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 57 luxury villa rentals

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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
  • Maison de Cortes, Los Cabos

    Sheldon James and the entire team delivered an exceptional, seamless experience from start to finish. From the moment we arrived, we were met with the warmest welcome and an incredible level of attentiveness that truly set the tone for...

    Lucylena C., January 2026
  • Akatsuki, Thailand

    This trip has been an exceptional experience from day one. A superb villa, clearly carefully curated, with easy lines of communication between us, Sheldon James and the villa concierge, meant that from the minute we arrived on the island there...

    Neil O., December 2025
  • Dolphin Manor, Hawaii

    Great house, as advertised. Nicely furnished. Pool is smaller than I thought from the pictures, but I should have looked more carefully. Activities and arranged chef were wonderful. The outreach from the concierge distinguished SJ and was much appreciated.

    Dave B., December 2025
  • Hokulani 825, Hawaii

    Great place and amazing service. Very profession team we loved them and our get away there in Maui 🙂

    Jamie E., May 2025
  • Just in Paradise, St. Martin

    Wade with Sheldon James was exceptional to work with. Everything was perfect!

    Lelah P, June 2024
  • Nevaeh, Anguilla

    Wade chose an amazing villa for us. This is the second time using him and he has been spot on each time. Tania was super helpful and everything was arranged perfectly and her recommendations were great. I thought the staff...

    Greg P., December 2025
  • We spent a great 10 days at Hacienda B5 in Punta Cana. We choose a villa experience to avoid the crowds of an all inclusive and we were not disappointed. The villa was perfect for our extended family of...

    David P, March 2024
  • Point View Place, Colorado

    Our Family recently stayed at Point View Place in Breckenridge, Colorado. Starting with our initial contact at Sheldon James (James D’Silva) the trip could not have been more Perfect! We have partnered with James D’Silva on a number of properties...

    Barbara G., August 2022
  • Villa Santa Cruz, Puerto Vallarta

    My team and I came to the Villa for a work retreat. What an absolute delight! Everything was wonderful, the staff were extremely accommodating and considerate. The food and villa itself were remarkable. An unforgettable experience – would definitely book...

    Lou K., November 2023

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.

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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.
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