Discover a selection of 175 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 air conditioning. Prices start at $105 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.
Top rated rentals — Anguilla
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 175 vacation rentals around Anguilla. From 96 villa rentals to 115 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:

  • Shoal Bay: 84 vacation rentals
  • The Valley: 126 vacation rentals
  • Island Harbour: 172 vacation rentals
  • Blowing Point: 116 vacation rentals
  • West End Village: 172 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:

  • Shoal Bay: 84 rentals
  • The Valley: 126 rentals
  • Island Harbour: 172 rentals
  • Blowing Point: 116 rentals
  • West End Village: 172 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:

  • The Valley (AXA-Clayton J. Lloyd Intl.): 176 vacation rentals
  • Gustavia (SBH-Gustaf III): 1,358 vacation rentals
  • Philipsburg (SXM-Princess Juliana Intl.): 780 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:

  • Wallblake House: 176 rentals
  • Meads Bay: 176 rentals
  • Anguillan Christian Fellowship Church: 176 rentals
  • Maundays Bay: 176 rentals
  • Scilly Cay: 176 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

Shoal Bay
84 vacation rentals
The Valley
126 vacation rentals
Island Harbour
172 vacation rentals
Blowing Point
116 vacation rentals
West End Village
172 vacation rentals
Sandy Ground
176 vacation rentals
South Hill
99 vacation rentals
East End Village
32 vacation rentals
Merrywing Bay
156 vacation rentals
Simpson Bay
783 vacation rentals
Orient Bay
801 vacation rentals
Cul de Sac
803 vacation rentals
Les Terres Basses
273 vacation rentals
Nettle Bay
805 vacation rentals
Grand Case
803 vacation rentals
781 vacation rentals
St. Barthelemy
1,358 vacation rentals
Anse Marcel
805 vacation rentals
Oyster Pond
792 vacation rentals
805 vacation rentals