Anguilla Vacation Rentals

Anguilla makes a great holiday destination, with many perfect vacation rental properties available for your enjoyment, catering to a wide range of specific needs - anything a visitor to Anguilla could possibly require. Select a destination or property from the list below for more information about the specific Anguilla vacation rental properties available in each location.

Vacation Home Rentals in Anguilla

Listings provided by
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    Anani - Kamique - , AI

    Villa DescriptionThis very spacious contemporary West Indian style 4 bedroom villa sits on a slight landscaped rise overlooking the Caribbean Sea, St. Martin\'s hills and beyond.  ANANI  has direct access through their own short private pathway to a cove with good gentle water  which is  protected by an outer reef.  Beach chairs, umbrellas and day beds are available for the guests use.   On the main first floor can be found two GRAND master bedrooms...

    • From 2,380 to 6,392 CAD Weekly
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Ani Estate - Travel Keys

    Perched on the breathtaking cliffs overlooking Anguilla's Little Bay, Ani Estate is 2 luxury villas (Ani North and Ani South) aimed at delivering a remarkable vacation experience. Designed with the highest level of detail in contemporary style, Ani Estate is a one-of-a-kind Caribbean island escape.This 10 bedroom estate, with 2 fully outfitted villas, is perfect for larger groups and family gatherings. The property includes facilities and amenities expected within a world-class resort...

    • From $9,460 to $17,738 Weekly
    • villa
    • 10 bedrooms, 10 bathrooms, sleeps 20
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    Aquamarie - Kamique

    With its southwestern position in Lock Rum Bay, the Villa Aquamarie - Kamique in Anguilla offers impressive scenery. A great view of the channel, and even of St. Martin in the distance, guarantees visitors that they have the kind of endless sea, sky, and breezes that define any Caribbean experience. However, the luxury and roominess of this four-bedroom villa are reason enough to choose it for a getaway.Crafted in the traditional style, but influenced by contemporary themes, the villa...

    • From 3,008 to 7,114 CAD Weekly
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Award-winning beach villa with 2 pools, all master suites. Chef. Great value.

    Named one of the top 15 villas in the Caribbean by both Ocean Home and Islands magazines, but an extremely economical alternative to a resort. Almost all 5 star villas on Anguilla have marketing firms. As the owner of the Bird of Paradise, we're able to offer you rates at least 30% below comparable villas. Living/Dining AreasFor gathering together, there is an interior living room with wet bar, an exterior living area with fireplace, a sundeck, and a covered veranda as well as hidden...

    • From $1,000 to $7,399 Monthly,Weekly
    • villa
    • 5 bedrooms, 5 bathrooms, sleeps 10
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    Beach Villa Holiday Special - Anguilla

    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 provides the ultimate location for a vacation. Mahogany Doors Welcome Guests into a Cool Interior - Large mahogany front doors welcome guests from the landscaped gardens at...

    • From 3,365 CAD
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Beautiful Anani Luxury villa

    This very spacious contemporary West Indian style four bedroom villa sits on a slight landscaped rise overlooking the Caribbean Sea and the mountains of St. Maarten beyond. Anani has direct access through their own short private pathway to a cove with good gentle water which is protected by an outer reef. Beach chairs, umbrellas and day beds are available for the guests use. On the main first floor can be found two grand master bedrooms with magnificent views in separate wings. Each with...

    • From $1,755 to $4,714
    • villa
    • 4 bedrooms, 4 bathrooms, sleeps 10
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    Beautiful Nevaeh Luxury villa

    Nevaeh is a supremely relaxing masterpiece that raises luxury to new heights with an elegant oversize kitchen, theater, media room, tennis/basketball court, eight bedrooms (including a master suite for guests with impaired mobility), a staff of ten, and a state-of-the-art golf simulator.Guests at Anguilla's newest top-of-the-line retreat, Nevaeh (pronounced "ne-vay-eh"), are greeted by antique Balinese temple doors that open to a serene, soothing Japanese courtyard and...

    • From $7,590 to $24,643 Weekly
    • villa
    • 8 bedrooms, 7 bathrooms, sleeps 16
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    Black Pearl - Anguilla

    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 waters of the Caribbean Sea.The distinctive Mediterranean design of Villa Black Pearl incorporates a domed roofline with verandas and pergolas interspersed throughout. The comfortable living area...

    • From 2,423 to 6,460 CAD Weekly
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Black Pearl - Anguilla

    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 conditioned bedroom has its own outdoor shower, indoor bathroom, flat screen TV, DVD player and stunning ocean view. 1000 Count Egyptian Cotton Bed Linens - ...

    • From 2,437 to 3,385 CAD
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Coyaba LockRum Bay - Vacation Rental

    Set in one of the most scenic parts of Anguilla, the Villa Coyaba (which is a native Arawak term for heaven) is a perfect choice for the discerning travelers. With six bedrooms and room for 12, this luxurious beachfront property has a tremendous array of amenities that make it an ideal Caribbean escape.Private and estate-like, the villa has extensive grounds, with mature plantings that include a lovely garden path to the beachfront. The amenities outside of the villa include an outdoor...

    • From 2,563 to 8,092 CAD Weekly
    • house
    • 6 bedrooms, 6 bathrooms, sleeps 12
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    Crystal Sunrise Villa

    Completed in December 2014, this four bedroom home has gorgeous views of St. Maarten and is just a two minute drive to Sandy Hill Bay beach or five minute walk. You know you have reached somewhere special as you drive up the house and park.The entrance is flanked with twin fountains and as you enter you see the beautiful spiral staircase leading to the upstairs bedrooms. On the main floor is a large kitchen and dining area, living room, guest bedroom with en suite and powder room. Sliding...

    • From $833 to $4,567 Weekly
    • villa
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Kishti Black Black Garden Bay

    Designed by a world-renown team of architects and designers, the impressive Villa Kishti Black sites above Black Garden Bay in Anguilla and offers families or groups an unprecedented opportunity for a truly luxurious, private and unforgettable Caribbean holiday.A five-bedroom villa, it has been designed on the concept of the "kishti" or arc, and you will detect the curved lines throughout. Whether it is the elegant curve of the stone terrace that wraps one edge of the identically...

    • From 3,768 to 9,613 CAD Weekly
    • house
    • 5 bedrooms, 5 bathrooms, sleeps 10
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    Kishti on Meads East

    Experience modern indoor/outdoor living in these sparkling new villas situated side-by-side on the pristine white sands of Anguillas Meads Bay. Floor to ceiling windows immerse guests in this breathtaking, world class location. Walk to top restaurants, charming beach cafes and enjoy a cocktail along a fabulous mile-long stretch of beach anchored by 5-star resorts on each end.Lounge on outdoor canopy beds, cool off in the private infinity pool or relax in a beachside hot tub. Kishti Villas on...

    • From $6,160 to $24,200 Weekly
    • villa
    • 6 bedrooms, 6 bathrooms, sleeps 12
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    Kishti on Meads West

    Experience modern indoor/outdoor living in these sparkling new villas situated side-by-side on the pristine white sands of Anguilla's Meads Bay. <br /><br />Floor to ceiling windows immerse guests in this breathtaking, world class location. Walk to top restaurants, charming beach cafes and enjoy a cocktail along a fabulous mile-long stretch of beach anchored by 5-star resorts on each end. Lounge on outdoor canopy beds, cool off in the private infinity pool or...

    • From $5,600 to $11,000 Weekly
    • villa
    • 6 bedrooms, 5 bathrooms, sleeps 12
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    Moonrise, Elsie Bay Luxury villa

    Gorgeous villa located on the rocky coastline in Little Harbour with Elsie Bay within walking distance. This beautiful villa has two masters and a guest bedroom on the main floor. Spacious pool deck with covered area for dining and relaxing and chaise lounges for sunning. Even a bocce court for a bit of fun.The living room has folding doors which open up the kitchen and dining area to the pool deck and the panoramic views of St. Maarten and the Caribbean Sea. The kitchen is very well...

    • From $550 to $1,500
    • villa
    • 3 bedrooms, 3 bathrooms, sleeps 6
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    Nevaeh - Travel Keys

    PACESETTING NEW RETREAT ON ANGUILLA: NEVAEH(Even with its name spelled backwards it's still HEAVEN) Nevaeh is a supremely relaxing masterpiece that raises luxury to new heights with an elegant oversize kitchen, theater, media room, tennis/basketball court, 8 bedrooms including a master suite for guests with impaired mobility, staff of 10 and a state-of-the-art golf simulator. Guests at Anguilla's newest top-of-the-line retreat, Nevaeh (pronounced...

    • From $8,349 to $27,107 Weekly
    • villa
    • 8 bedrooms, 8 bathrooms, sleeps 16
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    Sandcastle Villa - Anguilla

    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 provides the ultimate location for a vacation. Cars Included in Rental - There are 2 vehicles available for guests: a Jeep Wrangler 4 door convertable & a Chevey Tahoe...

    • From 2,504 to 4,350 CAD
    • house
    • 4 bedrooms, 4 bathrooms, sleeps 8
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    Sea Winds Villa Luxury villa

    A fantastic waterfront villa with classic Caribbean style. Sitting on .83 acre Sea Winds is well designed with an open living room, dining room and kitchen. There are two master suites that are mirror images and located on opposite sites of the main living area. In addition there is a third bedroom off the living room with adjoining bathroom. The kitchen has granite counters, GE appliances including a dishwasher. The bathrooms have marble double vanities and walk-in closets are in the two...

    • From $500 to $1,400
    • villa
    • 3 bedrooms, 3 bathrooms, sleeps 6
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    Solaire - Travel Keys

    Solaire is your personal glimpse into Anguilla. We sit you at the windowsill of a Caribbean getaway and beckon you to take it. Perched on Lockrum Bay, our eco-friendly luxury villas, all constructed from green building materials, and world-class accommodations are half of Solaire's story. The rest is the stay you make. Explore the island's powdered coastlines, corals and crystal-blue waters. Nearby St. Maarten, St. Barths and their tideswept beaches make Solaire's vistas among...

    • From $990 to $2,200 Weekly
    • villa
    • 2 bedrooms, 3 bathrooms, sleeps 4
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    Solaire Premier - , AI

    If you are part of the green revolution and you want to travel but also support those aligned with your cause, then the stunning Villa Solaire Premier in Anguilla is for you. Sitting over Lockrum Bay and offering truly unprecedented views of the sea and the islands in the distance, the two-bedroom villa is an eco-friendly property that is also as luxurious as it is environmentally-minded.Built of green building materials, it offers you a balance of indoor and outdoor living spaces, but the...

    • From 1,214 to 4,046 CAD Weekly
    • house
    • 2 bedrooms, 2 bathrooms, sleeps 4
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    Solaire Standard - , AI

    Are you an eco-friendly person? Most of know we have to start thinking about the environmental impact of many parts of our lives, including travel. This is why the Villa Solaire Standard is the environmentally friendly traveler's ideal find. Set on an astonishingly beautiful area of Anguilla, and overlooking Lockrum Bay, it was constructed of green materials that include stone and wood, and offers you private beach access and an idyllic retreat.From your wooden deck, recline on the sun...

    • From 791 to 2,636 CAD Weekly
    • house
    • 2 bedrooms, 2 bathrooms, sleeps 4
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    The Beach House - ANG

    The Beach House has an unparalleled beachfront location and is the ultimate in the Caribbean. It sits on the soft white sands of Meads Bay, one of the most beautiful beaches on Anguilla and possibly the world.Set within beautifully landscaped gardens and offering 8 spacious master bedrooms, 10 master baths and two powder rooms, the architecture of this inspired home is designed to capture the natural beautify of Anguilla, with its spectacular sunsets and ocean views. With more than a dozen...

    • From $11,785 to $27,972 Weekly
    • villa
    • 8 bedrooms, 11 bathrooms, sleeps 16
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    The Beach House - Anguilla

    Set right along the sands of Meads Bay in Anguilla, the stunning and contemporary Villa The Beach House offers classic tropical living with an added note of luxury. From the pool terrace to the interiors, you will find this villa a remarkable experience, and ideal setting for a group holiday.Like so many villas, this one does have an impressive pool terrace. It uses stunningly modernistic lines and features a long stretch of infinity edge pool that is backed by generously proportioned sun...

    • From 14,507 to 32,496 CAD Weekly
    • house
    • 8 bedrooms, 1 bathroom, sleeps 16
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    The Beach House Luxury villa

    The Beach House has an unparalleled beachfront location and is the ultimate in Caribbean living. It sits on the soft white sands of Meads Bay one of the most beautiful beaches on Anguilla and possibly the world. Elegant, modern and spacious, the Beach House has every conceivable facility with eight bedrooms and ten baths. However, the simply stunning architecture and position of the Beach House set it apart from other properties. Guests at the Beach House will be looked after by trained...

    • From $15,233 to $16,629 Weekly
    • villa
    • 8 bedrooms, 10 bathrooms, sleeps 16
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    Triton - Kamique - , AI

    With a southwest Anguilla location on Lockrum Bay, the Villa Triton provides visitors with some of the loveliest and most inspiring views. Not only of the constantly shifting spectrum of blue and turquoise sea, but also the rolling blue and purple hills of St. Martin in the near distance. It also has a private path that guests can take to reach their own private and sheltered cove where day beds, beach chairs, and umbrellas make for unforgettable days along the sand.Guests of this...

    • From 3,455 to 15,411 CAD Weekly
    • house
    • 6 bedrooms, 6 bathrooms, sleeps 13
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    Ultimacy Shoal Bay East

    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 well-suited to serving as an unforgettable location for a destination event.At the heart of the classic villa is the pool terrace. Surrounded in warmly colored stone, it also features a round whirlpool...

    • From 4,017 to 13,389 CAD Weekly
    • house
    • 8 bedrooms, 1 bathroom, sleeps 16
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    Ultimacy Villa Luxury villa

    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 villas. After the purchase of the property the owners immediately embarked on an extensive three million dollar renovation project which took a few years to complete. The superb villa...

    • From $4,200 to $12,000
    • villa
    • 8 bedrooms, 10 bathrooms, sleeps 16
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    Villa Colibri - Anguilla

    Villa Colibri is a striking, new, spacious and contemporary villa situated on the Southern coast of Anguilla. Five minutes' drive from the half mile of beach at Sandy Hill Bay. It's elevated position allows for the villa to benefit from the trade winds (assisted by the high ceilings throughout) and the stunning views of both Anguilla itself, and of the mountains of St Martin and St Barths and Statia. The luxurious and modern villa is designed for comfort and relaxation both inside...

    • From $1,540 to $3,300 Weekly
    • villa
    • 6 bedrooms, 7 bathrooms, sleeps 12
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    Villa Kishti- 4 bd waterfront villa with volcanic shoreline on Black Garden Bay

    Villa Kishti’s striking architectural design, with its angled and sloping roofs, is unique on Anquilla. The name is derived from the Urdu word meaning an ark or canoe.  The contemporary build and design are enhanced by an Asian touch; providing tranquilty and privacy in a spectacular waterfront location on a volcanic shoreline. Outdoor spaces and huge windows take advantage of panoramic Atlantic views throughout Villa Kishti. Outdoors guests find a large infinity-edged pool, a hot tub...

    • From $3,100 to $7,145 Weekly
    • villa
    • 5 bedrooms, 5 bathrooms, sleeps 10
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    White Cedars Villa - Travel Keys

    From every vantage point, White Cedars unique design provides breathtaking views of the Caribbean, the islands of St. Martin, St. Barths, Saba & St. Kitts, while capturing the prevailing tropical trade winds of this undiscovered paradise.The furnishings and interior design successfully blend natural elements of wood, granite and stone with contemporary sophistication. All three bedrooms feature super king beds using luxury white linen from England and are air-conditioned with screened...

    • From $859 to $1,925 Weekly
    • villa
    • 3 bedrooms, 3 bathrooms, sleeps 6
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    Zenaida - Anguilla - Vacation Rental

    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 property has true history and the location is where a 17th century Dutch fort once stood. As you can imagine the panoramic views are amazing over to St Martin and St Barths beyond...

    • From 3,276 to 6,143 CAD
    • house
    • 8 bedrooms, 9 bathrooms, sleeps 14
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    Zenaida Estate Luxury estate

    Zenaida Estate is nestled on three acres of lush tropical gardens where a 17th century Dutch fort once stood. Luxuriate in the white powdery sands of our deserted beach. Enjoy ultimate privacy in two separate villas and an adjoining garden cottage, all handsomely appointed featuring a total of seven air conditioned bedrooms and en suite baths, a vanishing edge pool, and hot tub. This splendid estate boasts a separate grand pavilion with double height ceilings, gourmet kitchen and wrap around...

    • From $1,300 to $7,150
    • estate
    • 7 bedrooms, 7 bathrooms, sleeps 16
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    Indigo Reef - PeriTwinkle

    This is a great deal for a new beautifully appointed two bedroom villa in the Indigo Reef development. Both bedrooms are large, equal in size, offering king or twin beds, and open onto a private deck or patio. Identical baths feature sunken showers. The living area and large cooks kitchen have everything you need, with multiple options for dining both inside and out. This villa makes for the perfect vacation. You will look forward to returning every year!

    • From $396 to $726 Weekly
    • villa
    • 2 bedrooms, 2 bathrooms, sleeps 4
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    Little Harbour Estates - Indigo

    Set within a private tropical garden of approximately 1.5 acres, Indigo is the perfect holiday hideaway. Located within idyllic Little Harbour, Indigo is sheltered by Cinnamon Reef, providing unrivaled panoramic views of the stunning Caribbean sea and the islands of St Barts and St Martin.<br /><br />Indigo's desirable location and flexible accommodation, offers guests luxury and the real opportunity of guaranteed privacy.<br /><br...

    • From $83,820 to $172,771 Weekly
    • villa
    • 10 bedrooms, 10 bathrooms, sleeps 20
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    Modena Villa - Travel Keys

    Contemporary architecture, miles of white sand beaches and the ultimate in privacy makes Villa Modena a rare find. Situated on 1.6 acres of lush surroundings, Modena is perfect for guests that desire privacy and luxury. When you pass through Modena's double gated entrances you are welcomed to over 10,800 square feet of indoor living space and 18,000 square feet of outdoor living space which can accommodate up to 125 guests for special events.<br /><br />Lounge...

    • From $5,000 to $9,500 Weekly
    • villa
    • 5 bedrooms, 5 bathrooms, sleeps 10
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    Sheriva - 2br Grand Villa Pool Suite

    An exhibition of modern architecture and Caribbeanesque vernaculars, the private enclave offers the serenity of understated elegance with contemporary luxuries. The exquisitely appointed interiors by Norma Chase Jobert offer a magnificent haven with a collection of unique art and custom furnishings. The lavishly oversized suites, sprawling terraces and decks, lush gardens, a total of 7 pools - all accented by generous use of fine marble, granite, exotic hardwoods, sea grass and banana leaf -...

    • From $1,870 to $2,750 Weekly
    • villa
    • 2 bedrooms, 2 bathrooms, sleeps 4
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    Sheriva - 3br Pool Suite

    An exhibition of modern architecture and Caribbeanesque vernaculars, the private enclave offers the serenity of understated elegance with contemporary luxuries. The exquisitely appointed interiors by Norma Chase Jobert offer a magnificent haven with a collection of unique art and custom furnishings. The lavishly oversized suites, sprawling terraces and decks, lush gardens, a total of 7 pools - all accented by generous use of fine marble, granite, exotic hardwoods, sea grass and banana leaf -...

    • From $2,750 to $3,850 Weekly
    • villa
    • 3 bedrooms, 3 bathrooms, sleeps 6
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    Thye Cottage II - Travel Keys

    A lovely West Indian cottage located on the beach, Thye House offers a perfect getaway from your busy life. This villa has spectacular views of the sea and Rendezvous Bay.A romantic hideaway surrounded by mature vegetation will give you the privacy you are looking for.There are wooden decks surrounding the living area and French doors that you can leave open during the day to let the outside in. A big comfy hammock or dinner by candle light awaits you on either side of the wrap around deck....

    • From $275 to $395 Weekly
    • villa
    • 1 bedroom, 1 bathroom, sleeps 2
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    Ultimacy - Travel Keys

    The grandeur of Ultimacy Villa belies its warmth and serenity. Ultimacy offers many secluded spots for quiet conversation, reflection and peaceful meditation to the pulse of the calming surf against the rocks.Ultimacy Villa can comfortably accommodate up to 16 guests in 8 bedrooms for small conferences and executive retreats, an entourage of your own staff, as well as family gatherings. The villa can also be staged as a 3 or 5 bedroom private getaway for couples and honeymooners for the...

    • From $4,400 to $11,000 Weekly
    • villa
    • 8 bedrooms, 8 bathrooms, sleeps 16