Anguilla

Why complicate things – villas in Anguilla tick every box, from style to substance. This island is known for offering seven-star luxury and being a bit of a hideaway, so if you’re looking to escape somewhere, Anguilla might just be it. Sheldon James offers luxury villas in Anguilla’s best secret corners. 

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

Discover our 19 luxury villa rentals

$1,400 - $5,000/nt
Round Rock Estate, Anguilla, Pelican Bay
12 Guests • 6 Bedrooms • 8.5 Bathrooms
$1,700 - $4,000/nt
Champagne Shores, Anguilla, Pelican Bay
10 Guests • 5 Bedrooms • 5.5 Bathrooms
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Villa Reviews

  • Aqua Dream, St. Martin

    The staff were Excellent,very knowledgeable and professional.My Experience was Excellent looking forward doing business again.

    Vernon M, March 2024

  • Mes Amis, St. Martin

    An experience truly unimaginable. Our villa, Mes Amis was a resort on its own. Although we were only a family of 10 celebrating a very special birthday, our villa was one of the, if not the largest in Terre...

    Stewart R, March 2024

  • Beach Enclave GB Oceanview Villa 6bdr, Turks and Caicos

    We had a great experience at beach enclave. 5 star property and service. The only confusion was at first when the villa number/size was slightly different than what we thought we signed up for, but nonetheless we had a...

    Matt P, February 2023

  • Just in Paradise, St. Martin

    Wade with Sheldon James was exceptional to work with. Everything was perfect!

    Lelah P, June 2024
Experienced by Our Team
$1,850 - $7,399/nt
Bird of Paradise, Anguilla, Sandy Hill Bay
10 Guests • 5 Bedrooms • 4.5 Bathrooms
Experienced by Our Team
$1,850 - $3,571/nt
Sandcastle Beach House, Anguilla, Limestone Bay
8 Guests • 4 Bedrooms • 4.5 Bathrooms
Experienced by Our Team
$2,000 - $8,000/nt
Sandcastle, Anguilla, Limestone Bay
12 Guests • 5 Bedrooms • 7 Bathrooms
$2,300 - $10,500/nt
Alkera, Anguilla, Shoal Bay East
10 Guests • 5 Bedrooms • 5 Bathrooms
$3,100 - $10,000/nt
Sand Villa, Anguilla, Long bay
12 Guests • 5 Bedrooms • 5 Bathrooms
Experienced by Our Team
$3,200 - $14,500/nt
Altamer – Antilles Pearl, Anguilla, Shoal Bay West
10 Guests • 5 Bedrooms • 6 Bathrooms

Anguilla is easy to love. Powder-soft beaches and glassy turquoise water are the order of the day here, and never too far away from our villas in Anguilla, if not just steps out your door. The island is on the sleepier side, but we can get your heart racing with watersports, sailing, golf and more. Gourmet restaurants and casual beach bars are also there to tempt you throughout the day. For something a little different, try an excursion from Anguilla to St Martin or St Barts.

$3,300 - $11,000/nt
Sea Villa, Anguilla, Long bay
11 Guests • 6 Bedrooms • 5.5 Bathrooms
Experienced by Our Team
$3,450 - $14,000/nt
Altamer – Blue Diamond, Anguilla, Shoal Bay West
11 Guests • 5.5 Bedrooms • 7 Bathrooms
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

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!

A Villa Expert will be in touch with you shortly. If you want to speak to someone immediately, please give us a call.

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

Vic Tool

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

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

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