Costa Rica

Costa Rica used to be very off the beaten path. Though the secret may be out now about this glorious tropical destination, don’t think you’ll be bumping elbows with other tourists here. There’s plenty of Costa Rica to go around, and luxurious privacy is the name of the game; just you, your villa, the parrots and the monkeys.

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

Discover our 51 luxury villa rentals

$373 - $2,254/nt
$400 - $2,300/nt
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.
$549 - $5,000/nt
$600 - $3,500/nt
$600 - $4,000/nt
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
  • Casa Napa, Riviera Maya

    Remarkable property that exceeds expectations in almost every way… start with location… the deck is literally a stones throw from the water…. Impeccably designed and maintained landscape, including plenty of coconuts… we asked Emilio to cut a couple down...

    Jon P., December 2025
  • 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
  • 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
$600 - $4,000/nt
$700 - $4,000/nt

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. Golfing and spa retreats are also very popular here.

$700 - $3,800/nt
$750 - $5,000/nt
$750 - $4,500/nt

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.