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.
Cute and quaint little cottage on a homestead.
This quaint country cottage in Anahola sits on acreage surrounded by fruit trees and tropical foliage. If you are looking for an authentic local experience, this is it. Far from resort vibes, Banana Hideaway is as real Kaua'i as you can get. Wake up to incredible...
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...
Kailua Beach Historic Renovated Cottage
This property is offered as a monthly rental. Although full-month occupancy isnot required, the monthly rate remains fixed and applies in full, regardlessof the number of nights stayed, as prorated rates are not available.One of the original homes on Kailua Beach, this...
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...
❤️PiH❤️ PARADISE AWAITS ★ Private Pool & Spa ★ Guest Cottage
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Awaits, a part of our Hawaiian Luxury Collection. Paradise Awaits at KaMilo is a wonderful, large, single-level 4 bedroom home that includes three bedrooms in the main house, each with a large primary...
Ocean View. Central AC, Parking is available. Multiple cottages to choose.
~Beautiful ocean, beach view ️ ~Balcony has dining furniture ️ ~Quiet central AC, quiet building ~Larger size cottages’s bedroom has view.~2 minutes walk to Duke‘s statue and Waikiki Beach ~Provide all kinds of kitchen appliances and cooking utensils. ️ ~Grocery stores,...
Hale Lo'i + Cottage: 5BR home +pool in Sunny Poipu
This bright, spacious, brand-new 5-bedroom, 4.5-bath compound has everything you’ll need for a flawless vacation—and luxurious perks galore, including a swimming pool and an outdoor lava-rock shower. The five bedroom house, which sleeps 10, consists of a 4-bedroom,...
Hale Lo'i Cottage: Luxury + Convenience in Poipu
This bright, spacious, brand-new 1-bedroom, 1-bath cottage has everything you could possibly need for a flawless vacation—and luxurious perks galore, including an outdoor lava-rock shower. Located in a quiet, upscale neighborhood, this charming tropical hideaway is...
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...
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...
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...
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...
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...
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,...
Makanui 711 - Garden/Mountain View
Summary:Ground-floor 1-bedroom retreat with garden and mountain views, just a short walk to Poipu Beach, Brennecke’s, and Shipwreck Beach. Features a king bedroom with portable A/C, queen sleeper sofa, full kitchen, in-unit laundry, beach gear, and access to both the...
Dream Vintage Surf Cottage TVNC 4301
Step back in time in this charming cottage by the beach. Built in the 1920's, this plantation style home will give you a true Hanalei experience. Just steps to the beach and a short stroll or bike ride to many restaurants and shopping. This is a dream location in the...
World Famous Kailua Beach Charming Cottage
Studio Cottage near Kailua Beach and Beach Park! Large, 200 square foot lanai, fully furnished. Nice neighborhood setting. You won't believe how close this is to the beach! Also close to Kalapawai Market and other Beach Shops & Food. All utilities - A/C, Cable,...
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...
Cottage with Private Salt Water Pool
30 night minimum This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu coast. Also, in very short...
Stunning oceanfront cottage
This beautifully restored one-of-a-kind oceanfront home has all the charm of yesteryear with the added conveniences and sustainability of today. Meticulously appointed and private, the views and location are spectacular. The Guardian newspaper has listed Kona Moana Hale...
ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC
International Colony Club 20 Fully Remodeled Hawaiian Cottage- Walk to Beach & Steps to the 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,...
Kukuiula Cottage #27 By Parrish Kauai
This handsomely designed and decorated Kauai cottage offers the details of early plantation days yet with the modern conveniences of central air conditioning, as well as everything else one needs to indulge themselves on a luxury Kauai vacation. Enjoy the lush garden...
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...
Lilikoi Cottage - In The Heart of Lovely Waimea
We have switched to renting for a longer term of a minimum of 6 months. Available from Oct 2023 onwards. Spacious artist's cottage in heart of Waimea. Rare find! Walking distance to coffee shop, celebrated restaurants, farmer's market, art galleries. 15 mins to the best...
Volcano Places Laukapu Forest Cottage
Laukapu Forest Cottage (LFC) is a spacious studio, vacation-rental cottage handcrafted as a "Work of Heart".LFC has a well-equipped kitchen, with refrigerator/freezer, electric range/oven, microhood, toaster, coffee and tea making supplies. LFC has a private bathroom,...
Lanikai Cottage: Charming Tropical Oasis with Private Pool
Just steps from the turquoise shoreline of Lanikai Beach, Lanikai Cottage by Gather is a beach-chic 3-bedroom, 2-bath retreat with two separate dwellings on one property and a brand-new private pool. Ideal for families or couples traveling together, this island holiday...
Ho'okipa Villa: Historic Home + Guest Cottage in Kahala
Tucked within the prestigious Kahala neighborhood, Ho‘okipa Villa by Gather blends vintage Hawaiian charm with modern comfort for the ultimate island retreat. Originally built in 1938 and lovingly restored, this five-bedroom, four-bathroom estate spans over 3,000 sq....
Haleiwa Oceanfront Cottage - Charming 1BR Retreat
Discover the delightful onebedroom getaway nestled right within Haleiwa. Nestled just a 22-minute drive from the renowned Banzai Pipeline and 24 minutes from the stunning Turtle Bay Beach, this cozy retreat offers the perfect base for your Hawaiian adventure. ocean...
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...
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...
Nestle Into Your Private Cottage After a Busy Day. Enjoy the Hottub - Permitted
Maui County Rental permit - STPH 2013/0024TA-091-083-1616-01TMK-270031060000Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the...
Your own private cottage, 60+ FIVE STAR exceptional reviews!
Hibiscus Hideaway is a licensed Bed and Breakfast, permit # BBKM 2015/0004TA-001-473-5360-01Hawaii Tax I.D. NO W01511848-01This beautiful one bedroom one bathroom cottage is completely brand new and is kept immaculate. Tile floors throughout, granite counter tops in 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...
Magical Kauai Cottage on North Shore TV5131 NCU
Hale Huna ('Hidden House') is a wonderful cottage on a hillside near the end of the road on the North Shore of Kauai. Located on hill and a quiet cul-de-sac with only a few other local houses. Very private and peaceful (It is NOT on/near the highway like many Kauai...
Naupaka Hale - Lanikai Beach Home & Cottage
NAUPAKA HALETA-151-566-1312-02THIS PROPERTY RENTS ONLY MONTHLY FOR 30 DAYS AND LONGER.Idyllic classic Hawaiian style vacation rental home on large lot with huge sandy beach right in front of your very eyes. This beautiful vacation rental home offers breathtaking views...
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Under the Warm Maui Sun - Permit#BBKM\2016\0004 Due to cancellation last moment special forMon, Oct 31 - Thu, Nov 10, 2022 $350/nightRegular rates 2022: April 1 - December 27 2022$410/nite for 2 personsWinter rates 2023: January 3 - March 31 $490/nite for 2...
Cottage on Beachfront Estate property, central Hanalei Bay
This amazing and completely refurbished home is situated on a stunningly beautiful one-acre, gated OCEANFRONT estate property, right in the middle of magical Hanalei Bay. It is, in fact, one of the ONLY vacation rental cottages on beachfront property to be found...
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Nestled on Baldwin Avenue, our plantation style one bedroom cottage provides convenient and comfortable accommodations for 2 people, with the amenities of Historic Paia Town and Paia Bay just a few minutes walk away and all areas of the Island within easy driving...
"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)...
Ocean View 1 BR Cottage on Oceanfront Property. Permitted
$340/night + tax 18.712%. Rate is for 1 or 2 persons.(Permit # CP2001/0018 & HT ID TA-003-079-5776-01 & TMK 2-6-009-008). Minimum stay 7 nights. Want to stay fewer days? At certain times of the year, or for last minute bookings, we might waive the minimum nights stay....
Cottage with Amazing View, Minutes to Dolphin Swimming, Very Private, Affordable
Please check out the main house on the same property for larger groups:vrbo 1542506This cottage is perfect for a couple looking to save money but still have a million dollar view. In Kealakekua Bay, just 3 minutes from some of the best snorkeling and wildlife viewing in...
North Shore Ocean View Cottage
This recently built comfortable cottage is located on the north shore of the island of Maui, tucked away in the quiet countryside of Haiku but relatively close to major attractions! Enjoy a relaxing vacation in a rich tropical setting with spectacular ocean views!The...
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
Pineapple Cottage enjoys a 5-star rating. Enjoy peace and quiet overlooking a private gulch and stream with a bit of with ocean view. Pineapple Cottage offers hardwood floors, shaker cabinets, granite countertops, newly purchased leather sofa, and a covered lanai with a...
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...
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...
Malaekahana Ocean Front Cottage (30 day min)
Beautiful and charming describes this tranquil and peaceful ocean front cottage.It sits on the 1st level, beach front, of a private estate home on over 3/4 acres of manicured lawn to the ocean. A view from every room!Fall asleep to the sound the ocean waves and wake to...
Paia Family Cottage - Walk to everything in Paia Town
Walk to everything in Paia Town. Paia Family Cottage is well equipped, with comfortable indoor, and sweet outdoor living spaces for everyone. There is AC in all bedrooms and living room. And a yard where kids can play, with views out over the green sugar cane fields....
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...
Spacious Ranch Cottage with private hot tub and VIEW!
Our Ranch House Cottage sits above the town of Kona with beautiful views of the Kona Coast. We are a 10-acre gated estate. This unit has a private Hot Tub/Jacuzzi with magnificent views. We a working farm with miniature goats, sheep and chickens. Fresh fruit and fresh...
Poipu Beach Plantation Style Cottage
This custom designed Hawaiian plantation style cottage is located just steps from Poipu Beach Park and Brennecke’s beach on a quiet dead end street. It is the perfect vacation retreat. Hale Honu was just completed in September of 2014 and was designed to fit in with...