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 58 luxury villa rentals

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Villa Reviews
  • Compass House, Costa Rica

    We had an amazing trip. The house was perfect. The outdoor pool area was ideal for our family, we had a hard time even leaving the house. The sunsets are better than anyone can imagine. We will definitley be...

    Chris M., March 2026
  • 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
  • Founders Villa, Dominican Republic

    James, who I have been working with for many years on our annual family vacations, is great to work with and he always gives me great properties. The Villa is exceptional and services five star.

    Alan M., May 2025
  • 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
  • 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
  • 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
  • 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
  • The One, Punta Mita

    The home is gorgeous with incredible attention to detail with all the amenities it was like your own private boutique hotel . The staff is absolutely a major highlight of this experience. They are at your every beck and call...

    Julie B., January 2026
  • Claudine, France

    The apartment in Paris was wonderful, comfortable and in a part of Paris that made for a very walkable and enjoyable experience. The staff at Sheldon James made planning for our Paris trip very effective and easy, so we...

    Jenny M, May 2024
  • 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

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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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.

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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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