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
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    €0
    €5,098 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travellers to Anguilla are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €115
    / Night
    View Details
    View Details
    1 / 23
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    From
    €7,591
    / Night
    View Details
    View Details
    1 / 23
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    From
    €7,591
    / Night
    View Details
    View Details
    1 / 23
    Little Harbour
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    From
    €7,281
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Parking
    • Internet Access
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee) This... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 23
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    From
    €7,591
    / Night
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool...
    • Shared Garden
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee) This... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 23
    Little Harbour
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    From
    €7,281
    / Night
    View Details
    View Details
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool...
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 10... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 23
    Little Harbour
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    From
    €7,281
    / Night
    View Details
    View Details
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Shared Garden
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 10... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 23
    Little Harbour
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
    From
    €7,281
    / Night
    View Details
    View Details
    Amenities & Details
    • Shared Outdoor Pool...
    • Parking
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Private Villa Rentals is a licensed & registered villa wholesaler. (TICO) #50020221. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.privatevillarentals.com/service-guarantee) This... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 23
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    From
    €7,591
    / Night
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Shared Garden
    • Internet Access
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Our Reservation Payment Protection Guarantee ensures you peace of mind. Preferred Escapes is a licensed & registered villa wholesaler. (TICO) #50020229. (http://www.tico.ca/) Our Service Guarantee ensures you the best villa experience. (http://www.preferredescapes.com/service-guarantee) This 10... View all property information
    Location Information
    Little Harbour, Anguilla
    1 / 32
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    €1,108
    / Night
    View Details
    View Details
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Three Dolphins, an elegantly furnished estate on Anguilla, provides a most private escape for the discriminating traveler. Overlooking its own secluded strand of white sand beach, with breathtaking views of the neighboring islands of St. Martin, St. Bart's and Saba, the villa offers a totally... View all property information
    Location Information
    Anguilla, Caribbean AI 2640
    5 of 5 stars Reviewed 26 March 2013
    We visited Three Dolphins villa for a third time this past January. I can not say enough about this villa - it is beautiful! It is very large and can accomodate several couples...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 63
    Little Harbour
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
    From
    €5,540
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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 / 22
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    From
    €2,925
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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
    1 / 25
    8 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
    From
    €2,571
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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 / 17
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
    From
    €2,123
    / Night
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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
    West End Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    €80
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    Location Information
    West End Village, Anguilla AI 2640