Costa Rica - Sheldon James

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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 57 luxury villa rentals

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

$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

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
Ani Dominican Republic, Dominican Republic

Once again, James has thought about everything my family is looking for in a Villa vacation. We had an amazing family vacation that exceeded our expectations. The Villa was beyond our imagination. It was pristine. The Staff was impeccable. They...

Debbie A, July 2024
Cabuya, Turks and Caicos

From the initial enquiry, James and his team were exceptional, responsive and organised. James helped us find the Villa that suited our taste and needs, and was patient while we reviewed each one and finally made a decision (recommended by...

Alyssa R, July 2024
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
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
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
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
Villa Aquazure, Turks and Caicos

Great experience, great location, and great service by Axel. My family and I had the best vacation.

Dragan N., November 2024
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
Villa Santa Cruz, Puerto Vallarta

My team and I came to the Villa for a work retreat. What an absolute delight! Everything was wonderful, the staff were extremely accommodating and considerate. The food and villa itself were remarkable. An unforgettable experience – would definitely book...

Lou K., November 2023

$600 - $4,000/nt

Villa Alegria, Costa Rica, Hacienda Pinilla

17 Guests • 6 Bedrooms • 6 Bathrooms

$600 - $4,000/nt

Villa Uana, Costa Rica, Flamingo Beach

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.

$604 - $4,250/nt

Casa Blanca, Costa Rica, Hacienda Pinilla

20 Guests • 6 Bedrooms • 6 Bathrooms

$700 - $4,000/nt

Cabaña 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

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.

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.

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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:

Discover our 57 luxury villa rentals in Costa Rica

THE SHELDON JAMES WAY

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