Guesthouse vacation rentals in Hawaiian Islands

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Top-rated guesthouse rentals in Hawaiian Islands

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Naalehu

4.86 out of 5 average rating, 250 reviews

The Ohana

Find your peaceful retreat by staying in a traditional Hawaiian style home, an Ohana. Get the full experience of what real Island lifestyle is in your stay in Na'alehu, world renowned as "The Southern Most Town" in Hawai'i and the USA! A perfect midpoint between Kona and Hilo maximizing your adventure choices and making the most out of tour time. Guaranteed treasured memories. NOW OPEN Self-Serving shop conveniently located just a few steps from your stay. Rentable surf board and beach gear.

Jun 21 – 28

G$22,200 GYD per night

Guest favorite

Guesthouse in Kula

4.98 out of 5 average rating, 166 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

Oct 18 – 25

G$55,001 GYD per night

Guest favorite

Guesthouse in Honokaa

4.96 out of 5 average rating, 182 reviews

Romantic waterfall cabin in the rain forest

Your own private log cabin and waterfall! Listen to the rushing stream as it cascades over your own private 50 foot high waterfall in your own private cabin. For the writer. For the dreamer. For the romantic getaway. Be inspired, transported and immersed into our Hamakua Coast rain forest oasis. Located next to the Waipio Lookout, our rain forest property is the perfect place to recharge and rejuvenate. We’re a ten minute drive to Historical Honoka’a Town. Our "Banana Belt" climate is perfect!

Mar 26 – Apr 2

G$40,797 GYD per night

Guest favorite

Guesthouse in Mountain View

4.97 out of 5 average rating, 561 reviews

Hawaii Volcano Coffee Cottage

We at Hawaii Volcano Coffee Company welcome you to stay at our beautiful studio cottage overlooking one of our many organic coffee orchards. We are located between two of the Big Islands most iconic areas; Hawaii Volcano National Park and Hilo's beaches, approximately both a 20-minute drive from the studio. Our road to cottage can be rough,it is old blacktop that need to be replaced. We are asking county for help but no response.Road be adventurous , but cottage is worth it. E Komo Mai (Welcome)

Mar 11 – 18

G$24,092 GYD per night

Superhost

Guesthouse in Pāhoa

4.88 out of 5 average rating, 449 reviews

Coconut Cottage/Sunrise Cottages Hawaii

Adorable ocean facing cottage has a true Hawaiian rainforest feel. The Coconut Cottage has a king sized bed, high end mattress, en suite bathroom and full kitchenette. 5 minute walk to Kehena beach with its beautiful black sand and stunning views. Hawai'i has many outdoor activities which include amazing nearby snorkeling at Shipman's Bay, miles of the world's newest beaches, Volcanoes National Park, beautiful Akaka & Rainbow Falls, and stunning Waipio Valley, are all within driving distance.

Dec 17 – 24

G$28,948 GYD per night

Guest favorite

Guesthouse in Hilo

4.95 out of 5 average rating, 168 reviews

Rain Forest Luxury Retreat

Here is a unique retreat, recently remodeled, set in the charming Hilo beach neighborhood of Keaukaha. A separate and private guest cottage that feels like the old Hawaii. Property is across the street from the ocean & surrounded by the rainforest. Beautiful, large (350 sqft) and Cozy room with private lanai, lots of windows, comfy queen bed, HD Smart TV, cable and high speed WiFi. Kitchenette includes small refrigerator, microwave, toaster and coffee maker. Clean, relaxing, and luxurious.

Sep 19 – 26

G$37,917 GYD per night

Guest favorite

Guesthouse in Hilo

4.99 out of 5 average rating, 175 reviews

NEW 2 bedroom hosted Tranquil Island Getaway

Enjoy up country Hilo at it's finest with a new, private home in a gated community. Our 1500' elevation makes a perfect cool, peaceful evening respite after a day of beach going, hiking at Volcano National Park and enjoying Hilo's dining and entertainment. The property features a distant ocean view, many fruit trees, aquaponics, gardens, plenty of animals including dogs, Angus cows, chickens and a macaw named Li'i! Interacting with the animals on our ranch is part of the property's charm.

Aug 5 – 12

G$43,987 GYD per night

Guest favorite

Guesthouse in Koloa

4.99 out of 5 average rating, 147 reviews

Poipu Tropical Retreat with AC & Pool/Gym Access

Discover beautiful Kauai from this spacious 1 bedroom vacation home, built in 2018, in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai, shops and restaurants. Create lifetime memories from this modern retreat with its tropical Asian decor. This is a stand alone house, very private, not an apartment. Enjoy a complimentary Poipu Beach Athletic Club membership.

Dec 23 – 30

G$134,684 GYD per night

Guest favorite

Guesthouse in Keaau

4.97 out of 5 average rating, 184 reviews

Magical Jungle Cabin with Pool

Nestled in a lush guava tree grove, this tropical sanctuary offers the nature sounds of camping with the comforts of a cozy bungalow. Perfect for a couple's getaway, a personal retreat, or a peaceful place to retire to after a full day of exploring. Wake up with an outdoor rainfall shower, soak up the Hawaiian sunshine while you float in the pool, grill locally caught fish in the kitchenette pavilion (hot plate and BBQ), and stargaze some of the darkest night skies. Primary residence.

Jul 18 – 25

G$32,155 GYD per night

Guest favorite

Guesthouse in Haiku-Pauwela

4.97 out of 5 average rating, 373 reviews

Quaint Cottage Near Coffee, Road to Hana/Haleakala

Located on the quiet north shore, 1 hour from the fire area- on the opposite side of the island. Ideal for returning visitors that like to explore during the day and relax quietly at night or exploring the road to Hana / Haleakala. Wander to the coffee shop for breakfast. Adventure the road to Hana, Haleakala or a nearby beach. Refresh in the warm outdoor shower. Admire the unique, colorful homemade decor. Imagine yourself living here forever. Repeat! (Daily guest cottage life!)

Feb 1 – 8

G$60,325 GYD per night

Superhost

Guesthouse in Wailuku

4.88 out of 5 average rating, 217 reviews

2B/2Bcottage/central/private/ historic town/wi-fi

2B/2B cottage , attached to a plantation home, in the heart of Maui, in historic Wailuku town...home of the famous Iao theater and minutes from Iao valley & the famed "Needle mountain ". Private, fully furnished, and equipped with all amenities needed for a comfortable short-term stay. Well located to connect you to all parts of the island within a 10-30 minute drive. It's great for business travelers doing business in Wailuku , hikers ,bikers, and true hawaiiana seeking tourists .

Mar 30 – Apr 6

G$51,716 GYD per night

Superhost

Guesthouse in Koloa

4.89 out of 5 average rating, 194 reviews

Luxury Beach Cottage, Sleep 4, walk to beach/shops

This 1 bed/ 1 full bath unit is nestled on the 2nd floor above the garage, with another home located on the property. It has a full kitchen, BBQ, split system AC, memory foam beds, and beach gear included. Poipu Beach is the best place to stay on Kauai. Within a few miles from the house you have, great surf spots, hiking, snorkeling, diving, fishing spots, world-class golfing, excellent restaurants and local boutique shops. Come to the south shore of Kauai for an ultimate get away.

Mar 15 – 22

G$69,203 GYD per night