Plan Your Anguilla Vacation


Displaying 71 villas in your search

Beaches Edge Villa
  • 5
  • 5.5

Starting From $1,490 USD / night

  • 9
  • 8

Starting From $17,847 USD / night

Cloud Cottage
  • 4
  • 3

Starting From $940 USD / night

  • 6
  • 6.5

Rate On Request

  • 10
  • 10.5

Starting From $8,190 USD / night

  • 4 - 6
  • 8

Starting From $3,740 USD / night

Kishti on Meads Bay
  • 11
  • 14.5

Starting From $10,490 USD / night

Kishti Villa East
  • 6
  • 7.5

Starting From $5,590 USD / night

Kishti Villa West
  • 5
  • 7

Starting From $4,890 USD / night

Anguilla Extravagant Relaxation

While her Caribbean sister, St. Martin is known for vibrant nightlife, Anguilla is the relaxed partner separated by the Anguilla Channel. Get away from all your cares on this 15-mile island and find your perfect Anguilla vacation rental. . Anguilla villa rentals all have their own easy chicness and commands style and comfort for guests.

This British territory is located east of Puerto Rico and the Virgin Islands and is the northern most Leeward Island. You'll find many attractions on "eel" island including colorful coral reefs perfect for scuba and snorkeling, white-sand beaches, and an 18-hole Greg Norman golf course. This warm, welcoming, Caribbean island is kissed by beautiful turquoise seas and blends unique high style with low key elegance. Anguilla is the best of the good life at a casual tempo. 

Anguilla Must-See

Colorful, creative, and passionate expressions can be found all around you from your Anguilla villa rental out to the sea and sky. Find anything from canvasses to driftwood carvings in one of the many galleries on this small island; or listen to the rhythmic beats of a steel pan paired with a guitar. This island reverberates with creativity through art, music, poetry, dance and life. 

Don't miss discovering the island's natural beauty, witness the history bleeding from the cultural landmarks. Find hidden gems just off the path or major points of interests along well traveled streets. Highlights include: the Valley Well, Ebenezer Methodist Church, The Old Court House, Wallblake House (property), the East Pond Conservation Area, Sandy Hill Bay, Sandy Ground, Old Salt Factory and Pumphouse, Fountain Cavern, Forest Bay and Big Spring Heritage Site. 

A must-do for your trip is to rent a car and take a leisurely drive around the island to see all it's treasures.

Anguilla Activities

The sea is central to life on Anguilla and you will find that represented in most Anguilla vacation rentals. The conditions on the island are ideal for snorkeling and scuba diving alike. A don't miss activity on your trip should be observing an island regatta as boat racing is the national sport. Book a day cruise or sail to some of the island's most pristine places - plan a picnic, sunset cruise or private excursion to one of the outer Cays. Any number of other watersports are in abundance on Anguilla: waterskiing, tubing and banana boat rides are some of our favorites. For the more adventurous, try kiteboarding, windsurfing, sailfishing or catamaraning. Care for a simple stroll? Try enjoying the island beaches on horseback, or simply take a moonlit walk. Golfers can enjoy the Greg Norman 18-hole course at CuisineArt Golf Club.

Anguilla Beaches

Anguilla is home to 33 beaches along twelve miles of pure white sand. The cobalt waters are perfect for strolling along Rendezvous Bay or to take a romantic moment at Little Bay.

All of Anguilla's beaches are open to the public yet are not crowded. Each stretch of aquamarine water and white sand carries unique characteristics ranging from rock and coal to picturesque tropical plants. 

Anguilla Entertainment

Sandy Ground is otherwise known as "the entertainment capital of Anguilla." At night, this area becomes alive with the imaginative beach bars, casual restarants become emboldened with live music and dancing. 

Your Anguilla vacation rental may feature a complete gourmet kitchen, but be sure you get out and visit some of Anguilla's world-class restaurants; you'll find cuisine for the most sophisticated international traveler. Native Anguillian and international chefs create truly elegant and creative cuisine fusing fresh local flavors with the abundance of the shore and sea. Foodies and connoisseurs will rejoice and enjoy the Angillian dining experience sans necktie and jacket. 

Find Karaoke and Disco on the island or sand mash (dance) your Sunday afternoon away on Shoal Bay. Enjoy raggae and other live music all over the island.

Anguilla Travel Tips

If you visit Anguilla during low season, you'll be able to see Leatherback, Green and Hawksbill turtles nesting along the shores. 

Peak travel season ranges from December to April; though hurricane season is considered to be June through November. Hurricane season also sees the hottest temperatures, mid-80s. Winter months typically average around 83 degrees Fahrenheit. Even during the hurricane season, the weather is known to be fairly pleasant, averaging 4-5 inches of rainfall per month.

Getting to your Anguilla villa rental is easily done by air from Puerto Rico St. Martin, Antigua and St. Kitts. You'll fly into Clayton J. Lloyd International Airport. Many of our villas offer airport transfers. Anguilla can be accessed by ferries as well - note, if you don't want to feel ocean spray, sit in the ferry cabin. 

Anguilla is a self-governing overseas British Territory so you will need a passport valid beyond your travel dates. Additionally, you may need a visa, for more information on visas, please see Anguilla's requirements here. 

Not only will you find your perfect Anguilla vacation rental, but you will fall in love with this friendly, English-speaking nation. U.S. currency is widely accepted, so get to know the locals. They are warm and welcoming and can share many of the island's secrets with you.