Hawaii is a true paradise! So I’ve rounded up the dreamiest vacation homes in Hawaii on the islands of Maui, Kauai, Oahu, and Big Island.

The Ultimate Hawaii Travel Guide

Pro Tip: Hawaii is a year-round destination. The closest thing Hawaii has to an off-season is February. You’ll have some of the lowest prices and crowd numbers this month because it’s after the holidays and before spring breaks.

Hawaii is also one of the Best Destinations To Visit In February because it’s the peak season for humpback whale-watching, so you’ll have lots of opportunities to see these impressive gals.

Here are the best vacation homes in Hawaii for your dream trip!

Romantic Cottage

Hanalei, Kauai

2 guests · 1 bedroom · 2 beds · 1 bath

This cottage is perched on a bluff overlooking the Wainiha River on an acre of lush gardens. You’ll have stunning views of the entire river valley. The private pool, hot tub, and patios take this property over-the-top, and the home is just two miles from some of the most beautiful beaches in the world.

Surf House

Haleiwa, Oahu

3 guests · 1 bedroom · 1 bed · 1.5 baths

If you want to walk out your door onto the beach and fall asleep listening to the waves, then this oceanfront house is for you. From your private yard, you’ll have stunning views from North Shore’s famed Pipeline all the way to Sunset Beach’s West Peak.

Luxury Villa

Kailua, Oahu

12 guests · 6 bedrooms · 7 beds · 8 baths

Presidents and celebrities have stayed in this mansion! The property has a Japanese-style garden and a lagoon pool with waterfalls, lava rocks, and beautiful rainforest foliage. You’ll also have a jacuzzi, BBQ, gourmet kitchen, two living rooms, and multiple indoor and outdoor dining spaces.

Check out all the best vacation homes in Oahu

The Dream Temple

Haiku, Maui

6 guests · 2 bedrooms · 3 beds · 1 bath

Immerse yourself in the natural beauty of Maui at this eco-designed bamboo cottage. There are three covered decks, a grill, a hot tub, and a resort-style pool. Plus, the home’s lush, tropical landscaping makes this a true jungle paradise.

Duke’s Cottage B&B

Makawao, Maui

2 guests · 1 bedroom · 1 bed · 1 private bath

This boutique bed and breakfast has a vintage Hawaiian theme with a modern twist. Your private room has a bathroom, kitchenette, and a patio. You’ll be able to enjoy the property’s pool, jacuzzi, fire pit, hammock, and outdoor seating areas, and the breakfast here is the perfect way to start your day.

Discover all of the Dreamiest Vacation Homes in Maui

Tropical Paradise

Captain Cook, Big Island

5 guests · 2 bedrooms · 3 beds · 2 baths

This modern-meets-Hawaiian-style home is perfectly located for exploring the island. There are incredible views of the ocean, vaulted ceilings, and a covered lanai. You’ll also love the six-person hot tub.

Volcano, Big Island

6 guests · 2 bedrooms · 3 beds · 4 baths

This home is in the rainforest on the slopes of the Kilauea volcano, right outside Hawaii Volcanoes National Park. You’ll be at an elevation of 3,750 feet, so you’ll want layers for the evenings and mornings. The house comes with large bedrooms, a luxurious covered porch, and a hot tub. 

Tiny House on a Lava Field

Kalapana, Big Island

5 guests · 2 bedrooms · 5 beds · 1 bath

If you’re looking for a truly unique and off-the-grid property, then this vacation home is for you. You’ll be at the foot of one of the world’s most active volcanos, and you can see Pele’s Orange glow from this property!

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