Haleiwa Vacation Rentals – Historic Surf Town Meets Beachfront Charm
Haleiwa vacation rentals immerse you in the heart of Oahu's North Shore surf culture. Stay steps from world-class beaches, local art galleries, food trucks, and historic charm – all in one of Hawaii's most beloved seaside towns.
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 discover why this surf town remains a timeless favorite for visitors to Oahu's North Shore.
North shore beachfront villa - garden view home
Plumeria House is a recently renovated traditional Hawaiian style plantation home found in Tropical Waters, a vacation rental retreat featuring three homes in a gated community on Oahu's North Shore. This house has a beautiful garden view along with your own private...
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North Shore
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Samurai House by GatherSamurai...
Shark's Cove Ocean View Extra Large 2BR Sleeps 10
The property is in the heart of North Shore, across from Shark's Cove and the start of the bike path to Log Cabins, Pipeline, and Rocky Point. Just a few minutes bike ride to Sunset Beach or a short walk to Waimea Bay. Fall in love with the views of the ocean and...
The Cedar House - Private Yard and Entrance!
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 sounds of nature, amidst coconut trees, bananas, and tropical plants. Local laws require a minimum 30-night booking, but...
Beach Unit! Unlimited ocean view-Beautiful reef protected sandy beach
Enjoy this bit of paradise at Haleiwa on Oahu’s legendary North Shore. This wonderful one-bedroom, two-bath condo offers the perfect North Shore home, with breathtaking ocean views that greet you the moment you walk through the door.Enjoy your private lanai for an...
Sunset Point Hawaiian Beachfront: Exclusive Beach Home w/Hot Tub/Surf Break Spot
Welcome to Sunset Point Hawaiian Beachfront by Gather, a captivating three-bedroom, one-and-a-half-bathroom Hawaiian home, perfectly situated on the pristine Sunset Beach in the picturesque North Shore of Oahu. This residence, known as one of the area’s finest,...
Hidden Jewel Beach front
Your Private Beachfront Retreat in Haleiwa – 30-Day Minimum StayEscape to your own slice of paradise at Haleiwa Beach on Oahu’s legendary North Shore. This charming one-bedroom, two-bath condo offers the perfect blend of comfort and island charm, with breathtaking...
Villa Bianca: Oceanfront Elegance w/ BBQ, Lanai, Stunning Ocean & Sunset Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Nestled in the picturesque town of Haleiwa,...
Relaxing family 4-bed/4 bath house in Sunset Beach- Book at Vrbo #687687
Unwind in Haleiwa at this lovely house. This amazing property features 4 bedrooms - 2 with king beds and 2 with twin beds. With 5 bathrooms equipped with showers, bathtubs, and hair dryers, guests will feel right at home. Enjoy all that Haleiwa has to offer when you...
Waimea Bay Cottage - Steps to beach, AC
**30 day rental**Nestled just steps from the pristine white sand beach, Waimea Bay Cottage offers an idyllic 3-bedroom, 2-bathroom retreat in one of the most coveted locations on the island. Conveniently situated near two of the best beaches in the world, including the...
Waimea Bay Getaway - Beachfront | AC
Escape to Waimea Bay Getaway, a spacious 3-bedroom, 2-bathroom retreat accommodating up to 6 guests with three luxurious Queen size beds and a cozy futon. Nestled within walking and biking distance of renowned beaches and surf spots, our home offers easy access to the...
Waimea Combo: Experience Twice the Island Charm!!
Discover the epitome of North Shore living with our exclusive Waimea Combo, boasting a total of 6 bedrooms and 4 bathrooms across two exquisite properties: Waimea Bay Cottage and Waimea Bay Getaway.Waimea Bay Cottage offers a charming 3-bedroom, 2-bathroom retreat just...
Kealoha Tropical Beach Villa: North Shore Surf Spot Retreat w/ Hot Tub & Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Aloha and welcome to Kealoha Tropical Beach...
Beachfront Home for 7 in North Shore
Discover paradise in this beachfront haven. With private access to the famous Sunset beach, this idyllic location is located directly in front of the popular surf spot, Rocky Point. Lounge comfortably on the spacious private balcony and listen to the lapping waves while...
Three Tables Bungalow, walking distance Waimea Bay, Three Tables, Sharks Cove
Three Tables Bungalow is a custom built 1 bedroom/1 bathroom, newly renovated & fully furnished unit with a private entrance. In a great location, safe & private residential cul-de-sac within walking distance to Three Tables, Waimea Bay, Sharks Cove, Foodland, Food...
Waimea Bay Tropical Retreat w/ pool & jacuzzi 2 min walk from the beach!
Waimea Bay Tropical Retreat is in a Great Location on a private residential cul-de-sac within walking distance to Waimea Bay, Three Tables, Sharks Cove, Foodland, Food Trucks. Close to the bike path & all of the best North Shore surf breaks & beaches. Neighborhood is...
Beachfront in Haleiwa, Sea Turtles and Sunsets!
Welcome to one of the most unique beachfront homes on Oahu’s north shore. Located directly on the breathtaking Laniakea beach, this location is well-known for spotting Hawaii’s endangered green sea turtles along the shore! Laniakea is also a lovely beach for...
Brand New Rocky Point Beach Cottage
Enjoy a brand new studio just steps from Rocky Point on Oahu’s North Shore. This charming and spacious spot offers private beach access, making it the perfect getaway for surf lovers and beachgoers alike.
Cozy downstairs Apartment located one block from beach in V-land.
Awesome cozy downstairs Apartment located one block from beach in Velzyland. Safe family friendly location in residential neighborhood . Across from Freddyland beach access . Longer bookings inquire about reduced monthly rate.The spaceCozy & simple One bedroom apt with...
Beachfront Studio in North Shore - Lower Unit
Discover a surfer's paradise at this beachfront studio located in Haleiwa, Oahu. With private access to the beach, this idyllic location is in front of a popular surf spot. Lounge comfortably on the porch and have lunch at the outdoor dining area right outside the...
Garden Studio -
Newly built, our super private guest suite is located at Sunset Beach, on Oahu’s North Shore. Short walk to the beach & Ted's Bakery.Parking is free & right by your front door.Kitchenette & bathroom are fully equipped.New appliances, blinds, mattress, sheets, towels...
Haleaha Road - Steps to the Beach in Hau'ula
Aloha and welcome to The Haleaha Road Home in Hau’ula on Oahu’s northeast shore. This spacious, renovated home features mountain views, sleeps 8, and is perfect for extended family stays. Just steps from an uncrowded beach, enjoy lush scenery, local farms, hiking,...
Shark's Cove Ocean View Deck near Pipeline 2BR
The property is in the heart of North Shore, across from Shark's Cove and the start of the bike path to Log Cabins, Pipeline, and Rocky Point. Just a few minutes bike ride to Sunset Beach or a short walk to Waimea Bay.
Private North Shore Studionn
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 loft bed) who want to enjoy the comforts of home while experiencing the North Shore culture. Walk distance to beautiful,...