Guesthouse holiday rentals in Honolulu

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Honolulu

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Superhost

A tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.

Guesthouse in Kailua

4.79 out of 5 average rating, 190 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

Superhost

The kitchen showcases a granite countertop with a breakfast bar accommodating three stools. Bright stained glass artwork adds color above. To the right, a doorway leads to additional spaces, and behind, cabinets and appliances are organized neatly along the walls.

Guesthouse in Manoa

4.61 out of 5 average rating, 67 reviews

Manoa Valley B - Lush with Diamond Head Views

You family will adore this lovely 2BR duplex whether there are just two or a group as large as five. The home is also pet friendly (for an additional fee of $250), which is difficult to find. Unique Craftsman touches include custom stained glass windows along with an outdoor shower that provides added convenience after a day at the beach. Find a second full living space on the enclosed lanai with panoramic views of Diamond Head and Honolulu City.

Guest favourite

A spacious sleeping area is highlighted by a king-size bed dressed in a white coverlet. A futon is positioned alongside, complemented by decorative pillows. Soft natural light enters through multiple windows, while indoor plants add a touch of greenery to the peaceful ambiance.

Guesthouse in Kailua

4.87 out of 5 average rating, 419 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.

Superhost

A serene beach scene features soft white sand leading to clear turquoise waters. Gentle waves lap against the shoreline under a bright blue sky with scattered clouds. Lush greenery borders the beach, providing a natural frame to the picturesque landscape.

Guesthouse in Kailua

4.8 out of 5 average rating, 162 reviews

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Superhost

A panoramic view captures the lush greenery of Manoa Valley, interspersed with residential homes. The iconic Diamond Head crater rises in the background, framed by a clear blue sky and gentle clouds, while solar panels can be seen on several rooftops.

Guesthouse in Manoa

4.88 out of 5 average rating, 90 reviews

Manoa Valley Duplex with Mountain and Ocean Views

Located on a hill overlooking Honolulu and the majestic Diamond Head crater, this two bedroom, two and half bath plus bonus sleeping space in Manoa Valley features gorgeous custom touches and a large lanai that’s perfect for a barbecue. The home is also pet friendly (for an additional fee of $250) which is difficult to find. Contact HVROAHU com for more information!

Guesthouse in Kailua

Kailua Hillside Retreat

Relax at this peaceful Ohana in Kalaheo Hillside, Kailua. Convenient location (0.7 miles) to Castle Beach (14 minute walk), Kailua Beach (1.7 miles), easy H3 access, restaurants, park, schools, Aikahi Shopping Center (Safeway, Starbucks) 2 blocks away, Kaneohe Marine Corps Base, and Kailua Town (2.5 miles). Perfect for walking and biking.

Superhost

A panoramic view captures the serene beauty of the ocean at sunset, with two small islands visible in the foreground. The sky is painted in shades of orange, pink, and yellow, reflecting on the water’s surface, while lush greenery and homes dot the landscape below.

Guesthouse in Kailua

4.91 out of 5 average rating, 138 reviews

Kailua Surf Shack: Your Hawaiian Adventure!

Snorkels, check! Beach chairs, check! Boogie boards, check! Surf boards, check! You relaxing on the sandy beach of Kailua, still pending! Welcome to your Hawaiian vacation in Kailua, Oahu! This property is nestled between the beach town of Kailua and is footsteps away from the ocean.