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Holiday Rentals and Villas in Island Harbour, Anguilla

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    Travellers to Island Harbour are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 12
    4.5 of 5 stars (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 15
    4.5 of 5 stars (10) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Private Garden
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    • Ocean Views
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    About this property
    Quiet neighborhood. Fully furnished, spacious air conditioned private apartment overlooking Island Harbour village, miles of ocean, and Scilly Cay. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. Second bedroom and second bathroom with... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 5
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    La Vanda is a charming romantic cottage. Very private part of a larger estate, with a walled back garden with outdoor shower, bar-b-que dinning area as well as sun bathing loungers. It is not on the waterfront, but is a very short walk about 3 meters to famous Shoal Bay East Beach. The area is... View all property information
    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed 13 March 2016
    We stayed at Lavanda from February 20 through March 5, 2016.....the pictures don't do the place justice! It was perfect for the two of us, we had never been to Anguilla before and...
    5 of 5 stars Reviewed 28 January 2016
    My wife and I absolutely loved Lavanda Cottage and would not hesitate to stay there again. We have traveled to many islands in the Caribbean and felt like Shoal Bay, and Lavanda...
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    1 / 35
    5 of 5 stars (57) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Waterfront
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    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
    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed 23 May 2016
    Our trip to the Almond Tree Villa was wonderful. We would have to concur with all the other excellent reviews. We enjoyed every part of the villa, coffee under the patio in the...
    5 of 5 stars Reviewed 10 May 2016
    This was our second visit to Almond Tree Villa and exceeded our expectations once again. Our friends Sue & Joe have thought of everything to make this villa a home away from...
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    1 / 29
    5 of 5 stars (42) Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    • Hot Tub
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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
    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed 23 May 2016
    We Just stayed at Moonraker with a group of 15. My husband and I along with our closest friends, my daughters and their boyfriends all helped us celebrate our 10 year...
    5 of 5 stars Reviewed 19 August 2015
    We (15) meet together from three states. The house was perfect for us and we had the most amazing time together. We all had space without being on top of each other. The...
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    1 / 7
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Balcony
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    About this property
    'JEMS' is beautifully situated with sweeping ocean views and magnificent sunsets. The villa offers the discriminating traveler 3 main bedrooms and 3 main baths with walk-outs to the lovely pool and galleries from the principal rooms. JEMS Villa has a wonderful garden for alfresco dining. Walk... View all property information
    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed 12 February 2014
    This is a tranquil vacation spot. The private pool is a perfect place to relax all day with a sun-hat and a good book. I spent 10 days decompressing from the stress of urban life...
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    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
    • x
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    About this property
    Our ocean front villa is open-air living in contemporary design. Verdant gardens, natural stone swimming pool, plunge pool and seaside gazebo in expansive private grounds. Your private hideaway in the rural tranquility of Island Harbour village. Since we lived in the villa for 15 years, we can... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 32
    5 of 5 stars (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • ?
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    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether... View all property information
    Location Information
    Island Harbour, Anguilla
    5 of 5 stars Reviewed 12 December 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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    1 / 27
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    • Waterfront
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    About this property
    Picturesquely situated on Anguilla's southeast shoreline, Ultimacy Villa is an eight bedroom super villa located in the upscale neighborhood of Sea Rocks, nestled between the villages of Shoal Bay and Island Harbour. This three story home is considered one of Anguilla's largest and most impressive... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 25
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Internet Access
    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
    Location Information
    Island Harbour, Anguilla
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
    • DVD Player
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    • Balcony
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    • Pet-friendly
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    About this property
    Villa Black Pearl on Anguilla is located just steps away from spectacular and sought after Shoal Bay East beach, considered the most magical beach in the entire Caribbean. This lovely private villa is situated at the very tip of the island, offering spectacular panoramic views of the turquoise... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 39
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Villa Amarilla on Anguilla sets the standard of excellence on a tropical island known for upscale accommodations. Enter through a welcoming lanai with a profusion of colorful bougainvillea flowers surrounding the intricately designed wrought iron doorway. Step into the grand foyer and prepared to... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 13
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    • Washer
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    • Smoking allowed
    • x
    About this property
    With impressive views of the Atlantic, the Villa Ultimacy is located in Anguilla and rests between Shoal Bay East and Island Harbor. Peaceful and secluded, it is an eight-room masterpiece of luxury and world-class amenities. It is a fabulous place for the ultimate family holiday, but is also... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 21
    2 Bedrooms, 8 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 24
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Satellite TV
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    • Internet Access
    • Grill
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Living up to its name, the Villa Beachcourt in Anguilla really does hold court over its own private beach in the sparsely populated Shoal Bay. It is considered one of the finest properties on the island and is large enough to house up to 16 guests comfortably in style and total privacy. Large and... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 21
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor...
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    Located just west of Shoal Bay East the views from the pool deck and upper balcony are panoramic and dramatic. Special touches throughout this lovely villa reflect the extensive efforts to make this villa comfortable and relaxing for guests. The home has four bedrooms, five bathrooms and has... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 21
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 21
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
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    Island Harbour, Anguilla
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    1 / 21
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 21
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Built on a hill forty feet above the water, Beachcourt Villa maximizes the stunning ocean views and breezes of Shoal Bay East in sunny Anguilla. Just seconds from the spacious decks of your villa lie the pristine waters, green foliage and white sands of this remote area of the island. Swimming,... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 8
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
    • Private Outdoor...
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Praised in Architectural Digest twice, this ultra modern villa is the ideal vacation spot for the well traveled who appreciate architectural beauty, unspoiled nature, tranquility, privacy, simple elegance and personalized service. Two four bedroom grand villas, four three bedroom villas and... View all property information
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    Island Harbour, Anguilla
    1 / 32
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
    • ?
    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether... View all property information
    Location Information
    Island Harbour, Anguilla
    1 / 32
    3 Bedrooms, 6 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior designer David Salem. Whether... View all property information
    Location Information
    Island Harbour, Anguilla