We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Smoking Allowed Holiday Rentals in Anguilla, Caribbean

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €2,654 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Anguilla are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 26
    West End Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    1 / 16
    4.5 of 5 bubbles (2) Very good
    Sandy Hill Bay
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    1 / 32
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    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. Indigo's... View all property information
    Location Information
    Little Harbour, Anguilla AI 2640
    1 / 17
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    Our newest 5 bedroom grandest villa, The Point at Covecastles offers spectacular views of St. Martin and the western Caribbean sea with extraordinary sunsets. The special features include a Grand 26 foot square master bedroom with twin decks and 20 foot ceiling, Grand master bath with jacuzzi, 2... View all property information
    Location Information
    Anguilla, Caribbean
    1 / 25
    8 Bedrooms, 9 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    This 8-bedroom residence style villa successfully harmonizes traditional Caribbeanesque style with subtle touches from the Far East. Only the finest materials accent almost every inch of this 14,000 square foot haven including exquisite marble floors and balustrades, exotic hardwood ceilings and... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    1 / 5
    Shoal Bay Village
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Central Heating
    • Ocean Views
    • Waterfront
    • Grill
    • DVD Player
    • Hot Tub
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Please contact us before booking because we have to confirm the availability! This stunning property takes us on a journey to paradise. Indoor and outdoor living spaces appear to hover over the sparkling blue waters of the Atlantic that is how close you are to the ocean. A semi-circular infinity... View all property information
    Location Information
    Shoal Bay Village, Anguilla 2640
    1 / 39
    West End Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    Location Information
    West End Village, Anguilla AI 2640
    1 / 45
    West End Village
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Going beyond luxury, the eight-bedroom Villa Nevaeh sets an entirely new bar in terms of opulence and amenities. Located along Long Bay in Anguilla, it features a full household staff, a golf simulator, a tennis and basketball court, and more. The Balinese inspired design and décor of the villa... View all property information
    Location Information
    West End Village, Anguilla
    1 / 22
    6 Bedrooms, 9 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    Overlooking Cove Lagoon and only two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Sheriva at Sheriton Estates is one of Anguilla's luxury boutique villa hotels in chic West End. Situated on a lush 10-acre alcove with stunning views of the Caribbean Sea... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 15
    Blowing Point
    10 Bedrooms, 10 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Ocean Views
    • Housekeeping...
    • Grill
    • Central Heating
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    To avoid cancellation please contact us before request booking to confirm the availability! Within the sea-side garden is a dining pavilion with seating for 10 and barbeque dining area on a private beach with beautiful white sand and direct access to the crystal clear sea. Is set within a private... View all property information
    Location Information
    Blowing Point, Anguilla