Plantation at Paradise Point

Oahu, Kailua

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

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Bali Estate

Oahu, Diamond Head

  • 3 Bedrooms
  • 2 Bathrooms
  • From at USD 2,000 - 2,500/nt

Take me there
Oahu Vacations

Oahu Villa Rentals

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Featured Oahu Villas

Plantation at Paradise Point

Plantation at Paradise Point
Oahu, Hawaii
5 Br, From $3,300 / nt.
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Plantation at Paradise Point, Oahu
Oahu Lani

Oahu Lani
Oahu, Hawaii
10 Br, From $5,200 / nt.
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Oahu Lani, Oahu
Paradise Cove Estate

Paradise Cove Estate
Oahu, Hawaii
7 Br, From $7,500 / nt.
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Paradise Cove Estate, Oahu

Oahu Vacation Rentals

Oahu villa rentals are some of the most luxurious and elegant estates offered by CaribbeanWay. This cosmopolitan and tropical wonderland attracts people from all over the globe with its famous natural beauty, award-winning surfer's beaches and gourmet restaurants, and Oahu villas are the perfect complement to its ambiance of barefoot luxury.

Oahu and villas in Oahu are especially ideal for travelers seeking a subdued retreat with amenities and activities within easy reach.

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