Anguilla Vacations & Trips from $3,244

Book a Hotel + Flight or Car together to unlock savings

Photo by Anguilla Tourist Board

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Two blue objects with flags and logos.
FlightsFlightsHotelsHotels

The Valley

The Valley

The Latest Anguilla Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $4,040, price is now $3,244 per person
$3,244
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9/10 Wonderful! (34 reviews)
stayed there in previous years, the hotel would need some upgrade. not to make it luxury, but not so „run out“. maybe depends on room you stay in, they have different standards/settings… location is quiet and probably most beautiful beach/spot, very private and relaxing.

Reviewed on May 15, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $6,151, price is now $3,690 per person
$3,690
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.6/10 Exceptional! (207 reviews)

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $6,248, price is now $4,539 per person
$4,539
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.6/10 Exceptional! (109 reviews)
GOAT Anguilla!

Reviewed on Nov 1, 2026

Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $14,533, price is now $11,640 per person
$11,640
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.8/10 Exceptional! (50 reviews)
Beautiful property and lovely staff. The room was clean and very comfortable. The location on the beach was perfect.

Reviewed on Oct 12, 2026

6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was $13,197, price is now $10,595 per person
$10,595
per person
Jan 25 - Feb 1
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
No reviews

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 lovers and outdoor enthusiasts, featuring stunning scenery and a range of activities. Visitors can enjoy resort stays, indulge in water sports, and explore educational experiences. For an unforgettable vacation, consider exciting island adventures, inclusive excursions, and vibrant entertainment options that highlight the charm of this beautiful Caribbean destination.

Shopping

In Anguilla, visit the charming shops at The Valley for local crafts and souvenirs. For a more vibrant experience, check out the local market in Sandy Ground, where you can find handmade goods and unique gifts that capture the island's spirit.

Recreation

At Aurora International Golf Club, immerse yourself in the serene outdoor vibes while enjoying a round of golf. The lush landscapes and stunning views create a perfect backdrop for relaxation and rejuvenation, making it an ideal spot for both leisure and wellness activities.

Adventure

Explore the stunning beaches of Shoal Bay, perfect for snorkeling and paddleboarding. Discover the thrill of kite surfing at Meads Bay, where the winds create ideal conditions. For hiking, trek to the breathtaking cliffs of Crocus Bay for panoramic views of the turquoise waters.

Nightlife

Experience the vibrant nightlife in Anguilla at places like The Dune Preserve, where live music and beach vibes create a lively atmosphere. For a more upscale scene, visit Viceroy Anguilla’s Sunset Lounge, perfect for cocktails with stunning views. Dance the night away at local beach bars for a true island experience.

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

Find the best attractions in Anguilla

Anguilla is a tropical paradise ideal for beach and outdoor enthusiasts, boasting stunning scenery and pristine shores. Visitors can explore popular points of interest such as picturesque bays, the famous Anguilla Arch, and some of the best beaches in the Caribbean. Whether you're seeking a relaxing beach getaway or adventurous activities, Anguilla offers an array of attractions that cater to every traveler's desire for sun-soaked adventures and scenic beauty.

  • Meads Bay: Experience the tranquil beauty of Meads Bay, a stunning stretch of beach known for its soft sand and clear turquoise waters. Ideal for sunbathing, swimming, and enjoying outdoor activities, this bay offers a serene atmosphere perfect for relaxation and scenic views.
  • Shoal Bay Beach: Renowned for its powdery white sand and vibrant azure waters, Shoal Bay Beach is a tropical paradise. The beach vibes here are perfect for sun-seekers, snorkelers, and those looking to unwind while soaking in the breathtaking surroundings.
  • Anguilla Arch: Marvel at the natural beauty of Anguilla Arch, a unique rock formation offering stunning scenery. This outdoor attraction provides fantastic photo opportunities and a chance to connect with nature while enjoying the picturesque coastal views.

Best time to go to Anguilla

The best time to visit Anguilla is dependent on what kind of holiday you are seeking. September is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. March is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January78.3°F (25.700000000000003°C)No RainMostly SunnySlightly HighAverage
February77.7°F (25.4°C)No RainMostly SunnyAverageSlightly High
March77.4°F (25.200000000000003°C)No RainMostly SunnyAverageSlightly High
April78.4°F (25.8°C)No RainMostly SunnyAverageSlightly High
May80.1°F (26.700000000000003°C)Light RainMostly SunnySlightly LowAverage
June81.5°F (27.5°C)Light RainMostly SunnyAverageAverage
July82.0°F (27.8°C)Light RainMostly SunnySlightly HighAverage
August82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
September82.9°F (28.3°C)Light RainMostly SunnySlightly HighSlightly Low
October82.4°F (28.0°C)Light RainMostly SunnySlightly LowSlightly Low
November81.1°F (27.3°C)Light RainMostly CloudySlightly LowAverage
December79.5°F (26.4°C)No RainMostly SunnyAverageAverage

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 to Anguilla during the low season (August to October) for more affordable options.
  • 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.

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

Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Rendezvous Bay Rendezvous Bay
$188 nightly
The price is $215 total per night from Nov 4 to Nov 5
$215 total
Nov 4 - Nov 5
Total with taxes and fees
Anguilla Great House Beach Resort
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
$1,251 nightly
The price is $1,394 total per night from Nov 10 to Nov 11
$1,394 total
Nov 10 - Nov 11
Total with taxes and fees
Four Seasons Resort and Residences Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Fully refundableReserve now, pay when you stay
$1,037 nightly
The price is $1,158 total per night from Dec 2 to Dec 3
$1,158 total
Dec 2 - Dec 3
Total with taxes and fees
Aurora Anguilla Resort & Golf Club
See all 351 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
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How do vacation package prices compare across popular destinations in Anguilla?
Rendezvous Bay has the lowest typical price for a week-long Anguilla vacation package, while Shoal Bay and West End Village run higher. A week-long trip typically costs around $2,000 per adult in Rendezvous Bay, around $3,850 per adult in West End Village, and around $4,100 per adult in Shoal Bay.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Anguilla vacation package?
When you bundle, you can save up to 30%*. To save money on a Anguilla package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in an Anguilla vacation package?
An Anguilla vacation package lets you combine flights, hotel stays, and rental cars, based in popular destinations like Rendezvous Bay, West End Village, and Shoal Bay. The main airport serving the region is The Valley (AXA-Clayton J. Lloyd Intl.).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
Which destinations in Anguilla offer the best-value vacation package deals?
Rendezvous Bay, Shoal Bay, and West End Village are some of the top destinations for cheap Anguilla vacation package deals. For an affordable trip, Rendezvous Bay is often among the most budget-friendly options, with package prices starting around $1,130 per adult. For notable bundle savings, West End Village is often among the best options, with flight-and-hotel bundles saving around $620 per adult.

Browse cheap vacation packages in Anguilla on Expedia to compare current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
When is the best time to visit the top destinations in Anguilla?
The best time for an Anguilla vacation package depends on which destination you choose.

West End Village sees peak bookings in February, June, and July. If you prefer fewer crowds, consider visiting during other months like August, September, or October.

Rendezvous Bay is busiest in February, April, and November, with April often hosting the Festival Del Mar. For a quieter experience, other months might be more suitable, such as August, September, or October.

Shoal Bay experiences high demand in February, June, and July. Travelers looking to avoid crowds might prefer different times of the year, including August, September, or October.
What package types are available across the top destinations in Anguilla?
Anguilla vacation packages offer diverse travel styles across its popular areas like Rendezvous Bay, West End Village, and Shoal Bay:
  • Family: In Rendezvous Bay, Anguilla Great House Beach Resort, a 3.5-star property, offers family rooms and an outdoor pool, with travelers often finding their overall experience absolutely amazing.
  • Couples: Aurora Anguilla Resort & Golf Club, a 5-star resort in Rendezvous Bay, is rated 9.3 out of 10 by travelers and features a hot tub and outdoor pool, with guests frequently praising its fabulous staff and best breakfast.
  • Luxury: Malliouhana Resort Anguilla, a 5-star property in West End Village, is rated 9.5 out of 10 by travelers and provides a hot tub and outdoor pool, with guests highlighting its amazing facilities and friendly staff.
  • Beach: Shoal Bay Villas in Shoal Bay, a 3.5-star property rated 9.2 out of 10 by travelers, is about a 5-minute walk from Shoal Bay Beach and includes an outdoor pool and kitchens.
  • Budget: Serenity Cottages in Shoal Bay, a 3.5-star property, offers kitchens and a restaurant, and travelers note its overall affordable experience.
Which destinations should I consider for an Anguilla vacation?
For an Anguilla vacation, your ideal destination depends on your preferred travel style:
  • West End Village: A popular choice for couples and luxury travelers, offering beach-focused packages and a range of outdoor activities.
  • Rendezvous Bay: Well-suited for beach lovers, couples, and families, with packages that highlight its scenic views and sports activities.
  • Shoal Bay: Another excellent option for couples and luxury seekers, providing beach-centric packages and opportunities for outdoor adventures.
  • The Valley: As the area with the most lodging choices, The Valley serves as a convenient base for exploring Anguilla's beaches and outdoor attractions.
Is Anguilla better suited for a beach vacation or a cultural trip?
Anguilla is primarily a beach and outdoor activities destination, known for its stunning coastlines and scenic views. Travelers on an Anguilla vacation can enjoy beautiful stretches of sand like Meads Bay, Shoal Bay Beach, and Maundays Bay, which are ideal for relaxation and water sports.

Beyond its natural beauty, Anguilla also offers a rich cultural history. The island's heritage is shaped by its Indigenous American roots, with ancient petroglyph sites like Big Spring and Fountain Cavern, and its colonial past, visible in structures such as the restored Wallblake House. Local traditions, cuisine, and music are celebrated through events like Lobster Fest and boat races, with the Anguilla National Trust working to preserve this heritage.

Overall, an Anguilla vacation package is best suited for those seeking a luxurious beach getaway with ample outdoor activities, complemented by opportunities to explore the island's unique cultural depth.
Which airports serve the main destinations in Anguilla?
For an Anguilla vacation, the primary gateway is Clayton J. Lloyd International Airport (AXA), located in The Valley. This airport serves the entire island, providing convenient access to all its destinations.
What are the top things to do across the destinations in Anguilla?
An Anguilla vacation offers a variety of activities spread across its distinct destinations:

Browse and book things to do in Anguilla on Expedia.
Are there family vacation packages in Anguilla with kid-friendly amenities?
Family vacation packages in Anguilla feature resorts with kid-friendly amenities across areas like Rendezvous Bay and West End Village:
  • Aurora Anguilla Resort & Golf Club: In Rendezvous Bay, this 5-star resort, rated 9.3 out of 10 by travelers, offers a playground and family rooms, with travelers often praising its fabulous staff and best breakfast.
  • Four Seasons Resort and Residences Anguilla: Located in West End Village, this 5-star property, rated 9.6 out of 10 by travelers, provides a kids club and babysitting services, and guests frequently highlight its comfortable rooms and fun pool.
  • Carimar Beach Club: Also in West End Village, this 3.5-star property, rated 9.4 out of 10 by travelers, features family rooms and a playground, making it a solid choice for families.
What luxury vacation packages are available in Anguilla?
Anguilla offers luxury vacation packages centered around high-end resorts in areas like West End Village, Maunday's Bay, and Rendezvous Bay:

Most Anguilla vacation packages pair the hotel with flights. Browse luxury vacation packages in Anguilla on Expedia to compare options.
When should I book vacation packages for the top destinations in Anguilla?
Booking times for an Anguilla vacation package vary by destination — most travelers book around 9 to 14 weeks before departure.

Travelers tend to book Anguilla trips most often February, April, from June to July, and November. If you're planning a spontaneous getaway, Expedia also offers last-minute Anguilla vacation packages.
How many days do you need for an Anguilla vacation?
Most Anguilla vacation packages last around 5 to 7 days, but the ideal trip length depends on where you're going and what you'd like to experience.

Rendezvous Bay, known for its beautiful beaches and scenic views, is well suited for a trip of around 7 days, with week-long stays being most popular — enough time to enjoy Rendezvous Bay Beach.

West End Village, also primarily a beach destination with outdoor activities, is worth around 6 days, with week-long trips being common to explore areas like Meads Bay.

Shoal Bay, another area primarily known for its beaches and scenic views, rewards a stay of around 5 days, with week-long trips being popular to experience Shoal Bay Beach.
Can I change or cancel my Anguilla vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Anguilla vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Anguilla vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Anguilla vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Anguilla?
To find last-minute vacation packages to Anguilla, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Anguilla vacation packages?
Free cancellation on a Anguilla vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Anguilla vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Anguilla getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Anguilla vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Stay near popular Anguilla attractions

A beach with white lounge chairs and blue umbrellas, a clear sky, and turquoise water.

Shoal Bay Beach

9.0/10 (796 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.
See properties

What to do in Anguilla

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

$81
per adult
78% of travellers recommend
High-Speed Ferry to St. Barths
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

$77
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Amazing Plane Spotting at Maho Beach

Amazing Plane Spotting at Maho Beach

$27
per adult
80% of travellers recommend
Amazing Plane Spotting at Maho Beach
See all activities in Anguilla
Explore a world of travel with Expedia

Other vacations you might like

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