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Vacation Rentals in Anguilla, Caribbean

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    Travellers to Anguilla are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 36
    5 of 5 bubbles (10) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
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    1 / 42
    5 of 5 bubbles (7) Excellent
    Blowing Point
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    1 / 22
    Little Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 23
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    Offering ocean views from a balcony or terrace, these spacious, air-conditioned suites have Caribbean-style décor, full kitchens, a comfortable living space, washer and dryer, and complimentary wi-fi access. There is a king-size bedroom and a separate living room that includes a flat-screen TV and... View all property information
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    Anguilla, Caribbean
    1 / 24
    South Hill
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Ambia is centrally located in Anguilla with spectacular views overlooking Sandy Ground and minutes away from the Island's 33 magnificent white-sand beaches. The Villa is newly renovated and available for rental beginning December 1, 2016. Ambia's Asian-style suites with Caribbean influence are the... View all property information
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    South Hill, Anguilla AI 2640
    1 / 21
    5 of 5 bubbles (2) Excellent
    The Valley
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Dear Paradise Researcher, We are very pleased to have your kind interest in our version of True Paradise! 2016 is a milestone for Elise & Paul as it marks their 30th year sharing their unique vacation homes with great folks like yourself. Whether a ski chalet at LOON MOUNTAIN, a bungalow on... View all property information
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    The Valley, Anguilla AI 2640
    1 / 4
    The Valley
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Lovely decor adorns this delightful two bedroom villa which includes an open kitchen, bar and dining room with vaulted ceilings; two equal air conditioned master bedroom suites, private hot tub, lush gardens and roof top sun lounge. Each master suite has memory foam beds with luxury linens, and is... View all property information
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    The Valley, Anguilla A1
    1 / 4
    The Valley
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Experience the luxury vacation of your dreams in the romantic ambiance of Gardenia Villa. Lounge on your private roof deck and enjoy the laid-back tropical lifestyle of Anguilla. Overlooking the sparkling azure waters of West End Bay, Gardenia is just a five minute walk from Shoal Bay West -... View all property information
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    The Valley, Anguilla A1
    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    For the ultimate in luxury, the Frangipani Beach Resort's new beachfront villa offers privacy with the benefit of access to Frangipani's exclusive amenities. This 5,000 square foot four-bedroom villa offers ocean facing bedrooms equipped with king-sized beds, plus a multipurpose room that can be... View all property information
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    Anguilla, Caribbean
    1 / 24
    Island Harbour
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Villa Soleil at Captains Bay is a fully air conditioned villa with luxury appointments throughout. . From every vantage point, the villa has the most spectacular views of any villa on the island. Breathtaking views of the ocean from the front and rear of the villa; view of seven islands including... View all property information
    Location Information
    Island Harbour, Anguilla AI 2640
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    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located in Shoal Bay East, Anguilla, British West Indies, this majestic 4 bedroom villa sits on one acre of stunning oceanfront property and is a short stroll to one of the finest beaches in the world. With more than 7,000 square feet of indoor and outdoor living space, Shoal Bay Pointe is designed... View all property information
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    Anguilla, Caribbean
    1 / 34
    Island Harbour
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Epic Beachfront Villa is located on a private and secluded beach, offering luxury living in a relaxing setting on the tropical island of Anguilla.This property has its own private helicopter pad where we can arrange for quick trips to St. Martin and St. Barthelemy. This family-friendly villa... View all property information
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    Island Harbour, Anguilla
    1 / 25
    Long Bay Village
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Golfer’s Eden is a beachfront vacation rental nestled in the crescent curve of Rendezvous Bay, and offers direct access to the Greg Norman 18-hole championship golf course. Guests staying here will have access to a secluded sandy cove and is within walking distance to the mile-long beach of... View all property information
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    Long Bay Village, Anguilla
    1 / 34
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Surrounded by wide open spaces, fresh air and amazing ocean views, this four bedroom villa combines the idyllic Caribbean lifestyle with five-star boutique luxury. CéBlue Villas & Beach Resort is perched atop a hillside overlooking the blue ocean waters of Crocus Bay, and the location is just steps... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 6
    The Valley
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Set into beautifully landscaped gardens, Mangrove Villa is on dramatic West End Bay and just a 5 minute walk from the powder white sands of Shoal Bay West. The magnificent roof top lounge is perfect for sun-bathing or having cocktails while watching the sun go down. The 50 x 20 foot freeform pool... View all property information
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    The Valley, Anguilla A1
    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Simpson Bay Penthouse is a top-level vacation rental that sits directly on Kim Sha and is minutes away from Simpson Bay Beach, Mullet Bay, and the infamous Sunset Beach Bar. You can walk to the drawbridge and watch the sailboats and mega yachts (in season) enter and exit the lagoon. The penthouse... View all property information
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    Anguilla, Caribbean
    1 / 30
    Island Harbour
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Fountain Beach Villa is located on Shoal Bay East on the tropical island of Anguilla and is a short walk to Shoal Bay Beach. The villa features four bedroom suites each with a private bathroom, an outdoor shower garden, air conditioning and a flat screen TV. Indoor spaces are full of verve and... View all property information
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    Island Harbour, Anguilla
    1 / 29
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    About this property
    Seaside Villa is located is located on a private beach shared by only four other villas, and is minutes away from Shoal Bay Beach and close to some of the island's best cuisine and market shopping. Included for our guests at Opus Destinations is a special shuttle available to take you to Shoal Bay... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 34
    Island Harbour
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Epic Beachfront Villa is located on a private and secluded beach, offering luxury living in a relaxing setting on the tropical island of Anguilla. This property has its own private helicopter pad where we can arrange for quick trips to St. Martin and St. Barthelemy. Designed to maximize the 20,000... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 26
    Rendezvous Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    • x
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    About this property
    Situated on the western end of the sparkling white sands and aquamarine waters of Rendezvous Bay, Anguilla, Arushi Villa brings private luxury to this stunning natural paradise. You’ll enjoy pampering and seclusion with the five-star amenities of Cusinart Resort at your service. And for golf... View all property information
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    Rendezvous Bay, Anguilla
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    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    This slice of paradise is perched on a hill overlooking the shimmering Crocus Bay on the island of Anguilla. Spectacular architecture and sensational tropical scenery, tasteful furnishings and a deluxe kitchen offers you unequaled comfort in a tropical paradise setting. The villa is sprawled out... View all property information
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    Anguilla, Caribbean
    1 / 12
    West End Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Step into a magical sea-view villa on the dramatic lush green hillsides of Anguilla's Long Bay, featuring sweeping panoramic views of the glittering turquoise waters that fill the expanse across the horizon. As one of the Caribbean's crowned jewels, the beaches of Anguilla provide picturesque... View all property information
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    West End Village, Anguilla
    1 / 30
    Sandy Hill Bay
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Villa Zenaida Beach & Tennis Estate sits on Anguilla’s highest elevation and is nestled in three acres of lush tropical gardens. The villa is reached entirely by paved road and is famous for its sweeping views of the Caribbean Sea, St. Martin and St. Barthelemy. Enjoy ultimate privacy in this five... View all property information
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    Sandy Hill Bay, Anguilla
    1 / 35
    8 Bedrooms, 9 Bathrooms, Sleeps 20 | Quick View
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    • Terrace
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    • x
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    About this property
    Luxury St. Martin Estate is nestled on a hilltop that faces the turquoise sea with extensive grounds and blossoming gardens. The villa is sprawled out over 12,000 square feet of grand living spaces and features eight bedroom suites, eight full plus one half bathrooms, sleeps 20 guests, and is... View all property information
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    Anguilla, Caribbean
    1 / 15
    West End Village
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Indulge the mind, body, and senses in an immerses luxury villa rental experience along the white-sandy shores of Long Bay on the pristine island of Anguilla in the Caribbean. Part of the Elements Estate in Long Bay, this Sea Villa is one of three architecturally-stunning properties set amidst the... View all property information
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    West End Village, Anguilla
    1 / 35
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • x
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    About this property
    Dramatically situated on one of the most coveted destinations in the Caribbean, CéBlue Villas & Beach Resort is built into the hillside overlooking the shimmering Crocus Bay on the island of Anguilla. Spectacular architecture and sensational tropical scenery, tasteful furnishings and a deluxe... View all property information
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    Anguilla, Caribbean
    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    This new log cabin is located in a private gated community and has all the amenities to make a memorable New Year. Wolf Creek is the perfect getaway for large families or groups traveling together and accommodates up to 16 guests. The unit comprises over 4,600 square feet with four bedrooms (plus... View all property information
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    Anguilla, Caribbean 84032
    1 / 34
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This vacation villa can be rented out separately by bedrooms. Fore more information on pricing, please contact our reservations team at *******-5511 or email us at [email protected] St. Barthelemy Luxury is the perfect “base camp” for all your activities on the Caribbean island and will exceed and... View all property information
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    Anguilla, Caribbean
    1 / 31
    West End Village
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Situated directly on Long Bay; Villa Nevaeh offers the pinnacle of refined comfort and privacy for guests who choose Anguilla for the ultimate Caribbean escape. This beachfront vacation villa boasts five bedrooms; including a finely-appointed guesthouse with a second full kitchen. Balinese... View all property information
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    West End Village, Anguilla
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Dreamy architecture, great outdoor amenities, and panoramic views of the Caribbean Sea makes this vacation home a perfect retreat for the whole group. The contemporary build and design are enhanced by an Asian touch; providing tranquility and privacy in a spectacular waterfront location on a... View all property information
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    Anguilla, Caribbean
    1 / 15
    West End Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Situated on the white sands of Long Bay Beach, perched just above the shoreline, capturing a panoramic 180-degree view of the turquoise waters of the Caribbean Sea just off the coast of Anguilla, this sumptuous Sand Villa, part of the Elements Estate, is sure to dazzle mind, capture the heart, and... View all property information
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    West End Village, Anguilla
    1 / 25
    Rendezvous Bay
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Situated on the white-sandy beaches of Anguilla's renowned Rendezvous Bay, boasting a commanding view of the sparkling turquoise waters of the Caribbean Sea, this sprawling white-washed estate oozes resort style elegance, in a luxurious and private setting. Immerse yourself in a five-star... View all property information
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    Rendezvous Bay, Anguilla
    1 / 16
    Little Harbour
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Comfortable villa in quiet neighborhood overlooking Little Harbor. Views include lovely sunsets over the harbor, St Martain and surrounding islands. There is access to Little Harbor for swimming and snorkeling. The villa has a spacious great room with high airy ceilings, full kitchen, dining and... View all property information
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    Little Harbour, Anguilla CARRIBEAN
    1 / 33
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Welcome to the resort that combines an idyllic, relaxed Caribbean lifestyle with this luxuriously appointed villa. Dramatically situated on one of the most coveted destinations in the Caribbean, CéBlue is built into the hillside overlooking the shimmering Crocus Bay on the island of Anguilla.... View all property information
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    Anguilla, Caribbean
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Perched high above Little Bay, overlooking the sparkling Caribbean waters, Ani Villas Anguilla North Estate is a spectacular luxury waterfront villa with a heated pool & jacuzzi. Take in the spectacular west-facing ocean views from virtually every square inch of this spectacular property. Enjoy... View all property information
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    Anguilla, Caribbean
    1 / 28
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    About this property
    PLEASE NOTE THIS VACATION RENTAL CAN BE RENTED OUT SEPARATELY. PLEASE CALL OR EMAIL OUR RESERVATIONS TEAM FOR MORE INFORMATION. Villa Ani is a fabulous Caribbean retreat for friends and family and is comprised of two spacious villas both offering unequaled comfort in a luxurious setting. There is a... View all property information
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    Anguilla, Caribbean
    1 / 45
    5 of 5 bubbles (4) Excellent
    Blowing Point
    10 Bedrooms, 12 Bathrooms, Sleeps 20 | Quick View
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    • Children's Pool
    • Mountain Views
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    About this property
    A PRIVATE RESORT, ALL TO YOURSELVES! ***One of the most affordable 10-bedroom options on Anguilla and near the island's desirable West End!!*** This professionally-managed, two-villa oceanfront estate with a small beach nearby is ideal for family reunions, destination weddings, corporate... View all property information
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    Blowing Point, Anguilla BWI
    1 / 32
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Resting majestically along the white sands of Meads Bay Beach, along the idyllic coastline of Anguilla, immersed in an endless seascape of shimmering turquoise waters and towering coconut palms, this six bedroom contemporary villa provides an immerse luxury experience in the Caribbean. Come enjoy... View all property information
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    Anguilla, Caribbean
    1 / 35
    West End Village
    7 Bedrooms, 9 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    This magnificent estate truly is beyond comparison. Long Bay Bliss offers its guests an exquisite accommodation for a special event, of a secluded Caribbean retreat with extraordinary amenities. The estate features one main house and two separate guest houses. The seven bedrooms are split over the... View all property information
    Location Information
    West End Village, Anguilla
    1 / 30
    10 Bedrooms, 11 Bathrooms, Sleeps 20 | Quick View
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    • Patio
    • Waterfront
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    A favorite VIP getaway, Little Harbour Grandeur is an exceptionally private Caribbean island retreat with five-star amenities and experiences. A spectacular choice for weddings or extended family gatherings, Little Grandeur has an adjoining sister property that can be booked to expand luxury... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 37
    Shoal Bay Village
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Tamarind Villa overlooks the Atlantic on the north eastern end of the island. This villa is just a five minute drive from Shoal Bay East, one of the most beautiful beaches in the Caribbean. With its large principle rooms and comfortable settings, its the perfect place for large family and... View all property information
    Location Information
    Shoal Bay Village, Anguilla AI 2640
    1 / 16
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Nestled in Little Bay, Ani Villas South Estate sits adjacent to its North relative, with a commanding presence overlooking the turquoise waters and white-sandy beaches of the Caribbean Sea. Oriented towards the westerly-facing views, Ani Villas South Estate's bedrooms and living spaces are front... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 33
    9 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Private Outdoor...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Imagine a resort equipped villa with breathtaking views, generous inclusions and a full staff... all exclusively yours. Ani Villas Anguilla was designed specifically to host large groups and families seeking a more pampered Caribbean escape. As the name suggest Àni North sits on the northern... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    1 / 24
    Shoal Bay Village
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Located just west of Shoal Bay East the views from the pool deck and upper balcony are panoramic and dramatic. Special touches throughout this lovely villa reflect the extensive efforts to make this villa comfortable and relaxing for guests. The home has four bedrooms, five bathrooms and has... View all property information
    Location Information
    Shoal Bay Village, Anguilla AI 2640
    1 / 28
    Rendezvous Bay
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Songbird Villa is a newly constructed villa with spectacular views of Rendezvous Bay the Caribbean Sea and St. Martin. This villa has a unique blend of contemporary and classic Caribbean architecture and provides a true island living experience. It is less than a minute's drive to the sands of... View all property information
    Location Information
    Rendezvous Bay, Anguilla AI 2640
    1 / 24
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    • Washer
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This 3700 sf. sprawling compound offers mature landscaping, a master bedroom, two additional bedrooms with private bathrooms, a 1900 sf. Great Room and the Entertainment Deck. Each bedroom offers private decks for sunning or just relaxing with a cocktail. If you don't want to go to the beach... View all property information
    Location Information
    Anguilla, Caribbean 12345
    1 / 26
    5 of 5 bubbles (28) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • DVD Player
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    Charming & affordable Bonnie & Isaiah's country cottage apartment: The monthly rent is US $1,200 is for 1-2 people staying 2 months or longer. The monthly rent is US $1,300 for 1-2 people staying 1 month only. Additional guests pay US $20 per night per person. One bedroom with king-sized bed,... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    1 / 26
    Little Harbour
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Washer
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Gorgeous villa located on the rocky coastline in Little Harbour with Elsie Bay within walking distance. This beautiful villa has two masters and a guest bedroom on the main floor. Spacious pool deck with covered area for dining and relaxing and chaise lounges for sunning. Even a bocce court for a... View all property information
    Location Information
    Little Harbour, Anguilla AI 2640
    1 / 14
    Rendezvous Bay
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The home is outfitted with all modern amenities and fully furnished and decorated to reflect a thoughtful sense of place and style. Fully air conditioned, with en suite bathrooms in each bedroom, the villa combines the best of the natural tranquility of the beach, with the luxury that discerning... View all property information
    Location Information
    Rendezvous Bay, Anguilla
    1 / 32
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Waterfront
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The villa is a contemporary 5 000 square foot beach house on secluded Lover's Cove, Dropsey Bay on the southern shore of Anguilla. It overlooks the Caribbean Sea and the mountains of St. Martin beyond. Whilst accessible to all the conveniences of modern living, Tequila is a private retreat that... View all property information
    Location Information
    Anguilla, Caribbean AI 2640