Guesthouse vacation rentals in Pupukea

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Pupukea

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

%{current} / %{total}1 / 1
Guest favorite
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
4.8 out of 5 average rating, 202 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

Top guest favorite
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 Makaha Valley
5 out of 5 average rating, 29 reviews

Studio Nene - Ocean, King bed, Tropical Garden

Aloha! Come and rejuvenate yourself in this serene retreat in the beautiful Makaha Valley in Hawaii. Studio Nene (360-ft) has elegant interior design and lush tropical garden. Highlights: A highly-praised extra comfy king bed, the cute kitchenette, ensuite washer/dryer, and a desk by the window with mountain view. It’s near a 7-mile stretch of pristine beaches, you can enjoy the beauty of the coast as well as the tranquility of the mountains. We can assist if cancellation in 48 hrs is needed.

Guest favorite
Guesthouse in Makaha Valley
4.9 out of 5 average rating, 109 reviews

Chic Private Guest House • Pool • Gym • Hikes

Escape to this cozy, intimate studio in Makaha Valley’s exclusive Mauna Olu Cottages, a gated community with 24-hour security. 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 favorite
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 Makaha Valley
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 favorite
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 Makaha Valley
4.93 out of 5 average rating, 159 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.

Top guest favorite
Guesthouse in Kailua
4.87 out of 5 average rating, 449 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
4.78 out of 5 average rating, 174 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.

Guesthouse in Haleiwa

Beach house with Garden stroll to beach

Our unit offers a peaceful home base for families with a young child or couples. Uncrowded beaches, local eateries, are easily accessible, while Haleiwa is close by and provides great dining and activities. We offer all the basic amenities and a calm, private backyard, it’s a comfortable home away from home for respectful guests seeking relaxation and island style living.

Guest favorite
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
4.92 out of 5 average rating, 154 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.

Superhost
A cozy living area is presented with a gray sofa adorned with white and yellow pillows. A round dining table is set with green-patterned napkins on dark plates. Open shelving above the kitchen counter displays various dishes and utensils, creating an inviting space.
Guesthouse in Haleiwa
4.75 out of 5 average rating, 68 reviews

Newly & Cozy 1 Bed & 1 Bath in Vland - 90 days Min

Located at Velzy Land Beach. A perfect place for a couple or 2 friends to come and experience the quiet side of Oahu.

Superhost
A spacious bedroom features a Queen bed with a premium mattress, accented by artful octopus-themed wall decor. Natural light filters in through the windows, and a cozy seating area is complemented by a neutral color palette. An adjacent bathroom is visible through an open door.
Guesthouse in Makaha Valley
5 out of 5 average rating, 3 reviews

He’e Hideout Studio - Rare Find!

Rarely Available !! - He’e Hideout Studio An addition to our luxury Hideout Collection Homes here in Mākaha Valley!

Popular amenities for Pupukea guesthouse rentals

Quick stats about guesthouse rentals in Pupukea

  • Total vacation rentals

    Explore 20 vacation rentals in Pupukea

  • Nightly prices starting at

    Pupukea vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 2,280 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Pupukea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pupukea rentals

  • 4.9 Average rating

    Pupukea stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Pupukea's top spots, include Waimea Valley, Sharks Cove, and Banzai Pipeline

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Pupukea
  6. Guesthouse rentals