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Rentals for Seniors 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 / 29
    5 of 5 stars (11) Excellent
    Shoal Bay Village
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 21
    5 of 5 stars (2) Excellent
    West End Village
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    5 of 5 stars (1) Excellent
    West End Village
    5 Bedrooms, 14 Bathrooms, Sleeps 10 | Quick View
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    1 / 23
    5 of 5 stars (11) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • x
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    About this property
    This 3700 sf. sprawling compound offers mature landscaping, a master bedroom, two additional bedrooms with private bathrooms, a 1900 sf. Great Room and the Entertainment Deck. Each bedroom offers private decks for sunning or just relaxing with a cocktail. If you don't want to go to the beach... View all property information
    Location Information
    Anguilla, Caribbean 12345
    5 of 5 stars Reviewed March 21, 2016
    Villa was in a perfect location with a great view of St Martin, and easy walk to Rendezvous Bay and the Blowing Point Ferry Terminal. Villa was clean and well equipped. We were...
    5 of 5 stars Reviewed March 11, 2016
    Well this is the 4th year we have stayed at this great Villa. The kids loved the pool, everyone has a lot of privacy, and the view to St. Maarten is exquisite. We were well...
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    West End Village
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    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,... View all property information
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    West End Village, Anguilla AI2640
    1 / 12
    5 of 5 stars (9) Excellent
    The Valley
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Come and enjoy wonderful accommodations on the island of Anguilla. Our wonderful property on Rendezvous Bay is a perfect getaway with friends or family. Up to three bedrooms, with wonderful living areas provide special back drops for your special days on Anguilla. Whether it's just two of you... View all property information
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    The Valley, Anguilla AI2640
    5 of 5 stars Reviewed May 21, 2016
    We stayed in Chinaberry, the one bedroom cottage portion of the Bayberry-Chinaberry property, which can be rented as a whole or as individual units. Bayberry and Chinaberry have...
    5 of 5 stars Reviewed March 2, 2016
    We have just returned from two wonderful weeks at Chinaberry! While not on the beach (one does need a car, the view from the deck over Rendezvous Bay is truly fabulous...
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    1 / 25
    5 of 5 stars (12) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • ?
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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... View all property information
    Location Information
    Anguilla, Caribbean ANGUILLA
    5 of 5 stars Reviewed December 8, 2015
    Once again, my wife and I visited Anguilla and Villa B on The Sea. We absolutely love both. The accommodations are wonderful (2 pools,entertainment deck,media room) and the...
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    1 / 20
    5 of 5 stars (3) Excellent
    Long Bay Village
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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
    Location Information
    Long Bay Village, Anguilla AI 2640
    1 / 13
    5 of 5 stars (1) Excellent
    Shoal Bay Village
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • Private Indoor Pool
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    • x
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    About this property
    Ambrosia Villa: the pinnacle of luxury travel accommodations in Caribbean rental homes. Boasting an oceanfront villa with unobstructed views of calm turquoise waters and pristine white sand beaches, Ambrosia Villa embodies the private island getaway best out of all Anguilla luxury rentals. Nestled... View all property information
    Location Information
    Shoal Bay Village, Anguilla AI21640
    1 / 94
    5 of 5 stars (15) Excellent
    The Valley
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • x
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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
    Location Information
    The Valley, Anguilla NONE
    5 of 5 stars Reviewed June 18, 2016
    Oceana is a beautiful villa in a perfect location looking over Crocus bay. My wife and I stayed here for a week during June 2016 and we couldn't have picked a better Villa for our...
    5 of 5 stars Reviewed February 2, 2016
    This is our 3rd year at Oceana and it continues to be a fantastic choice , perfect for two couples, not too big for my husband and me when we're on our own. The site is...
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    1 / 45
    5 of 5 stars (3) Excellent
    Blowing Point
    10 Bedrooms, 12 Bathrooms, Sleeps 20 | Quick View
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    • Children's Pool
    • Mountain Views
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    • x
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    About this property
    A PRIVATE RESORT, ALL TO YOURSELVES! ***One of the most affordable 10-bedroom options on Anguilla and near the island's desirable West End!!*** This professionally-managed, two-villa oceanfront estate with a small beach nearby is ideal for family reunions, destination weddings, corporate... View all property information
    Location Information
    Blowing Point, Anguilla BWI
    5 of 5 stars Reviewed August 5, 2015
    My family stayed at Beaches Edge for my wedding. This location is just amazing. The photos do not begin to describe how beautiful the location really is. The ocean is...
    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...
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    1 / 20
    5 of 5 stars (1) Excellent
    West End Village
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Washer
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    • x
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    • 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.<BR><BR>Bow Green is a beautiful home... View all property information
    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 / 24
    4.5 of 5 stars (3) Very good
    West End Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    "Palm Shores Villa"--the name says nearly all of it! This quiet, private Anguilla villa is sited in a stunning Caribbean location with scrumptious views of St Martin and St Barts. Situated at 6 feet (!) above sea level on a point of land between two small bays, it has sweeping vistas. Centrally... View all property information
    Location Information
    West End Village, Anguilla N A
    4 of 5 stars Reviewed February 15, 2015
    on Forest Bay with a view of St Maarten. Villa is basic, nicely maintained and furnished. We could not have asked for more from a property. As much as we like to walk the long...
    4 of 5 stars Reviewed March 16, 2014
    Palm Shores villa is a budget-friendly, extremely private villa with the most amazing view! Accommodations are exactly as pictured: simple and clean. Sure, it could use some...
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    1 / 29
    5 of 5 stars (42) Excellent
    Island Harbour
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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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 AI 2640
    5 of 5 stars Reviewed May 23, 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 August 19, 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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    Blowing Point
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Blowing Point, Anguilla ANGUILLA
    1 / 25
    5 of 5 stars (2) Excellent
    The Valley
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • ?
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    About this property
    Recently featured in Robb Report, Islands Magazine and Maco. Ani Villas goal is for our guests to leave the everyday world and their worries behind. letting our team help shape memorable escapes of relaxation and adventure. We strive to introduce our guests to the best our destinations have to... View all property information
    Location Information
    The Valley, Anguilla AI 2640
    Little Harbour
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Private Yard
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Little Harbour, Anguilla BWI
    1 / 5
    5 of 5 stars (2) Excellent
    Island Harbour
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Private Yard
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    • Pet-friendly
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    • ?
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    • x
    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 AI 2640
    5 of 5 stars Reviewed March 13, 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 January 28, 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 / 11
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • ?
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    • x
    About this property
    The Sandyhill Beach Club is a small development (24 units) consisting of rentals as well as residents. It is a few steps to Sandyhill Bay beach with excellent snorkeling as well as quiet waters for swimming and sunbathing. The condo is tastefully decorated with custom fabrics in the turquoise... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    5 of 5 stars Reviewed November 18, 2015
    I was in anguilla for a few days on business and stayed at the Romantic Oceanfront Condominium. This is a one bedroom unit facing onto the pool and the ocean (which is just past...
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    1 / 20
    5 of 5 stars (12) Excellent
    The Valley
    10 Bedrooms, 14 Bathrooms, Sleeps 20 | Quick View
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    • Hot Tub
    • Waterfront
    • Outdoor Dining Area
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Ultimate Luxury, pampered and fully serviced - Recently featured in ROBB REPORT, ISLANDS MAGAZINE, HUFFINGTON POST AND MACO... CONDE NAST JOHANSEN'S PREFERRED PROPERTY !!! 30,000 square feet of pure bliss. The Estate consists of 10 Bedrooms, 6 of them are luxuriously oversized Master Suites.... View all property information
    Location Information
    The Valley, Anguilla AI 2640
    5 of 5 stars Reviewed November 20, 2015
    My family thoroughly enjoyed our week at Ani Villas. The 5 of us (and one baby) stayed in the north villa. As they advertise, all rooms have a terrific view. The roof top...
    5 of 5 stars Reviewed April 21, 2015
    When you travel as much as we do, vacations have a high bar. Ani Villas met an exceeded our expectations. From the service to the accommodations to the food, nothing disappointed.
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    West End Village
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    'Octagon' 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 amenities.... View all property information
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    West End Village, Anguilla AI 2640
    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Mountain Views
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    • x
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    About this property
    CéBlue Villas on Crocus Bay Anguilla, is in the heart of the beach studded island in a secluded west coast locale. The new award-winning villa resort is set in over five acres of tropical hillside fronted by exquisite beachfront, with spanning views of five-thousand-foot-stretching tranquil... View all property information
    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 / 20
    5 of 5 stars (2) Excellent
    The Valley
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Waterfront
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Brand new lavish Luxury Estate in Anguilla. PRIVACY Guaranteed 3 Kings + 2 Twins + 2 Full Ultra Luxurious and fully staffed Private Chef and Butler Services Gym and Tennis Court View all property information
    Location Information
    The Valley, Anguilla AI 2640
    Little Harbour
    6 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    • Washer
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Your dream island escape awaits you at Triton, an exquisite 6-bedroom, 6.5-bath vacation rental villa at Kamique, settled on Anguilla’s South Shore with its own secluded beach cove and commanding views of the mesmerizing mountains of St. Martin.  Welcome to Triton’s beachfront estate, one of... View all property information
    Location Information
    Little Harbour, Anguilla 00000
    1 / 11
    Little Harbour
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    About this property
    This very spacious contemporary West Indian style, four bedroom villa sits on a rise overlooking the Caribbean Sea and the mountains of St. Maarten beyond. Aquamarie has direct access to a cove via a private pathway. Beach chairs, umbrellas and day beds are available for the guests use. On the... View all property information
    Location Information
    Little Harbour, Anguilla
    South Hill
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Patio
    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Irie Heights is a lovely and very safe apartment on Back Street. The space has natural sunlight and good breeze coming through all the time. Tons of space and open floor plan with a cozy back patio. The neighborhood is in a brilliant location and close to several amenities and beaches. Best of all,... View all property information
    Location Information
    South Hill, Anguilla AI 2640
    South Hill
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    Ambia is centrally located in Anguilla with spectacular views overlooking Sandy Ground and minutes away from the Island's 33 magnificent white-sand beaches. The Villa is newly renovated and available for rental beginning December 1, 2016. Ambia's Asian-style suites with Caribbean influence are the... View all property information
    Location Information
    South Hill, Anguilla AI 2640