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 57 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
  • Villa Cascade, Turks and Caicos

    10 stars rating!! It was the most luxurious place I have ever stayed in, and I loved walking out my bedroom door each morning to see my swimming pool.
    The staff was incredible, and made me feel like a queen....

    Jessi, January 2026
  • 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
  • Sunset Point, Turks and Caicos

    I have worked with James on many Villa vacations over the past 8 years. They are always exceptional. James has learned what my family is looking for in a holiday and is very particular in which Villa’s he sends...

    Debbie A, March 2025
  • 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
  • Amandara, St. Martin

    The villa was fantastic, spacious and well kept. Everyone found the experience unique. We did not want to go out, we had everything we needed including sports and entertainment. Chef Tim was incredible, really attentive and aware of everybody’s taste,...

    Carole G, February 2026
  • 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
  • We’ve been using Sheldon James for all of our villa rentals and this was yet another perfect experience! The team really knows what they’re doing and always find the perfect villa for our events.

    Norm L, June 2023
  • Villa Bash, Turks and Caicos

    WOW, WOW,WOW. This was our first trip through Sheldon James. Unfortunately no outer vacation will ever live up to what we experienced. We rented Villa Bash in Turks and Caicos for my wife’s 50th birthday with 5 other couples. We...

    Alex D., December 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.

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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