Villa Holidays

Villa Holidays are the perfect holiday solution for large groups and multi-generational families. They offer privacy and comfort, and eschew the hustle and bustle of many resort hotels. Simply Caribbean Luxury Holidays features a range of villa options to across most of the islands to ensure that you’ll be able to find the perfect villa.

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    Cap Juluca, A Belmond Hotel, Anguilla

    Anguilla
    • 4 Restaurants
    • 66 Rooms 44 Suites
    • Cocktail Bar
    • Infinity Pool
    • Off-site golf course
    • Spa
    • Watersports
    • 10 minutes from the Airport
    Belmond Cap Juluca is a dream-like escape, spread across the Caribbean’s most beautiful beach. Feel the breeze blowing across your private terrace. Every room is a beachfront haven. From the pristine sands of our famed platinum beach to the inviting, cool interiors of our rooms and restaurants, every part of this luxury Anguilla hotel is
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    Sugar Beach Resort

    St. Lucia · From £3,190 per adult for seven nights
    Up to 25% off for 2023 & 2024
    • Babysitting Facilities
    • Butler Service
    • Complimentary Landsports
    • Fitness Centre
    • Large Swimming Pool
    • The Rainforest Spa
    • Weddings
    • All Inclusive Option Available
    • Children's Learning Centre
    • Complimentary Non-motorised Watersports
    Sugar Beach, St. Lucia, is a proud member of the world-renowned Viceroy Resort Group. The hotel is located at the foot of the majestic Piton Mountains, parallel to one of St. Lucia’s best sandy beaches. With a sparkling white sand beach in the foreground and a lush, green rainforest behind, this 5 star resort will
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  • Labrelotte Bay

    Windjammer Landing

    St. Lucia
    Up to 50% Off in 2023 & 2024 on B&B and All Inclusive Rates! Plus children between the ages 0-11 eat free when sharing accommodation with adults on the All Inclusive Package.
    • 2 Bars
    • 5 Restaurants
    • Babysitting
    • Fitness Studio
    • Jacquot Children's Club
    • Mini-mart
    • Serenity Spa
    • 4 swimming pools (3 adult 1 child)
    • Beach with excellent Water sports
    • Luxury Villa accommodation some with private pools
    • Mini-Bus shuttle around the resort
    Windjammer Landing sits on the hilltop above the sparkling waters of Labrelotte Bay, St. Lucia. The hotel has been a family favorite destination for years, and recent renovations have only added to Windjammer’s appeal. With a plethora of world-class amenities available, including 7 restaurants, 3 bars, 5 pools, watersports, and a luxurious spa, no guest
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  • Beachfront Villa North Shore

    Beach Enclave

    Turks and Caicos
    Early Booking Offer- Up to 20% off
    • 5 Star Luxury
    • All with Ocean Views
    • Four Properties
    • Private Pools
    • Watersports
    • Large Villas Up to 7 Bedrooms
    Recently voted TripAdvisor Travelers’ Choice Best of the Best for 2023, Beach Enclave takes a fresh, modern approach to luxury travel. The bespoke collection includes a collection of private villas, beach houses and estate homes located across distinctive, beachfront communities on Providenciales. Each butler-serviced villa provides space, privacy, and exclusivity, paired with unparalleled amenities and
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    Coral Hill Bequia

    St Vincent & The Grenadines
    • 30ft Infinity Pool
    • 4-5 Bedrooms
    • 6 Bathrooms
    • Butler
    • Gym Suite
    • Lounge Gazebo & Sun terrac
    • Petit Nevis & Friendship Bay
    • Private access to Friendship beach
    • Private estate with gated access & security
    • Spectacular 180 degree views of Mustique
    Coral Hill Bequia is perched above Villa ONE with sweeping views of Mustique & the Southern Grenadines, with over 6,000 SqFt of internal living area, 4-5 en-suite bedrooms sleeping 8-10 guests. Coral Hill offers a Master Suite occupying the entire upper floor with unmatched privacy and outdoor living space. Bedrooms There are 5 bedrooms at
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    The Shore Club, Turks & Caicos

    Turks and Caicos
    • 3 Bars
    • 4 Restaurnts
    • Beachfront Location
    • Great Spa
    • Gym
    • Kids Club
    • Suites & Villas
    • Tennis Court
    • Up to 6 Bedroom Villas
    • Watersports
    The Shore Club is a 38-suite and 110 room resort where units have been designed to invite views of the beautiful landscape, and a private, luxurious, and relaxing retreat. Pamper yourself and your family in a magnificent suite (with optional butler service). The resort has over 800 feet of beachfront on Long Bay, the most
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    Waverly House

    Barbados
    • 2 Bathrooms
    • 3 Bedrooms
    • Air Conditioned Bedrooms
    • Barbeque
    • Beach Shower
    • Plunge Pool
    • Watersports Upon Request
    • WiFi
    3 Bedrooms 2 Bathrooms This gorgeous coral stone villa sits on the serene shores of Gibbs Beach in Barbados and enjoys panoramic views of the bay and perfect privacy. Built-in the traditional Barbadian style the villa encourages outdoor living with large open doorways drawing the views into every room. The open-plan living and dining areas
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    Arc En Ciel Villa, St Lucia

    St. Lucia · Prices from $1900 per night
    • BBQ
    • Caribbean Sea View
    • CD player
    • DVD player
    • Gazebo
    • Near Beach
    • Near Golf Course
    • Near Water Sports
    • Private Pool
    • Safe
    • Security Safe
    • TV
    • Washing Machine
    • WiFi
    • 1 - 5 Bedrooms Air-conditioned bedrooms
    Arc En Ciel is a luxury 5 bedroom 6 bath villa situated in the valley between the impressive Piton mountains in Beau Estate, Soufriere. This contemporary home features open, airy living areas, with a large verandah and patio; perfect for admiring the views of the Caribbean Sea and the majestic Petit Piton. The villa is
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    Villa Ashiana

    St. Lucia · Prices from $720pn
    • Air Con
    • Air Conditioned Bedrooms
    • BBQ
    • Cable TV
    • CD player
    • Dishwasher
    • DVD player
    • Hair Dryer
    • Near Beach
    • Safe
    • Security system
    • Telephone
    • TV
    • Washing Machine
    • WiFi
    Location: Marigot, St Lucia Villa Ashiana is located on a hill overlooking the historic, scenic Marigot Bay, a long established yacht haven. The villa contains 5 bedrooms spread over 2 stories, and is beautifully appointed with plentiful lounge space for entertaining and dining. The upper floor houses the air-conditioned bedrooms, three of which have en suite
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    Blue Waters – Pelican House

    Antigua
    • Complimentary Wi-Fi
    • Concierge service
    • Exercise Classes
    • Infinity Edge Pool
    • Luxurious Living Areas
    • Tennis Courts
    • Water Sports on Request
    • 3-6 Air conditioned bedrooms
    • Bed and Breakfast and All Inclusive available
    • Twice daily housekeeping service
    Location: Blue Waters Resort, St Johns Bay, Antigua No expense has been spared when it comes to making Pelican House one of the most luxurious and exclusive villas in the Caribbean. From its crisp and airy décor to its social and dining areas, you will feel like royalty during your stay here. The two semi-detached
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    Blue Waters – Rock Cottage

    Antigua
    • Complimentary Wi-Fi
    • Concierge service
    • Gym
    • Infinity Edge Pool
    • Luxurious Living Areas
    • Tennis Courts in Resort
    • Water Sports on Request
    • 5 Air conditioned bedrooms
    • Bed and Breakfast and All Inclusive available
    • Exercise Classes in Resort
    • Twice daily housekeeping service
    Towering above the Caribbean Sea, providing breathtaking views of the turquoise waters, Rock Cottage is a shining example of Caribbean luxury accommodations. Ideal for a family reunion, couple’s retreat or high profile guests, Rock Cottage will shower its guests with sea, sun and serenity. Rooms Seclusion meets decadence at Rock Cottage, one of the Caribbean’s
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    Blue Waters – Turtle Cottage

    Antigua
    • Air Conditioned Bedrooms
    • Complimentary Wi-Fi
    • Concierge service
    • Exercise Classes
    • Luxurious Living Areas
    • Private Pool
    • Water Sports on Request
    • 4 Air conditioned bedrooms
    • Bed and Breakfast and All Inclusive available
    Turtle Cottage beautifully combines effortless Caribbean luxury with modernity. Savour stunning views of the Caribbean Sea, cook up a storm in your private kitchen or simply relax in your private swimming pool – the choice is up to you. Design Turtle Cottage spans 4200 square feet and enjoys stunning views of the Caribbean Sea. No
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    Bonavista

    Barbados · From US$1280 per night per person
    • Barbeque
    • Beach Shower
    • Beachfront
    • DVD player
    • Hair Dryers
    • iPod Dock
    • Stereo
    • TV with Cable
    • Wet Bar
    • Wi-Fi
    • Holetown (West Coast) nearby
    • Speightstown (West Coast) nearby
    Bonavista sits on a quiet stretch of white, sand beach on the stunning West Coast of Barbados. Upon arrival, guests enter a paved courtyard complemented by lush Caribbean greenery. An arched doorway provides a dramatic “window to the sea” offering tempting views of the shimmering Caribbean waters. As you walk through the hallway, glimpses of
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    Brise De Mer Villa

    St. Lucia
    • Air Conditioned
    • BBQ
    • Beach nearby
    • Caribbean Sea View
    • Coffee Maker
    • Electric Kettle
    • Electronic Gates
    • Flat screen TV
    • Fridge/Freezer
    • Outdoor Shower
    • Private Pool
    • Security system
    • Washing Machine and Dryer
    • WiFi
    Brise De Mer is a stunning, 4 bedroom, 4.5 bath villa in the historic Cap Estate with panoramic views of the Caribbean sea. Favorite Features: A short distance to the beach All four bedrooms, living room & dining are air conditioned Amazing panoramic views Large pool & pool deck, great to entertain Great for a family
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    Colibri Cottage, Soufrière

    St. Lucia
    • Bar-B-Q
    • Caribbean Sea View
    • Gazebo
    • Smart TV
    • Sun Loungers
    • High Speed (ADSL) Internet - Wireless
    • Private Infinity Edge Pool
    • Washing Machine & Dryer
    Location: Malgretoute Bay, Soufriere. 2 – 6 Bedrooms Smart TV, Sun Loungers, Washing Machine & Dryer, Bar-B-Q, Caribbean Sea View, Ceiling Fan, Solar Water Heating, Gates, Gazebo, High Chair, High Speed (ADSL) Internet – Wireless, Infinity Edge Pool, Near Beach, Outdoor Shower, Safe, Telephone Pool Types: Infinity Edge Pool, Swimming Pool Description: Colibri Cottage is situated on
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    Crystal Spring

    Barbados
    • Beach Shower
    • Cable TV & DVD Player
    • Ceiling Fans
    • Fax Machine
    • Guard (12hr shifts)
    • Gym
    • Home Theatre
    • iPod Dock
    • Security Safes
    • Speedboat
    • Stereo
    • Tennis & Golf Nearby
    • Water sports
    • Wi-Fi
    Only a privileged few get to experience the joy and pleasure of staying at Crystal Springs, one of the premier beachfront properties on the stunning Caribbean island of Barbados. First built in the 1940s, the villa was then redesigned by Oliver Messel in the 1960s, with the current owners dutifully maintaining the theatrical ambiance. Guests
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