Italy

Countless movies have been set in Italy – scroll our villas’ pictures and you’ll understand why. Italy is a scene-stealer, each vista more picture-perfect than the next, from the rolling, cypress-lined hills of Tuscany to the cliffsides of the Amalfi Coast.

Italy’s vistas are more picture-perfect than the next, from Tuscany to the Amalfi Coast.

Discover our 42 luxury villa rentals

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Villa Reviews
  • 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
  • Claudine, France

    The apartment in Paris was wonderful, comfortable and in a part of Paris that made for a very walkable and enjoyable experience. The staff at Sheldon James made planning for our Paris trip very effective and easy, so we...

    Jenny M, May 2024
  • Villa Embrace, St. Barts

    Embrace St Barts exceeded our expectations. The view and sunsets were beyond amazing. The home was impeccably designed, inviting and comfortable THE ARTWORK amazing. Dorian was so helpful to be sure we experienced all the island had to offer....

    Boyd M, March 2024
  • Casa Minitas, Dominican Republic

    Great working with Alba who was attentive and prompt for each follow up.

    Marco, February 2026
  • 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
  • Villa Buena Vida, Dominican Republic

    Liv was amazing at helping us coordinate this incredible trip! We will definitely look her up again if we plan something similar!

    Rajat K., February 2026
  • 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
  • Maison de Cortes, Los Cabos

    The home was truly amazing, the staff was friendly and polite. The chef we had made amazing food and the group couldn’t have been happier. This was the best house we have stayed at in Cabo with great build...

    Fabio C, November 2024
  • Villa Tartaruga, Dominican Republic

    Villa Tartaruga is possibly the nicest property we’ve ever stayed at as a family. The staff was outstanding, attentive, friendly, fun….the food cooked by the wildly talented Melania was an absolute treat, every single meal. We had beautiful weather and...

    Thomas T., July 2025
  • 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

Don’t fill your calendar with activities — this ancient region should be enjoyed slowly, with a stroll down cobbled villages, a bike ride to the closest gelato shop, or a languid lunch of fresh pasta and cold Vernacchia white. When you’re really ready to relax, your villa in Italy will welcome you back with classic style.

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THE SHELDON JAMES WAY

We don’t have to work hard to make an Italian villa holiday something to remember, but we still will. At Sheldon James our goal is to take your luxury vacation to the next level, through high-end services and a custom itinerary of activities.

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

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