Guesthouse holiday rentals in Oahu

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Top-rated Guesthouses in Oahu

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

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Guest favourite

A serene beach scene captures the sun setting between two islands, casting a warm glow over the water. Gentle waves lap against the shore, while smooth rocks are visible in the foreground, providing a natural frame to the tranquil view.

Guesthouse in Kailua

4.93 out of 5 average rating, 136 reviews

Lanikai Oasis, Cozy Cottage 5 Min to Lanikai Beach

Lanikai Oasis, A Peaceful Island Retreat Tucked away in one of the most private and peaceful neighborhoods on Oʻahu, Lanikai Oasis is a serene cottage retreat just 5 minutes from Lanikai Beach, consistently ranked among the most beautiful beaches in the world. Perfect for a clean, calm, and relaxing vacation, this newly remodeled ohana unit offers modern comfort in a lush island setting. ideal for couples or quiet travelers seeking paradise. Hawaii Tax IDs GE-159-110-0416-01, TA-159-110-0416-01

Superhost

Guesthouse in Hauula

4.77 out of 5 average rating, 44 reviews

The Jungle Bungalow - AC - Smart TV - 30 Day stays

🌺 Escape the tourist crowds and experience the real Hawai‘i in a peaceful local neighborhood. Just a block from the ocean and the famous tipping palm tree—where seals often rest—you’ll also be within walking distance of the Hau‘ula Loop Trail. Minutes from beaches, surf spots, food trucks, PCC, and BYUH. Perfect for families of up to 4 with 2 queen beds, kitchen, AC, Wi-Fi, smart TV, patio, walk-in closet, shared laundry, and 1 parking spot maximum. Absolutely NO smoking. No large van parking.

Guest favourite

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

4.81 out of 5 average rating, 209 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

Guest favourite

Guesthouse in Waianae

4.89 out of 5 average rating, 113 reviews

Chic Private Guest House • Pool • Gym • Hikes

Escape to this cozy, intimate studio in Makaha Valley’s exclusive gated resort community The Cottages at Mauna’Olu Surrounded by lush, tropical landscapes, this private retreat offers the perfect blend of comfort and tranquility your area is not shared with the main house it’s private and fenced away from each other. Unwind on famous Makaha Beach, just 4 minutes away, explore nearby hiking trails, or simply relax to the soothing sounds of the mountains. With thoughtful amenities 🌿

Guest favourite

A sandy beach stretches along the shoreline, gently meeting the ocean waves. Palm trees are visible in the background, framing the tranquil scene. The sky is partly cloudy, casting soft light over the peaceful landscape, inviting moments of relaxation and enjoyment.

Guesthouse in Kapolei

4.91 out of 5 average rating, 137 reviews

Aloha Living Near Ko’olina + WiFi/Sleeps 4

Our Guest House sits in a unique & safe neighborhood. You’ll have your own private entrance. Shared entrance will only be through the front gate. We live on the property, but Privacy is always respected. Ko’olina Beach Lagoons & Golf Course is just a 3 minute drive (Free Parking is usually available there for early bird beach goers), Shopping centers, grocery stores, and luaus. A great space for your island get away, especially away from the busy hustle & bustle of town life.

Guest favourite

An entrance is displayed, featuring a smooth wooden deck with two outdoor chairs positioned beside the door. Soft lighting illuminates the entryway, while lush greenery provides a tropical ambiance against the backdrop of a colorful sunset sky.

Guesthouse in Waianae

5 out of 5 average rating, 35 reviews

Studio Nene - Ocean, King bed, Tropical Garden

Aloha! Welcome to Studio Nene, a serene, luxury guesthouse retreat in breathtaking Makaha Valley. Perfect for couples or solo travelers, this stunning space features a plush king bed, high-end finishes, and a private tropical garden. Wake up to stunning mountain views, enjoy your morning coffee surrounded by trade winds, and stargaze at night. Enjoy resort-style community pool, jacuzzi, and gym. Just minutes away from pristine west-side beaches. Guaranteed cancellation in 48 hrs.

Top Guest favourite

A spacious bedroom features wooden beam ceilings and is adorned with a coral-patterned bedspread draped over a king-size bed. A small desk is positioned near the window, and natural light filters through sheer curtains. A large area rug with a nautical design enhances the coastal theme.

Guesthouse in Kailua

4.97 out of 5 average rating, 33 reviews

Private 1 Bedroom Cottage

Welcome to our 1-bedroom legal short term private cottage centrally located in the heart of Kailua. Walking distance to Kailua Beach, Kailua Town, boutique shops, cafes, restaurants, bars, breweries. Private yard, lusciously landscaped garden, BBQ with outdoor and indoor dining. Hawaiian inspired accommodations are top notch. We thought of everything so you can enjoy your stay. Kailua is a bike friendly town. Many main island attractions are 15-45 minute drive. 1990/NUC-1815

Superhost

Two white Adirondack chairs sit on a wooden deck overlooking the ocean. The scene captures a serene sunset with soft hues of orange and yellow blending into the horizon, while gentle waves lap at the shore and mountains are visible in the background.

Guesthouse in Hauula

4.57 out of 5 average rating, 14 reviews

Mai Tide: New N. Shore Oceanfront, 30 Day, AC

Mai Tide is a beautiful North Shore guest home with 30'+ of ocean frontage, spectacular sunrises & majestic mountain views. Dine on the lanai with turquoise ocean waters so close you can almost touch it. Our home overlooks the sea & mountains (a rare & gorgeous view). We are at the water's edge with a private lanai & seating where sea turtles can often be seen. 1 house from ocean access, minutes from Pounders & Kokololio Beaches, white sand gems with fantastic body surfing.

Guest favourite

The studio features a kitchenette with dark wooden cabinets and a microwave, accompanied by a dining area with a small table and chairs. A spacious queen-size bed and a pull-out bed are visible in the background, with a TV mounted on the wall allowing for entertainment options.

Guesthouse in Waianae

5 out of 5 average rating, 31 reviews

Beautiful Mountain Studio Retreat

Imagine vacationing in a brand new studio set in a peaceful valley. You're surrounded by Ka’ala & Waianae mountains, towering palms, mango trees, wild peacocks, & famous beaches. You take a sunrise/sunset stroll around the gated neighborhood (w/24hr security) and return home for a peaceful dinner. Studio is fully equipped w/a comfortable queen-size bed, pull-out bed, TV, a kitchenette, mini-fridge, microwave, coffee maker, & bathroom w/ tub & shower.

Guest favourite

An outdoor seating area is featured, with a wooden table and four white metal chairs. A comfortable lounge area, furnished with a wooden bench and colorful cushions, is visible to the right. The background includes lush greenery, enhancing the setting's natural feel.

Guesthouse in Haleiwa

4.94 out of 5 average rating, 175 reviews

Dreamy Surf Shack

If you are looking for a dreamy modern surf shack on the North Shore of Oahu then this is the ultimate spot! Located on a quiet private street across from the famous surf breaks and the best beaches. Sunset Beach, BackYards and Velzyland - which offers perfect swimming in the summer and amazing surf all winter, turtle sighting on the sand and spectacular sunsets are all only a 3 minute bike ride away and about a 5-10 minute walk away. @dreamysurfshack

Superhost

The kitchen area features white cabinetry, a black refrigerator, and stainless-steel appliances. A butcher block countertop serves as a preparation space, complemented by a wooden island and a black stool. Natural light fills the room through windowed doors, enhancing the modern design.

Guesthouse in Hauula

4.94 out of 5 average rating, 93 reviews

Modern 1 Bed by the Beach w/Stay Discounts

Kick back and relax in this calm, stylish space. Located on the relaxing north east shore of Oahu, you're a minutes walk across the street to a beautiful and uncrowded sandy beach. Or take a drive 15 minutes up the road to the world famous surfing beaches of the north shore. If you want to stay in a bit, no problem either. Completely redone in 2022, this one bedroom apartment has a light modern feel that makes it a pleasure to just hang around.

Guest favourite

A cozy studio space features a spacious bed with white linens and decorative accents. A kitchenette with wood cabinetry, appliances, and a dining area is visible. An armchair sits nearby, and large windows offer views of the outdoors, contributing to a bright and open atmosphere.

Guesthouse in Waianae

4.93 out of 5 average rating, 165 reviews

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.