If you’re planning a trip to Hawaii, you’re in for a treat. Dramatic natural scenery, friendly locals, delicious cuisine, and exceptional vacation rentals are a small taste of what’s to come.
The Hawaiian Islands offer top-notch vacation rentals. From treehouse hideaways to extravagant beach villas, there’s something for everyone here. Depending on the area you choose to visit, and what type of vacation you’re after (whether it be an active hiking holiday or a family beach vacay), each of the archipelago’s six main islands has its own unique and incredible atmosphere to offer.
Whatever you’re after, the vast array of vacation rentals in Hawaii are sure to not disappoint. Let’s dive in and take a look at the best of the best!
Quick Answer: These are the Top 5 Vacation Rentals in Hawaii
Beautiful Gated 6 Bed Oceanfront Villa
- > $$$$
- > 15 Guests
- > Bright and regal home
- > Located on a private beach in Northeast Oahu
Funky Colorful Ocean View Studio for 2
- > $
- > 2 Guests
- > Hip and vintage condo with retro furniture
- > Centrally located in the heart of Honolulu
Secluded Rainforest Hideaway for 2
- > $$$
- > 2 Guests
- > Studio cottage in the rainforest
- > Located in a small residential neighborhood nearby a local village.
Authentic 2 Bed Rainforest Home
- > $
- > 4 Guests
- > Designed in a homey style with warm wooden tones
- > Hidden in the tropical rainforest
Ultra-Modern Villa with 5 Bedrooms
- > $$$$
- > 14 Guests
- > This modern luxury vacation rental in Hawaii has a heated infinity pool
- > Located on the beach in Puako
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Looking for other types of accommodation? Check out our guide to Where to Stay in Hawaii.
Types of Accommodation in Hawaii
Choose from rustic sugar plantation homes in Kauai, beach houses overlooking world-class surf on the North Shore of Oahu, or a high-rise condo in the tropical metropolis we call Honolulu.
With some of the most beautiful beaches of all the islands, Maui naturally has some outstanding beach houses scattered around its coastline. More interested in natures’ erupting volcanoes than relaxing on a beach? There’s heaps of awesome accommodation in the Big Island, with loads of secluded treehouses and cabins nestled in the inland tropical rainforest.
Villas and Estates
Villas and estates are large luxury vacation rentals in Hawaii, usually located in prestigious and well-connected regions. These ultra-fancy homes can range in size from three to ten bedrooms. They are known for being extravagantly designed and furnished with top-of-the-range furniture and appliances.
Often boasting panoramic ocean views and lush green lawns, Hawaiian villas and estates are usually fitted with large swimming pools, Jacuzzis, and outdoor dining and seating areas. These luxury vacation rentals in Hawaii are typically reserved for groups of high-end vacationers who aren’t restricted to a tight budget.
Beach Houses and Cottages
Some of the top beach vacation rentals in Hawaii can be found scattered along the coastlines of all six islands. Perched atop rocky cliffs, set in quiet residential neighbourhoods or amongst the hustle of trendy beach districts, beach accommodation ranges in size, quality, and price.
The variation in offerings makes beach vacation rentals in Hawaii appropriate for couples, small families, and groups of friends. Whether you seek quiet tranquillity or busy beach vibes, you’ll be sure to find the perfect beach house or cottage in Hawaii.
Typically found on Hawaii’s Big Island in the region by the Volcanoes National Park, there’s an abundance of cottages and rainforest treehouses in Hawaii.
The remote location of these homes makes them some of the best vacation rentals in Hawaii for romantic visits and honeymoons. They are also ideal rentals for outdoor lovers looking to embark on hiking, kayaking, and waterfall adventuring activities. Surrounded by forest and boasting unrivalled privacy, a huge benefit of inland accommodation is the reduced price in comparison to beachfront properties.
Top 20 Vacation Rentals in Hawaii
Best Overall Vacation Rental in Hawaii | Beautiful Gated 6 Bed Oceanfront Villa
This stunning beachfront home features a Greek interior influence, with white arches, bougainvillaea climbers, and blue detail. The villa is pretty luxurious and on the upper end of the price scale, but it’s absolutely worth it. Each room is complimented with 180-degree views of surrounding islands and has magnificent sea views. This home includes a main house and a detached cottage which can be rented out together or separately.
Best Budget Vacation Rental in Hawaii | Funky Colorful Ocean View Studio for 2
Hip mid-century furniture meets tropical wallpapers and retro kitchen appliances in this studio rental overlooking the ocean. Equipped with full catering and laundry facilities and a private balcony, this rental has everything you might need from a vacation rental in Hawaii. Its central location puts you within walking distance of Waikiki’s coolest shops and restaurants, making it the ideal vacation rental for anyone visiting Hawaii on a budget.
Budget Tip: Dorms in Hawaii start from $10USD per bed. They’re the cheapest accommodation in the city. Search for hostels in the area!
Most Beautiful Vacation Rental in Hawaii | Extravagant 6 Bed Villa on the Ocean
This magnificent villa is perched overlooking some of Hawaii’s most beautiful beaches. A front courtyard with impressive water features leads into a spacious open-plan living area. The shared living space boasts a chef-level fully-equipped kitchen and large dining area – all of which open into the undercover cabana and lush lawns of the front yard.
The home is designed to look like a Balinese villa, showcasing exposed wooden beams, natural tones, indoor plants, and traditional Hawaiian art.
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Most Luxurious Vacation Rental in Hawaii | Ultra-Modern Villa with 5 Bedrooms
This opulent villa is designed in an ultra-modern architectural style mixed with unique wooden features and concrete slabs. Fitted with only top-of-the-range interiors, including steam showers, Miele appliances, and four outdoor showers, this is one of the most luxurious beach vacation rentals in Hawaii.
The home includes concierge services and daily housekeeping. Other luxury amenities include a heated infinity pool, a private tennis court, and a sand volleyball.
Best Vacation Rental in Hawaii for Families | Authentic 2 Bed Rainforest Home
This home is a safe and secure spot to experience the gems of Hawaii with your family. The two-bedroom home is tucked away in the pristine rainforest on the Big Island. You’ll feel right at home here and can enjoy classic wooden furnishings, spacious, bright rooms, and authentic decor. We love that there are skylights throughout, and the indoor/outdoor shower is a feature everyone will love.
Best Vacation Rental in Hawaii for a Friends Getaway | Private 4 Bed Estate with Lush Gardens
Large lawns, a panoramic deck, and an azure blue swimming pool overlooking the pristine ocean epitomize luxury in this estate. It’s a great place to stay in Maui if you’re travelling with mates and comes complete with an indoor and an outdoor dining area, as well as a chef-standard kitchen.
Each of the four luxury suites has a private television lounge ares, en-suite bathrooms, and ocean-view balconies. It’s ideal for enjoying a peaceful private space between gathering with friends.
Best Vacation Rental in Hawaii for a Weekend | Private 1 Bed Condo with Ocean Views
Sometimes, you just need to escape to Hawaii for a couple of days. If you’re in need of a tropical getaway, then this vacation rental is the best place to base yourself. Simply decorated and well located, this one-bedroom condo has been furnished with cozy furniture and linen and includes a fully-equipped kitchen with a double burner gas stove. With balcony ocean views and an easily accessible location
Best Vacation Rental in Hawaii with a Pool and Jacuzzi | 9 Bed Estate with Waterfall and Waterslide
This spectacular holiday rental in Hawaii is the ultimate luxury at its best. The 9-bedroom estate sits in a prime location on the beach, but we won’t blame you for not wanting to leave the house! Decorated with traditional Hawaiian opulence, this home exudes over-the-top beauty and has plenty of fantastic features.
The best thing about this property is its pool area, which overlooks the ocean and includes a Jacuzzi, waterfall feature, and a child-friendly water slide.
Super Accessible Vacation Rental in Hawaii | Gorgeous Contemporary Condo for 2
This affordable condo includes a large open-plan living space beside a private bedroom. Complete with dark wood finishes and decorated with warm furniture and lighting fixtures, it provides a cosy and homely atmosphere. It’s a truly accessible option, whether you’re looking to stay in Hawaii for a couple of days or a longer visit.
Most Central Vacation Rental in Hawaii | 1 Bed High-Rise Condo with Ocean Views
Towering over the city, this place offers some of the coolest accommodation in Honolulu! The apartment overlooks the ocean, providing unrivalled sunrise views and morning sunshine from the outside balcony. The bedroom is fitted with two single beds which can be set up as you please. The central living area offers two spacious sofa beds, which can easily sleep additional guests.
Best Vacation Rental in Hawaii with a View | Stylish Treehouse with 360-Degree Views
Luxurious isolation – that’s what comes to mind when walking through this paradise treehouse overlooking the ocean and jungle. Walk around living trees strung with lights and soak in the Jacuzzi beneath the treehouse. From this breathtaking Hawaii vacation rental, guests can admire panoramic mountain, jungle, and ocean views. The treehouse has one bedroom, making for a gorgeous eco-retreat in Hawaii.
Most Remote Vacation Rental in Hawaii | Secluded Forest Home for 4
This spacious home with a shared sleeping area has 360-degree forest views. It’s ideal for a family or a group of friends, but keep in mind you will be sharing one bedroom. Appreciate the private yet convenient location, tucked away in the forest just minutes from Hilo town.
The kitchen is well equipped with top-of-the-range appliances and has been recently renovated in a modern style. Clean marble countertops meet wooden floors and tropical colours in this contemporary forest home.
Because of its epic forest views, this is one of our favourite places to stay near Hilo.
Most Unique Vacation Rental in Hawaii | Remote Outdoor-Living Glamping Tent
Hidden between the leafy trees of Kona, this unique tent accommodation can comfortably sleep two adults and one child. The shared living space is completely outdoor (although undercover), and includes a simple kitchenette with a grill, dining area, and lounge space. A private enclosed wooden bathroom allows for late night stargazing from the bathtub.
Best Vacation Rental in Hawaii for Honeymooners | Romantic Jungle Cottage for 2
This gorgeous Hawaiian cabin is designed to look like a European cabin. It boasts wooden walls and cabinetry yet is furnished with tasteful contemporary pieces, creating a cosy and charming atmosphere. If you’re worried about missing those tropical island vibes, don’t fret – you’ll have the jungle right on your doorstep.
This is the ideal vacation rental in Hawaii for a honeymoon, as it offers plenty of things to do and lots of privacy.
Best Vacation Rental in Hawaii for Nightlife | Contemporary 1 Bed Waikiki Studio
Located within the hustle and bustle of a world-renowned beach, this condo offers some of the best accommodation in Waikiki! It’s close to some of the island’s most revered eateries, bars, and nightclubs, making a convenient spot to retreat to after a big night out on the town.
The pet-friendly home also has brilliant internet connection and is fitted with a fully-equipped kitchen and laundry facilities. This makes it a great option for digital nomads or long-stay visitors who need a reliable internet connection.
Most Romantic Vacation Rental in Hawaii for Couples | Secluded Rainforest Hideaway for 2
Walk into this tropical cottage with your number one and you’ll feel like you are the only two people in the world. The home is finished with warm wooden tones and decorated with Japanese and Hawaiian fusion styles, blending interesting textures, linens, and artwork. This hexagonal structure is a beautiful escape for a romantic getaway. Step outside into the rainforest to access a traditional Japanese bathtub and shower, hidden beneath the dense trees.
Your hosts will even drop off a prepared continental breakfast selection for you to enjoy each morning.
Best Vacation Rental in Hawaii for Digital Nomads | Rustic 3 Bed Cottage on Ocean Cliffs
Tucked away in a lush forest, this rustic cottage boasts practical amenities and unique touches. It’s decorated with quirky cushions and art and has fast internet connection, making this jungle paradise the perfect spot for a digital nomad. The home is well supplied with everything you might need from a self-catering vacation rental in Hawaii. Located beside the ocean, digital nomads will be able to enjoy peace and quiet during work hours while still enjoying a beach environment when off the clock.
Best Treehouse Vacation Rental in Hawaii | Bird Themed Forest Treehouse for 2
Built on stilts and painted in bright blue and yellow canary colours, this bird-themed treehouse attracts some of the best birdlife in Hawaii. The home is built using wooden panels and fitted with a modern and clean kitchen, dining area, and cosy living area. This colourful and newly renovated treehouse will exceed all expectations. Keep your eyes peeled for the bird-inspired art, fabrics, and furniture that is scattered throughout the treehouse.
Best Vacation Rental in Hawaii for Stargazing | Isolated Contemporary Forest Treehouse for 2
Different shades of wood, concrete and exposed iron ceilings, and an abundance of glass make this a modern treehouse of architectural dreams. It’s placed in a jungle environment surrounded by flora and features large glass windows and skylights to invite the wild outdoors in. A simple self-catering kitchenette offers everything you need to cook a home-cooked meal, which you can enjoy out on the balcony.
Don’t Forget Your Hawaii Travel Insurance
ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.
They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.
SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!
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Final Thoughts on Hawaii Vacation Rentals
Hawaii’s main islands are best known for their natural beauty, excellent beaches, and awesome volcanoes. Alongside the culture and heritage of the islands, there are plenty of places to go in Hawaii to learn more about this epic destination.
Whether visiting with a large family, a group of friends, or a romantic partner, Hawaii is flooded with extraordinary vacation rentals for every type of visitor. From treetop oases overlooking never-ending rainforests to villas hanging over dramatic cliff faces, you’ll have no issue finding the right accommodation to suit your budget and desires!
And for transparency’s sake, please know that some of the links in our content are affiliate links. That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!