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Rentals with Pool in Anguilla, Caribbean

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    Travelers to Anguilla are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 25
    5 of 5 stars (5) Excellent
    South Hill
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    South Hill
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    1 / 10
    5 of 5 stars (12) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Hot Tub
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    • Water Views
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    About this property
    Bird of Paradise, named one of the top villas in the Caribbean by both Islands Magazine and Ocean Home magazines, was recently recognized by Conde' Nast. The reasonably-priced villa is designed in an Asian tropical style with indoor/outdoor living and two lagoon-style pools, which weave amongst... View all property information
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    Anguilla, Caribbean 00000
    5 of 5 stars Reviewed May 25, 2015
    There is absolutely nothing not to love about the Bird of Paradise. The house is exceptional and the staff is great. We have stayed at a number of villas throughout the Carib...
    5 of 5 stars Reviewed August 2, 2012
    zoe is property manager, genius chef, leader of the most amazing staff...how could one of the most beautiful places on earth also be graced by such wonderful people. Magnificent...
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    1 / 89
    5 of 5 stars (11) Excellent
    The Valley
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • DVD Player
    • Stereo System
    • Watersports Nearby
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Internet Access
    • Private Outdoor...
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    • Pet-friendly
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    About this property
    Oceana, Anguilla offers tranquility, romance, and casually elegant tropical living. The villa's open design maximizes sea views and ocean breezes, inviting you to experience a private vacation retreat. Set on a breezy hillside overlooking picturesque Crocus Bay, this bright and airy villa provides... View all property information
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    The Valley, Anguilla NONE
    5 of 5 stars Reviewed May 31, 2014
    Perfection is the word that sums it up. This was the nicest villa that we've ever rented, anywhere. The location was perfect, quiet with stunning views. The villa was high end...
    5 of 5 stars Reviewed December 12, 2012
    From the minute you walk in the front door your eye is drawn to the beautiful view outside! The water is so blue and amazing! The home is wonderful, the furnishings are so well...
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    1 / 32
    5 Bedrooms / 6 Bathrooms / Sleeps 12
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    • Shared Outdoor Pool...
    • Grill
    • Satellite TV
    • Air Conditioning
    • Water Views
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • ?
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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
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    5 of 5 stars (1) Excellent
    West End Village
    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Ocean Views
    • Staffed Property
    • DVD Player
    • Wi-Fi
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Golden sun, aquamarine sea, azure sky, soft white sand, beautiful unspoilt and uncrowded beach at Rendezvous Bay Beach, Bow Green Villa with swimming pool , fantastic haute cuisine of Anguilla near by,and indulgent luxury Spa near by are waiting for you. Bow Green is a beautiful home walking... View all property information
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    Location Information
    West End Village, Anguilla A12640
    5 of 5 stars Reviewed September 8, 2014
    Would recommend this to anyone! Of all the tropical islands I've visited this is my favourite. its the most picture perfect paradise island of them all. I have stayed at Bow...
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    1 / 29
    5 of 5 stars (41) Excellent
    7 Bedrooms / 7 Bathrooms / Sleeps 18
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    • Hot Tub
    • Internet Access
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Private Outdoor...
    • Playground
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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    About this property
    MOONRAKER - The ultimate villa in Anguilla for Luxury, Seclusion and Value. Rated overall as '5 star” and loved by all our valued customers. Rated 'Excellent' on Tripadvisor and awarded 'Top Vacation Rental' on Flipkey/Tripadvisor Moonraker Villa awaits you; a signature, 7 suite, 15,500 sq ft... View all property information
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    Anguilla, Caribbean AI 2640
    4 of 5 stars Reviewed January 22, 2015
    This was an amazing place to stay!! For sharing purposes, here are the pros and cons, in my opinion: Pros: - Amazing decor; awesome floor plan - Pool is beautiful - Amazing...
    5 of 5 stars Reviewed September 24, 2014
    Sorry for the delay in writing up this review, however better late than never! 12 of my clsest friends and myself traveled to the Moonraker at the end of July. Upon arrival the...
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    1 / 35
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Washer
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Grill
    • Gym
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
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    1 / 8
    4.5 of 5 stars (5) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
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    • Private Outdoor...
    • Stereo System
    • Ocean Views
    • Waterfront
    • Deck
    • TV
    • DVD Player
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Mainstay is a privately owned villa situated on a ½ acre right on the Caribbean Sea. It offers 3 bedrooms, 2 full baths and a 1/2 bath. Our lovely pool and large deck offers spectacular southern views of St. Martin & other neighboring islands. Mainstay is a very spacious and well appointed... View all property information
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    Anguilla, Caribbean ELSIE BAY
    5 of 5 stars Reviewed March 22, 2015
    I stayed here with my family in February 2015. This is a beautiful, spacious villa with a stunning view. It has a charming vibe. The Pattersons were very helpful with their...
    5 of 5 stars Reviewed February 21, 2015
    We have vacationed at Mainstay several times over the past few years and could not imagine a more perfect experience. The location provides the most breathtaking view on the...
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    1 / 20
    5 of 5 stars (3) Excellent
    Long Bay Village
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Water Views
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    The Retreat @ Moonraker is a fully secure private retreat that allows full privacy and interaction with the perfect serenity of its surroundings. Fully opening expanses of glass optimize the stunning views from all elevations The Retreat @ Moonraker Villa awaits you; a signature 15,500 sq ft villa... View all property information
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    Location Information
    Long Bay Village, Anguilla AI 2640
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    $375
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    1 / 15
    5 of 5 stars (7) Excellent
    Shoal Bay Village
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    travelers have booked this property
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    • Deck
    • Dryer
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Take in the beautiful panaromic views of St. Martin, the beautiful ocean and parts of the island while sitting on the deck drinking your morning coffee or cocktail! Large open air living space with dining room, sitting area as well as chaises to enjoy your day. Two large beautifully appointed... View all property information
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    Location Information
    Shoal Bay Village, Anguilla 00000
    5 of 5 stars Reviewed April 10, 2015
    We truly enjoyed our stay at the villa. It’s a beautiful place with magnificent views. There are amazing views of St. Martin from almost any point in the villa. The villa is...
    5 of 5 stars Reviewed April 3, 2015
    The view will stop you in your tracks the moment that you walk into the house. The living room is filled with comfy couches and lounges to sit and stare out at the distant islands...
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    5 of 5 stars (67) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Reviews (67) Make Inquiry
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    • Air Conditioning
    • Watersports Nearby
    • Ocean Views
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Children's Pool
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Dear Paradise Researcher, before you do read on, know the safe and serene island of Anguilla and the stunning Grand Outlook Castle WILL exceed you and your party's expectations. No image or description can ever replicate the experience of the beauty and friendly people of Anguilla and the event... View all property information
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    Anguilla, Caribbean N A
    5 of 5 stars Reviewed July 16, 2015
    Paul and Elise made us feel like we were borrowing a friend's home, instead of renting a vacation house. Their attention to details about our arrival, stay, and departure made...
    5 of 5 stars Reviewed May 31, 2015
    This was our second stay at the castle. Both vacations were fantastic! Paul and Eileen were very responsive to everything. The house and views are absolutely breathtaking! my...
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    $2,200
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    1 / 19
    5 of 5 stars (1) Excellent
    West End Village
    5 Bedrooms / 14 Bathrooms / Sleeps 10
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    Amenities & Details
    • Ocean Views
    • Staffed Property
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • TV
    • Private Outdoor...
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    ARUSHI means ' Ray Of Sunshine' This exquisite beach front property situated in the West of Anguilla at the CUISINART GOLF RESORT & SPA, this exclusive villa is one of only 12 homes on this beautiful estate.Located on a 4,400 foot long stunning white sandy beach. A Greg Norman designed golf course... View all property information
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    Location Information
    West End Village, Anguilla AI2640
    5 of 5 stars Reviewed March 6, 2015
    We had the pleasure of staying at Arushi Villa and the property exceeded our expectations. The privacy, the accommodations, and the breathtaking views made for a remarkable...
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    1 / 14
    Studio / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Water Views
    • Shared Outdoor Pool...
    • Internet Access
    • Microwave
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Take an unforgettable vacation at The Fountain Residences in this luxury, over-sized studio. The Fountain Residence is located on Shoal Bay East, and is only a short five minute walk to the white sandy beaches and blue ocean water. The studio offers flexible seating and conversation areas with... View all property information
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    Anguilla, Caribbean
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    $249
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    1 / 19
    Island Harbour
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Water Views
    • Wi-Fi
    • TV
    • Housekeeping...
    • Watersports Nearby
    • Waterfront
    • Ocean Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    CATALINA VILLA- Shoal Bay Village, Anguilla; PERFECT FOR ONE OR TWO COUPLES OR A FAMILY WITH 1-3 CHILDREN!! This cute Caribbean Style newly built (2012-14) home has two beautiful Bedrooms and each has its own En Suite Bathroom with Shower and double vanities. Perfect for two couples or one... View all property information
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    Location Information
    Island Harbour, Anguilla XXXXXX
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    $425
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    1 / 18
    West End Village
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Housekeeping...
    • Ocean Views
    • TV
    • Watersports Nearby
    • Water Views
    • Private Outdoor...
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    LOCATED DIRECT WATERFRONT STUNNING VIEWS OF SHOAL BA.Y EAST AND REEFS BEYOND! SHOAL REEF Villa has four (4) one bedroom suites with 4.5 beautiful Bathrooms, Waterfront, Washer, TV, Preferred Lifestyle, Pool, Microwave, Maid Service, Internet, Hair Dryer, Dryer, Dish Washer, Coffee Maker, Ceiling... View all property information
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    Location Information
    West End Village, Anguilla XXXXXXXXXX
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    $777
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    1 / 25
    Blowing Point
    3 Bedrooms / 10 Bathrooms / Sleeps 9
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    • Sauna
    • Ping Pong Table
    • Housekeeping...
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    BRAMASOLE - Pelican Bay, Anguilla Location: Anguilla 1 - 3 Bedrooms, 3.5 Baths , Air Conditioning Whole House, BBQ, Blender, Cable, Ceiling Fans, Coffee Maker, Dish Washer, Dryer, DVD, Hair Dryer, Ice Maker, Internet, Maid Service, Microwave, Pool, Preferred Lifestyle, Safe, TV, Washer Villa... View all property information
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    Blowing Point, Anguilla XXXXXXXXXX
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    1 / 49
    5 of 5 stars (5) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Stereo System
    • Private Outdoor...
    • Water Views
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Three Dolphins, Anguilla is an Elegantly furnished Small Estate on the British West Indies Isle of Anguilla and provides a most private escape for the discriminating traveler. Overlooking its own secluded strand of white sand beach directly in front of the house it also has breathtaking views of... View all property information
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    Location Information
    Anguilla, Caribbean A12640
    5 of 5 stars Reviewed April 21, 2013
    We just returned from a fantastic week at Three Dolphins. The house is absolutely spectacular. The main house has three air conditioned "master suites", all equally beautiful. The...
    5 of 5 stars Reviewed March 25, 2013
    We enjoyed another fabulous week on Anguilla with friends at Three Dolphins villa - this was our third stay there. I am posting some pictures from our recent trip. I highly...
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    $2,100
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    1 / 17
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Parking
    • Dishwasher
    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Shared Yard
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 6... View all property information
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    Anguilla, Caribbean
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    $1,050
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Staffed Property
    • Watersports Nearby
    • Wi-Fi
    • Game Room
    • Ping Pong Table
    • Housekeeping...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    CéBlue Villas on Crocus Bay Anguilla, is in the heart of the beach studded island in a northwestern locale. The new property is set in over ten acres of tropical hillside, with spanning views of five-thousand-foot-stretching tranquil coastline. The entire resort's vibe is Capri meets Santorini... View all property information
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    Location Information
    Anguilla, Caribbean 1264
    5 of 5 stars Reviewed June 18, 2015
    My partner and I stayed at CeBlue for five nights and six days, we travel allover and it was the most stunning resort/villa we have ever been to. The staff was so friendly and...
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    1 / 16
    5 of 5 stars (2) Excellent
    West End Village
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Water Views
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bow Green is walking distance to Rendezvous Bay Beach which is one of the best beaches in Anguilla. Great views of St Martin and close to Anguilla Great House and Cuisinart Golf Resort. It is three bedroom villa and sleeps six and has a very private large walled swimming pool. We offer... View all property information
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    Location Information
    West End Village, Anguilla A12640
    5 of 5 stars Reviewed June 13, 2015
    Overlooking a stunning 2 mile long powder white sandy beach, named Rendevous Bay, stands Bow Green Villa which is set within half an acre of private land. The exclusivity of the...
    5 of 5 stars Reviewed October 8, 2014
    Beautiful beaches and superb family-oriented accommodation. Comfortable air-conditioned rooms, fitted kitchen with all mod cons. Private swimming pool and wonderful views of the...
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    The Valley
    3 Bedrooms / 10 Bathrooms / Sleeps 9
    Overview Make Inquiry
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    • Waterfront
    • Housekeeping...
    • Mountain Views
    • Watersports Nearby
    • Swingset
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Villa Description Nearest Beach: Blowing Point Beach Beach Proximity: On the Sea, Steps to Sandy Blowing Point Beach; St. Martin Views! Bramasole Villa is a jewel perched on the waters edge, located on a private cul-de-sac at Pelican Bay, with the beach just steps away from the pool gate.... View all property information
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    Location Information
    The Valley, Anguilla AI2640
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    $1,250
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    1 / 25
    Island Harbour
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    traveler have booked this property
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Water Views
    • DVD Player
    • Stereo System
    • Waterfront
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Island Harbour, Anguilla AI 2640
    From
    $3,500
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    1 / 30
    Island Harbour
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Gym
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool...
    • TV
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee) This... View all property information
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    Location Information
    Island Harbour, Anguilla
    From
    $487
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    West End Village
    4 Bedrooms / 9 Bathrooms / Sleeps 8
    Overview Make Inquiry
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    • TV
    • Housekeeping...
    • Water Views
    • Wi-Fi
    • Waterfront
    • Private Outdoor...
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The 'Abbey' comprises of four (4) bedrooms, one bedroom being in a different separated wing and three on the other side, all bedrooms have ensuite bathrooms, three with ocean views... The living room doors open up to a perfectly situated outside area, overlooking the ocean in all its beauty. The... View all property information
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    Location Information
    West End Village, Anguilla AI 2640
    From
    $2,500
    / Night
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    1 / 21
    8 Bedrooms / 14 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Nestled in three acres of lush tropical gardens, where a 17th century Dutch fort once stood, Zenaida Tennis and Beach Estate offers gracious island living. Enjoy ultimate privacy in two separate villas and an adjoining garden cottage, all handsomely appointed featuring a total of seven... View all property information
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    Location Information
    Anguilla, Caribbean A12640
    From
    $1,375
    / Night
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    1 / 27
    5 of 5 stars (7) Excellent
    Shoal Bay Village
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Ocean Views
    • Private Outdoor...
    • Satellite TV
    • Private Fishing...
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    **Quick Villa Azure info: Villa Azure is a 5 Star Luxury Villa overlooking Anguilla's best Beach- Shoal Bay Beach • It is the most luxurious Villa with the most amenities in the Shoal Bay Beach area • The best sea views on the island are framed in each doorway with endless shades of blue • One of... View all property information
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    Location Information
    Shoal Bay Village, Anguilla 00000
    5 of 5 stars Reviewed March 9, 2014
    Villa Azure provides a 5+++ Star vacation accommodation with all the privacy and comfort of a private home. Villa Azure's location and staff are beyond compare. If you are...
    5 of 5 stars Reviewed July 12, 2013
    Our family spent a week at Azure and it was more than we expected. The pictures on the website don’t do this view justice. When looking for a vacation villa, you can’t help but...
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    From
    $1,800
    / Night
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    1 / 21
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Gym
    • Grill
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    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.... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $633
    / Night
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Safe
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    BRAZEPJ is ideally located just a 5 minute walk to Meads Bay Beach. Malliouhana Hotel, Blanchards Restaurant and other hotels and restaurants are also within walking distance along the beach. The main floor consists of a separate kitchen and dining area, living area with its unique wooden doors... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $4,250
    / Night
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    1 / 22
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Gym
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Children's Pool
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    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 Modenas double gated entrances, you are welcomed to over 10,800 square feet of indoor living space and 18,000... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $1,000
    / Night
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    1 / 16
    4.5 of 5 stars (2) Very good
    Blowing Point
    7 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • TV
    • Internet Access
    • Gym
    • Grill
    • DVD Player
    • Stereo System
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This 6/7 bedroom, 7,000 square foot gated property with large oceanfront freshwater pool sits on a landscaped 3.5 acre estate situated right on the Caribbean Sea with the mountain of St. Martin/St. Maarten beyond. The villa's protected harbor with boat dock and small cove are located directed out... View all property information
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    Location Information
    Blowing Point, Anguilla
    From
    $1,455
    / Night
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    1 / 14
    4.5 of 5 stars (2) Very good
    Little Harbour
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Stereo System
    • Shared Outdoor Pool...
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Sitting on Anguillas 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. Dramatically nestled in the rolling... View all property information
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    Location Information
    Little Harbour, Anguilla
    From
    $1,850
    / Night
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    1 / 19
    Little Harbour
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Dryer
    • Internet Access
    • DVD Player
    • Stereo System
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Sitting on Anguillas 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. Dramatically nestled in the... View all property information
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    Location Information
    Little Harbour, Anguilla
    From
    $490
    / Night
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Freezer
    • Refrigerator
    • Stove
    • Wi-Fi
    • Satellite TV
    • Microwave
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Palm Villa is located within the Indigo Reef Development in the West End of Anguilla. Indigo Reef is a group of one to four bedroom homes with a community pool and barbecue area and steps away from the small and quiet West End beach. Shoal Bay West is just a ten minute walk or two minute drive.... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $2,400
    / Night
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    1 / 11
    Long Bay Village
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool...
    • Hot Tub
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Unwind in Sand Villas glamorous accommodations. Its 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. The infinity-edged pool with an adjoining jacuzzi and lounge area is a... View all property information
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    Location Information
    Long Bay Village, Anguilla
    From
    $2,400
    / Night
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    1 / 12
    3 of 5 stars (1) Average
    Long Bay Village
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Gym
    • DVD Player
    • Parking
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Spend a memorable holiday in this spacious villa on one of the Caribbeans safest and most charming islands. Perched above Long Bays sugar white sands, Sea Villa is one of our top Anguilla villa rentals for beach lovers. Cool off in the infinity-edged pool during the day, and then lounge at night in... View all property information
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    Location Information
    Long Bay Village, Anguilla
    From
    $2,100
    / Night
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    1 / 32
    5 of 5 stars (2) Excellent
    Island Harbour
    5 Bedrooms / 7 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Stereo System
    • Dryer
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Villa Amarilla is a Caribbean gem influenced by subtle European and North African charms. The international sensibilities of the conceptualizers are revealed in the yellow stucco walls, turquoise shutters and red tile roof reminiscent of the Italian countryside, while the cool island interiors made... View all property information
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    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed December 12, 2011
    This villa was quite spectacular. The kitchen was very nice and spacious. All the bedrooms were very big and each had their own balcony which was really nice! The pool are was...
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    From
    $1,375
    / Night
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    1 / 19
    5 of 5 stars (5) Excellent
    Shoal Bay Village
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Grill
    • Stereo System
    • Internet Access
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Location, location, location! Villa Azure overlooks fabulous Shoal Bay Beach, Anguilla’s most celebrated beach. With its coveted position, exquisite attention to detail and tailoring to the desires of our guests, Villa Azure has cumulated in the perfect holiday retreat. Villa Azure was created to... View all property information
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    Location Information
    Shoal Bay Village, Anguilla
    5 of 5 stars Reviewed July 12, 2012
    We have visited Anguilla 3 times now and twice have stayed at Villa Azure. When you drive through the gates and step through the big wooden doors into the living room, the views...
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    From
    $480
    / Night
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    1 / 13
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Stove
    • Satellite TV
    • Wi-Fi
    • Dryer
    • Balcony
    • Refrigerator
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Lovely new three bedroom villa located in popular West End just a short walk from Meads Bay Beach, Malliouhana Hotel & Spa, Frangipani Resort and Blanchards Restaurant. The two bedrooms are located on each side of the villa with the living, dining, kitchen area in the center affording each bedroom... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $450
    / Night
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    1 / 35
    5 of 5 stars (53) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (53) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Watersports Nearby
    • Housekeeping...
    • Private Outdoor...
    • Staffed Property
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Offering stunning panoramic views of the down islands ( St. Maarten, St. Barths, Statia, St. Kitts and Nevis), this luxury 1 Bedroom Villa is among the largest of the 1 bedroom villas on the island with 1100 sq. ft. of living area and nearly 3000 sq. ft. of outdoor patio and pool deck area.... View all property information
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    Location Information
    Anguilla, Caribbean AI 2640
    5 of 5 stars Reviewed May 11, 2015
    Everything was seamless, from booking the villa to checking in and out. Sue and Joe are gracious hosts and do not miss any attention to detail. The villa is nicely appointed and...
    5 of 5 stars Reviewed April 29, 2015
    I worked with Sue for nine years and was always fascinated by the twice yearly island sojourns to this place called "Anguilla." I had never even heard of it! We decided to...
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    From
    $1,250
    / Night
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    1 / 43
    5 of 5 stars (3) Excellent
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Housekeeping...
    • Children's Pool
    • Watersports Nearby
    • Wi-Fi
    • Air Conditioning
    • Staffed Property
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Beaches Edge Anguilla Villas -- One of the most private and affordable 5 bedroom luxury villa options on Anguilla. Guests call this set of two luxury Anguilla villas, 'the most peaceful place on earth... Rent 1 or Both Villas Beaches Edge Anguilla's East and West Villas are two spacious 5... View all property information
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    Location Information
    Anguilla, Caribbean BWI
    5 of 5 stars Reviewed August 11, 2014
    Words truly cannot describe our stay at Beaches Edge Anguilla. But I will try.. From the serene private setting with amazing views of the ocean to the full service staff(which...
    5 of 5 stars Reviewed July 28, 2014
    I had the pleasure of staying at Beaches Edge (East Villa) with my husband. Once we first entered into the villa our breath was taken away instantly! We truly felt we were in our...
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    From
    $2,400
    / Night
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    1 / 43
    5 of 5 stars (2) Excellent
    10 Bedrooms / 12 Bathrooms / Sleeps 20
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Staffed Property
    • Waterfront
    • Hot Tub
    • Housekeeping...
    • Children's Pool
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    *SPECIAL 2-VILLA OFFER! Rent both the Beaches Edge Anguilla East and West Villas for at least 4 nights and enjoy the 5th night in both villas for FREE! Plus receive a $500 credit toward a professional island photoshoot! Capture your destination wedding moments or Anguilla vacation memories, or... View all property information
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    Location Information
    Anguilla, Caribbean BWI
    5 of 5 stars Reviewed June 25, 2015
    My boyfriend & I stayed at Beaches Edge villa for a week with another couple this past April. Neil, Christina, & Michelle all of their team was beyond accommodating and helpful...
    5 of 5 stars Reviewed March 16, 2015
    Beaches Edge is a wonderful place to stay. I definitely give it 5 stars. We couldn't have been more pleased with the villas, the staff and Anguilla. I am on the board of a...
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    From
    $385
    / Night
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    1 / 10
    5 of 5 stars (1) Excellent
    West End Village
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Water Views
    • Satellite TV
    • DVD Player
    • Internet Access
    • Deck
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    About this property
    West Green Villa is just a mere 15' from Anguilla's prestigious Cuisinart Golf Course. Spectacular views of St. Martin, the ocean, and the golf course now await your next stay in Anguilla. West Green Villa set in a wonderful garden, has three large and stunning bedrooms all with walk outs to patios... View all property information
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    Location Information
    West End Village, Anguilla AI 2640
    5 of 5 stars Reviewed April 17, 2014
    I rented this amazing house for my family for my wedding. We also used the house as our meeting place for all of guests that came to Anguilla. It's spacious and comfortable. The...
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    From
    $1,600
    / Night
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    1 / 42
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • TV
    • Hot Tub
    • Balcony
    • Internet Access
    • Gym
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee) This... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $650
    / Night
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    1 / 27
    5 of 5 stars (9) Excellent
    Long Bay Village
    5 Bedrooms / 5 Bathrooms / Sleeps 11
    Overview Reviews (9) Make Inquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Water Views
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Private and Secluded, VILLA GARDENIA is perfect for a FAMILY, a GROUP OF FRIENDS or COUPLES looking for a retreat in Anguilla. The architectural design is sophisticated, contemporary and has a versatile layout to accommodate your needs. Rent 1,2,3,4,or all five bedrooms Villa Gardenia consists... View all property information
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    Location Information
    Long Bay Village, Anguilla 2640
    From
    $23,100
    / Week
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    1 / 16
    6 Bedrooms / 9 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Dishwasher
    • DVD Player
    • Satellite TV
    • Stereo System
    • Shared Outdoor Pool...
    • Microwave
    • Safe
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Villa Mystique, reputed to be the largest villa on the island at 21,000 square feet, is home to four Grand Villa Suites, three pools and a full gym. There is a Loft Junior Suite with a generous outdoor roof terrace and an optional Garden Suite which is perfectly suited for a guest's personal staff.... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $20,300
    / Week
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    1 / 23
    7 Bedrooms / 9 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Balcony
    • Hot Tub
    • Satellite TV
    • Dishwasher
    • Stereo System
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    An exhibition of modern architecture and Caribbeanesque vernaculars, the private enclave that is Sheriva Boutique Villa Hotel offers the serenity of understated elegance with contemporary luxuries. The exquisitely appointed interiors by Norma Chase Jobert offer a magnificent haven with a collection... View all property information
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    Location Information
    Anguilla, Caribbean
    From
    $440
    / Night
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    1 / 29
    5 of 5 stars (7) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Water Views
    • Internet Access
    • Air Conditioning
    • Deck
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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
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    Location Information
    Anguilla, Caribbean 12345
    5 of 5 stars Reviewed January 13, 2015
    We stayed at Villa Fay over Christmas 2014, with 3 related families, and 2 babies. And it was just marvelous. Despite the fact there were 10 persons, we felt completely home. The...
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    From
    $1,330
    / Night
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    1 / 18
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • TV
    • Internet Access
    • Parking
    • Shared Yard
    • Grill
    • Shared Outdoor Pool...
    • Dishwasher
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 6... View all property information
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    Location Information
    Anguilla, Caribbean