Private suite holiday rentals in Pupukea

Kailua Pineapple Studio. Walk to Beach! PERMITTED

Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.

Location · Family · Hospitality

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks

Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other deck has a partial ocean view between the houses

Value · Family · Cleanliness

Aloha suite

NOTE: UPDATE Oct 2025: Temporary construction equipment parked next door is being vacated. Barrier fence is still in place while grass is being restored. Some noise may occur. See photos. Only registered guests allowed on property. Welcome to our home! We are a legal vacation rental (TA-188-004-1472-01, 90/BB-0102,420200220000) hosting guests for more than 30 years. We are an environmentally-conscious family doing our share to "Live Lightly" so our natural resources are protected.

Value · Family · Biking

by the sea

Perfect for a couple or small family that wants to wind down at the end of the day! Away from the noise and city life, you can feel safe outside with the kids! If you are looking for a peaceful place this cottage is for you. 5 min walk to a secluded beach! Very friendly and safe neighborhood. Only 10 minutes away from Hawaii’s number one attraction (PCC). 3 minutes from the famous kahuku food trucks that has a variety of food to enjoy! Located on Oahu’s famous North Shore!

Location · Family · Indoor spaces

Gem btwn Mountain & Ocean - Minitues to Beach

Unique and tranquil getaway! Refresh your soul with your eyes lifted up to the mountain and ocean! Newly built, fully furnished. AC, TV, queen bed, nightstands with dimmable touch-controlled lamps... We have done our best to create a Haven for your Hawaii vacation! Special Declaimer: 1. It is a studio attached to the main house in a gated community. 2. Owner is a licensed real estate agent with Coldwell Banker Realty. 3. Homelessness is present along the west coast.

Location · Value · Cleanliness

Slice of Paradise-Studio-Sleeps 4-Same$ for 4 as 2

Enjoy this beautiful, private, brand new studio nestled in the mountains of Makaha Valley. This is located in a gated community with 24 hour security. Minutes from year round surfing and golfing. This is a LEGAL vacation rental. Private yard on a perimeter lot with unobstructed ocean and mountain views and just a few minutes drive to many clean, sand bottom beaches. Any combination of 4 guests is okay as long as there is a max of 2 adults.

Family · Value · Amenities

Hauula Studio

Hauula Hale Studio quietly sits against the mountains in the small town of Hauula, which is just a 5 minute drive from Laie and the Polynesian Cultural Center. Located in the charming country setting of Oahu's windward coast, you can enjoy a quiet and relaxing stay in our comfortable studio. With only a 5 minute walk to hiking trails or the beach or a 20 minute drive to the beautiful North Shore, there is plenty to explore and do.

Location · Value · Check-in

Modern Beach Home Laie North Shore - 30 Day Stays

Beautiful ocean-view unit in a modern "Dwell" style home. This 2-bed 1-bath guest unit sleeps up to six guests. Fully stocked kitchen with high-end appliances. Sandy, crystal-clear beach is just three houses down. Due to local regulations, this home can only be rented for periods of 30 days or longer. No breakdown in pricing or calendar settings in Airbnb shall suggest that this home can be rented for a shorter period.

Family · Location · Parks

DIAMOND ON DIAMOND HEAD

Located on the slope of Diamond Head, our apartment is at a walking distance of Waikiki beach, restaurants, nightlife, public transport. You’ll love my place because of the coziness, the location. I put a special attention on having the mattress spray monthly for bugs and also the apartment for insects. It is very important for me to offer a super clean, cozy, comfy and secure apartment. TA-182-790-8096-01

Family · Value · Cleanliness

Papaya Paradise "Mauka" Poolside Studio *Licensed*

Relax in our private, air-conditioned Poolside Mauka Room, tucked beside our tranquil saltwater pool. The room offers its own entrance and private bathroom, plus access to a shared kitchenette and covered outdoor lanai (patio) for dining or morning coffee. Just minutes from the beaches, shops, and laid-back charm of Kailua, it’s ideal for couples or solo travelers seeking a peaceful tropical escape.

Location · Value · Getting around

Living Local Style with Aloha

Any questions please feel free to contact us first. Aloha! Stay at Our Local peaceful getaway spot to experience real beauty of Oahu. Enjoy your own private studio apt with bathroom and Patio. Enjoy gazing at the stars and the fresh air of the windward side. Located on the North East Shore, escape the noise of Honolulu and enjoy the quiet, secluded, serene beaches and hikes nearby.

Value · Location · Quiet

Steps to beach!!

**Please note that due to Honolulu County ordinance, rentals must be 30 days or more. Enjoy a part of real Hawai'i in our newly remodeled 1 bd/1 bath unit, across the street from the beach in a truly local community. Wile away the hours on the secluded beach or in the hammock under the mango tree. Surf, fish or relax and rejuvenate!

Family · Location · Access