Costa Rica
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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

Experienced by Our Team
$1,200 - $6,500/nt
Compass House, Costa Rica, Tamarindo
18 Guests • 9 Bedrooms • 9 Bathrooms
Experienced by Our Team
$1,500 - $5,500/nt
Andaz 2 Bedroom Papagayo Suite, Costa Rica, Papagayo
6 Guests • 2 Bedrooms • 2 Bathrooms
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Experienced by Our Team
$2,490 - $4,990/nt
Casa Alang Alang, Costa Rica, Tamarindo
20 Guests • 8 Bedrooms • 9 Bathrooms
Experienced by Our Team
$2,600 - $8,500/nt
Andaz 3 Bedroom Penthouse, Costa Rica, Papagayo
8 Guests • 3 Bedrooms • 3 Bathrooms
Experienced by Our Team
$15,000 - $28,900/nt
The Hive, Costa Rica, Papagayo
16 Guests • 6 Bedrooms • 8 Bathrooms
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

  • Tremblant Village Walk, Quebec

    Wade and the Sheldon James team were incredibly helpful and provided a true 5-star service and product. Their chalet recommendation was a perfect fit for our needs and the attention to detail during our entire stay was impeccable including the...

    Bernard A, April 2025

  • 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

  • Villa Pacifica, Punta Mita

    Excellent facilities & great staff!

    David R., February 2025

  • 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

  • Nevaeh, Anguilla

    Wade chose an amazing villa for us. This is the second time using him and he has been spot on each time. Tania was super helpful and everything was arranged perfectly and her recommendations were great. I thought the staff...

    Greg P., December 2025

  • 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

  • Casa Familia, Punta Mita

    The house was great! Beautiful grounds and really nice beach below. The staff was excellent. Reminded me of the 6 star service you get on a yacht charter. Helen was wonderful as always. Will definitely consider booking again in the...

    Greg P., December 2024

  • Villa Embrace, St. Barts

    I have been working with James for over 10 years to locate beautiful homes for our special family vacations across the world. He has a gift of listening to his clients and is the most patient human being on this...

    Carol W., March 2024

  • Serena, St. Martin

    Beautiful villa on the Baie de Rouge beach,

    Pearly C, November 2025
Experienced by Our Team
$24,000 - $40,000/nt
Villa Avellana, Costa Rica, Papagayo
23 Guests • 10 Bedrooms • 13 Bathrooms
$400 - $2,300/nt
Casa Tamarindo, Costa Rica, Tamarindo
10 Guests • 4 Bedrooms • 3 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.

$549 - $5,000/nt
Casa Descanza, Costa Rica, Tamarindo
12 Guests • 6 Bedrooms • 5 Bathrooms
$600 - $4,500/nt
Casa de Sophie, Costa Rica, Playa Conchal
14 Guests • 4 Bedrooms • 4 Bathrooms
$600 - $3,500/nt
Jade, Costa Rica, Tamarindo
8 Guests • 4 Bedrooms • 4 Bathrooms

Ready to go?

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Send us your inquiry and one of our Villa Experts will reach out as soon as possible. Or call to speak to someone immediately.
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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.

Internal Info

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Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

Internal Info

Supplier:
Commission Value:
Link to Rates:
Price & Villa Details:
Villa Status:
Villa Status Description:
Sales Pitch (INTERNAL VIC TOOL):
Look Before You Book Details:
Whitelabel URL:

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