Bali Hale

Maui, Lahaina

  • 4 Bedrooms
  • 5.5 Bathrooms
  • From at USD 1,800 - 3,800/nt

Take me there

Plantation at Paradise Point

Oahu, Kailua

  • 5 Bedrooms
  • 5.5 Bathrooms
  • From at USD 3,300 - 6,000/nt

Take me there

Ali'i Villa

Big Island, Mauna Lani Resort

  • 3 Bedrooms
  • 3.5 Bathrooms
  • From at USD 675 - 900/nt

Take me there
Hawaii Vacations

Hawaii Villa Rentals

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Featured Hawaii Villas

Hale Nana Kohola

Hale Nana Kohola
Big Island, Hawaii
4 Br, From $2,600 / nt.
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Hale Nana Kohola, Big Island
Honolulu Sky Villa

Honolulu Sky Villa
Oahu, Hawaii
4 Br, From $1,000 / nt.
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Honolulu Sky Villa, Oahu
Horizon of Gold

Horizon of Gold
Maui, Hawaii
4 Br, From $2,995 / nt.
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Horizon of Gold, Maui

Hawaii Vacation Rentals

CaribbeanWay's selection of villas in Hawaii occupies some of the most coveted real estate on earth. These islands evoke a unique nostalgia in people who have never even visited the area and, for people who have been lucky enough to visit Hawaiin villas before, they have a tendency to call you back more than once.

Holidays at villas in Hawaii can be as peaceful or action-packed as guests would like. Surfing, hiking across volcanoes, pineapple plantation tours and golfing are just some of the activities enjoyed by guests of our Hawaii villa rentals.

One-on-one Villa Rental Planning

Our top priority is making sure you're 100% thrilled with your villa vacation, every step of the way. Our Villa Specialists are exceptionally keen guides who will help you find the Caribbean villa that's perfect for you. And once you've found it, our detail-oriented Concierges will take care of all the arrangements. Put your plans in our ex

What can your Concierge arrange? Here are some ideas:

  • Pre-stocking the villa with food
  • Door-to-door luggage delivery
  • Private yoga instructor
  • Private tour guides
  • Poolside massages
  • Personal chefs
  • Car rentals
  • Theme parties