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 48 luxury villa rentals

$373 - $2,254/nt
Casa Kenia, Costa Rica, Tamarindo
14 Guests • 5 Bedrooms • 5 Bathrooms
$400 - $2,300/nt
Casa Tamarindo, Costa Rica, Tamarindo
10 Guests • 4 Bedrooms • 3 Bathrooms
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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

  • Serena, St. Martin

    We had an amazing vacation in St. Martin staying at the Villa Serena. Our group of 10 had very specific requests on the type and location of a villa. Wade listened to all our “wishes” and found the best...

    Beth E, March 2024

  • Round Rock Estate, Anguilla

    Neil O, December 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
$549 - $5,000/nt
Casa Descanza, Costa Rica, Tamarindo
12 Guests • 6 Bedrooms • 5 Bathrooms
$600 - $3,500/nt
Jade, Costa Rica, Tamarindo
8 Guests • 4 Bedrooms • 4 Bathrooms
$600 - $4,000/nt
Villa Alegria, Costa Rica, Tamarindo
17 Guests • 6 Bedrooms • 6 Bathrooms
$600 - $4,000/nt
Villa Uana, Costa Rica, Tamarindo
16 Guests • 6 Bedrooms • 6 Bathrooms
$700 - $4,000/nt
Cabana de Playa, Costa Rica, Tamarindo
12 Guests • 6 Bedrooms • 6 Bathrooms
$700 - $3,800/nt
Puesta del Sol, Costa Rica, Tamarindo
16 Guests • 6 Bedrooms • 6 Bathrooms

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.

$750 - $5,000/nt
Soul House, Costa Rica, Tamarindo
14 Guests • 4 Bedrooms • 4 Bathrooms
$750 - $4,500/nt
Villa Sakura, Costa Rica, Playa Conchal
11 Guests • 4 Bedrooms • 4.5 Bathrooms
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.

Thank you for contacting us!

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Toll Free: 1-888-277-8882
International: +1 514-400-5151

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