Discover Charming Cottage Vacation Rentals Across Hawaii

Hawaii cottage vacation rentals provide a peaceful escape in lush settings or near the ocean. These cozy retreats are perfect for couples, solo travelers, or families seeking a relaxing island stay. Enjoy tropical gardens, private lanais, and authentic Hawaiian charm across the islands.

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New Custom Hawaiian Cottage - Poipu Beach- Koloa, Hi

New Custom Hawaiian Cottage - Poipu Beach- Koloa, Hi

The Sea Glass Cottage offers an unforgettable Garden Isle vacation. This custom-designed Hawaiian style Cottage is located just steps from Poipu Beach. The 2-bedroom, 2 bath Sea Glass Cottage graciously combines the beauty and simplicity of a classic Hawaiian home with all the conveniences of the 21st century.

2 bedroom
2 bathroom
Sleeps 4

from $808

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ICC 16 Kaanapali 2BD Plantation Cottage w AC Near Beach

ICC 16 Kaanapali 2BD Plantation Cottage w AC Near Beach

FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental.

2 bedroom
2 bathroom
Sleeps 4

from $347

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Charming Cottage

TVR 4181: Charming cottage above historic Koloa Town, about 20 minutes from Lihue airport.
Front door opens into expansive screened-in lanai with dining table. Living room includes comfortable furnishings, seating area and a pune'e, Hawaiian style couch, that can sleep one.

2 bedroom
2 bathroom
Sleeps 5

from $330

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$Rainbow Deluxe - 2 BR\/2 BA Cottage - Simply Wonderful!$

Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful!

'RAINBOW DELUXE' is a 700 square foot standout 2 bedroom / 2 bath fully licensed vacation home conveniently located in Maui Meadows, along the south shore of Maui, Hawaii. Our luxury Polynesian pole cottage sits on its own quarter acre, ideally nestled in a peaceful neighborhood on the foothills of Mt.

2 bedroom
2 bathroom
Sleeps 4

from $428

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Ocean Views, Private Hot Tub, Swimming Pool Access, Historic Cottage

Ocean Views, Private Hot Tub, Swimming Pool Access, Historic Cottage

) This home offers three bedrooms and sleeps 6. It has been lovely restored and is a very special place to vacation in Hawaii.

Soak in the private cedar hot tub after a busy day at the beach or hiking.

The Cowboy House has a long lanai with big ocean Views and a big tree swing for grown ups and kids!

3 bedroom
2 bathroom
Sleeps 6

from $624

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Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-

Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-

Ocean front- Nestled between Historic He`eia Bay and Keauhou Bay- Kinohi at He`eia

Welcome to He`eia Bay Hale. Comfortable and bright, this house and guest cottage has 5 bedrooms and 3 bathrooms in the main house and two queen size sofa beds and bathroom in the guest cottage.

6 bedroom
4 bathroom
Sleeps 14

from $1,490

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Charming Beach Cottage by Mama's Beach

Grom's Hideaway is a charming cottage nestled in the heart of Kuau Point, the last little neighborhood 1 mile outside Paia(a 5 min drive), as you head out on Hana Highway.
Grom's has 3 bedrooms (king, queen and two twins) and 1 Bath with an indoor and a Very Private Outdoor shower.

3 bedroom
2 bathroom
Sleeps 6

from $447

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Cottage on a 3 acre estate, spa, fireplace, cozy, park like setting, fruit trees

Cottage on a 3 acre estate, spa, fireplace, cozy, park like setting, fruit trees

Hale O' Makani, is located in upper Paauilo cool temperatures for a comfortable nights sleep, lots of mature trees, including fruit trees, vegetable garden,surround this property, very cozy cedar cottage ,with 1 bedroom, queen size bed, full kitchen, bathroom with tub and shower, walk in closet, gas fireplace in living room for those chilly nights, beautiful deck with spa, this cottage only accommodates 2 guests maximum, 25 min.

1 bedroom
1 bathroom
Sleeps 2

from $236

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Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Tat # TA-031-786-3936-01 The perfect Maui vacation cottage that is legal. Hale Manu Mele offers you the best of Maui: Quality, Comfort, Quiet Privacy, Convenient Location, And Affordability. The 720 sf House is a beautiful remodeled 2 br/1 bath with an outside shower.

2 bedroom
1 bathroom
Sleeps 4

from $597

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ICC 37 Remodeled Plantation Cottage Near Beach

ICC 37 Remodeled Plantation Cottage Near Beach

2 bedroom
2 bathroom
Sleeps 6

from $371

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Tiki Hut Cottage - Lush Tropical Garden, ;Walk to Tunnels Beach TVNCU#5161

Tiki Hut Cottage - Lush Tropical Garden, ;Walk to Tunnels Beach TVNCU#5161

Capture the magic of this romantic cottage. Large picture windows, open beam ceilings and sky lights bring views of lush tropical gardens with towering Cook pines. Two covered lanais for pupus, mai-tais and outside dining. After an adventurous day on the Kalalau Trail, you can star gaze in your private hot tub under the moonlight in this serene, beautiful , private, half acre surrounding.

1 bedroom
1 bathroom
Sleeps 2

from $464

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Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

This very spacious ocean and pool view cottage has everything you need to truly relax and
enjoy the serenity of Maui. Designed in a vintage Hawaiian theme with a modern twist, this
room offers a unique tribute to the great Hawaiian Surfer, Duke Kahanamoku.

1 bedroom
1 bathroom
Sleeps 2

from $501

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$Special Rate 1\/12\/25-3\/9\/25! Escape to our Cozy 2 BR\/1BA COTTAGE in Kihei!$

Special Rate 1/12/25-3/9/25! Escape to our Cozy 2 BR/1BA COTTAGE in Kihei!

Located in central Kihei, nestled on the northern end of beautiful Halama Street. Family-owned and operated legal short-term rental. A cozy 2 bedroom, 1 bath cottage with a large deck for sunbathing or BBQS. Less than a three-minute walk on the property will take you to a large spacious green lawn with swaying coconut palm trees and to a seemingly private sandy beach.

2 bedroom
1 bathroom
Sleeps 4

from $455

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Beautiful One Bedroom AC Beach Cottage

Our one bedroom beach cottage is located on a quiet one lane road leading to the ocean. While in a quiet location it is still just a few minutes drive from downtown Hilo, supermarkets, restaurants, airport, medical centers, and scenic parks and beaches.

1 bedroom
2 bathroom
Sleeps 2

from $340

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Sweeping Ocean Views, Very Private Cottage

Sweeping Ocean Views, Very Private Cottage

Charming 1930's Authentic "Hawaiian Paniolo" bungalow on our private ocean view ranch. Less than a mile from the shore line with 180º sweeping ocean, green pastures and Maui views.

Our historic bungalows are stocked with everything you need to enjoy your home away from home.

2 bedroom
2 bathroom
Sleeps 4

from $629

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Private cottage above Kona surrounded by coffee farms.

Private cottage above Kona surrounded by coffee farms.

Experience living in Hawaii lush garden property. Very private fully remodeled 1bed/1bath cottage on 2 acre property in Holualoa, just above Kailua Kona. Cooler elevation, surrounded by coffee farms. Hike to a famous Kona Coffee farms like : Heavenly Hawaiian and Buddha's Cup.

1 bedroom
1 bathroom
Sleeps 4

from $252

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Spectacular Oceanfront Puako Cottage

Your oceanfront authentic Hawaii vacation destination awaits you! The Reef House is a perfect place to get away from it all. With breathtaking views, a paradise of snorkeling at your back door and a lush tropical yard to relax in and soak it all in.

3 bedroom
2 bathroom
Sleeps 6

from $963

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$Entire Cottage w\/ Private Plunge Pool, A\/C, BBQ$

Entire Cottage w/ Private Plunge Pool, A/C, BBQ

Air Conditioning is in the living room and principal bedroom. Guest bedroom has a ceiling fan only. A private freestanding cottage with its own Private Heated Plunge Pool. Air Conditioning, a rare amenity on Kaua'i, cools the space for a restorative nights sleep.

2 bedroom
2 bathroom
Sleeps 4

from $620

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Oceanfront Cottage 5A

You can't beat the views and privacy from 5A!
Perfectly situated on the lot, with picture-perfect views of sunsets, Kaiaka rock, and Oahu.

Your cottage has a new kitchen (January 2023) and offers amazing natural light and sense of space from 3 walls of windows/doors and 20 foot vaulted ceilings.

1 bedroom
1 bathroom
Sleeps 4

from $306

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Charming Country Cottage with WiFi and Smart TV in Kula!!!

Charming Country Cottage with WiFi and Smart TV in Kula!!!

Stay comfortably in lower Kula at this 1-bedroom cottage. Located in lower Kula, this property is situated on a small 2-acre organic fruit orchard. Enjoy views of Haleakala, Maui’s Central Valley, West Maui mountains, Maalaea Harbor, and parts of North Kihei as you walk around the orchard.

1 bedroom
1 bathroom
Sleeps 3

from $350

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Kihei Beach Cottage - 1 Block to the Beach!

Kihei Beach Cottage - 1 Block to the Beach!

This cozy 2-bedroom, 1-bathroom cottage is just one block from the beach, offering a peaceful and private retreat. Perfect for a relaxing vacation or remote workers, traveling healthcare professionals, snowbirds or those in transition to longer-term accommodation.

2 bedroom
1 bathroom
Sleeps 4

from $371

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ICC 28 Remodeled 2BD Cottage in Kaanapali Walk to Beach and Pool

ICC 28 Remodeled 2BD Cottage in Kaanapali Walk to Beach and Pool

FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)
*One ticket per activity per day.

2 bedroom
2 bathroom
Sleeps 4

from $492

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Sweet Rustic Cottage ~ Ocean View ~ Short walk to beach

Sweet Rustic Cottage ~ Ocean View ~ Short walk to beach

A Classic Kauai Cottage on Acres of Beautiful Grounds. Away from developments and the public. More Island Artsy Than Corporate. Two ceiling fan's in living room and one ceiling fan in bedroom. One floor fan. Nice, natural breeze normally.

Watch the sunrise off the ocean horizon from bed.

1 bedroom
1 bathroom
Sleeps 2

from $307

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ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC

ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC

2 bedroom
2 bathroom
Sleeps 6

from $411

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$UALANI RETREAT. Spacious Ocean\/Mountain View Cottage.Private Tropical Sanctuary.$

UALANI RETREAT. Spacious Ocean/Mountain View Cottage.Private Tropical Sanctuary.

UALANI RETREAT
Fully Licensed & Permitted
Locally Owned & Operated B&B
Permit # BBPH 2012/0002
SUP2 2012/0001

Terrific Discounts Thru October.

2 bedroom
1 bathroom
Sleeps 4

from $276

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Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

Beautifully built and decorated luxury private cottage in a tropical garden with ultra-quiet split AC systems and ceiling fans in every room, whole house water filtration system, resort-style landscaping and lighting.
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Located in sunny South Maui, Maui's South Shore boasts the most variety and breathtakingly beautiful beaches of all Hawaiian Islands.

1 bedroom
1 bathroom
Sleeps 2

from $498

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Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

The International Colony Club is a collection of uniquely "Hawaiian" cottages situated on meticulously landscaped grounds located right in the middle of the North Kaanapali Golf Course. Kaanapali beach, famous for incredible beauty and some of Maui's best snorkeling is only a few minute walk from the property.

2 bedroom
2 bathroom
Sleeps 4

from $441

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Hale Kokio: A Magical, Romantic Cottage, on North Shore Kauai #4212

Hale Kokio: A Magical, Romantic Cottage, on North Shore Kauai #4212

Welcome to Hale Kokio, a well loved getaway, designed for two. This is the place to stay on North Shore Kauai for relaxation, privacy and island living. Enjoy a quiet setting and a convenient location. The newly updated cottage is designed with your comfort in mind.

1 bedroom
1 bathroom
Sleeps 2

from $469

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Kope Cottage -1 BR -1B-Endless Views

The Cottage sleeps 3 people in 600 sq ft. It is a true one bedroom and not a studio. It has 1 full size bed and 1 queen size bed. It also has a queen-size pull-out sleeper bed as outlined above. There is also a modern washer/dryer in the Kitchen area.

1 bedroom
2 bathroom
Sleeps 3

from $337

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KBM Resorts | FREE CAR | International Colony Club | 2-Bedroom Cottage, True Essence of Hawaii! ICC-11

KBM Resorts | FREE CAR | International Colony Club | 2-Bedroom Cottage, True Essence of Hawaii! ICC-11

Plantation-style 2BR cottage near Ka'anapali's Airport Beach with high beam ceilings, updated kitchen, and lush tropical gardens. Walk to the beach or relax by the pool in authentic Hawaiian charm.

*Special Offer - Book any KBM rental home in Hawaii for 6 nights or more with an arrival date between Jan 1 - Dec 31, 2025 & receive a complimentary 4-door rental car from Hertz, Alamo, Avis, or Budget.

2 bedroom
2 bathroom
Sleeps 4

from $1,550

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Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage

Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage

Studio with oceanview, full kitchen and bathroom, queen size bed, plus small couch for one child or small adult. Perfect for couples. The property offers 1 mile private rainforest trail, pool, steam vents, two steam vent hot springs and private retreat setting surrounded by forest.

1 bedroom
1 bathroom
Sleeps 3

from $251

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KAUAI'S Plantation-style Paradise for 2! Peaceful North Shore Cottage 5-STAR!

KAUAI'S Plantation-style Paradise for 2! Peaceful North Shore Cottage 5-STAR!

**THIS RENTAL IS EXCLUSIVE TO VRBO - DO NOT RENT OFF CRAIG'S LIST OR ANY OTHER WEB SITE**

If you are looking for the ultimate Kauai experience, then look no further! Located on the North Shore, the most desirable area of Kauai, known for its tropical lushness, sandy beaches, snorkeling, surf and beautiful sunsets.

2 bedroom
1 bathroom
Sleeps 2

from $290

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Charming 2-bedroom cottage in Kula with AC, WiFi. Relax and unwind

Charming 2-bedroom cottage in Kula with AC, WiFi. Relax and unwind

Located in lower Kula, this cottage is a dream. It is situated on a small 2+ acres organic fruit orchard with 6 varieties of avocados, 28 varieties of citrus, with other exotics like soursop, lychee and longan. There are 2 king beds in the cozy bedrooms and a living room with a very comfortable queen sofa bed, this retreat is perfect for small groups or families.

2 bedroom
1 bathroom
Sleeps 6

from $588

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Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Welcome to Lanikai Hale ~ Two Hawaiian style cottages (which can be rented together or separately) on a large fenced-in property in the heart of Lanikai, just 2 miles from Kailua Town on the Windward side of Oahu.
There is plenty of parking and sleeping space for a group of 10 to 12 people.

5 bedroom
3 bathroom
Sleeps 12

from $972

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Romantic Private Garden Cottage B&B Within Walking Distance to the Beach!

Romantic Private Garden Cottage B&B Within Walking Distance to the Beach!

Aloha and welcome,

We invite you to come and relax in our cottage with a tropical garden and private entrance, as well as a view of Haleakala Mountain.

This is a beautiful, resort quality environmentally green built, private cottage.

1 bedroom
1 bathroom
Sleeps 2

from $211

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Hana's Heaven - a charming 2 bedroom cottage with spectacular ocean views

Hana's Heaven - a charming 2 bedroom cottage with spectacular ocean views

Hana's Heaven - a charming 2 bedroom cottage complete with full kitchen, living room and 3 lanais. Wake every day to the sunrise and ocean expanse. Off the beaten track, this home away from home is quiet and serene, the perfect place to relax and enjoy nature.

2 bedroom
2 bathroom
Sleeps 4

from $405

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The Ohana Cottage is perfectly situated in Hilo town close to all amenities.

The Ohana Cottage is perfectly situated in Hilo town close to all amenities.

This two-bedroom / one-bathroom house is located in a cool, safe, and quiet neighborhood in the Hilo District. The property is centrally located from the main attraction sites. 5 miles to the University of Hawaii, 1 mile to Imaloa Center, 5 miles to Hilo Downtown and to Rainbow Falls, and a short drive from all the main waterfalls and Park Beaches.

2 bedroom
1 bathroom
Sleeps 4

from $181

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Private Renovated Manoa Cottage

Go back in time to this renovated 1950's Hawaiian Cottage located in luscious Manoa Valley on the Island of Oahu. Lounge indoors on mid century Hawaiian koa furniture or outdoor on either the dining patio or the sitting patio. A short drive to shops, restaurants, beaches, Manoa Falls Hike, and other activities.

2 bedroom
1 bathroom
Sleeps 4

from $195

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$\"Hale Maluhia\" - Cottage with expansive ocean views in central Kailua Kona.$

"Hale Maluhia" - Cottage with expansive ocean views in central Kailua Kona.

Enjoy our hosted private 1 bedroom, 1 1/2 bathroom accommodations. Beautifully detailed with a king size bed, tv, wireless internet, laundry, closet, and large covered lanai. Everything my mom needs for her month long stays with our family!

1 bedroom
1 bathroom
Sleeps 2

from $229

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Ohia Cottage: Your Coastal Retreat near Napoopoo Beach

Ohia Cottage: Your Coastal Retreat near Napoopoo Beach

Ohia Cottage is a well-appointed guest house on a secluded private farm in the heart of Kona s coffee belt.
Our cottage is a perfect setting to host honeymooners celebrating their love or simply hosting a family of 3 that would love a secluded getaway in the tropics!

2 bedroom
1 bathroom
Sleeps 3

from $321

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Lazy Lehua Cottage

Serenity, peace, and rejuvenation await you at this private cottage on a half-acre of upcountry rainforest. Lazy Lehua Cottage is for quiet or adventurous couples, small families, honeymooners, artists, poets, musicians, scientists, and writers.

1 bedroom
2 bathroom
Sleeps 4

from $239

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$Kona Awesome Tropical PoolCottage\/AC\/GreatLocation$

Kona Awesome Tropical PoolCottage/AC/GreatLocation

E komo mai !

Our guests highly recommend the mail in VAULT Covid test. You mail it UPS and your results are emailed to you within 72 h. com/covid

We look forward to welcoming you to our home and our newly established Ohana/ Studio in a beautiful neighborhood of Kona Palisades.

1 bedroom
1 bathroom
Sleeps 4

from $374

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Paradise Found: Spacious & Comfortable Hawaiian Cottage

Paradise Found: Spacious & Comfortable Hawaiian Cottage

Spacious, well-appointed comfortable cottage in a lovely garden setting has two large, well-appointed, sunny king and twin bedrooms, a large primary bath and a fully remodeled, enlarged guest bath. Bedroom walls are sound-proofed - no shoji doors.

2 bedroom
2 bathroom
Sleeps 4

from $394

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$Gorgeous Home Across from Beach - 5 BR + Opt. Cottage \/ 4 Bath \/ AC$

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

PLEASE READ PRIOR TO BOOKING: If you have more than 10 guests the cottage will need to be booked as Maui's rental permit law requires 2 guests per room. That includes children over the age of 2 years old. Children under the age of 2 can stay with their parents in the same room and not count toward the occupancy rate.

6 bedroom
4 bathroom
Sleeps 12

from $1,575

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Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast

Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast

Aolani House & Coffee Cottage – Your Private Hawaiian Sanctuary
Nestled in the serene coffee farms of Holualoa, Aolani House & Coffee Cottage offers an exclusive retreat for relaxation and rejuvenation. Perched on 5 private acres of Kona Coffee and Macadamia Nut farms, this resort-style property features panoramic 180° ocean views, stunning sunsets, and ultimate tranquility.

6 bedroom
6 bathroom
Sleeps 12

from $2,180

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Romantic, Private Cottage Nestled Away in Volcano

Romantic, Private Cottage Nestled Away in Volcano

This is a private cottage located in one of the prettiest parts of Volcano Village. This one bedroom cottage is perfect for honeymooners, a special anniversary, or as a writer or artist's retreat.

Enjoy natural beauty and incredible privacy.

1 bedroom
1 bathroom
Sleeps 2

from $179

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Lovely 2 Bedroom Cottage Near Brenneckes Beach! Best Location in Poipu!

Lovely 2 Bedroom Cottage Near Brenneckes Beach! Best Location in Poipu!

Beachfront Paradise Across from Brennecke’s Beach – Hot Tub, Ocean Views, EV Charger!

Enjoy your dream Kauai escape at this beautiful two-bedroom beachfront home directly across from Brennecke’s Beach and Poipu Beach Park—famous for boogie boarding, body surfing, and swimming.

2 bedroom
2 bathroom
Sleeps 6

from $887

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NEW Charming Kapaa Cottage - 1 Block to the Beach!

NEW Charming Kapaa Cottage - 1 Block to the Beach!

Welcome to your home away from home in beautiful Kapa'a! This enchanting 2-bedroom cottage offers the perfect blend of Hawaiian charm and modern comfort, nestled in a tranquil garden setting just steps from local attractions. Experience the magic of Kauai from this perfectly positioned retreat.

2 bedroom
1 bathroom
Sleeps 4

from $474

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Hale O Imi Loa 3br 2ba Cute PrincevilleCottage

Hale O Imi Loa 3br 2ba Cute PrincevilleCottage

Welcome to Hale O Imi Loa. This 3br 2ba home has been in Princeville since 1986 and is a local treasure. Recently remodeled, the owners of this home have taken great care to ensure that guests can enjoy a beautiful Hawaiian Vacation here at the home dedicated to their late son.

3 bedroom
2 bathroom
Sleeps 6

from $448

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On the Edge of a Gulch, Privacy, Charm, Unique Style Cottage - Permitted

On the Edge of a Gulch, Privacy, Charm, Unique Style Cottage - Permitted

Maui County Rental permit - BBPH 2011/0001
TA-063-891-2512-01/ GE-063-891-2512-01
TMK-270360090000
Romantic, unique, charming coral rock cottage perched on the edge of Maliko Gulch. Swing in the hammock, or play tennis on the clay court.

2 bedroom
1 bathroom
Sleeps 4

from $442

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