Kris Scott is the executive editor at Cheapism and has previously covered food, design, and lifestyle. Her work has previously appeared in Food & Nutrition, Modern in Denver, and Dallas-based Advocate Magazines. She lives in Colorado with her family and two heelers.
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If you've been wanting to take a Hawaiian vacation for some time, there is probably no better way to experience any of the islands than from the comfort of your very own private beachfront vacation rental. While there are thousands of properties in Oahu, Maui, the Big Island, and Kauai, not all are created equal — here are some of the best in the most prime coastal Aloha State locations.
Prices and availability are subject to change.
Hana, Maui | Sleeps 2
This oceanfront studio condominium is just 100 feet off the water, with a balcony offering wonderful views of Hana Bay and Waikoloa Beach. Enjoy your morning coffee on the balcony as you watch the sunrise over the water, and enjoy amenities like a fully equipped kitchen, private lanai, gorgeous landscaped grounds, a beachside barbecue, and more. The location is a short drive away from great Maui destinations such as Ohe'o Gulch, Haleakalā National Park, and Waimoku Falls.
Hana, Maui | Sleeps 8
For something a little larger and more luxurious on Maui's east side, check out this warm and well-appointed three-bedroom, two-bath property. Situated between Hamoa and Koki beaches and picturesque Alau Island, this Hawaii vacation rental includes an acre of oceanfront property, a hot tub, an expansive sundeck lanai, cathedral ceilings, and more.
Lahaina, Maui | Sleeps 36
Is it pricey? Yes. But, split between a few families, it becomes less so, and it's tough to beat the fact that this Maui location is mere feet from the water. In addition, this nearly 12,000-square-foot, 11-bedroom and 11-bath house has amenities such as a full outdoor kitchen and barbecue, outdoor ping pong, corn hole, its own fitness center, a media room, and more. Also note that while the listing says this property can sleep 32, the fine print says it can sleep up to 36.
Related: Vacation Rentals for Large Groups & Family Reunions
Honolulu | Sleeps 8
For something a little larger right in Honolulu, consider this three-bedroom, three-bath Oahu condo featuring floor-to-ceiling "infinity" doors that open onto two lanais with sweeping views of the nearby mountains, coastline, Honolulu skyline, and more. Guests here get to enjoy the amenities at the adjacent Outrigger Reef hotel, which include restaurants, shops, a pool, spa, hot tubs, and a fitness center.
Kihei, Maui | Sleeps 4
Located within the Royal Mauian, this modern condo is a stone's throw away from two white sand beaches that offer snorkeling, surfing, and other activities. The King suite offers gorgeous beach views, while the shared living space includes a fully-stocked kitchen, cable TV, and a washer and driver. The Maui Ocean Center, Maui Brewing Co., and The Shops at Wailea are a quick 15-minute drive away if you've had enough of the beach for the day.
Paia, Maui | Sleeps 4
This light-filled cottage on Maui's north shore is perfect for a small family or couple. Head to the nearby beach to surf or splash around, then take a trip into town to dine at Mama's Fish House Restaurant. If you'd rather cook at home, pay a quick visit to Kuau Store to pick up groceries, then spread out in the cottage's cozy kitchen which seamlessly blends into a communal dining area.
Honolulu | Sleeps 7
Take in spectacular beach views from this luxury condo, which boasts high-end furnishings, expansive standing showers, and dimmable recessed lighting to help set the mood. Multiple balconies invite couples and families to enjoy meals overlooking the ocean, and each room is equipped with air conditioning to keep guests cool on sweltering days.
Waialua, Oahu | Sleeps 10
Vacationers seeking a secluded getaway can head straight to this Oahu rental, located in a low-key, family neighborhood. The four-bedroom, three-bathroom space boasts a ping pong table, foosball, and ocean and mountain vistas that can be seen from around the house. Relax on the nearby white sand beach, or go for a tranquil walk throughout the serene suburb.
Ewa Beach, Oahu | Sleeps 6
Get away from it all at this ocean-facing home near popular Ewa Beach, south of Kapolei, on the leeward coast of Oahu. With three bedrooms and two baths, this rental has ocean views from both the master bath and living room, is air-conditioned, has a grass yard, and includes amenities like beach supplies, a dedicated workspace, a TV, and more.
Waianae, Oahu | Sleeps 8
Get a beach-facing grassy front yard and natural-stone lanai filled with chairs and hammocks at this four-bedroom, two-bath Oahu vacation home. A secluded sandy beach is just steps beyond, and the home itself makes the most of indoor-outdoor living with huge nesting doors and large windows. Amenities include a fully equipped kitchen, dedicated workspace, and TV.
Hauula, Oahu | Sleeps 8
Get ready for some spectacular outdoor spaces with this rental, which includes a beachside lanai, outdoor barbecue, hammocks, chaise lounge chairs, and an array of beach gear. The house looks just as comfortable inside as out, with three bedrooms, three baths, and amenities like air conditioning, a dedicated workspace, washer and dryer, and a well-equipped kitchen.
Haleiwa, Oahu | Sleeps 6
With 180-degree views of Sunset Beach, this two-story, two-bedroom rental is a dream for Oahu visitors looking for privacy and serenity in Hawaii. The gated property's main bedroom opens up to an outside balcony (hello, breakfast with a view), while everyone can gather around the gas grill for a barbecue on the patio deck. In need of a tan? Take a quick walk to Sunset Beach, Rocky Point, and Pipeline to soak up some rays and a stellar sunset.
Kawela Bay, Oahu | Sleeps 8
This three-bedroom, two-bathroom beachfront property is within walking distancing to quiet sandy beaches, swimming areas, surfing, and walking trails on the North Shore, though you'll have just as much fun hanging around the beautiful vacation home. Wash the sand off your swimsuit at the outdoor shower, then fire up the grill and enjoy an evening sunset from the outdoor dining area.
Kailua, Oahu | Sleeps 10
Located on the east side of Oahu, this stunning five-bedroom, three-bathroom property seamlessly blends indoors with outdoors. Open sliding glass doors onto a spacious patio where you can relax, dine, or take a dip in the pool. A private gate leads visitors to a beach path that provides access to Kailua Beach, and Makapu’u Point Lighthouse, Nuuanu Pali Lookout, and the beaches of Waimanalo are a quick jaunt away.
Waimea, Hawaii | Sleeps 10
Located beachside right off Waialea Bay on the Big Island's west side, this five-bedroom, four-bath house offers an open layout with "a bit of old Hawaii mixed with a modern style and design." The home features lots of outdoor living space, a small grassy yard, and a separate guest house — aka an ohana — that can act as a private room.
Pahoa, Hawaii | Sleeps 4
Declared an Airbnb Plus property for its stylish decor, this Balinese-style one-bedroom, one-bath beach house is located on the Big Island's Southeast coastline near the gorgeous Kaimū Beach Park. Amenities include an ocean-facing deck, a dedicated workspace, and some nearby black lava fields to explore.
Kailua-Kona, Hawaii | Sleeps 10
Enjoy indoor/outdoor Big Island living with this four-bedroom, two-bath vacation property, which boasts a great location across the street from Kahalu’u Beach and is also conveniently located near surf shops, food trucks, and the Kona Trolley Stop. Amenities include a hot tub, outdoor shower, and beach gear, and each bedroom has a 42-inch TV.
Captain Cook, Hawaii | Sleeps 2
Another property with a Balinese vibe, this one-bedroom, one-bath private guesthouse is just steps from Kealakekua Bay and also within walking distance of Manini Beach. It includes a fully equipped outdoor kitchen, outdoor shower, dedicated workspace, and some beach essentials.
Hilo, Hawaii | Sleeps 3
This Big Island one-bedroom, one-bath condo is close to great swimming spots and next door to Carlsmith Beach Park. Guests have access to the complex pool, and other amenities include a washer/dryer, TV, full kitchen, and private balcony.
Kapaa, Kauai | Sleeps 4
Just steps from the water's edge, this two-bedroom, two-bath condo rental on Kauai's east side is adjacent to Lae Nani Beach. Enjoy views of the ocean and landscaped grounds from your private balcony, or take a dip in the shared pool. Inside, amenities include a dedicated workspace and TV.
Hanalei, Kauai | Sleeps 12
Spend your vacation at this newly remodeled home within walking distance from Hanalei Beach. Perfectly for multiple families, the five-bedroom getaway boasts a wraparound porch, fully-stocked kitchen, a hot tub, and ping pong table. Be sure to take advantage of the boogie boards and snorkeling gear on hand, along with the fruit trees that offer lemons, limes, and bananas when in season.
Hanalei, Kauai | Sleeps 8
Also situated on the cusp of Hanalei Bay is this dual-structure rental, which includes a three-bedroom, two-bath home, and a one-bedroom, one-bath guest cottage (you get both with your rental). Enjoy your morning coffee in the sunroom with walls of windows or dine on the private lanai with views of the lush grounds and bay. Other amenities include a washer and dryer and TV.
Anahola, Kauai | Sleeps 10
Located on Kauai's coast north of Lihue, this four-bedroom, three-bath beach house is newly remodeled with a comfy and modern vibe. Loads of windows provide vistas of Aliomanu Bay, and you can take in those views, too, from the covered lanai while you barbecue some dinner. Accordion-style doors provide the ultimate indoor/outdoor living, and other amenities include a dedicated workspace, washer and dryer, and TV.
Koloa, Kauai | Sleeps 8
On Kauai's southern coast just west of Poipu, this four-bedroom, three-bath rental has ocean and coastal views from nearly every room, as well as amenities like a spa, pool, air conditioning, outdoor barbecue, washer/dryer, and dedicated workspace. The location is also close to Kauai's National Tropical Botanical Garden, and many tours of the Nā Pali Coast State Wilderness Park depart from Poipu.
Lahaina, Maui | Sleeps 6
If mountain and ocean views for days are your idea of a great Hawaii vacation, this two-bedroom, two-bath Maui rental gives you both those and much more. Amenities include free parking, a washer and dryer, a dedicated workspace, some beach gear, plenty of outdoor space on the large lanai, and access to the complex pool.
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Kapolei, Oahu | Sleeps 6
The ground-floor location of this rental villa will appeal to many people, especially with its ocean, mountain, and sunset views. The property also includes easy access to the community pools and beach bar, as well as an on-site sauna, fitness center, steam room, surf and bike storage, and more.
Related: The Coolest Mountain Hideaways You Can Rent Across America
Kaneohe, Oahu | Sleeps 10
Relax on comfortable seating under covered lanais or post up at the outdoor home bar at this five-bedroom, four-bathroom getaway. With stunning views of Kaneohe Bay, the rental offers spacious common areas, a pool, and kayaks to take out on the water. Need to get out of the house for a bit? A theater, mall, restaurants, and grocery stores are all five minutes away.
Kilauea, Kauai | Sleeps 6
Located just east of ritzy Princeville, this two-bedroom, two-bath, 1,600-square-foot-plus home offers something a little more low-key. In a secluded neighborhood with just a few other homes, you can be on the beach or wading in the ocean from this rental within just a few seconds, and the home's warm island decor combines with dramatic ocean views for a truly Hawaiian vibe. Amenities include a covered lanai and a large, fully equipped kitchen, but take note — no TV.
