Ultra Luxury Anguilla Holidays
Anguilla is host to many excellent resorts and hotels, where guests are treated like royalty by the excellent staff and luxury amenities and facilities are found around every corner, offering pure holiday bliss that is totally unbeatable.
Beyond your hotel, Anguilla is a haven of exploration. You’d be remiss not to taste some of the local cuisine at nearby restaurants or feel the buzz from a robust rum-based cocktail. History buffs and nature lovers – Anguilla’s got you covered. Nature trails and historical sites are second-to-none here and will perfectly round off your Caribbean experience.
Ideal for jetsetters searching for an off-the-radar adventure or travellers wanting to be pampered and beautified, Anguilla has it all. If you’re a sporty type and love a rush of endorphins, there are many activities available throughout the island to suit you. Golf, water sports, and morning hikes through tropical gardens are the perfect way to get stuck in and discover the island’s natural beauty.
Your chosen hotel will be a haven of perfection, but Anguilla is an island that beckons exploration. How about renting a car and discovering the island in your own time? Be your own tour guide as you glide through the Caribbean streets and feel the tropical breeze blow through your hair. This economical option means you don’t need to take taxis everywhere too!
Anguilla is host to many excellent resorts and hotels, where guests are treated like royalty by the excellent staff and luxury amenities and facilities are found around every corner, offering pure holiday bliss that is totally unbeatable.
Beyond your hotel, Anguilla is a haven of exploration. You’d be remiss not to taste some of the local cuisine at nearby restaurants or feel the buzz from a robust rum-based cocktail. History buffs and nature lovers – Anguilla’s got you covered. Nature trails and historical sites are second-to-none here and will perfectly round off your Caribbean experience.
Ideal for jetsetters searching for an off-the-radar adventure or travellers wanting to be pampered and beautified, Anguilla has it all. If you’re a sporty type and love a rush of endorphins, there are many activities available throughout the island to suit you. Golf, water sports, and morning hikes through tropical gardens are the perfect way to get stuck in and discover the island’s natural beauty.
Your chosen hotel will be a haven of perfection, but Anguilla is an island that beckons exploration. How about renting a car and discovering the island in your own time? Be your own tour guide as you glide through the Caribbean streets and feel the tropical breeze blow through your hair. This economical option means you don’t need to take taxis everywhere too!
Anguilla is host to many excellent resorts and hotels, where guests are treated like royalty by the excellent staff and luxury amenities and facilities are found around every corner, offering pure holiday bliss that is totally unbeatable.
Beyond your hotel, Anguilla is a haven of exploration. You’d be remiss not to taste some of the local cuisine at nearby restaurants or feel the buzz from a robust rum-based cocktail. History buffs and nature lovers – Anguilla’s got you covered. Nature trails and historical sites are second-to-none here and will perfectly round off your Caribbean experience.
Ideal for jetsetters searching for an off-the-radar adventure or travellers wanting to be pampered and beautified, Anguilla has it all. If you’re a sporty type and love a rush of endorphins, there are many activities available throughout the island to suit you. Golf, water sports, and morning hikes through tropical gardens are the perfect way to get stuck in and discover the island’s natural beauty.
Your chosen hotel will be a haven of perfection, but Anguilla is an island that beckons exploration. How about renting a car and discovering the island in your own time? Be your own tour guide as you glide through the Caribbean streets and feel the tropical breeze blow through your hair. This economical option means you don’t need to take taxis everywhere too!
Anguilla boasts 33 world-class beaches including Rendezvous Bay, Shoal Bay, and Maundays Bay. Lose yourself on warm sands fringed by pristine waters, all sitting blissfully under clear-blue skies.
Life’s A Beach
Anguilla boasts 33 world-class beaches including Rendezvous Bay, Shoal Bay, and Maundays Bay. Lose yourself on warm sands fringed by pristine waters, all sitting blissfully under clear-blue skies.
Food is a huge part of Anguilla’s identity. Hundreds of restaurants and eateries pervade the island, from elegant resort fine dining to casual beach joints, and everything in between.
Tastes to Remember
Food is a huge part of Anguilla’s identity. Hundreds of restaurants and eateries pervade the island, from elegant resort fine dining to casual beach joints, and everything in between.
With an eclectic nightlife, Anguilla promises sundown fun every evening. Discover ambient jazz haunts, laid-back beach bars, and spirited sandy dancefloors for a party like no other.
After Dark Entertainment
With an eclectic nightlife, Anguilla promises sundown fun every evening. Discover ambient jazz haunts, laid-back beach bars, and spirited sandy dancefloors for a party like no other.
next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.
START A WHATSAPP CHATLuxury Anguilla Hotels
Luxury Anguilla Hotels
Cap Juluca, A Belmond Hotel
Maundays Bay, Anguilla
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Four Seasons Resort & Residences Anguilla
Barnes Bay, Anguilla
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Malliouhana
Meads Bay, Anguilla
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Start Your Journey
Plan your Anguilla holiday with help from our top reads, favourite hotels and inspiring tour ideas.
10 reasons to book with Winged Boots
You'll soon understand why we're a leading luxury travel specialist
Cap Juluca, A Belmond Hotel
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Four Seasons Resort & Residences Anguilla
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Antigua & Anguilla, 11 Days
Experience paradise with a 10-night Caribbean getaway to Antigua and Anguilla, featuring luxurious stays at Carlisle Bay and Cap Juluca, exquisite local cuisine, a powerboat tour, and exciting watersports amidst breathtaking oceanfront settings.
10 reasons to book with Winged Boots
You'll soon understand why we're a leading luxury travel specialist
Winged Boots Interviews: Claire Baker, Luxury Concierge for Winged Boots
From reservations to romantic proposals, see how our dedicated personal experience team can add some extra sparkle to an already incredible travel experience.
Anguilla in a Nutshell
Golden sands, blue skies and a whole lot of happiness can be found at Rendezvous Bay. Once the location of a key battle between the English and French for colonial control over the island, you can now simply enjoy lounging on the shore and dipping in and out of the sparkling ocean.
Food is king in Anguilla, and you can enjoy a wide range of local and international cuisines all over the island. Step right into the heart of Rome at Dolce Vita Restaurant in Sandy Ground, an award-winning establishment specialises in delicious Italian cuisine. This open-air eatery with bay views features classic dishes such as linguine, fresh local lobster and speciality risotto dishes, all served to smooth jazz playing softly in the background.
For views that live up to the name, Sunset Lounge at the Four Seasons Resort and Residences exceeds every expectation. Exquisite Japanese cuisine – including arguably the island’s best sushi – delicious cocktails, live music, and unbeatable Caribbean scenery make this the prime location for friends and loved ones to come together and enjoy the very best of luxury island life.
Non-stop music and flowing cocktails can be found at the iconic Johnno's Place in Sandy Ground. A laid-back beach bar by day and a club by night, visitors and locals alike have been joining together for a good time here since it opened its doors in the mid-80s. Try the legendary whole snapper, freshly caught and cooked to perfection, followed by ‘The Famous Punch’, which truly lives up to its name – a concoction full of delicious local rum that does indeed pack some clout!
End your evenings in style by immersing yourself in Anguilla’s low-key yet electrifying nightlife. After a relaxing day on Rendezvous Bay Beach you can head to the Dune Preserve, a music bar opened by Bankie Banx, Anguilla’s very own reggae music star. Enjoy a steady stream of drinks and excellent live music from the man himself for an unforgettable evening. Banx and his band perform live on Wednesday and Friday nights, and every March sees his annual ‘Moonsplash’ festival take place, bringing reggae rhythms and the full moon together in perfect harmony!
Elvis’ Beach Bar is another essential stop on your night-time outings. Located right on the beach in Sandy Ground, this popular haunt offers an eclectic mix of entertainment that varies from one evening to the next. Saturdays are filled with all-night dancing – sometimes complete with a limbo stick – and an energetic atmosphere, while other nights take on a more chilled vibe with smaller groups sat down enjoying a backdrop of gentle reggae sounds.
Golden sands, blue skies and a whole lot of happiness can be found at Rendezvous Bay. Once the location of a key battle between the English and French for colonial control over the island, you can now simply enjoy lounging on the shore and dipping in and out of the sparkling ocean.
Food is king in Anguilla, and you can enjoy a wide range of local and international cuisines all over the island. Step right into the heart of Rome at Dolce Vita Restaurant in Sandy Ground, an award-winning establishment specialises in delicious Italian cuisine. This open-air eatery with bay views features classic dishes such as linguine, fresh local lobster and speciality risotto dishes, all served to smooth jazz playing softly in the background.
For views that live up to the name, Sunset Lounge at the Four Seasons Resort and Residences exceeds every expectation. Exquisite Japanese cuisine – including arguably the island’s best sushi – delicious cocktails, live music, and unbeatable Caribbean scenery make this the prime location for friends and loved ones to come together and enjoy the very best of luxury island life.
Non-stop music and flowing cocktails can be found at the iconic Johnno's Place in Sandy Ground. A laid-back beach bar by day and a club by night, visitors and locals alike have been joining together for a good time here since it opened its doors in the mid-80s. Try the legendary whole snapper, freshly caught and cooked to perfection, followed by ‘The Famous Punch’, which truly lives up to its name – a concoction full of delicious local rum that does indeed pack some clout!
End your evenings in style by immersing yourself in Anguilla’s low-key yet electrifying nightlife. After a relaxing day on Rendezvous Bay Beach you can head to the Dune Preserve, a music bar opened by Bankie Banx, Anguilla’s very own reggae music star. Enjoy a steady stream of drinks and excellent live music from the man himself for an unforgettable evening. Banx and his band perform live on Wednesday and Friday nights, and every March sees his annual ‘Moonsplash’ festival take place, bringing reggae rhythms and the full moon together in perfect harmony!
Elvis’ Beach Bar is another essential stop on your night-time outings. Located right on the beach in Sandy Ground, this popular haunt offers an eclectic mix of entertainment that varies from one evening to the next. Saturdays are filled with all-night dancing – sometimes complete with a limbo stick – and an energetic atmosphere, while other nights take on a more chilled vibe with smaller groups sat down enjoying a backdrop of gentle reggae sounds.
Golden sands, blue skies and a whole lot of happiness can be found at Rendezvous Bay. Once the location of a key battle between the English and French for colonial control over the island, you can now simply enjoy lounging on the shore and dipping in and out of the sparkling ocean.
Food is king in Anguilla, and you can enjoy a wide range of local and international cuisines all over the island. Step right into the heart of Rome at Dolce Vita Restaurant in Sandy Ground, an award-winning establishment specialises in delicious Italian cuisine. This open-air eatery with bay views features classic dishes such as linguine, fresh local lobster and speciality risotto dishes, all served to smooth jazz playing softly in the background.
For views that live up to the name, Sunset Lounge at the Four Seasons Resort and Residences exceeds every expectation. Exquisite Japanese cuisine – including arguably the island’s best sushi – delicious cocktails, live music, and unbeatable Caribbean scenery make this the prime location for friends and loved ones to come together and enjoy the very best of luxury island life.
Non-stop music and flowing cocktails can be found at the iconic Johnno's Place in Sandy Ground. A laid-back beach bar by day and a club by night, visitors and locals alike have been joining together for a good time here since it opened its doors in the mid-80s. Try the legendary whole snapper, freshly caught and cooked to perfection, followed by ‘The Famous Punch’, which truly lives up to its name – a concoction full of delicious local rum that does indeed pack some clout!
End your evenings in style by immersing yourself in Anguilla’s low-key yet electrifying nightlife. After a relaxing day on Rendezvous Bay Beach you can head to the Dune Preserve, a music bar opened by Bankie Banx, Anguilla’s very own reggae music star. Enjoy a steady stream of drinks and excellent live music from the man himself for an unforgettable evening. Banx and his band perform live on Wednesday and Friday nights, and every March sees his annual ‘Moonsplash’ festival take place, bringing reggae rhythms and the full moon together in perfect harmony!
Elvis’ Beach Bar is another essential stop on your night-time outings. Located right on the beach in Sandy Ground, this popular haunt offers an eclectic mix of entertainment that varies from one evening to the next. Saturdays are filled with all-night dancing – sometimes complete with a limbo stick – and an energetic atmosphere, while other nights take on a more chilled vibe with smaller groups sat down enjoying a backdrop of gentle reggae sounds.
frequently asked questions
What other activities are on offer in Anguilla?
What is the time difference between Anguilla and the UK?
When is the best time to travel to Anguilla?
next trip today
Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.