I’ve been lucky enough to visit Hawaii three times, exploring its islands and staying in some seriously breathtaking vacation homes. Whether you’re dreaming of a beachfront villa on Maui, a jungle hideaway on the Big Island, or a luxury retreat on Oahu, these 13 stunning homes on Airbnb and VRBO are perfect for soaking in all the beauty Hawaii has to offer.
From private pools with ocean views to lush tropical settings, each spot has something special that will make your stay unforgettable. I can’t wait to share my favorite finds with you—get ready for some serious island inspiration!
The 13 Coolest Vacation Rentals in Hawaii
Here are the best Airbnbs and VRBOs in Hawaii by category, considering factors such as amenities, trip types, and budgets. The following sections will cover each listing in more detail.
- Top Overall: Pineapple Cottage Farm Stay
- Best Luxury Villa: Unique Beachfront Estate
- Most Romantic: Hale Kokio Home
- Best for Large Groups: Hawaii Beachfront Home
- Top Cheap VRBO: Peace of Paradise Jungle Getaway
- Coolest with a Pool: Treehouse with Hot Tub and Swimming Pool
- Top Beach House: Kilauea Oceanfront Accommodation
- Best with a View: Hawai’i Villa for Rent
- Most Unique: Hale Hubner Treehouse Cottage
If romantic island getaways, beach houses, and luxury rentals in Hawaii all sound good to you, you’re in for a treat! Below are some of the most unique stays in HI:
Guest Post by Charity De Souza from charitydesouza.com
1. Pineapple Cottage at Hulili Tropical Fruit Farm – Among the Best Hawaii Vacation Rentals
Location: Hakalau, Hawaii
Rates from: $135 per night
Accommodates: 4 guests
One of the most unique vacation rentals on the Big Island of Hawaii, this adorable Pineapple Cottage is simply magical. Admire the sweeping ocean views from a comfy rocking chair or queen-size swinging bed from the gorgeous lanai, then sit back and enjoy the cottage’s soundtrack of beautiful birdsong.
Inside this Hawaii vacation rental, there’s a master suite with a king-size bed and full-size futon so up to four guests can fit comfortably. Take a stroll through the orchards of the private farm, which boasts a citrus grove with lemons, limes, and oranges, then dig into your sweet treats while enjoying a gorgeous sunset. It’s easy to see why this is among the coolest rentals in Hawaii!
2. Beachfront Estate with Private Hot Tub – A Top Beach House for Rent in Hawaii
Location: Anahola, Hawaii
Rates from: $841 per night
Accommodates: 6 guests
This luxury beachfront rental in Hawaii offers 5-star amenities, featuring a magazine-worthy interior and sliding glass doors that open out onto a spacious lanai. You might be tempted to stay here forever with its gorgeous views, while this stylish three-bedroom home also boasts luxurious amenities such as a hot tub, modern kitchen, BBQ grill, and beautifully landscaped yard.
Best of all, a secluded shoreline is within steps from your front door, offering a tranquil shoreline perfect for swimming, strolling, and basking in the sunshine. What more could you want in a top Hawaii Airbnb or VRBO?
3. Hale Hubner Treehouse Cottage – One of the Coolest Treehouse Rentals in Hawaii
Location: Volcano, Hawaii
Rates from: $130 per night
Accommodates: 4 guests
A stress-free alternative to big resorts, this whimsical treehouse cottage in Hawaii is a wonderful retreat for nature lovers. Surrounded by bright green foliage, it’s nestled in the lush hapu’u fern and ohia rainforest. The studio-style space accommodates up to four guests comfortably, with its large picture windows with nature views, 20-foot-high vaulting ceilings, and spacious sun deck with a BBQ grill among its biggest highlights.
While the setting feels remote and private, the Hawaii treehouse rental is actually close to a variety of popular attractions on the Big Island, including Volcanoes National Park. Is this one of the coolest Hawaii house rentals? It sure is!
4. Affordable Beach House Rental in Hawaii, Steps to the Ocean
Location: Haena, Hanalei, Hawaii
Rates from: $335 per night
Accommodates: 5 guests
Offering tropical island-style lodging, this Beachcomber bungalow on the north shore of Kauai can accommodate up to five guests in its three-bedroom layout. Only a one-minute walk from the beach, this peaceful sanctuary boasts a bright and airy atmosphere with wood and tile floors, high beam ceilings, and skylights.
Let the sound of the ocean lull you to sleep, then wake up and take advantage of the epic snorkeling, swimming, and shell collecting available at the white sandy beach. Just a short drive away is the gateway to the spectacular Na Pali Coast. With so much to see and do nearby this is definitely one of the best Hawaii beach houses for rent, especially for families!
5. Peace of Paradise Jungle Getaway – One of the Most Unique Vacation Rentals in Hawaii
Location: Hawaiian Paradise Park, Keaau, Hawaii
Rates from: $85 per night
Accommodates: 2 guests
A romantic retreat for two, this jungle hideaway vacation home in Hawaii is surrounded by an acre of tropical landscaping with citrus, mango, lychee, and starfruit trees. The serene atmosphere of the bungalow is complemented by its large floor-to-ceiling windows and stylish interior with a cozy living and entertainment room and ensuite master bedroom.
Escape the stressors of everyday life and reconnect with nature while enjoying the garden views from your lush soaking tub, then explore everything the Big Island has to offer. Though there’s a lot to see and do throughout the island, after stepping foot inside this unique Hawaii rental on Airbnb and VRBO, it will be hard to leave!
6. Luxury Hawaiian Island Rental with Hot Tub + Sauna
Location: Volcano, Hawaii
Rates from: $225 per night
Accommodates: 6 guests
This gorgeous two-bedroom beach cottage in Hawaii has everything you need for a relaxing getaway in Hawaii. Set on two acres, it features a large Jacuzzi, detached outdoor sauna imported from Finland, and two outdoor hot showers, as well as a garden trail with koi ponds. There’s even an Imu house where you can hire experienced locals to prepare a traditional Hawaiian luau.
If that’s not enough luxury for you, the chic cottage also boasts a gourmet kitchen, four fireplaces, and wrap-round upper and lower decks with incredible rainforest views. I can’t imagine a better HI vacation rental than this one in the jungle.
7. Hawaii Villa Rental with Magnificent Mountain Views near Beach & Village
Location: Princeville, Hawaii
Rates from: $335 per night
Accommodates: 6 guests
This Kauai vacation home for rent in Hawaii is an idyllic retreat for up to six guests, offering gorgeous mountain views. The three-bedroom townhouse features a breezy indoor/outdoor lanai overlooking Mount Namahana, as well as a covered area with a hot tub, reading room, modern kitchen, and outdoor grill.
Don’t worry about keeping cool, as each of its rooms has air conditioning and beach essentials such as bikes, boogie boards, beach chairs, and umbrellas are complimentary. It’s just 15 minutes from Hanalei Bay and five minutes from Princeville shopping, while Queen’s Bath, Hideaways, and Anini Beach are within walking distance. Is this among the coolest Hawaii vacation properties? 100%!
8. Peace of Heaven in Kona Paradise – Among the Top Hawaii Beach Homes to Rent in Kona
Location: Kona Paradise, Captain Cook, Hawaii
Rates from: $135 per night
Accommodates: 6 guests
Dubbed “A Little Peace of Heaven”, this picture-perfect beachfront house in Hawaii boasts incredible island views and a professionally decorated interior. Relax on the lanai and enjoy the panoramic ocean views while relaxing on comfy sun loungers or dine alfresco on the charming dining set. A picnic table offers the perfect spot to appreciate the beautiful tropical landscaping, while you can also bathe under the stars in the outdoor shower.
High-speed Wi-Fi and Netflix are available at the house, but it will be tough to pull yourself away from the private black pebble beach and popular snorkeling sites nearby, including Two Step, Captain Cook Monument, and Hookena Beach Park. With so much charm and personality, this is one of the best Hawaii houses for rent on the beach, hands down.
9. Hawaiian Dream Temple with Private Hot Tub & Shared Pool
Location: Pauwela, Haiku, Hawaii
Rates from: $427 per night
Accommodates: 6 guests
Easily one of the most unique vacation rentals in Hawaii, this Asian-style bamboo cottage is not your typical overnight stay. The custom-designed eco-friendly cottage features 1,800 feet of living space, including three large covered decks.
Enjoy the postcard-worthy views of tropical flowers and the peaceful sound of local birds from the private hot tub or unwind with a soak in the bathroom’s oversized Jacuzzi tub. Afterward, take a dip in the shared 40-foot-long freshwater swimming pool with a lava rock waterfall. Visiting the surf town of Paia, hiking to a waterfall, and watching windsurfers at Ho’okipa Beach are popular activities nearby. Though after spending time at this Hawaiian beachfront rental, it will be hard to leave!
10. Hawaiian Charm Just Steps From the Ocean – A Top Rental Vacation Home in Hawaii for Families
Location: Kekaha, Hawaii
Rates from: $235 per night
Accommodates: 4 guests
Nestled on the sunny West Side of Kauai, the “Nene Nest” is a beautiful sugar plantation-style cottage. The two-bedroom property features an adorably charming pale yellow exterior and is just 152 steps from the ocean (to be exact).
Wake up and sip your morning coffee on the gorgeous lanai, relax in the comfy living room or dig your toes in the longest white-sand beach in the Hawaii Islands. Other perks include a pillow-top king and queen beds, outdoor hot shower, gourmet kitchen, and air conditioning. Take advantage of the area’s laid-back beach atmosphere away from the tourist crowds and easy access to Waimea Canyon, the Grand Canyon of the Pacific. If you’re seeking a top Hawaii beach house for rent, it truly doesn’t get any better than this!
Read next: Top Hidden Gems in America
11. Hale Kokio: A Hawaii House Rental for Romantic Getaways
Location: Kilauea, Hawaii
Rates from: $300 per night
Accommodates: 2 guests
A perfect escape for honeymooners or couples looking for a private oasis, this charming cottage in Kauai, HI is designed with comfort in mind. This Hawaii beach house rental offers an ideal home base for scenic road trips on the island, with a relaxing hot tub, spacious lanai, and sun loungers ready for your return.
Take a nap in the hammock tucked away in the banana patch, catch a flick on the Smart TV on the cozy sofa, or get out and explore the nearby town of Kilauea just five minutes away. Complimentary beach chairs, towels, snorkel equipment, and an umbrella are convenient for visiting nearby beaches such as Pila’a, Rock Quarry, Kalihiwai, and Anini. As far as Hawaii vacation rentals go, this is among the very best!
Read next: Island of Molokai Travel Guide
12. 2-Bedroom Cottage with Waterfall Pool
Location: Kihei, Hawaii
Rates from: $285 per night
Accommodates: 5 guests
Offering easy access to Maui’s top attractions, this beautiful two-bedroom Hawaii house rental is a tropical retreat for up to five guests. Two sliding glass doors lead to its outdoor oasis, which features a private deck, gas BBQ grill, outside shower, and heated pool surrounded by sun loungers and a covered seating area.
The modern house to rent in Hawaii has tons of perks for families, including a full kitchen, remote control ceiling fans in every room, and a washer and dryer, while all travelers will appreciate its prime location just one mile to the island’s best beaches. As such, it’s no wonder this is among the most unique Hawaii beach houses for rent on Maui!
13. Hawaiian Beach Home with Breathtaking Ocean Views
Location: Kalihiwai, Kilauea, Hawaii
Rates from: $850 per night
Accommodates: 8 guests
You can vacation in style in this lavish Hawaii home for rent, which is perched on one-half acre above the picture-perfect beaches at Kalihiwai Bay. The luxury HI vacation rental offers some of the best Pacific Ocean, beach, and mountain views on Kauai, where waterfalls can be seen in the distant Mount Namahana Range.
The hot tub and covered lanai are the best spots to take in the incredible island views, where you’ll have a chance to spot dolphin or whale sightings down below. Aside from its epic views, the air-conditioned house features four bedrooms and is close to the island’s award-winning golf courses, shops, restaurants, and beaches. Spend a weekend here, and you’ll quickly see why this is one of the coolest beach houses for rent in Hawaii for large groups!
Top House Rentals in Hawaii: Coolest Cottages and Beach Houses for Rent in the Hawaiian Islands
Have you ever stayed in a unique Airbnb or VRBO house rental in Hawaii? Let me know in the comments or on Insta, as I’m always looking to add to this round-up of the most unique beach house rentals in Hawaii!
Looking for more adventures around the US? Check out these dreamy destinations:
– Unique Rentals across the USA
– Best Lake Winnipesaukee Vacation Rentals
– Top Airbnb Homes in New England
ABOUT THE AUTHOR: Charity De Souza is a freelance travel writer from Orlando, Florida. Traveling full-time as a digital nomad for over a decade, her favorite travel memories include skydiving in Switzerland, eating sushi in Japan, and snorkeling with sea turtles in Indonesia. She currently resides in Porto, Portugal with her husband. You can follow her adventures at www.charitydesouza.com and on Instagram @marriednomads.
