Costa Rica

Costa Rica used to be off the beaten path. Though the secret may be out now about this glorious destination, don’t think you’ll be bumping elbows with other tourists. There’s plenty of Costa Rica 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

BE IN THE KNOW
Sign up for access to our private portfolio.
Pocket listings, early access, new villas and more.
VIP ACCESS STARTS HERE
EXCLUSIVE ACCESS ACTIVATED
Thank you and stay tuned.
Your insider news and more are on the way.
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
  • 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
  • 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
  • West Enclave 8, Los Cabos

    Our friends & family had a magnificent time at the villa. The staff was superb, the decoration was right on point, the beds were comfortable, the cooking was delicious, and the whole experience was entertaining and relaxing.

    Mark C, December 2023
  • Serena, St. Martin

    Beautiful villa on the Baie de Rouge beach,

    Pearly C, November 2025
  • Just in Paradise, St. Martin

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

    Lelah P, June 2024
  • 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
  • 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
  • Maui Ocean Breeze, Hawaii

    The property, as always, was very comfortable and enjoyable. We had been apprehensive about returning to Maui in light of the fire that had destroyed much of Lahaina, but it really did not impact our visit. Kapalua, Ka’anapali, and...

    Jim P, September 2024
  • 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

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.

Ready to go?

So are we.

Send us your inquiry and one of our Villa Experts will reach out as soon as possible. Or call to speak to someone immediately.
Inquire now
Toll Free: 1-888-277-8882
International: +1 514-400-5151
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.
Client-first focusHand-select villasA trusted network

explore the world

We have much more than you see here. Want to escape to Thailand or an exclusive villa in Mykonos? We can do that.