Anguilla Villas & Vacation Rentals

Looking to rent a villa in Anguilla?

Anguilla’s breathtaking vacation homes redefine luxury in the Caribbean, offering an extraordinary escape for couples or groups seeking an unforgettable getaway. Imagine waking up to panoramic ocean views in your private villa, complete with an infinity pool, a personal chef, and exclusive beachfront access. These stylish retreats combine privacy with indulgence, setting the stage for magical moments in a paradise of powder-white sands, turquoise waters, and vibrant island charm.

These are the 88 most popular villa rentals in Anguilla. Narrow your search above.

  • From $1,400 to $8,900 per night
  • Pool
  • AC
  • From $6,050 to $28,000 per night
  • Beachfront
  • Pool
  • AC
  • From $11,500 to $32,760 per night
  • Beachfront
  • Pool
  • AC

ANI Anguilla

10 Bedrooms
10 Bathrooms
  • From $14,000 to $32,000 per night
  • Pool
  • AC
  • From $549 to $3,000 per night
  • Pool
  • AC
  • From $529 to $1,082 per night
  • Near Beach
  • Pool
  • AC
  • From $9,200 to $26,160 per night
  • Beachfront
  • Pool
  • AC
  • From $5,200 to $16,000 per night
  • Beachfront
  • Pool
  • AC
  • From $3,500 to $8,900 per night
  • Near Beach
  • Pool
  • AC
  • From $1,100 to $6,000 per night
  • Beachfront
  • Pool
  • AC
  • From $4,500 to $12,600 per night
  • Near Beach
  • Pool
  • AC
  • From $450 to $1,500 per night
  • Near Beach
  • Pool
  • AC
  • From $5,600 to $14,500 per night
  • Beachfront
  • Pool
  • AC

Kandara

8 Bedrooms
8+ Bathrooms
  • From $3,750 to $15,854 per night
  • Near Beach
  • Pool
  • AC
  • From $850 to $2,200 per night
  • Near Beach
  • Pool
  • AC
  • From $1,500 to $5,500 per night
  • Beachfront
  • Pool
  • AC
  • From $469 to $1,135 per night
  • Near Beach
  • Pool
  • AC
  • From $815 to $2,300 per night
  • Pool
  • AC
  • From $1,950 to $4,862 per night
  • Beachfront
  • Pool
  • AC
  • From $1,650 to $6,000 per night
  • Near Beach
  • Pool
  • AC
  • From $1,400 to $3,600 per night
  • Pool
  • AC
  • From $1,775 to $4,900 per night
  • Near Beach
  • Pool
  • AC
  • From $1,500 to $4,200 per night
  • Near Beach
  • Pool
  • AC
  • From $549 to $2,000 per night
  • Pool
  • AC
  • From $1,075 to $2,530 per night
  • Beachfront
  • Pool
  • AC
  • From $1,850 to $7,400 per night
  • Near Beach
  • Pool
  • AC

Indigo Villa

10 Bedrooms
10 Bathrooms
  • From $5,300 to $23,040 per night
  • Beachfront
  • Pool
  • AC
  • From $7,500 to $30,500 per night
  • Beachfront
  • Pool
  • AC
  • From $800 to $3,000 per night
  • Pool
  • AC
  • From $1,100 to $4,655 per night
  • Beachfront
  • Pool
  • AC

About Anguilla

Anguilla is a Caribbean gem, renowned for its luxury, privacy, and natural beauty, making it the perfect destination for villa rental vacations. The island’s serene atmosphere and exclusivity create an idyllic escape for those seeking relaxation or adventure. With 33 pristine beaches, Anguilla offers a slice of paradise for every visitor. Shoal Bay’s powdery sands and vibrant coral reefs, Meads Bay’s calm, inviting waters, and Little Bay’s secluded charm are just a few of the highlights along its stunning coastline. 

Water enthusiasts can dive into crystal-clear waters to snorkel among colorful marine life, paddleboard along tranquil bays, or sail to nearby hidden cays on private charters. For those seeking cultural immersion, Anguilla offers a lively music scene, friendly locals, and historical sites like the Heritage Collection Museum. 

Stay in one of the island’s world-class luxury villas, each offering unparalleled privacy and breathtaking ocean views. Anguilla’s exceptional dining scene ranges from casual beachfront restaurants to fine dining establishments, all showcasing fresh seafood and local flavors. Whether you’re savoring a sunset dinner or exploring the island’s natural and cultural treasures, Anguilla is the ultimate destination for an unforgettable villa holiday, blending tranquility, adventure, and sophistication in a truly unique way.

What's special about Anguilla?

Anguilla, a jewel of the Caribbean, is celebrated for its powdery white-sand beaches and crystalline turquoise waters. This tranquil island offers a serene escape for travelers seeking a relaxing yet luxurious vacation. With 33 pristine beaches to explore, from the lively Shoal Bay East to the secluded sands of Little Bay, Anguilla is the ultimate beach lover’s paradise. Stay in one of the island’s private villas and wake up to the soothing sounds of the ocean, with sweeping views of the Caribbean right from your terrace. Anguilla’s luxury villas provide a perfect blend of comfort and elegance, offering an unparalleled vacation experience with amenities like infinity pools, private chefs, and personalized concierge services.

Beyond the beaches, Anguilla enchants visitors with its rich culture, world-class dining, and warm, welcoming locals. Enjoy fresh seafood at beachfront restaurants, dance to the rhythm of live reggae, or explore the island’s vibrant art galleries and heritage sites. From the lively festivities of Carnival to the quiet charm of its coastal villages, Anguilla offers a unique mix of relaxation and cultural richness. With an array of luxury vacation rentals and holiday homes to choose from, this Caribbean haven guarantees an unforgettable retreat tailored to your every desire.

Anguilla FAQ

Q: What is the best time to visit Anguilla?
A: The best time to visit Anguilla is between November and April, when the weather is warm, dry, and perfect for beach activities. If you prefer fewer crowds and better rates, consider visiting during the off-season from May to August, but note that hurricane season peaks between September and October.
Q: What are the must-see attractions in Anguilla?
A: Anguilla is famous for its stunning beaches like Shoal Bay, Meads Bay, and Rendezvous Bay. Other highlights include Sandy Island, a tiny offshore paradise, Little Bay, a secluded cove accessible only by boat, and The Heritage Collection Museum, which offers a glimpse into Anguilla’s history.
Q: What are the best outdoor activities to do in Anguilla?
A: Anguilla is a haven for water sports and outdoor adventures. Popular activities include snorkeling and diving at Prickly Pear Cays, sailing to secluded beaches, kayaking through the mangroves, and exploring the island by bike or ATV. Deep-sea fishing and kite surfing are also popular.
Q: What is the local cuisine like in Anguilla?
A: Anguilla’s cuisine blends Caribbean flavors with fresh seafood. Must-try dishes include grilled lobster, crayfish, conch fritters, and Johnny cakes. For a true island experience, head to local beach shacks like Blanchards Beach Shack or enjoy gourmet dining at restaurants like Veya and Straw Hat.
Q: How do I get to Anguilla?
A: Anguilla does not have major direct international flights, so most travelers arrive via St. Maarten (SXM) and take a 20-minute ferry or a short flight. You can also fly into Puerto Rico (SJU) or Antigua (ANU) and take a connecting flight. Private charters are available for a more exclusive experience.