Anguilla

Why complicate things – villas in Anguilla tick every box. This island is known for offering 7-star luxury and is a bit of a hideaway, so if you’re looking to escape, Sheldon James Villas offers luxury villas in Anguilla’s best secret corners.

Anguilla offers 7-star luxury, beautiful beaches and a ton of privacy.

Discover our 27 luxury villa rentals

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Villa Reviews
  • 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
  • Round Rock Estate, Anguilla

    Neil O, December 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
  • 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
  • Turtle Nest, St. Martin

    Turtle Nest exceeded our expectations. The house was just perfect for the 8 of us, ages 8-73, with common both areas and secluded areas. Alba the concierge was incredibly helpful before we arrived as were Gio (concierge) and Chana (housekeeper)were...

    Suzanne S., March 2026
  • Amandara, St. Martin

    The villa was fantastic, spacious and well kept. Everyone found the experience unique. We did not want to go out, we had everything we needed including sports and entertainment. Chef Tim was incredible, really attentive and aware of everybody’s taste,...

    Carole G, February 2026
  • Twin Palms Villa, Turks and Caicos

    The house was unbelievable and the staff and chef were incredible. Everyone was so nice. Whatever we needed all day and night we got as soon as we requested and everyone was so happy. Kids loved it! Location was great...

    Ally V., March 2026
  • Casa Minitas, Dominican Republic

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

    Marco, February 2026
  • Sea 2 Infinity, Grand Cayman

    This was our third visit to Grand Cayman, and this time we stayed for two wonderful weeks (+ 3 extra days due to bad weather at home) at Sea 2 Infiniti in Rum Point. What a beautiful home! From the...

    Debbie W., January 2026
  • 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

Anguilla is easy to love. Powder-soft beaches and glassy turquoise water are the order of the day here, often just steps out of your Anguilla villa’s door. The island is on the sleepier side, but we can get your heart racing with watersports, golf and more. For something a little different, try an excursion to St Martin or St Barts.

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THE SHELDON JAMES WAY

Sheldon James has stayed and played at our Anguilla villas and can guide you through choosing the best home for your next holiday. When you arrive, our trusted on-island partners will help us deliver an unforgettable experience.

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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