House vacation rentals in Pupukea

4.86 out of 5 average rating, 436 reviews

A covered patio area is viewed, featuring a large umbrella providing shade over a small table. The entrance to the unit is visible in the background, framed by a railing and surrounded by greenery.

Home in Kailua

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

A scenic view of a paved road lined with tall palm trees swaying gently in the breeze. Lush greenery and colorful tropical flowers frame the roadway, enhancing the natural beauty of the surroundings. Soft sunlight filters through the clouds, casting a warm glow over the landscape.

4.93 out of 5 average rating, 123 reviews

Beautiful 4-BR Home| Near Beach| Mountain View

A tastefully designed 4 bed/2.5 bath home in a gated community (built in 2022), nestled in the beautiful Makaha Valley. Private back yard with breathtaking Wai’anae Mountain view and peek-a-boo oceanview. Enjoy quality time with your family and friends at this stylish, cozy home. Experience true taste of paradise on western side of Oahu, away from hustle and bustle of city. The endless beaches along the coastline, amazing sealife, and magnificent mountains will make your vacation memorable!

4.97 out of 5 average rating, 112 reviews

A serene bedroom features a spacious bed with crisp white linens, complemented by soft, natural textures. Large windows showcase ocean views, while two woven light fixtures add warmth. A dresser provides additional storage, and a neutral rug enhances the calming atmosphere.

Home in Waikiki

Waikiki Gem, Stunning Ocean View, Parking Included

Wake up to breathtaking ocean views from our newly renovated 1BR, 1BA condo. Relax on the lanai, let in the gentle breezes, and soak in the picturesque surroundings. With enough space for up to 4 guests, this retreat is perfect for couples, small families, or close friends seeking solace and tranquility. Immerse yourself in the calming ambiance of modern furnishings and a soothing color palette. Convenient parking included. Discover a blissful sanctuary where serenity and relaxation harmonize.

4.89 out of 5 average rating, 72 reviews

A sandy beach curves along a clear, blue ocean, with gentle waves lapping at the shore. Sunbathers and swimmers are scattered across the beach, while umbrellas provide shade in certain areas. Lush green hills rise in the background, contrasting with the golden sands.

Home in North Shore

Steps to SURF and Beaches w/ Ocean Views!

Here on the North Shore, this unique Balinese influenced 2 leveled home is Located directly across the street, just steps from breathtaking beaches and epic surf spots Here you'll find yourself in the middle of Haleiwa and Pipeline. 3 mi in each direction. In the winter months the excitement of the Big surf draws spectators and surfers to this area. Historic Haleiwa Town you will find great restaurants, shops and amazing food trucks Farmers Markets. Placed in a nice quiet neighborhood.

The image captures a modern home set against a vibrant sunset sky, with hues of pink and orange. Lush green grass surrounds the property, which features a welcoming entrance and a three-car garage. Nearby mountains are visible in the background, enhancing the serene atmosphere.

4.98 out of 5 average rating, 121 reviews

Kalo Homes ~ Makaha Valley Oasis!

Escape to paradise in this brand new vacation rental located in the secluded Makaha Valley. Just a short drive away from some of the world's most beautiful beaches, enjoy endless opportunities for hiking, golfing, and soaking up the sun. Surrounded by lush mountains and pristine nature, this rental offers the perfect retreat from the hustle and bustle of everyday life. Take in the breathtaking ocean and mountain views and create unforgettable memories in this ultimate tropical getaway.

Top guest favorite

A golden beach at sunset is framed by tall palm trees and gentle waves. Smooth, dark rocks are visible along the shoreline, contrasting with the soft sand. The tranquil scene embodies a serene atmosphere, inviting restful moments amidst nature.

Home in Kahuku

4.95 out of 5 average rating, 43 reviews

Ocean Pearl

Ocean Pearl is a luxurious retreat nestled in the heart of scenic Turtle Bay Resort, offering a perfect blend of comfort, convenience, and breathtaking views. With three full bedrooms and two full Jack & Jill bathrooms, this spacious abode provides ample accommodation for families or groups seeking an unforgettable getaway. As you step inside, you're greeted by a warm and inviting atmosphere, featuring a 3 bedroom home with ample space. Tasteful decor and modern amenities throughout.

A bright living room features modern furniture with a dark gray couch and two vibrant purple chairs. Natural light fills the space from large windows, framed by sheer curtains, and a piece of scenic artwork is displayed on the wall. A small coffee table holds decorative items.

4.95 out of 5 average rating, 106 reviews

Oahu Perfect Vacation •Pool, Near Beach, Sleeps 14

Aloha! Welcome to Paradise Mahalo! Nestled in stunning mountains and ocean views, enjoy our modern, luxurious and cozy home located in the majestic Mākaha Valley. Whether it's a few rounds of golf, a hiking trails near by or a five minute drive down to the world famous Mākaha Beach - you got it all. From the mountains of Yosemite to the beaches of Gulf Shores, my family and I will provide you with the best experience for any vacation and occasion! (Pool available May 7th, 2025)

A private hot tub is situated beside a lush backyard, with a mountain view in the background. The yard features well-maintained landscaping, including plants and ornamental stones. In the distance, a dining table with chairs is set for outdoor gatherings under a clear blue sky.

4.96 out of 5 average rating, 108 reviews

Family Oceanview Oasis, Hot Tub, 5min to beach

Why guests LOVE our home? Why guests find it such a great VALUE? - Free parking for 5 cars (save $40–$100/car nightly) - Private SPA & BBQ, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds and 2 bathroom - Repeat guest favourite, peaceful spot near beaches & away from Waikiki crowds. - Gated community with Oceanview pool, gym & mountain views, - Filtered water (no bottled runs), - Washer/dryer to travel light

4.74 out of 5 average rating, 19 reviews

The living area features a comfortable seating arrangement with a rattan sofa and coffee table, situated on a textured area rug. A staircase leads to the loft area, with wooden railings and ample natural light enhancing the open design. Decor includes wall art and tropical accents.

Home in Kahuku

Peek-a-Boo Ocean View

Reconnect with loved ones in this family-friendly place. My unit is on the West side and is a 10 minute walk by to Turtle Bay Resort by sidewalk. Resort has restaurants and dining, the beach, family-friendly activities, nightlife. The pool at the resort is for Hotel guests only. Our condo has Cable TV'S in all rooms with upper channels. We will be charging you a $250 security deposit on booking. If there is no damages the $ will go back to your account.

4.91 out of 5 average rating, 121 reviews

An aerial view captures a sandy beach stretching along the coast, bordered by clear turquoise waters. Colorful umbrellas dot the beach, while small boats can be seen in the water. Lush green hills rise in the background, complementing the scenic landscape.

Home in Makaha Valley

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

Enjoy time w/family at this new 3 bdr 2.5 bath house in the mountains of Makaha Valley in a gated community. Minutes from year round surf&golf. This is a LEGAL vacation rental. Private yard on perimeter lot with unobstructed ocean&mountain views & just a few min. drive to clean, sand bottom beaches. Please note there is an attached studio on the property but everything is separate&private. Any combination of 10 guests is OK as long as no more than 8 adults.

5 out of 5 average rating, 5 reviews

A screened-in lanai showcases a wooden bench and a comfortable armchair, with views of a lush green lawn and a lagoon. The scene is framed by tropical plants and partially cloudy skies, creating a tranquil outdoor space for relaxation.

Home in Kahuku

~NEW~ Hale Aloha at Turtle Bay Golf Course

Brand New Listing! Relax in this beautiful and spacious getaway on the North Shore and be the first to review this 5-star Guest Favorite listing that is new to our portfolio! This spacious newly updated 3-bedroom unit has beautiful lagoon views of the Turtle Bay Golf Course and lush green North Shore mountain range. Comfort and style are the focal points of this exclusive property adjacent to the resort and a scenic walk to several beautiful beaches.