North Shore Tropical Hale by Gather | Spacious w/ Private Pool & Tropical GaFrom $845/night · Sleeps 8
North Shore Surf Town
Haleiwa Vacation Rentals
Why Stay in Haleiwa?
Haleiwa is a gateway to Oahu's legendary North Shore and offers a unique blend of natural beauty, small-town hospitality, and world-class surf. Whether you're catching waves at Waimea Bay or shopping for local art, this town delivers a true Hawaiian vibe.
Top Attractions in and Around Haleiwa
- Matsumoto Shave Ice – A local landmark since 1951
- Haleiwa Harbor – Book snorkeling, shark diving, or fishing charters
- Waimea Bay & Valley – Surf in winter, swim at the falls in summer
- Puʻu o Mahuka Heiau – Ancient Hawaiian sacred site with ocean views
- Laniakea Beach – Famous for sea turtle sightings
Key Features of Haleiwa Vacation Rentals
- Beach cottages and ocean-view homes steps from the sand
- Full kitchens, lanais, A/C, and local-style furnishings
- Walkable to shops, art galleries, restaurants, and surf spots
- Pet-friendly and family-friendly options available
- Peaceful locations with quick access to adventure
Who Should Book a Haleiwa Rental?
- Surfers chasing the North Shore's world-famous breaks
- Couples seeking a romantic, small-town coastal vibe
- Families who want outdoor fun with local flavor
- Travelers looking for authentic, non-resort-style Hawaii
Explore More Nearby
Want to expand your North Shore stay? Check nearby listings in Ehukai Beach, Kuilima Estates, and Sunset Beach for more surfside vacation rentals. You can also explore local farms, shrimp trucks, and secluded beach paths just minutes from town.
Browse our curated selection of Haleiwa vacation rentals below and find why this surf town remains a timeless favorite for visitors to Oahu's North Shore.
Rental Listings
Haleiwa Vacation Rentals Listings
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Haleiwa Vacation Rentals Map
North Shore Tropical Hale by Gather | Spacious w/ Private Pool & Tropical GaFrom $845/night · Sleeps 8
Kaunala Retreat | 4BR Oasis w/ Sauna, Lanai, Steps to Velzyland BeachFrom $1,167/night · Sleeps 8
Private North Shore StudioFrom $193/night · Sleeps 2
The Surf ShackFrom $199/night · Sleeps 2
Surfers Paradise w/ Oceanview 29+ nightsFrom $199/night · Sleeps 10
Best View in V Land! Incredible North Shore home!From $199/night · Sleeps 7
Country Chic Tiny Home in HaleiwaFrom $199/night · Sleeps 6
Lovely 5-bedroom house in Sunset beach vland for your dream vacationFrom $199/night · Sleeps 8
Shark's Cove Front/Sea View/Large 2BR/Full KitchenFrom $236/night · Sleeps 6
The Cedar House - Private Yard and Entrance!From $257/night · Sleeps 5
Wonderful 4-bedroom house with AC across from the beachFrom $387/night · Sleeps 6
HaleGator Oceanfront Home w/Surfbreak Views and AccessFrom $602/night · Sleeps 6
Hale Nalu (Lower Level) by Gather: Oceanfront w/ Lanai, Grill & ViewsFrom $708/night · Sleeps 7
Sunset Beach Hideaway by Gather: North Shore Retreat w/ Walk to Beach, Lanais &From $782/night · Sleeps 8
Sunset Point Hawaiian Beachfront: Exclusive Beach Home w/Hot Tub/Surf Break SpotFrom $1,031/night · Sleeps 6
Ka Hale Hau’oli by Gather: Gated North Shore Home w/ Pool+Hot Tub, Lanai & ViewsFrom $1,047/night · Sleeps 8
Gardenia @ Ke Iki Beach Bungalows ~ Daily Free Yoga~Sauna~Cold Plunge~ACFrom $1,065/night · Sleeps 4
You found Paradise! Relax in Luxury, A/C, Ocean, Valley, Forest VIEWS! PupukeaFrom $1,082/night · Sleeps 10
Maluhia Beach House by Gather: Beachfront Home w/ Lanai & ViewsFrom $1,113/night · Sleeps 10
Beachfront in Haleiwa, Sea Turtles and Sunsets!From $1,187/night · Sleeps 8
Luxury family villa 5bd - Ocean Views - Center of North ShoreFrom $1,222/night · Sleeps 10
Bird Of Paradise TVU-1868 - Ke Iki Beach BungalowsFrom $1,225/night · Sleeps 5
Hibiscus @ ke Iki Beach Bungalows~Daily Yoga~Sauna~Cold plunge~ACFrom $1,225/night · Sleeps 5
7 Mile Miracle Beach HouseFrom $1,227/night · Sleeps 10
Lilikoi @ Ke Iki Beach Bungalows, Daily Free Yoga~Sauna~Cold Plunge~ACFrom $1,332/night · Sleeps 6
Beachfront North Shore Oahu Estate | Sunset BeachFrom $1,363/night · Sleeps 10
Hale Pua Male at Ke Iki BeachFrom $1,529/night · Sleeps 10
Beach-front Estate - North Shore, private setting, close to Haleiwa & surf spotsFrom $1,804/night · Sleeps 6
Large Luxury Beachfront Family Estate Chun's Reef A/C Hot TubFrom $1,914/night · Sleeps 14
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North ShoreFrom $2,270/night · Sleeps 11
Top of the Line Beachfront Home in North Shore OahuFrom $3,769/night · Sleeps 12
North Shore Rustic Country Lodge 2-Story Yurt By Beach Waialua Haleiwa GlampingFrom $482/night · Sleeps 11
North Shore Tropical Studio with breathtaking mountain views!From $284/night · Sleeps 3
From $845/night
North Shore Tropical Hale by Gather | Spacious w/ Private Pool & Tropical Ga
Haleiwa, Hawaii
★★★★★ 1 reviews
This spacious Haleiwa retreat offers a serene base for exploring Oahu’s famed North Shore. With over 4,000 square feet of living space and lush...
From $1,167/night
Kaunala Retreat | 4BR Oasis w/ Sauna, Lanai, Steps to Velzyland Beach
Haleiwa, Hawaii
★★★★★ 1 reviews
Tucked within a private gated community just four homes from beach access, Kaunala Retreat blends modern island design with tropical serenity. This...
From $193/night
Private North Shore Studio
Haleiwa, Hawaii
Our newly renovated attached studio is located between Sunset Beach & V-land one block to the beach. Well suited for a single guest or couple (queen...
From $199/night
The Surf Shack
Haleiwa, Hawaii
Our cozy “Surf Shack” is locate steps away from the Historic Haleiwa town. Facing Anahulu River, come paddle the famous Rainbow Bridge accessing...
From $199/night
Surfers Paradise w/ Oceanview 29+ nights
Haleiwa, Hawaii
Lovely Hawaiian Pole House w/ oceanview on 1.1 Aces w/ fruit trees and ample parking on the property. Up on the hill of Pupukea -- one of the most...
From $199/night
Best View in V Land! Incredible North Shore home!
Haleiwa, Hawaii
The best view in V land! This incredible home is located right across the street from the coveted V Land beach oh Oahu's North Shore. With enough...
From $199/night
Country Chic Tiny Home in Haleiwa
Haleiwa, Hawaii
This brand new tiny home in Historic Haleiwa town is the perfect tropical country retreat. Just minutes from restaurants and shopping in Haleiwa town...
From $199/night
Lovely 5-bedroom house in Sunset beach vland for your dream vacation
Haleiwa, Hawaii
Your Haleiwa adventure begins at this delightful 5-bedroom house. With 4 queen beds and 1 full bed, this charming property is perfect for a group...
From $236/night
Shark's Cove Front/Sea View/Large 2BR/Full Kitchen
Haleiwa, Hawaii
- Washer, fully equipped kitchen for home cooking, coffee maker, dishwasher. - Air conditioning and ceiling fan in every room. -Comfortable workspace...
From $257/night
The Cedar House - Private Yard and Entrance!
Haleiwa, Hawaii
Welcome to The Cedar House! Just 5 minutes from world-class beaches and surf breaks. Enjoy country living with cool mountain breezes and the soothing...
From $387/night
Wonderful 4-bedroom house with AC across from the beach
Haleiwa, Hawaii
Located in Haleiwa, enjoy what this 4-bedroom house has to offer. This adorable home features three queen beds and a cozy sofa bed, perfect for...
From $602/night
HaleGator Oceanfront Home w/Surfbreak Views and Access
Haleiwa, Hawaii
HaleGator is a surfer's haven, an oceanfront home on Oahu's legendary North Shore, designed to blur the line between indoors and out. Set directly...
From $708/night
Hale Nalu (Lower Level) by Gather: Oceanfront w/ Lanai, Grill & Views
Haleiwa, Hawaii
At Hale Nalu (Lower Level), the Pacific Ocean stretches out from your backyard while the famous beaches of O'ahu’s North Shore frame your days. This...
From $782/night
Sunset Beach Hideaway by Gather: North Shore Retreat w/ Walk to Beach, Lanais &
Haleiwa, Hawaii
Discover the relaxed rhythm of Oahu’s North Shore at Sunset Beach Hideaway, a spacious 3-bedroom holiday home tucked into a quiet Haleiwa...
From $1,031/night
Sunset Point Hawaiian Beachfront: Exclusive Beach Home w/Hot Tub/Surf Break Spot
Haleiwa, Hawaii
Welcome to Sunset Point Hawaiian Beachfront by Gather, a captivating three-bedroom, one-and-a-half-bathroom Hawaiian home, perfectly situated on the...
From $1,047/night
Ka Hale Hau’oli by Gather: Gated North Shore Home w/ Pool+Hot Tub, Lanai & Views
Haleiwa, Hawaii
Set above the North Shore coastline in Pupukea, Ka Hale Hau’oli is a private, gated four-bedroom, three and one half bath retreat designed for...
From $1,065/night
Gardenia @ Ke Iki Beach Bungalows ~ Daily Free Yoga~Sauna~Cold Plunge~AC
Haleiwa, Hawaii
Pictures speaks louder then words! The Gardenia Bungalow has a king bed in the bedroom and a Twin Bed in the living room. The outside deck is...
From $1,082/night
You found Paradise! Relax in Luxury, A/C, Ocean, Valley, Forest VIEWS! Pupukea
Haleiwa, Hawaii
Since 2025, NorthShoreSunsets.com has been providing exceptional hospitality services to guests and visitors to the iconic North Shore of Oahu. We...
From $1,113/night
Maluhia Beach House by Gather: Beachfront Home w/ Lanai & Views
Haleiwa, Hawaii
Nestled along Oahu’s storied North Shore, Maluhia Beach House is an oceanfront retreat that blends barefoot luxury with effortless island living....
From $1,187/night
Beachfront in Haleiwa, Sea Turtles and Sunsets!
Haleiwa, Hawaii
This Laniakea beachfront retreat is a stunning 4-bedroom, 3-bath home set directly on Oahu's famous Laniakea Beach, known for its resident green sea...
From $1,222/night
Luxury family villa 5bd - Ocean Views - Center of North Shore
Haleiwa, Hawaii
Luxury North Shore Villa – 3 Bedroom with 5 bed | 5 Bath | Ocean Views | Sauna | Welcome to your dream getaway on the iconic North Shore! This...
From $1,225/night
Bird Of Paradise TVU-1868 - Ke Iki Beach Bungalows
Haleiwa, Hawaii
The Bird of Paradise Bungalow has a king sized bed in the beachfront bedroom. The garden side bedroom has a queen size bed. The living room has two...
From $1,225/night
Hibiscus @ ke Iki Beach Bungalows~Daily Yoga~Sauna~Cold plunge~AC
Haleiwa, Hawaii
The Hibiscus Bungalow is our most private beachfront end unit. This bungalow has a king bed in the beachfront bedroom and a queen bed in the garden...
From $1,227/night
7 Mile Miracle Beach House
Haleiwa, Hawaii
Beautiful fully furnished home on the very famous and highly coveted Ke Nui Road. It has direct beach access in front of Gas Chambers, and also...
From $1,332/night
Lilikoi @ Ke Iki Beach Bungalows, Daily Free Yoga~Sauna~Cold Plunge~AC
Haleiwa, Hawaii
The Lilikoi Bungalow is our largest bungalow on the beach. The large dining area and living room has a twin bed. There is a large full size kitchen...
From $1,363/night
Beachfront North Shore Oahu Estate | Sunset Beach
Haleiwa, Hawaii
New! Oceanfront North Shore Luxury Estate | Sunset Beach & Private Access | A/C | Bedroom Balconies | Surfboards, Bicycles, Beach Gear5 Beds • 5...
From $1,529/night
Hale Pua Male at Ke Iki Beach
Haleiwa, Hawaii
Hale Pua Male at Ke Iki BeachExperience true oceanfront living on Oʻahu’s legendary North Shore at Hale Pua Male at Ke Iki Beach. Located directly on...
From $1,804/night
Beach-front Estate - North Shore, private setting, close to Haleiwa & surf spots
Haleiwa, Hawaii
Beautiful, private beach-front estate on near-private beach...except for daily turtle visits. Close-to-town convenience but behind the front gate it...
From $1,914/night
Large Luxury Beachfront Family Estate Chun's Reef A/C Hot Tub
Haleiwa, Hawaii
6 Bedrooms | 6 Full Bathrooms | Sleeps 14 GuestsWelcome to your exclusive North Shore beachfront sanctuary! Perched 15 feet above Oahu's iconic...
From $2,270/night
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North Shore
Haleiwa, Hawaii
Samurai House is a stunning Japanese-inspired luxury estate perched on an oceanfront point on Oahu's North Shore. This 4-bedroom + bunk area,...
From $3,769/night
Top of the Line Beachfront Home in North Shore Oahu
Haleiwa, Hawaii
Disclaimer: The calendar is not perfect and we encourage clients to make an inquiry first to check the availability before booking.Please inquire...
From $482/night
North Shore Rustic Country Lodge 2-Story Yurt By Beach Waialua Haleiwa Glamping
Waialua, Hawaii
★★★★★ 10.0/10 · 1 reviews
Escape to this Tropical North Shore Island Nature Rental Retreat! 2.5 blocks to the beach & famous surf breaks. Rental is a 2-Story Yurt with a...
From $284/night
North Shore Tropical Studio with breathtaking mountain views!
Waialua, Hawaii
★★★★★ 9.4/10 · 51 reviews
This beautiful studio apartment with stunning mountain views is a perfect place to unwind for your North Shore get-away. The studio features a queen...