Discover a selection of 161 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 private pools. Prices start at $142 per night, and houses and villas 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.

How many vacation rentals are available around Anguilla?

Our 2022 property listings offer a large selection of 161 vacation rentals around Anguilla. From 119 house rentals to 91 villa 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:

  • Blowing Point: 163 vacation rentals
  • The Valley: 163 vacation rentals
  • Shoal Bay: 159 vacation rentals
  • Sandy Ground: 163 vacation rentals
  • Sandy Hill: 163 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:

  • Blowing Point: 163 rentals
  • The Valley: 163 rentals
  • Shoal Bay: 159 rentals
  • Sandy Ground: 163 rentals
  • Island Harbour: 159 rentals

For other cities, 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:

  • Scilly Cay: 163 rentals
  • Old Prison: 163 rentals
  • Anguillan Christian Fellowship Church: 163 rentals
  • National Trust of Anguilla: 163 rentals
  • Scrub Island: 163 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

Blowing Point
163 vacation rentals
The Valley
163 vacation rentals
Shoal Bay
159 vacation rentals
Sandy Ground
163 vacation rentals
Island Harbour
159 vacation rentals
West End Village
161 vacation rentals
East End Village
159 vacation rentals
South Hill
163 vacation rentals
Cove Bay
146 vacation rentals
Merrywing Bay
141 vacation rentals