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Holiday Rentals with Pools in Anguilla

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    Travellers to Anguilla are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    159 Matching Rentals in AnguillaView all 320 rentals
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    Oceana Villa Anguilla - Brand New 2 bedroom1 / 92
    (15)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Stunning Sea Feathers Villa1 / 29
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Bonne View Villa1 / 30
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    SHOAL REEF1 / 18
    (4)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The place was just wow, we felt like stars on vacation, we couldn't have chosen a better place for our family vacation, the breathtaking entrance view of the pool and the ocean...
    Reviewed 26 April 2017
    My family just returned from a week with this property. It had been 17 years since we were last on Anguilla and the island did not disappoint as it remains as beautiful as we...
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    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...
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    West End Village, Anguilla XXXXXXXXXX
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Internet Access
    • Balcony
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fantastic, well-appointed 2BR 2BA condo available for December 2017. This property is centrally located on the Island of Anguilla and is convenient to some of the most sought-after beaches and restaurants in the Caribbean. Ocean Terrace Condos overlooks the Island of St. Maarten, The view is...
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    The Valley, Anguilla AI 2640
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coconut Palm Villa -Twin Palms Villas at Meads Bay1 / 45
    (5)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Ocean Views
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2017
    This villa was the stay of a lifetime for my husband and I! We were lucky enough to be part of the wedding party for my cousin's wedding. It was truly paradise everywhere we...
    Reviewed 6 June 2017
    We stayed at Coconut Villa the week of our wedding. The villa is spotless, and very beautiful, the views are spectacular and it is very private.. The staff is very friendly and...
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    About this property
    Coconut Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla. * 3 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter kitchen * exquisitely...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Beach Palm Villa - Twin Palms Villas at Meads Bay1 / 32
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Patio
    • Wi-Fi
    • Ocean Views
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    The accommodations were absolutely wonderful! The villa was extremely comfortable and spacious. The private pool was a great feature that was used frequently, and housekeeping...
    Reviewed 5 April 2017
    This was a family vacation of nine people. We stayed at these two adjoining villas and had a great time. The Twin Palm Villa was perfectly equipped with everything, from the...
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    About this property
    Beach Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla * 2 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter kitchen * exquisitely...
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    Long Bay Village, Anguilla AI 2640
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Housekeeping Included
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Island Harbour, Anguilla XXXXXX
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    BEST VIEWS- ANGUILLA BWI... TRUE! 86 REVIEWS... Just read reviews & just VISIT1 / 98
    (87)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Children's Pool
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    This was our second stay in beautiful Anguilla with Paul and his fantastic team. This time we had the pleasure of staying at the G.O.C. and it certainly did not disappoint...
    Reviewed 17 April 2017
    Beautiful well equipped villa ,spacious and had everything you need to have a perfect holiday.we ate in most of the time as the kitchen was excellent and the barbecue area very...
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    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...
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    Sandy Ground, Anguilla N A
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bow Green Rendezvous Anguilla1 / 20
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2017
    Bow Green was the ideal place to enjoy Anguilla for a number of reasons:Location - situated less than 100m from Rendez-vous beach (my favourite beach on the island). There are...
    Reviewed 8 September 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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    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.<BR><BR>Bow Green is a beautiful home...
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    Location Information
    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bonne View Villa is located on South Hill Anguilla with a beautiful view of St Maarten and St Barts<BR><BR>Recently completed Villa, fully private property with a gated entrance • Two (2) Bedroom Villa, with the possibility of linking them together, with a total surface area of 3000 sq ft , and...
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    South Hill, Anguilla PO BOX 5179
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Black Pearl Villa Shoal Bay East Anguilla Mediterranean Pergolas, Domes & Verandas Black Pearl Villa has been designed in a cool Mediterranean style and features an exotic dome roof, a curved barrel roof, romantic pergolas and breezy verandas. 4 Bedroom Suites with Outdoor Showers Each air...
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    Shoal Bay Village, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Anguilla Bow Green Villa on Rendezvous Bay Beach1 / 22
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2017
    The villa is just a few minutes walk from Rendevous Beach, the best beach on the Island with fine golden sands and clear turquoise sea, the ideal setting where we chose to hold...
    Reviewed 13 June 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...
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    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, Sun Shine Shack and Cuisinart Golf Resort. It is three bedroom villa and sleeps six and has a very private large walled swimming pool....
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    West End Village, Anguilla A12640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Washer
    • Ocean Views
    • Grill
    • Children's Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SONGBIRD VILLA - Rendezvous Bay, Anguilla, British West Indies<BR><BR>Location: Anguilla<BR>2 - 4 Bedrooms, 4.5 Baths , Air Conditioning Bedrooms Only, Answering Machine, BBQ, Beach Chairs, Blender, Cable, Ceiling Fans, Coffee Maker, Dish Washer, Dryer, DVD, Golf, Gym, Ice Maker, Internet, Jacuzzi,...
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    West End Village, Anguilla AI2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location: Anguilla 7 Bedrooms, 6.5 Baths , Washer, TV, Preferred Lifestyle, Pool, Microwave, Maid Service, Internet, Hair Dryer, Dryer, Dish Washer, Coffee Maker, Ceiling Fans, Cable, Blender, Beach Chairs, BBQ, Air Conditioning Bedrooms Only Villa Description Nearest Large Beach: Shoal Bay East...
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    Island Harbour, Anguilla AI2640
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    Zenaida - Anguilla1 / 10
    (1)Excellent
    8 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2016
    The delightful staff was phenomenal - very welcoming and they all delivered exceptional service. We were made to feel special and like family. The villa and grounds were...
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    Zenaida East End Village Anguilla A luxury Private Estate with Beach and Tennis courts and wonderful service on the East End of Anguilla. Everything is Cool about the location - guests have the advantage of the most elevated point on Anguilla. Zenaida is one of Anguilla’s highest villas this...
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    East End Village, Anguilla
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Castle Villa Limestone Bay Anguilla Beachfront 4 Bedroom Villa Sand Castle Villa boasts 4 bedrooms, 2 kingsize, 1 Queensized and a twin room, perfect for a group of friends or large family to enjoy. Close to the stunning Anguillan coast and blessed with its own beautiful pool this villa...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Indoor Pool
    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Octagon' is new to the rental market and its unique design is welcoming, homely, elegant and attention to detail can be seen throughout. As soon as you enter one of the entrance gates you are greeted with a sense of tranquility. With three (3) bedrooms all with ensuites, living room, half bath,...
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    West End Village, Anguilla AI2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quixotic Villas, Harbour Ridge, Island Harbour, Anguilla Quixotic Villas are a collection of private retreats that nestle amongst Harbour Ridge offering stunning ocean views and relaxing, comfortable Caribbean accommodations. There are four definitive villas, Villa Amor, Villa Elegante, Villa...
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    Island Harbour, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ani North Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa quality bathrooms, AC, WiFi and an all inclusive...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Papillon Villa Little Harbour Anguilla 21st Century Family Home This state of the art privately owned family home was designed and built 3 years ago and combines an elegant mix of architectural styles and luxury to provide a spacious and comfortable vacation villa with landscaped gardens, tennis...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Ani South Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa quality bathrooms, AC, WiFi and an all inclusive...
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    Anguilla, Caribbean
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 11 Bathrooms, Sleeps 9 Quick View
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    • Sauna
    • Waterfront
    • Hot Tub
    • Mountain Views
    • Housekeeping Included
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Blowing Point, Anguilla XXXXXXXXXX
    Holiday Rental House - 3 Bedrooms, 11 Bathrooms, Sleeps 9
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Wi-Fi
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shoal Reef West is new to the rental market and its unique design is welcoming, relaxing; yet elegant with unique attention to detail can be seen throughout. As soon as you enter one of the entrance gates you are greeted with a sense of tranquility. A rooftop deck completes the recreational...
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    West End Village, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the golf course of the St Regis Resort, Westgreen villa with its beautiful attention to detail & fabulous open airy feel, is the perfect getaway. Built on two levels, the villa offers tiled floors and tasteful interiors that feature a mix of wood, rattan and upscale fabrics.  With three...
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    West End Village, Anguilla
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect Villa Layout This 4 bedroom villa offers the perfect layout for a relaxed, entertained, worked out and pampered experience in Anguilla. At the heart of the villa is a cool and impressive atrium area. The top floor houses the 2 master suites each with kingsize beds, ensuite bathrooms and...
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 1 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Maundays Bay Beach Proximity: Near the Beach Situated in the western part of Anguilla and overlooking Cap Juluca and Altamer, Panarea is just minutes away from two white sandy beaches, the three-bedroom luxury home combines pure elegance with state-of-the-art broadband technology and...
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    Anguilla, Caribbean
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 1
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Modena Cove Bay Anguilla Comfortably Sleeps 10 Guests Villa Modena is private and palatial and  set upon one acre of land near the Cap Juluca Hotel on Cove Bay. A combination of a two storey main house and a one storey clubhouse provides 5 stunning bedrooms with private bathrooms sleeping 10...
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    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Nirvana Villa - Anguilla1 / 8
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    After a long search, I chose Villa Nirvana for a friends getaway. This was our 5th trip to Anguilla, but the first for our group of friends. We had such a great time and the...
    Reviewed 20 March 2017
    Getting to our Nirvana Villa was simplified by Paul and Elise who organized all the transfers etc. Our plane was delayed so it was late when we got to the villa. Much to our...
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    About this property
    Nirvana Villa Shannon Hill aka Seafarer's Ridge Nr Sandy Ground Anguilla 4 Bedrooms 4 Bathrooms Private, Elevated Location above Sandy Ground This beautiful villa has been designed to fit perfectly upon its elevated position and present the best possible panoramic views from every room and terrace....
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    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Lotus Blossum Villa The Valley Anguilla 2 Double Bedrooms & 1 Double Studio Lotus Blossum is a peaceful, relaxing property, prisitne, light and beautifully finished with 2 double bedrooms and a self contained studio on the lower level. The bedrooms have contemporary art on the walls, bespoke...
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    The Valley, Anguilla
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • Parking
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Separated from the ocean’s shore by Anguilla’s fascinating; limestone rocks, towers Crystal Sunrise Villa. Coastally aligned, this beauty over the horizon offers you the most picturesque views; from its roof top, open deck panoramic patio to the poolside. Why sleep indoors? When you can sleep under...
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    Sandy Hill Bay, Anguilla AI 2640
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Three Dolphins  Lockrum Bay, Anguilla  BWI1 / 51
    (11)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    I have been to Europe, Asia, India, Mexico, Bermuda, and Hawaii. I have stayed in some very beautiful homes, but none so stunning as Three Dolphins Villa. For my fiftieth...
    Reviewed 17 February 2017
    My wife and I and our three kids ages 11 to 16 stayed here for about a week. The pool was really nice and got a lot of use even though one of the floatie chairs was broken...
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    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...
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    Location Information
    Little Harbour, Anguilla A12640
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beaches Edge Villa Pelican Bay, Anguilla Sleek Crisp Lines & Comfort for 10 Guests Located close to the sandy beach of Pelican Bay, Beaches Edge Villa has been designed with striking attention to detail and clean contemporary lines throughout both the interior and exterior. Supreme service and...
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    Location Information
    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oceana Villa Anguilla Close to Sandy Beaches Anguilla famously has 33 beaches and Oceana is close to several: one of the nearest is Crocus Bay.  Viewed from Oceana and just a five minute drive this is a long, relatively untouched, quiet beach, except for the Da Vida restaurant at its eastern end. ...
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    Location Information
    The Valley, Anguilla
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Grand Outlok Castle #1 Guest Rated Rental EXHALE!1 / 21
    (2)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • Housekeeping Included
    • Children's Pool
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 January 2017
    Just returned from our 2nd stay at the "Castle" with 3 other couples. Along with the most spectacular view and sunsets, the villa is perfect in every way. The...
    Reviewed 23 October 2016
    Grand Outlook Castle was everything all the other reviewers said. Paul and Elise managed all the details that made our arrival, stay, and departure effortless. Relaxing...
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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...
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    Location Information
    The Valley, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
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    LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS1 / 61
    (16)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Children's Pool
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    If you’re looking for a Paradise vacation, you should reserve the Luxury Villa 'B on the Sea' Oceanfront. It is perfect for sharing with family, friends with 5 spacious...
    Reviewed 2 July 2017
    We absolutely loved Anguilla and "B on the Sea". The house was stunning, perched up on the hill on a gorgeous bay overlooking St Marteen and the other islands. We were...
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    About this property
    Villa "B on the Sea" is a luxurious villa overlooking the Caribbean Sea with expansive views of surrounding island! The villa is specificaly designed to be the ultimate entertainment Mecca for an exceptional paradise experience. This exclusive villa features simple luxury, breathtaking views and...
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    Anguilla, Caribbean ANGUILLA
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Zenaida Beach and Tennis Estate1 / 21
    (4)Excellent
    8 Bedrooms, 14 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2016
    An absolutely wonderful property that has everything you potentially need. Very private and the service staff are incredible. Would definitely go back again.
    Reviewed 22 July 2016
    Our family of "10" had the vacation of a lifetime at the beautiful Zenaida Beach and Tennis Resort. From the moment of our arrival, we were taken in by the warmth of...
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    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...
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    Location Information
    Anguilla, Caribbean A12640
    Holiday Rental House - 8 Bedrooms, 14 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched 150 feet above sea level on the east end of Anguilla, the Wesley House features complete privacy, luxury, and a panoramic view of five islands. Air-conditioned bedrooms, a uniquely designed tropical architecture, expansive bougainvillea covered decks and plush eclectic and British colonial...
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    Location Information
    Little Harbour, Anguilla AI 2640
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beaches Edge East - Anguilla1 / 10
    (1)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2016
    We have been coming to Anguilla for years and usually stay on the other side of the island. This time we were traveling with 4 other couples and needed a much bigger place. We...
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    About this property
    Beaches Edge East Pelican Bay, Anguilla Sleek Crisp Lines & Comfort for 10 Guests Oceanfront Villa close to sandy beach of Pelican Bay, this 5 bedroom Villa has been designed with striking attention to detail and clean contemporary lines throughout both the interior and exterior. Supreme service...
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    Location Information
    Anguilla, Caribbean
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Wesley House - Anguilla1 / 10
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2013
    We really enjoyed our stay In Wesley House, the entire house is perfect in every way, well equippted, spacious, clean and indeed very comfortable, the outside decks are well...
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    About this property
    Wesley House Near Captain's Bay, Anguilla Beautiful location Located 150 feet above sea level, Anguilla's Wesley House is a private, luxury property.  It has amazing panoramic views over 5 islands, and from this rental guests are sure to fall in love with the Caribbean.  The nearest beach is a 5...
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    Location Information
    Anguilla, Caribbean
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    WEDDINGS, FAMILIES Enjoy 2 Full Oceanfront Villas!1 / 45
    (5)Excellent
    10 Bedrooms, 12 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Children's Pool
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had a fantastic experience at Beaches Edge for our four night vacation with our closest family and friends that culminated in our wedding! Michelle was very responsiveness...
    Reviewed 10 February 2017
    Not easy to find a place that can take care of such a large group. But these villas did that and some. Managers were very helpful lining up rental cars. Fishing trips. Our...
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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...
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    Blowing Point, Anguilla BWI
    Holiday Rental House - 10 Bedrooms, 12 Bathrooms, Sleeps 20
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waves on Shoal Bay is an oceanfront vacation rental that offers tranquility, splendor, romance, and casually elegant tropical living. The villa’s central location makes it the perfect Anguilla rental, as it is ideally situated between the high-end resorts and restaurants in Shoal Bay, and overlooks...
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    Shoal Bay Village, Anguilla AI 4620
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Private Garden
    • Grill
    • Parking
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our retreat, Lockrum Point Villa (LPV). Literally, steps from Lockrum Bay, this amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. The villa comes with breath-taking views of the sea and St. Martin, a private pool and a range of luxury amenities for...
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    Little Harbour, Anguilla BWI
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 1 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Long Bay Beach Beach Proximity: On the Beach FOR RENT: Sky Villa one of the three most luxurious rental properties in Anguilla.   Sky is the embodiment of its namesake. Interior hues of aquamarine and royal blue with yellow accents set an ethereal tone throughout its 6,500 sq. ft. of...
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    Location Information
    Anguilla, Caribbean
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 1
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    Mainstay Villa at Elsie Bay1 / 14
    (13)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    If you are planning a trip to Anguilla (first or return visit) this is a must Villa to stay. Great view of St Marteen while you relax in the pool with a beverage. Close...
    Reviewed 3 weeks ago
    My wife and I, along with another couple, stayed at Mainstay Villa and were blown away by the place! To wake up every day to that view is amazing. The housekeeper was helpful...
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    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...
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    Anguilla, Caribbean ELSIE BAY
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    8 Bedrooms, 9 Bathrooms, Sleeps 1 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearest Beach: Maundays Bay (2-3 minutes drive) Beach Proximity: Near the beach Infinity is yet another luxury villa located at Sheriva West End. This seven bedroom property is overlooking the Cove and only three minutes away from beautiful and scenic Maundays Bay. Situated on a lush 10-acre...
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    Location Information
    Anguilla, Caribbean
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 1
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    South Hill, Anguilla AI 2640
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    NEW UPGRADES! Beach, Pool, Gym! Beaches Edge West1 / 39
    (1)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    Beaches Edge exceeded all our expectations. The views, space, amenities and location made this a vacation my family will never forget. We have 4 teenage children and one...
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    About this property
    Vacation in style and comfort in Beaches Edge Anguilla's West Villa. This sleek and modern 5-bedroom/5.5 bath oceanfront home with path to a small beach, is now even more luxurious! We've added a gorgeous new pool, expanded oceanfront terrace with pergola, and new private gym. The villa's...
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    Location Information
    Blowing Point, Anguilla ANGUILLA
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    COUPLES ONLY RETREAT - Stunning Panoramic Ocean Views - Private Pool1 / 38
    (59)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • Housekeeping Included
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    Paradise accommodations on a Paradise Island. We loved the huge wrap around outdoor patio with sun and shade, the pool and sitting at the high table overlooking the...
    Reviewed 9 June 2017
    This Villa was a real find!!!!!. This is my husband's and I second trip to Almond Tree Villa, and now I remember why I came back, Enjoyed breakfast and cocktails everyday on...
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    About this property
    A couples only retreat, 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...
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    Location Information
    Island Harbour, Anguilla AI 2640
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kiki Villa Shoal Bay Anguilla 10 minute stroll from Shoal Bay Beach This stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just a 10 minute stroll away from Kiki Villa and...
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    Location Information
    Island Harbour, Anguilla
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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