Costa Rica

Though the secret may be out about this glorious destination, don’t think you’ll be bumping elbows with crowds in Costa Rica. There’s plenty of beauty to go around, and luxurious privacy is the name of the game; just you, your villa, and the monkeys.

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

Discover our 59 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
  • Solara, Turks and Caicos

    The home was beautiful, the staff was lovely and very accommodating. Dan was our right hand man the whole trip, making sure our cups were never empty and that we were always happy. He took great care of us...

    Cam N, May 2024
  • Villa Azetes, St. Barts

    Loved it! Excellent work to get the two villas near each other. cleaning people were great. Loved the food they brought us

    David K, December 2025
  • Kishti East, Anguilla

    Our week in Anguilla was perfect. The villa was exactly as described. The location, the staff — magnificent. The food blew us away. (Dinner out was more of an activity though we should’ve taken advantage of the villa chef more.)...

    Emma J, December 2024
  • Casa La Laguna, Los Cabos

    The house was stunning! Every person on the staff was wonderful and took such great care of us. Whatever we needed, they made sure they got…down to the beer pong we asked for! Would definitely vacation here again.

    Kyle L., January 2024
  • 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,
  • Turtle Nest, St. Martin

    Turtle Nest exceeded our expectations. The house was just perfect for the 8 of us, ages 8-73, with common both areas and secluded areas. Alba the concierge was incredibly helpful before we arrived as were Gio (concierge) and Chana (housekeeper)were...

    Suzanne S., March 2026
  • Ani Dominican Republic, Dominican Republic

    Visiting Villa Ani was one of the best family trips we have ever taken. Working with Wade to find new places is always such a pleasure. Sheldon James properties never disappoint and one of the aspects that make it...

    Brown, March 2024
  • Villa Pacifica, Punta Mita

    Excellent facilities & great staff!

    David R., February 2025
  • Tremblant Village Walk, Quebec

    Wade and the Sheldon James team were incredibly helpful and provided a true 5-star service and product. Their chalet recommendation was a perfect fit for our needs and the attention to detail during our entire stay was impeccable including the...

    Bernard A, April 2025

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.

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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.

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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.

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

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