Holiday rentals in Pupukea

An outdoor seating area is presented with a circular fire pit at the center. Comfortable, cushioned seating surrounds the fire pit, offering views of the ocean and palm trees in the background. The tranquil setting is enhanced by a clear, blue sky.

4.91 out of 5 average rating, 190 reviews

Magical Skies Hale at Turtle Bay

Tropical Paradise! This Cozy Condo has it all. Comfortable Furniture. Fully Equipped Kitchen. Remodel bath & lots of Privacy! Surrounded by Turtle Bay Golf Course & Beautiful Views. Wake to the sounds of the Native Hawaiian Birdsong. Take in the Magical Skies from our cozy screened-in patio. Sunsets & Beach are just a short walk away! 2 A/C units provided, but most guests open windows & doors to enjoy the refreshing trade winds & fragrant tropical air. 2 Smart TV, High Speed WiFi & Island Charm

5 out of 5 average rating, 33 reviews

Home in North Shore

Hibiscus Hale on Gated Estate + Walk to the Beach

Take it easy at this tranquil getaway on Oahu's North Shore. This eclectic container-turned-guesthouse is insulated & cooled with 2 split A/C units, has a cozy queen bed with all the amenities - Wifi, smart TV, off-street parking right in front of your unit & outdoor dining and gazebo area. Located on a large orchard, you'll be literally surrounded by avocado, mango and lemon trees that are free for the picking. The beach for surfing, snorkeling, shell-collecting is an easy 10 minute walk away.

5 out of 5 average rating, 19 reviews

Flat in Kawela Bay

North Shore Hideaway

Elevated, design-forward retreat at Turtle Bay. This stylish, retro surf–inspired condo overlooks the golf course and mountains, filled with natural light and calming, earthy tones. AC in living room & bedroom, high-speed Wi-Fi, Samsung Frame TV, Quince linen bedding, premium Slowtide towels, and a fully stocked kitchen. Enjoy pools, tennis & pickleball courts, plus walk to Ritz-Carlton dining. Surf, snorkeling, hikes, horseback rides, & golf right here. Adventure, comfort, and serenity await.

4.89 out of 5 average rating, 261 reviews

A two-story building is framed by lush greenery and large windows. A white staircase leads to the upper level, while balconies are visible. The exterior showcases a light-colored facade that blends with the natural surroundings, creating a serene residential setting.

Flat in Kawela Bay

Turtle Bay Corner Condo With A Fairway View!

Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th w/cool breezes, new washer & dryer, and A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax there and enjoy a true authentic Hawaiian experience!

A modern kitchen and living area are depicted in the image. The kitchen features sleek white cabinets and a spacious island. A stainless steel refrigerator and stove are visible. Natural light fills the area through large sliding glass doors, overlooking a green landscape.

4.99 out of 5 average rating, 336 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

4.98 out of 5 average rating, 41 reviews

Flat in Pupukea

A/C PONO Studio 3 minutes walk to the beach #B

Enjoy a stylish experience at the Central located place 3 minutes walking to the beach new studio W A/C on 1 acre property This is the country side off Oahu in the heart of North Shores 7 mile miracle. is perfect for beach vacation with the beach walking distance away, shopping, snorkeling, restaurants, groceries and food trucks nearby. This cute beach studio is a prime surfing location. Walk to pipeline and catch a breath taking sunset every evening. It’s a true surfer Paradise

4.98 out of 5 average rating, 105 reviews

Aerial view of a coastal property lined with homes along a sandy beach. Lush greenery and palm trees are visible, leading to a backdrop of mountains under a partly cloudy sky. Gentle waves lap against the shore, creating a serene beach environment.

Home in North Shore

Haleiwa Waterfront House

Location, location, location! This lovely DUPLEX home is perfectly situated on a beautiful white sandy beach and at the end of a quiet cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic Haleiwa Town rests in the heart of the north shore with Haleiwa being a 3 minute drive away and all the beautiful surf/swim beaches if not in front of the house then a mere 5 - 15 minute drive away (35 minute drive to the airport) .

The living room features a dark leather sofa with decorative pillows, positioned beside a wooden coffee table on a plush area rug. Wall art includes wooden paddles and displayed artwork. The staircase leads to the upper level, with a washer and dryer conveniently located in a nearby nook.

4.94 out of 5 average rating, 241 reviews

Turtle Bay Condo. Cozy retreat for two.

* North Shore * Pristine beaches * Rocky shores * Beautiful mountains * 2 PGA golf courses * Horseback riding * Surfing/kayaking/paddle board * Hiking/biking trails * Activity rentals * Restaurants/bars * Entire condo * Comfortable living space * Outdoor amenities * Gated entry * Assigned parking * On-site security guard * Three swimming pools * 2 tennis courts * 4 Pickle ball courts Suitable for couples, adventurers, business travelers, and families.

4.94 out of 5 average rating, 175 reviews

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.

Guest house in Pupukea

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

A modern kitchen is featured with light wood cabinetry and natural stone countertops. Three rattan bar stools are positioned at the breakfast bar. Pendant lights with woven shades hang above. Fresh greenery is placed on the counter, enhancing the spacious and airy feel of the room.

4.93 out of 5 average rating, 236 reviews

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

4.76 out of 5 average rating, 123 reviews

Home in North Shore

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm. Check my profile for other rentals!

4.86 out of 5 average rating, 63 reviews

A serene view of a sandy beachfront is framed by lush greenery and palm trees. Gentle waves roll onto the shore under a clear blue sky dotted with soft clouds, showcasing a peaceful coastal setting.

Cottage in Pupukea

Banzai Pipeline Beachfront home

Location, Location, Location Oahu-Rentals offers this gated, sandy beachfront (100ft frontage) property located along the famous North Shore's 'Banzai Pipeline' and offers panoramic breath taking views. The home was fully remodeled and can sleep up to 5 people AC is available but not included, if required it can be added anytime for an additional $20 per day. Please inquire for shorter stays as other options may be available

Popular amenities for Pupukea holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pupukea

4.75 out of 5 average rating, 68 reviews

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.

Guest house in Haleiwa

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

4.95 out of 5 average rating, 21 reviews

Tiny home in North Shore

Peaceful NorthShore Farm cottage

A light-filled living area is presented with a cozy white sofa, accented by decorative pillows featuring ocean-themed designs. Two rattan chairs flank a small glass table, while natural light filters through flowing sheer curtains. A potted plant brings a touch of greenery to the space.

4.85 out of 5 average rating, 420 reviews

Luxe Loft at Turtle Bay

4.88 out of 5 average rating, 154 reviews

The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.

Cottage in North Shore

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

4.88 out of 5 average rating, 82 reviews

Flat in Kawela Bay

Hidden gem at North Shore Turtle Bay

5 out of 5 average rating, 27 reviews

Home in Kawela Bay

Newly Renovated Villa Walk to Beach + Pool

A modern open-concept living space features a comfortable sofa and a decorative coffee table. The dining area includes a sleek kitchen island with bar stools. Natural light brightens the room through a large decorative mirror, while stylish accents and greenery enhance the coastal aesthetic.

4.97 out of 5 average rating, 202 reviews

Honu Hideout at Turtle Bay