Telephone: 0207 1019 219
Email: holidayrentals@luxuryretreats.com
Home

Anguilla Luxury Holiday Villas (Caribbean)

Order villas by:

Barnes Bay

Barnes Bay, Anguilla, Caribbean
9 br, 8.5 ba (7 Ensuite)

Cerulean may be named for—and decorated in—a rich shade of blue, but you’ll be feeling anything but after a stay at this one-of-a-kind beachfront property. With nine suite-style bedrooms, sophisticated interiors by New York designer Scott Salvator, and amenities ranging from chauffeur and cook service to water sports equipment and a putting green, the villa is your own private resort on Anguilla’s picture-perfect Barnes Bay Beach.

From
US$14285 - 35714 /nt

View Villa Cerulean Villa and Private Spa
Barnes Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Set high above Barnes Bay, the substantially sized Four Bedroom Bluff Top Villa with partial ocean views is part of the splendid Four Seasons Anguilla Resort & Residences Community. With sumptuous dining and living areas, a full gourmet kitchen and luxurious custom-designed four-poster king beds with marble en-suites, you can expect to be pampered.

From
US$2550 - 13000 /nt

View Villa 4 BR Villa, Blufftop at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
3 br, 3 ba (3 Ensuite)

The splendid Three Bedroom Penthouse gazes down over dazzling Barnes Bay and is part of the Four Seasons Anguilla Resort & Residences Community. Stylish and well established the Penthouse is perfect for entertaining, offering you and your guests spectacular views from its private and expansive terrace.

From
US$1800 - 11100 /nt

View Villa 3 BR Penthouse, Ocean view at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
3 br, 3.5 ba (3 Ensuite)

Sophisticated and well appointed, the Three Bedroom Residence with Ocean View boasts luxurious indoor and outdoor amenities for your utmost comfort. Being part of the superb Mediterranean style Four Seasons Anguilla Resort & Residences your stay is sure to be ultra-relaxing and truly memorable.

From
US$1550 - 9000 /nt

View Villa 3 BR Residence, Ocean View at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
2 br, 2.5 ba (2 Ensuite)

Chic and well established the spacious Two Bedroom Residence with Ocean View boasts marvelous living and relaxing spaces and features a full gourmet kitchen and sumptuous custom-designed four-poster king bed. Set within the jaw-dropping modern Mediterranean style resort of Four Seasons Anguilla, all the amenities you need are in place for a memorable vacation.

From
US$1250 - 7500 /nt

View Villa 2 BR Residence, Ocean View at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
5 br, 5.5 ba (5 Ensuite)

This sumptuous Five Bedroom Beachfront Villa is part of the Four Seasons Anguilla Resort & Residences Community, known for being a superb modern Mediterranean style resort. The private villa has beachfront on exclusive Barnes Bay and Meads Bay.

From
US$3600 - 6600 /nt

View Villa 5 BR Villa, Beachfront at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Perfectly positioned in the fabulous Four Seasons Anguilla Resort, the generously sized Four Bedroom Beachfront Villa includes private decks overlooking glamorous Barnes Bay. The Villa possesses a sumptuous dining and living room, gourmet kitchen, and exceptional custom-designed four-poster king beds with handsome marble en-suites.

From
US$3225 - 6100 /nt

View Villa 4 BR Villa, Beachfront at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Part of the superb Mediterranean style resort, Four Seasons Anguilla Resort & Residences Community, the generously sized Four Bedroom Oceanfront Villa sits proudly on Barnes Bay. The Villa includes luxury custom-designed four-poster king beds, lavish marble bathrooms, a full gourmet kitchen and sumptuous dining and living areas.

From
US$2850 - 5100 /nt

View Villa 4 BR Villa, Oceanfront at the Four Seasons Anguilla Resort & Residences
Barnes Bay, Anguilla, Caribbean
1 br, 1.5 ba (1 Ensuite)

The deluxe One Bedroom Residence with Ocean View is part of the Four Seasons Anguilla Resort & Residences Community, a superlative modern Mediterranean style resort. The private One Bedroom Residence boasts wonderfully relaxing indoor and outdoor living with marvelous and luxurious features including a gourmet kitchen and custom-designed four-poster king bed.

From
US$1075 - 4114 /nt

View Villa 1 BR Residence, Ocean View at the Four Seasons Anguilla Resort & Residences

Black Garden Bay

Black Garden Bay, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

The spirit of Villa Kishti is captured in the elegant luxury offered by the combination of an exceptional location harmoniously blended within an idyllic tropical environment. This unique villa provides a setting of natural beauty in which service excellence and the privacy of guests are paramount.

From
US$2650 - 7142 /nt

View Villa Kishti Blackgarden
Black Garden Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

A true tropical paradise, Sunset Beach House is nestled in a floral garden, designed by Anguilla's award-winning gardener. Drive thru the iron gates and down past the limestone rock floral walls which light up this incredible property in the evening.

From
US$700 - 4150 /nt

View Villa Sunset Beach House

Blowing Point

Blowing Point, Anguilla, Caribbean
7 br, 5 ba (4 Ensuite)

Treat yourself to the holiday you deserve in sunny Anguilla. Villa Paradise is a seven bedroom villa located in the coveted Blowing Point area of this idyllic tropical island.

From
US$1000 - 8571 /nt

View Villa Villa Paradise
Blowing Point, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

Welcome to Beaches Edge West, a private oceanfront estate in Blowing Point that has been exquisitely designed to embrace its captivating island surroundings. A twin located next door, Beaches Edge East, can be rented separately, or together for a total of ten bedrooms – perfect for a large family holiday or destination wedding party.

From
US$1400 - 3900 /nt

View Villa Beaches Edge West
Blowing Point, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

Welcome to Beaches Edge East, a private oceanfront estate in Blowing Point that has been exquisitely designed to embrace its captivating island surroundings. A twin located next door, Beaches Edge West, can be rented separately, or together for a total of ten bedrooms – perfect for a large family holiday or destination wedding party.

From
US$1250 - 3500 /nt

View Villa Beaches Edge East

Cove Bay

Cove Bay, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

A shimmering mirage or a feat of modern design? Contemporary architecture, miles of white sand beaches and the ultimate in privacy makes Villa Modena a rare find. When you pass through Modena’s double gated entrances, you are welcomed to over 10,800 square feet of indoor living space and 18,000 square feet of outdoor living space which can accommodate up to 125 guests for special events.

From
US$4250 - 9500 /nt

View Villa Modena Villa

Crocus Bay

Crocus Bay, Anguilla, Caribbean
8 br, 8.5 ba (8 Ensuite)

Viewfort Estate blends the unpretentious spirit of the West Indies with the refined and unparalleled natural beauty of Anguilla. Set on the island’s highest point overlooking the turquoise waters of Crocus Bay, this luxury Caribbean vacation rental effortlessly blends a 200-year-old heritage property with a modern addition to create a refined contemporary estate.

From
US$7000 - 15750 /nt

View Villa Viewfort Estate

Cul De Sac

Cul De Sac, Anguilla, Caribbean
4 br, 4 ba (4 Ensuite)

Influenced in design by centuries old Tuscan architecture and buzzing with state of the art amenities, Villa Alegria offers effortless beach access with breathtaking views of St Martin. With the amenities of a resort and the privacy that comes with an exclusive villa, you will be perfectly poised for tropical fun in sunny Anguilla, a laid back island with friendly locals.

From
US$1375 - 4500 /nt

View Villa Villa Alegria

Forest Bay

Forest Bay, Anguilla, Caribbean
3 br, 4 ba (3 Ensuite)

Set on an acre of lush tropical gardens and white sand beach, L’Embellie Beach Villa and Cottage is an elegant and secluded getaway destination in Anguilla. Surround yourself with the fragrances of lime trees, pineapples, plantain and banana plants.

From
US$575 - 1750 /nt

View Villa L Embellie Beach Villa and Cottage

Island Harbor

Island Harbor, Anguilla, Caribbean
5 br, 6.5 ba (5 Ensuite)

Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem.

From
US$2100 - 5000 /nt

View Villa Villa Amarilla

Limestone Bay

Limestone Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Like an ivory showpiece glinting in the sun, Sandcastle is your private palace right by the sands of the Caribbean Sea. Welcome to sunny Anguilla, a magical island known for its watersports, nightlife and friendly local vibration.

From
US$1600 - 6122 /nt

View Villa Sandcastle

Little Bay

Little Bay, Anguilla, Caribbean
10 br, 10 ba (10 Ensuite)

 


Like a towering ivory sculpture perched on the majestic cliffs overlooking Anguilla’s Little Bay, Ani Estate is comprised of two equally magnificent villas – North and South – that have been designed and fitted to offer an unforgettable Caribbean vacation. With wheelchair access and an elevator, the estate is perfect for diverse groups and multigenerational families.

From
US$8600 - 16125 /nt

View Villa Ani Estate
Little Bay, Anguilla, Caribbean
4 br, 4 ba (4 Ensuite)

 


Like a towering ivory sculpture perched on the majestic cliffs overlooking Anguilla’s Little Bay, the four bedroom Ani North has been designed and fitted to offer an unforgettable Caribbean vacation. Unique to Ani North is the home’s dramatic stair atrium with massive skylight above and water feature below.

From
US$5100 - 16125 /nt

View Villa Ani North
Little Bay, Anguilla, Caribbean
6 br, 6 ba (6 Ensuite)

 


Like an ivory sculpture on the majestic cliffs overlooking Anguilla’s Little Bay, the six bedroom Ani South has been designed to offer an unforgettable Caribbean vacation. Unique to Ani South is its configuration, accessible to guests via an elevator, roll-in showers, pool lift and wheelchair access – all subtly designed within the home’s conceptualization.

From
US$6400 - 16125 /nt

View Villa Ani South

Little Harbor

Little Harbor, Anguilla, Caribbean
20 br, 20.5 ba (20 Ensuite)

Let the lush gardens, white sands and turquoise waters of the Caribbean be the backdrop to a family getaway or special occasion at Little Harbour Estate. Set in the lovely lee of Cinnamon Reef in Little Harbor, the estate has its own beach and is comprised of Indigo villa and Le Bleu villa.

From
US$15180 - 32895 /nt

View Villa Little Harbour Estate
Little Harbor, Anguilla, Caribbean
10 br, 10 ba (10 Ensuite)


 

Located on two and half acres of beautiful tropical gardens, Le Bleu overlooks the clear turquoise waters of the Caribbean Sea. With a private beach cove, the scenic blue skies and myriad colors of the ocean will captivate your senses and your soul.

From
US$7750 - 20285 /nt

View Villa Le Bleu
Little Harbor, Anguilla, Caribbean
10 br, 9.5 ba (9 Ensuite)

 


Let the lush gardens, white sands and turquoise waters of the Caribbean be the backdrop to a family getaway or special occasion at Indigo. Set in the lee of Cinnamon Reef on Little Harbor, the villa is tucked into 1.

From
US$6860 - 17857 /nt

View Villa Indigo
Little Harbor, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Sitting on Anguilla’s South Shore, Aquamarie - Kamique commands stunning views of a secluded beach cove and the mountains of St Martin. You will be just paces away from a private swath of cool white sand, complete with padded sun loungers, shaded day bed and gazebo.

From
US$1850 - 7551 /nt

View Villa Aquamarie - Kamique
Little Harbor, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Sitting on Anguilla’s South Shore, Anani - Kamique commands stunning views of a secluded beach cove and the mountains of St Martin. You will be just paces away from a private swath of cool white sand, complete with padded sun loungers, shaded day bed and gazebo.

From
US$1455 - 6735 /nt

View Villa Anani - Kamique

Lockrum Estate

Lockrum Estate, Anguilla, Caribbean
6 br, 6 ba (6 Ensuite)

Named after the Arawak word for “heaven,” Coyaba Villa assures a divine time in sunny Anguilla filled with joy and peace. This luxurious villa rests on the scenic southern coast, overlooking the breathtaking mountains of St.

From
US$960 - 8571 /nt

View Villa Coyaba Villa

Long Bay

Long Bay, Anguilla, Caribbean
8 br, 8 ba (8 Ensuite)

Find your own Caribbean paradise at Nevaeh. Set on a private, gated lot that stretches down to a half-mile of golden sand on Anguilla’s Long Bay, this luxury oceanfront vacation rental boasts stunning views and pampering service.

From
US$5200 - 24642 /nt

View Villa Nevaeh
Long Bay, Anguilla, Caribbean
7 br, 7 ba (7 Ensuite)

The lush estate of Santosha is split over three unique properties and offers you absolute beachfront luxury with magnificent views over Long Bay. Your staff is on hand to tend to your every need, while full time security ensures complete privacy.

From
US$8857 - 17857 /nt

View Villa Santosha
Long Bay, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

Spend a memorable holiday in this spacious villa on one of the Caribbean’s safest and most charming islands. Perched above Long Bay’s sugar white sands, Sea Villa is one of our top Anguilla villa rentals for beach lovers.

From
US$2400 - 11000 /nt

View Villa Sea Villa
Long Bay, Anguilla, Caribbean
4 br, 4 ba (4 Ensuite)

Unwind in Sand Villa’s glamorous accommodations. It’s one of our top Anguilla villa rentals for beach lovers, thanks to its idyllic setting surrounded by tropical greenery and perched above the sugar white sands of Long Bay Beach.

From
US$2400 - 10000 /nt

View Villa Sand Villa
Long Bay, Anguilla, Caribbean
4 br, 4 ba (4 Ensuite)

Like an ivory showpiece perched above the fabled white sands of Anguilla, Sky Villa is a four bedroom bijou destination that will take your breath away. Terraces that open to the infinity edge swimming pool and the ocean beyond induce a natural lightness of being, while ivory, rust, burgundy, pewter and muted green interiors keep guests happily anchored to earth.

From
US$2200 - 9000 /nt

View Villa Sky Villa

Long Path

Long Path, Anguilla, Caribbean
3 br, 3 ba (3 Ensuite)

Stretching across the horizon like an ivory sculpture, White Cedars villa offers all the perks required for a truly memorable island holiday. Allow the sensual features of this private three bedroom villa to overtake your senses and soul.

From
US$589 - 2500 /nt

View Villa White Cedars

Maundays Bay

Maundays Bay, Anguilla, Caribbean
22 br, 24.5 ba (19 Ensuite)

The award-winning Sheriva Estate offers the serenity of understated elegance alongside elite level amenities and perks. Recognized as both a Condé Nast Johansens “Recommended Property” and a AAA 4-Diamond Property, Sheriva Estate will satisfy even the most distinguished traveler.

From
US$16100 - 45000 /nt

View Villa Sheriva Estate
Maundays Bay, Anguilla, Caribbean
8 br, 9.5 ba (6 Ensuite)

Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve.

From
US$2900 - 15000 /nt

View Villa Harmony at Sheriva
Maundays Bay, Anguilla, Caribbean
8 br, 9.5 ba (6 Ensuite)

Located in Maundays Bay in Anguilla, Infinity at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the rest and relaxation you deserve.

From
US$2900 - 15000 /nt

View Villa Infinity at Sheriva
Maundays Bay, Anguilla, Caribbean
6 br, 6 ba (6 Ensuite)

Overlooking Cove Lagoon and just two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Mystique at Sheriva is one of Anguilla’s top luxury boutique villas. Located in the chic West End, the villa is situated on a lush 10-acre alcove with stunning views of the Caribbean Sea and St.

From
US$995 - 15000 /nt

View Villa Mystique at Sheriva

Meads Bay

Meads Bay, Anguilla, Caribbean
8 br, 10.5 ba (8 Ensuite)

Located on the soft white sands of Meads Bay, The Beach House offers an unparalleled beachfront location and the ultimate in breezy Caribbean living. Book your stay with Luxury Retreats today, and you will soon be in Anguilla on one of the most beautiful beaches in the world.

From
US$10714 - 25428 /nt

View Villa The Beach House
Meads Bay, Anguilla, Caribbean
11 br, 11.5 ba (11 Ensuite)

Double the fun with a stay at Kishti on Meads. With two chic contemporary villas set on the beautiful white sands and turquoise waters of Meads Bay, the property can host the whole family for a Caribbean getaway or act as an idyllic setting for a special event.

From
US$11200 - 22000 /nt

View Villa Kishti on Meads
Meads Bay, Anguilla, Caribbean
6 br, 7.5 ba (6 Ensuite)

Treat yourself to a beautiful beach, pampering service, great contemporary design and five-star shopping and dining at Kishti on Meads East. Not only is the villa set on the sugary sands of Meads Bay Beach, it’s just a short walk from the restaurants and bars along the bay.

From
US$4200 - 11000 /nt

View Villa Kishti on Meads East
Meads Bay, Anguilla, Caribbean
5 br, 5 ba (5 Ensuite)

Gorgeous, mile-long Meads Bay is now the venue of choice for island foodies with its array of beachy and upscale restaurants, bars, anchored at each end of the beach by 5-star resorts – all within easy strolling distance of the new Kishti six bedroom beach enclave. The newcomers, designed by renowned international Interior Architects Cecconi Simone Inc.

From
US$4200 - 11000 /nt

View Villa Kishti on Meads West
Meads Bay, Anguilla, Caribbean
2 br, 2 ba (2 Ensuite)

Deny yourself nothing with a stay at Malliouhana - An Auberge Resort. Long a favorite of the Caribbean jet set, the resort was recently renovated, offering retro-chic interiors in a rainbow of pastel hues and floral prints.

From
US$1345 - 2750 /nt

View Villa Malliouhana - An Auberge Resort

Rendezvous Bay

Rendezvous Bay, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Stretching across the horizon like an ivory sculpture, Seabird villa offers all the perks required for a truly memorable island getaway experience. Allow the sensual features of this private four bedroom villa to overtake your senses and your soul.

From
US$650 - 3720 /nt

View Villa Seabird

Sandy Hill

Sandy Hill, Anguilla, Caribbean
5 br, 4.5 ba (4 Ensuite), Pool

Like the extraordinary orange and purple flower with which this residence shares its name, Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first class resort.

From
US$1975 - 7399 /nt

View Villa Bird of Paradise Villa
Sandy Hill, Anguilla, Caribbean
7 br, 8 ba (7 Ensuite)

Little could be more invigorating than beach fun and tennis on the sunny island of Anguilla. Zenaida Estate offers both brilliant activities right at your fingertips! This resplendent villa is located in the coveted area of Sandy Hill and is nestled on three acres of lush tropical gardens with sweeping views of the Caribbean Sea and the mountains of St.

From
US$1300 - 7150 /nt

View Villa Zenaida Beach and Tennis Estate
Sandy Hill, Anguilla, Caribbean
3 br, 3.5 ba (3 Ensuite)

Located on a secluded beach on Anguilla’s southern shore, Tequila Sunrise is a spacious and contemporary beach house on Lover’s Cove in Dropsey Bay. The villa overlooks the Caribbean Sea and offers stunning views of the mountains of St Martin.

From
US$900 - 3200 /nt

View Villa Tequila Sunrise

Shoal Bay East

Shoal Bay East, Anguilla, Caribbean
4 br, 4.5 ba (4 Ensuite)

Located on spectacular Shoal Bay East in the idyllic island paradise of Anguilla, Villa Black Pearl offers privacy, relaxed elegance and exquisite views. Just steps to one of the Caribbean’s most beautiful beaches, you will be perfectly positioned for the ultimate Caribbean holiday.

From
US$1000 - 4800 /nt

View Villa Villa Black Pearl
Shoal Bay East, Anguilla, Caribbean
8 br, 8 ba (8 Ensuite)

Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island.

From
US$1100 - 4655 /nt

View Villa Beachcourt Villa

Shoal Bay West

Shoal Bay West, Anguilla, Caribbean
8 br, 9.5 ba (8 Ensuite)

The African Sapphire is a generously proportioned beachfront property with a very large living and entertaining area that allows dining for 18, and offers superb 360 degree views of the Caribbean Sea and St Martin.

The African Sapphire is four stories high and 14,000 square feet sumptuously appointed villa.

From
US$3571 - 13571 /nt

View Villa African Sapphire at Altamer
Shoal Bay West, Anguilla, Caribbean
5 br, 7 ba (5 Ensuite)

This generous and luxurious beachfront villa features incredible views of the Caribbean Sea and St Martin. The spacious living and dining area is ideal for gatherings of family and friends or for entertaining business associates.

From
US$3357 - 12857 /nt

View Villa Blue Diamond
Shoal Bay West, Anguilla, Caribbean
5 br, 6 ba (5 Ensuite)

Antilles Pearl at Altamer is an extravagant three-floor villa reserved only for those who appreciate the finer things in life. Located in lovely Shoal Bay West on the island of Anguilla, this massive seaside estate boasts amazing views of the crystal clear Caribbean Sea.

From
US$3214 - 12142 /nt

View Villa Antilles Pearl at Altamer