Anguilla Vacations & Trips from $1,583

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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.

The Latest Anguilla Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $2,104, price is now $1,583 per person
$1,583
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
8/10 Very Good! (251 reviews)
Friendly, breakfast cimplimentary, great beach to swim. Power went out 2x. Once in mid nite, pitch black, could not even see in room

Reviewed on Oct 26, 2025

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $3,255, price is now $2,203 per person
$2,203
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
9.6/10 Exceptional! (172 reviews)
Beautiful place, beautiful people! Excellent resort for a family vacation.

Reviewed on Oct 25, 2025

Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $25,265, price is now $17,210 per person
$17,210
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
No reviews
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $7,090, price is now $4,903 per person
$4,903
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
9.4/10 Exceptional! (89 reviews)
A beautiful property on Meads bay. Great service. Restaurant is a wellness comparing to Four Seasons nearby

Reviewed on Aug 2, 2025

Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $2,992, price is now $2,414 per person
$2,414
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
9.2/10 Wonderful! (24 reviews)
Beach here is amazing and the surf is so easy to get in/out of. Rooms are nice and have everything you need. The hotel is relatively isolated and there is nowhere nearby to get dinner, so a rental car is needed or be prepared for an expensive taxi ride. A few beach restaurants for lunch are available. Breakfast is basic, comes to you in your room. Staff is wonderful and they will help you get whatever you need.

Reviewed on May 14, 2025

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

Find the Best Anguilla Vacation Packages

Anguilla Essential Information

Language
English
Currency
East Caribbean dollars
Closest Airport
Clayton J. Lloyd Intl. Airport (AXA)
Top Sights
Shoal Bay Beach, Maundays Bay and Anguilla Arch

Anguilla Hotel Deals

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay, West End Village
$851 nightly
The price is $948 total per night from Oct 30 to Oct 31
$948 total
Oct 30 - Oct 31
Total with taxes and fees
9.6/10 Exceptional! (237 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
$480 nightly
The price is $532 total per night from Oct 30 to Oct 31
$532 total
Oct 30 - Oct 31
Total with taxes and fees
9.6/10 Exceptional! (176 reviews)
Beautiful place, beautiful people! Excellent resort for a family vacation.

Reviewed on Oct 25, 2025

Aurora Anguilla Resort & Golf Club
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay, Rendezvous Bay
$208 nightly
The price is $232 total per night from Oct 30 to Oct 31
$232 total
Oct 30 - Oct 31
Total with taxes and fees
7.8/10 Good! (254 reviews)
Friendly, breakfast cimplimentary, great beach to swim. Power went out 2x. Once in mid nite, pitch black, could not even see in room

Reviewed on Oct 26, 2025

Anguilla Great House Beach Resort
See all 349 properties in Anguilla
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Kid Friendly Vacations
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Frequently asked questions

How much does an Anguilla vacation package cost?
Live it up in Anguilla from as little as $1,583. 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

Meads Bay

Meads Bay

4.5/5(56 reviews)

Commune with nature and explore the great outdoors at Meads Bay during your travels in West End Village. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Meads Bay
Shoal Bay Beach

Shoal Bay Beach

4.5/5(249 reviews)

If a restful vacation is part of your travel plans, Shoal Bay Beach might be the perfect place to seek out during your trip to Shoal Bay. You can enjoy the restaurants while in the area.

Shoal Bay Beach
Maundays Bay

Maundays Bay

5/5(19 reviews)

Commune with nature and explore the great outdoors at Maundays Bay during your travels in Maunday's Bay.

Maundays Bay

What to do in Anguilla

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

$139
per adult
100% of travellers recommend
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
St Maarten Shore Excursion: Maho Beach Round-Trip Transfer

St Maarten Shore Excursion: Maho Beach Round-Trip Transfer

$28
per adult
100% of travellers recommend
St Maarten Shore Excursion: Maho Beach Round-Trip Transfer
Coastal off-roading

For cruise passengers: Guided ATV Tour of Dutch & French St. Maarten

$120
per traveler
For cruise passengers: Guided ATV Tour of Dutch & French St. Maarten
See all activities in Anguilla
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.