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
  • 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
  • Beach Enclave GB Oceanview Villa 6bdr, Turks and Caicos

    We had a great experience at beach enclave. 5 star property and service. The only confusion was at first when the villa number/size was slightly different than what we thought we signed up for, but nonetheless we had a...

    Matt P, February 2023
  • Twin Palms Villa, Turks and Caicos

    The house was unbelievable and the staff and chef were incredible. Everyone was so nice. Whatever we needed all day and night we got as soon as we requested and everyone was so happy. Kids loved it! Location was great...

    Ally V., March 2026
  • 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
  • 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
  • The Resort, Spain

    The Sheldon James team knocked it out of the park again for our annual trip. We are typically confirming late into the rental season but Wade and his team always comes through with a great rental property for our large...

    Hillary Fujii, June 2024
  • Indigo (formerly Greatview), Jamaica

    Sheldon James was truly i n c r e d i b l e to work with. James and Alba planned a very special family reunion trip to Jamaica and took...
    Sophie G, March 2026
  • Aqua Dream, St. Martin

    The staff were Excellent,very knowledgeable and professional.My Experience was Excellent looking forward doing business again.

    Vernon M, March 2024
  • Villa Embrace, St. Barts

    Embrace St Barts exceeded our expectations. The view and sunsets were beyond amazing. The home was impeccably designed, inviting and comfortable THE ARTWORK amazing. Dorian was so helpful to be sure we experienced all the island had to offer....

    Boyd M, March 2024

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.

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.

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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.

Our mission is to transform our experience and relationships into a unique offering for you.
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