Anguilla Vacations & Trips from $1,092

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Your Anguilla Vacation

Secure a vacation package to Anguilla and experience travel on your own terms. You'll be charmed by its coastal beaches, underwater activities and views. A trip to Anguilla promises plenty to see and do. Not sure where to begin your travels? The Valley is one of the most popular cities to stay here. Expedia has flights, hotels, car rentals and more to help you create your own customized Anguilla vacation today.

Top destinations in Anguilla

The Latest Anguilla Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse
Sheriva Luxury Villas and Suites
Malliouhana Resort Anguilla
Coralito Bay Suites & Villas
Rendezvous Bay Hotel

Best Places to Vacation in Anguilla

1. Book your ideal West End Village with a vacation package

West End Village in Anguilla offers a unique and captivating outdoor vacation experience. With its stunning beaches, crystal-clear waters, and beautiful islands, it is the perfect destination for beach lovers. The local atmosphere is filled with luxury and relaxation, making it an ideal spot for those seeking a peaceful getaway. Whether you want to indulge in delicious dining options, go sailing or surfing, or simply relax on the white sand beaches, West End Village has it all. Get ready to immerse yourself in the beauty of nature and enjoy a truly unforgettable vacation in this tropical paradise.

  • The peak season is from November to January
  • The off-peak season is from February to April
  • Travelers tend to stay 5 days in West End Village

2. Plan your dream getaway to Rendezvous Bay

Rendezvous Bay in Anguilla offers a perfect outdoor vacation experience with its stunning sandy beaches, trendy resorts, luxurious spas, and beautiful golf courses. The island's serene atmosphere and picturesque landscapes make it an ideal destination for relaxation and romance. Whether you're looking to soak up the sun on the pristine beaches or indulge in rejuvenating spa treatments, Rendezvous Bay has it all. With its geographic affinities and range of recreational activities, this Caribbean paradise promises a memorable and blissful vacation for all.

  • Travelers tend to stay 5 days in Rendezvous Bay

3. Explore Shoal Bay with a vacation package

Shoal Bay in Anguilla offers a fantastic beach vacation experience with a vibrant local atmosphere. The beach is perfect for activities like dancing, fishing, and enjoying live music. There are also opportunities for snorkeling and exploring nearby islands. Visitors can indulge in spa treatments and enjoy delicious dining options. Shoal Bay is known for its luxury accommodations and vacation packages, making it an ideal destination for a memorable vacation. With its geographic affinities and range of entertainment options, Shoal Bay has something for everyone seeking a beach getaway in a beautiful setting.

  • The peak season is from May to July
  • The off-peak season is from October to December
  • Travelers tend to stay 4 days in Shoal Bay

4. Experience Maunday's Bay with a travel package

The Valley in Anguilla offers a unique and captivating atmosphere for beach vacation seekers. With its stunning geographical affinities, visitors can enjoy the beauty of pristine beaches, explore the enchanting islands, delve into the rich historical heritage, indulge in the vibrant art scene, embark on exciting boating adventures, and engage in birdwatching activities. The small-town charm adds to the overall experience, while snorkeling enthusiasts can discover the wonders of the sea. After a day of exploration, relax and unwind at the local beachside bars, immersing yourself in the true essence of this tropical paradise.

  • Travelers tend to stay 4 days in Maunday's Bay

6. Find your perfect South Hill vacation

South Hill in Anguilla offers a unique and idyllic atmosphere for a beach vacation. With its stunning geographic affinities, including pristine beaches, crystal-clear seas, and picturesque islands, it is a true paradise for beach lovers. The locals are known for their friendliness and hospitality, making visitors feel welcome and at ease. Whether you're sipping coffee at a charming café, dining at a gourmet restaurant, or indulging in luxury accommodations, South Hill offers a relaxing and rejuvenating experience. The scenic views and vibrant port add to the overall charm of this coastal town, making it an ideal destination for a beach getaway.

  • Travelers tend to stay 4 days in South Hill

5. Discover The Valley with our vacation deals

Maunday's Bay in Anguilla offers a serene and picturesque atmosphere for an outdoor vacation. With its crystal-clear turquoise waters and pristine white sand beaches, it provides the perfect setting for relaxation and sunbathing. The bay is surrounded by lush tropical vegetation, creating a tranquil and natural ambiance. Visitors can enjoy various water activities such as swimming, snorkeling, and paddleboarding. The bay also offers stunning views of the Caribbean Sea and the neighboring islands. Whether you're looking to unwind on the beach or explore the underwater beauty, Maunday's Bay promises an unforgettable outdoor vacation experience.

  • The peak season is from February to April
  • The off-peak season is from November to January
  • Travelers tend to stay 5 days in The Valley

Things to do in Anguilla

Anguilla offers a perfect getaway for beach and outdoor enthusiasts, featuring stunning scenery and a variety of activities. Enjoy thrilling water sports, explore educational experiences, and indulge in luxurious resorts. Key highlights include island adventures, inclusive excursions, and vibrant entertainment options. Whether you're looking for relaxation or excitement, Anguilla promises unforgettable beach vacations and memorable experiences for every traveler.

Shopping

In Anguilla, visit the charming shops at the Valley, where you’ll find unique local crafts and souvenirs. For a more vibrant experience, check out the local markets like the Road Bay Market, offering fresh produce and handmade goods that capture the island's spirit.

Recreation

At Aurora International Golf Club, experience a serene golfing getaway surrounded by lush landscapes. Enjoy the outdoor vibes while playing on a beautifully maintained course, perfect for both relaxation and recreation. After a round, unwind with refreshing drinks at the clubhouse, soaking in the stunning views.

Adventure

Explore the stunning beaches of Anguilla while kayaking through crystal-clear waters or try stand-up paddleboarding for a unique perspective of the coastline. For thrill-seekers, snorkeling at the coral reefs reveals vibrant marine life, and hiking along scenic trails offers breathtaking views of the island's natural beauty.

Nightlife

In Anguilla, enjoy vibrant nightlife at venues like The Dune Preserve and Elvis’ Beach Bar, where live music and dancing create a lively atmosphere. For a more laid-back vibe, visit Sandy Ground for beachside bars and local entertainment, perfect for soaking in the island's charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Anguilla

Anguilla is an idyllic vacation spot perfect for beach lovers and outdoor enthusiasts, featuring beautiful beaches, scenic bays, and stunning islands. With a range of attractions, visitors can enjoy beach getaways, explore local tourist sites, and experience the breathtaking Anguilla Arch. This Caribbean paradise offers a perfect blend of relaxation and adventure, making it an ideal destination for those seeking sun and surf.

  • Meads Bay: Experience the serene beauty of Meads Bay, where soft white sands meet crystal-clear waters. This tranquil bay offers a perfect setting for sunbathing, swimming, and indulging in local cuisine at beachfront restaurants, all while enjoying breathtaking scenery.
  • Shoal Bay Beach: Renowned for its stunning stretch of powdery sand and vibrant turquoise waters, Shoal Bay Beach is a tropical paradise. Ideal for relaxation and water sports, the beach's laid-back vibe and natural beauty make it a must-visit destination for sun seekers.
  • Anguilla Arch: Marvel at the natural wonder of Anguilla Arch, a striking rock formation that provides spectacular views of the coastline. Perfect for photography and exploration, this site invites visitors to enjoy the scenic outdoors and witness the beauty of nature.

Tips to save on your trip to Anguilla

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Anguilla.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Anguilla.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Anguilla Hotel Deals

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay, West End Village
9.6/10 Exceptional! (234 reviews)
"Best place we have been to. The hospitality, staff, food, and the beach was the best. You feel safe in and out of the water lol. The manager David and Chavez made sure all went well. Definitely coming back!"

Reviewed on Aug 11, 2025

Four Seasons Resort and Residences Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay, Rendezvous Bay
$448 nightly
The price is $496 total per night from Sep 1 to Sep 2
$496 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (166 reviews)
"Gorgeous gorgeous resort! water park was fantastic, staff was the most friendliest we've met. Justin Time was most accommodating for us in every way. The valet was great, the rooms smelled amazing and were very clean. Food was also exceptional. There was a cafe in the lobby which we went to quite ..."

Reviewed on Aug 11, 2025

Aurora Anguilla Resort & Golf Club
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Shoal Bay East, Shoal Bay
9.6/10 Exceptional! (240 reviews)
"Transportation for outside activity is limited. taxis are at least 30 USD one way. One round-trip outside venture would pay for a rental car."

Reviewed on Aug 9, 2025

Zemi Beach House, LXR Hotels & Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does an Anguilla vacation package cost?
Live it up in Anguilla from as little as $1,092. Choose from a great selection of flights, rental cars and hotels to suit your travel style. Pick up even more discounts when you add a couple of sightseeing tours to your package.
How do I get a cheap travel package to Anguilla?
You'll save a ton of money if you combine your hotels, flights and car rentals into an Anguilla travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels globally, so you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
What are the top hotels in Anguilla?
When it comes to properties in The Valley, Aurora Anguilla Resort & Golf Club and Turtles Nest Beach Resort  are two fantastic options. If you're also staying in West End Village, Four Seasons Resort and Residences Anguilla and La Vue Boutique Inn will make you feel right at home.
How far in advance should I book my Anguilla vacation?
Travelers can normally browse international airfares on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it's still possible to score a cheaper ticket just weeks before your flight.
What does an Expedia Anguilla travel package include?
From hotels and flights to car rentals, Expedia can help you put together an Anguilla package that fits you. Vacationing for a week or longer? Look into a hotel, flight and rental car bundle. If you can only squeeze in a quick getaway, a hotel and flight deal could be more your style. Activities can also be added after you've booked. Our packages make it a breeze to plan and save.
What should I know before booking an Anguilla travel package?
Bundling your bookings into an Anguilla vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with an Anguilla Expedia vacation package?
Yes, the choice is yours. We offer more than 550 airlines across the globe, so you can tailor your Anguilla trip according to your travel needs.
Does Expedia offer Book Now, Pay Later Anguilla vacation packages?
Any trip away can become expensive, so it's nice to know that Expedia is able to make things easier. Thanks to our partnership with online lender Affirm, you can now get the most out of your hard-earned dollars with a Book Now, Pay Later vacation package.
If I'm not able to travel, can I cancel my Anguilla vacation package?
It is possible to cancel your Anguilla booking if your plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Discover the most popular places to visit in Anguilla

What to do in Anguilla

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.