Costa Rica

Costa Rica used to be very off the beaten path. Though the secret may be out now about this glorious tropical destination, don’t think you’ll be bumping elbows with other tourists here. There’s plenty of Costa Rica to go around, and luxurious privacy is the name of the game; just you, your villa, the parrots and the monkeys.

There’s plenty of Costa Rica to go around, and luxurious privacy is the name of the game.

Discover our 51 luxury villa rentals

$373 - $2,254/nt
$400 - $2,300/nt
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$549 - $5,000/nt
$600 - $3,500/nt
$600 - $4,000/nt
Villa Reviews
  • The Point Luxury Villa, Costa Rica

    Another fabulous vacation in a first-class villa in a spectacular location in Costa Rica. Excellent service from Sheldon James and all the onsite staff. Highly recommended.

    Anne P., February 2025
  • Makena Kai, Hawaii

    Our family has worked with James D’Silva for several years to create perfect villa vacations that perfectly meet our needs. We have booked vacations with him in Hawaii, Cabo San Lucas, Jamaica, etc. He and his team are always customer...

    Brian M, July 2021
  • Baraka Point, Virgin Gorda

    My family has a great time and Wade was a true professional. The trip was everything Wade said it would be. The staff on Baraka Point was unreal and made me and my family feel very comfortable. and a...

    Zachary Z, November 2023
  • Casa Cervo, St. Martin

    If you’re looking for a well organized, customer focused, competitively priced luxury villa rental agency you won’t find anyone better than Sheldon James. We are repeat satisfied customers, and most recently (last week) were blown away by one of their...

    Norm L,
$600 - $4,000/nt
$700 - $4,000/nt

Costa Rica can be as adventurous or as relaxed as you wish…or both, all in the same day. Known for its protected and biodiverse jungle and quiet beaches lining a rugged coast, especially in the Pacific provinces of Guanacaste and Puntarenas, activities on land and on the water abound. Golfing and spa retreats are also very popular here.

$700 - $3,800/nt
$750 - $5,000/nt
$750 - $4,500/nt

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THE SHELDON JAMES WAY

Holidays shouldn’t be hard work. At Sheldon James, we’ll think about all the details so you can just get busy dreaming (and packing). With a guest-forward focus, our goal is to go beyond the booking and create an end-to-end villa experience to remember.

Our guest-first focus

You’re always our top priority–we’ve got you covered on all your travel needs before, during and after your stay.

Hand-selected villas

Our standards are high. Each and every villa we offer has been visited or thoroughly reviewed by a member of our team.

A trusted network

We only work with partners we know and trust, so you can count on them to reflect our values and standards.

Our mission is to transform our experience and relationships into a unique offering for you.
Client-first focusHand-select villasA trusted network

explore the world

We have much more than you see here. Want to escape to Thailand or an exclusive villa in Mykonos? We can do that.