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
  • Sugar Kube, Turks and Caicos

    It was an amazing Villa loved every moment of our honeymoon. The staff were amazing they provided such a great service from Housekeeping to our 2 masseuse Melanie and Marie and your chefs Juan and Emara, Great food. We will...

    Luis R, December 2024
  • Beach Cake, Turks and Caicos

    We’ve utilized the expertise of James D’Silva for all of our high end traveling for years. His knowledge, integrity, and genuine level of care are unmatched. The memories created in the villas he has recommended have been equally priceless.

    Greg H, January 2022
  • Serena, St. Martin

    We had an amazing vacation in St. Martin staying at the Villa Serena. Our group of 10 had very specific requests on the type and location of a villa. Wade listened to all our “wishes” and found the best...

    Beth E, March 2024
$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

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