Discover a selection of 285 vacation rentals in Anguilla that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $224 per night, and villas and houses are popular options for a stay in Anguilla. Either way, you'll find a rental for everyone's needs.
Destination guide

Sand and palm paradise in Anguilla

The picturesque white beaches of Anguilla invite vacationers to slip off their sandals and take a walk on the soft sand, or lounge under a swaying palm tree, with the sound of waves for company. The Lesser Antilles island is small, just 25 kilometers long and 5 kilometers wide at its largest, but with a number of offshore islands and cays a short boat ride away, you'll never run out of sea views to enjoy. Once you've selected your ideal Anguilla vacation rental, perhaps with an ocean view, it's off for kayak rides in the clear waves and a round of golf at the local greens.

Things to do

Island hopping around Anguilla

After checking out all the beaches and bays up and down the main island of Anguilla, a short boat ride can take you to one of the more remote offshore spots for hiking or relaxing away from the crowds. The 5-square-kilometer Scrub Island, off the eastern point, has an abandoned air field, with a plane wreck you can walk to. Snorkeling along here, you might encounter some of the sea turtles and stingrays that fill the waters. Sandy Island, a tiny cay to the west of Anguilla, earns its moniker with perfect white-sand beaches that invite you to relax in a hammock.


Waterfront fun in Anguilla

While it may be tempting to spend every day of your Anguilla vacation spread out on the beach, soaking up the warm sun, carve out some time to take in the views from the sea, while enjoying a number of water sports. Local rental companies can outfit you with a selection of boats and boards, whether you prefer kayaking in a glass-bottomed vessel, watching sea creatures swimming below or taking kitesurfing lessons to learn how to the master the wind and waves. Sailing excursions and cruises are available to explore some of the nearby islands and snorkel away from shore.


Warm winters on the beaches of Anguilla

Year-round warmth in Anguilla means that any season can be spent outdoors, enjoying swims in the ocean and sunbathing on the sand. June through November is hurricane season, with fall seeing the most rain, so if you're all about the sun, visit in the drier months between December and April, when you'll enjoy pleasant 80-degree afternoons. If you plan your trip during winter or early spring, reserve your Anguilla vacation rental early in order to secure your ideal dates, as this is the busier season for travelers and you'll want to make sure you nab one of the many properties with ocean views.

Natural features

Island habitats in Anguilla

There are plenty of natural environs and wildlife to discover around your Anguilla vacation rental, both on land and in the waters beyond, which are full of sea turtles and tropical fish. The Anguilla National Trust preserves some of the island's important natural sites, including the Big Spring Heritage Site, where you can see old petroglyphs, Fountain Cavern National Park, with its historic caves, and a number of birding areas. East End Pond is an ideal place for birdwatchers, as the 13-acre body of water is home to herons, egrets and an array of shorebirds that you can spy on from designated viewing areas.

How many vacation rentals are available around Anguilla?

Our 2020 property listings offer a large selection of 285 vacation rentals around Anguilla. From 144 villa rentals to 58 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Anguilla?

There are many lovely places to stay for a holiday trip or just for a weekend in Anguilla. From Vrbo travelers, the top most popular destinations to visit are:

  • West End Village: 45 vacation rentals
  • The Valley: 106 vacation rentals
  • Island Harbour: 274 vacation rentals
  • Blowing Point: 50 vacation rentals
  • East End Village: 46 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Anguilla! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Anguilla?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Anguilla:

  • Island Harbour: 274 rentals
  • Sandy Ground: 284 rentals
  • Merrywing Bay: 255 rentals
  • St. Barthelemy: 1,727 rentals
  • Simpson Bay: 951 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Anguilla?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Anguilla are:

  • Wallblake Airport (AXA): 284 vacation rentals
  • Princess Juliana International Airport (SXM): 952 vacation rentals
  • Saint Barthelemy Airport (SBH): 1,727 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Anguilla?

Vrbo offers a large selection of rentals near lovely places in Anguilla. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Captain's Bay Beach: 284 rentals
  • Shoal Bay Beach: 285 rentals
  • Meads Bay: 284 rentals
  • Scilly Cay: 284 rentals
  • Sandy Hill Beach: 284 rentals

But there are many other points of interest around Anguilla listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Anguilla

West End Village
45 vacation rentals
The Valley
106 vacation rentals
Blowing Point
50 vacation rentals
East End Village
46 vacation rentals
Shoal Bay Village
68 vacation rentals
Sea Rocks
24 vacation rentals
Pelican Key
178 vacation rentals
Les Terres Basses
426 vacation rentals
Indigo Bay
45 vacation rentals
414 vacation rentals
Oyster Pond
30 vacation rentals
Almond Grove
20 vacation rentals
Oyster Pond
183 vacation rentals
Mont Vergna
155 vacation rentals
427 vacation rentals
Dawn Beach Estates
179 vacation rentals
La Savane
82 vacation rentals
Red Pond Estates
136 vacation rentals
Lower Prince's Quarter
21 vacation rentals
Tamarind Hill Estates
168 vacation rentals