Hawaii Cottage Vacation Rentals
Hawaii cottage rentals are ideal for travelers seeking privacy, tranquility, and local charm. Nestled in tropical gardens, on the slopes of volcanoes, or just steps from golden beaches, these cozy hideaways offer an authentic island experience with all the comforts of home.
Our curated collection of Hawaii cottage vacation rentals includes quaint beach cottages, upcountry plantation homes, and serene rainforest escapes. These accommodations are perfect for couples seeking romance, solo travelers on retreat, or families looking for quiet space close to nature. Most cottages offer private lanais, BBQ areas, fully equipped kitchens, and proximity to scenic trails or snorkeling spots.
Whether you're relaxing near Hapuna Beach, stargazing in Volcano Village, or exploring waterfalls on Hilo's lush east coast, cottages let you experience the magic of Hawaii away from busy resorts. They're a favorite for extended stays, wellness retreats, and anyone looking to unplug in comfort.
Key Features of Hawaii Cottage Rentals
- Private lanais, outdoor showers, and garden settings
- Full kitchens and open-air living spaces
- Great for romantic getaways or peaceful retreats
- Located near beaches, waterfalls, and nature trails
- Often hosted by local owners for a personal touch
Browse our island collections by destination, including Upcountry Maui cottages, Waimea countryside stays, or cozy retreats near Hanalei Bay on Kauai.
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...
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. (W1)*One ticket per...
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...
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...
Ocean Views, Private Hot Tub, Swimming Pool Access, Historic Cottage
'The Cowboy House' is a very charming & historic home built by Plantation working families at the turn of the century.(1870''s!) 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...
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...
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...
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...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
We do not Rent on Craigs list if you find this on any other site it is a scam be careful there are lots of scams ,NEVER wire money ..Please READ the whole Description below about the pool below,Mahalo Hale Manu Mele B&B permit #BBKM2013/0001.Tat # TA-031-786-3936-01 The...
ICC 37 Remodeled Plantation Cottage 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. (W1)*One ticket per...
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,...
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
This very spacious ocean and pool view cottage has everything you need to truly relax andenjoy the serenity of Maui. Designed in a vintage Hawaiian theme with a modern twist, thisroom offers a unique tribute to the great Hawaiian Surfer, Duke Kahanamoku. The cottage...
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. There is a small...
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...
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...
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. Ideally located,...
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. Relax...
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...
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. The...
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...
ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC
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...
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 2012/0001Terrific Discounts Thru October. Enjoy your own PRIVATE DETACHED HOME at this lush tropical Hawaiian paradise. A refreshing place to nurture your spiritNicely...
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.Check out our VIDEO on YouTube MauiHome4Rent:...
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...
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. A...
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.In the cottage, it...
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...
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...
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...
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...
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. We are a legally licensed with the...
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. Nearby...
The Ohana Cottage is perfectly situated in Hilo town close to all amenities.
Embark on your dream vacation at this enchanting two-bedroom, one-bathroom cottage nestled in the tranquil Hilo District of Hawaii. Perfectly blending authentic island charm with modern comfort, this cozy retreat invites travelers to experience the unparalleled spirit...
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,...
"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!The large lanai (covered deck)...
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.How amazing would it be to wake up and smell the coffee in Hawaii?! Our cottage is a perfect setting to host honeymooners celebrating their love or simply hosting...
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. The native birds sing...
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. https://www.vaulthealth.com/covidWe look forward to welcoming you to our home and our newly established Ohana/ Studio in a beautiful...
Hoaloha Hale - Gorgeous Kihei Home Across from Beach
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...
Secluded Oceanfront Cottage- in Princeville – Private Hot Tub & Stunning Views
For less than half the price of a standard hotel room, this private ocean bluff Cottage-Studio offers a luxurious and romantic experience—giving you more space, more privacy, and more of Kauai’s magic. Instead of a crowded resort, you’ll wake up to the sound of...
Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast
Aolani House & Coffee Cottage – Your Private Hawaiian SanctuaryNestled 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,...
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. Step out the front door and...
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,...
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...
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...
On the Edge of a Gulch, Privacy, Charm, Unique Style Cottage - Permitted
Maui County Rental permit - BBPH 2011/0001TA-063-891-2512-01/ GE-063-891-2512-01TMK-270360090000Romantic, unique, charming coral rock cottage perched on the edge of Maliko Gulch. Swing in the hammock, or play tennis on the clay court. This is a property for nature...
Beach Front Estate With Guest Cottage Sandy Beach Heated Pool/Spa
30 Day Minimum Stay Required Share the romance and beauty of the North Shore with your entire family: 2 separate fully appointed living spaces with high end amenities great your every moment of your vacation.Swing open the gate to our Sandy Beach, sink your toes into...
Aolani Coffee Cottage | #1 AirBnb | Condé Nast | AC
🌺 Aolani Coffee Cottage | Private Hot Tub + Ocean Views + ConciergePeaceful Holualoa Farm Stay | 12 Min to Kona + Beaches | Luxury Escape🏡 About This SpaceWelcome to Aolani Coffee Cottage, a serene and stylish retreat nestled in the heart of Kona’s lush coffee...
Hale Nalu: Tropical Cottage in Poipu-Walk to Beach
Scenically situated on the Green Belt pedestrian pathway, this enchanting island-style home combines the casually elegant charm of a country-plantation retreat with an ideally convenient location. Not only is it close to everything—an easy stroll to beaches and...
Romantic Cottage, Stunning Ocean Views, Whales are jumping!
James Cottage is a historic home that has been completely restored for our guests to enjoy. Located with in The Historic Puakea Ranch, your bungalow was once home to the paniolos who lived and worked at Puakea 100 years ago. Ocean views, light filled, airy and...