfing, bodyboarding, shelling, swimming, and sunbathing.

• 4 bedroom
• 4 bathroom
• Sleeps 11

Hawaii> Kilauea

from $2,102 

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