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.

Holiday Rentals and Homes in Woodlands, Montserrat

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
    €155 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Woodlands is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    Applied filters:
    Nearby
    Clear All
    Woodlands
    5 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
    Owner online now
    From
    €1,324
    / Week
    Payment Protection
    View Details
    View Details
    1 / 14
    5 of 5 stars (6) Excellent
    Woodlands
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    €231
    / Night
    View Details
    View Details
    Woodlands
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    other traveller has booked this property
    From
    €229
    / Night
    Payment Protection
    View Details
    View Details
    1 / 14
    5 of 5 stars (12) Excellent
    Woodlands
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Owner online now
    From
    €197
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Ocean Views
    • DVD Player
    • Private Outdoor...
    • Waterfront
    • Housekeeping...
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Min-y-Don is a privately owned villa in a secluded location perched on the cliff with breathtaking views of Redonda and Nevis across the Caribbean, as well as the Montserrat hills inland. Situated at the end of a small road, the only sounds you will hear are from the sea and the wildlife - birds,... View all property information
    Location Information
    Woodlands, Montserrat MSR 100
    5 of 5 stars Reviewed 5 May 2015
    We spent a fantastic week at this villa. It is beautiful in all respects. Very quiet, except for the sound of the sea and wildlife all around. Rooms are superb, large, airy and...
    5 of 5 stars Reviewed 10 January 2015
    This is the third time I have stayed at Min Y Don with my wife, mother, and other friends/family members, and it has been a delight every time. Beautiful house, pool, location...
    See all reviews
    Woodlands
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    €148
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Outdoor...
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Light, spacious and airy villa with stunning views of the caribbean sea and a path leading down to Woodlands Bay Beach. Recently renovated and with plenty of indoor and outdoor space to relax in. Enjoy sunset from the daybed on the terrace and refresh yourself in the pool. Bedroom 3 can be 2 x... View all property information
    Location Information
    Woodlands, Montserrat MSR1330
    1 / 10
    4.5 of 5 stars (7) Very good
    Woodlands
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    €135
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Balcony
    • Private Outdoor...
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fabulous 2 bedroom villa with pool and fantastic sea views located on Montserrat the idyllic and untouched Caribbean Island. The villa is located on a half an acre lot of lush rainforest in the most exclusive Woodlands area of the island. The beach is just a short 7 minute walk down the hill, while... View all property information
    Location Information
    Woodlands, Montserrat MSR 1330
    4 of 5 stars Reviewed 16 November 2015
    Had a great stay - the view off the terrace is superb. We eat out 4 times and were able to cater ourselves easily with the kitchen being very well equipped - especially...
    4 of 5 stars Reviewed 4 December 2014
    We stayed a Crowsnest Villa for one week. The views are spectacular and it is very close to a wonderful and secluded beach that has a very nice small reef for those who like to...
    See all reviews
    1 / 11
    5 of 5 stars (39) Excellent
    Woodlands
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    €90
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Private Outdoor...
    • Washer
    • DVD Player
    • Waterfront
    • Housekeeping...
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Overlooking Woodlands Beach to the South with the rhythms of the waves landing on the rocks below, Palm Loop Cottage offers an idyllic Caribbean setting for your home away from home. On this property, you will enjoy Montserrat's striking sunsets, the sounds of the sea, the refreshing pool, charming... View all property information
    Location Information
    Woodlands, Montserrat MSR1330
    5 of 5 stars Reviewed 20 December 2015
    We can not say enough good things about this property and Kristina and Sunny who look after it. Sun picked us up at the ferry dock, drove us to the police station to get our...
    5 of 5 stars Reviewed 21 April 2015
    Palm Loop cottage is ideally located on Montserrat with spectacular ocean vista views. We were six adults and it worked perfectly with three bedrooms, three bathrooms and a great...
    See all reviews
    Woodlands
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
    other travellers have booked this property
    From
    €72
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Private Garden
    • Secure Parking
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Oasis villa is sets in a lush tropical secluded garden in Woodlands Montserrat ,approximately 10 min. walk from beautiful Woodlands Beach. Oasis has one large bedroom with ensuite, a large swimming pool, living room dining room, kitchen a second bathroom and large porch overlooking the garden and... View all property information
    Location Information
    Woodlands, Montserrat MSR01
    Woodlands
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    €314
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Mountain Views
    • Private Garden
    • Grill
    • Private Outdoor...
    • Ocean Views
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Grandview Villa is located in the beautiful Woodlands Beach area on the island of Montserrat, just a few minutes walk from one of the most popular beaches. The villa is facing west with sunset views, has 3 bedrooms and 3 bathrooms, pool, lots of deck area, comes fully furnished, and there's a... View all property information
    Location Information
    Woodlands, Montserrat MS1110
    Woodlands
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Owner online now
    From
    €808
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Waterfront
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Restful and relaxing home on low keyed island awaiting your visit. Quiet area near Woodlands beach just .8 km down the hill or take a drive to Isle Bay Beach and enjoy the newly opened beach bar and swimming facilities there. Do as much or as little as you want! Soufrière Hills Volcano... View all property information
    Location Information
    Woodlands, Montserrat MSR1350
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing

    The following rentals are within 10 kilometers of Woodlands, Montserrat.

    Old Town
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    €224
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Private Outdoor...
    • Mountain Views
    • Ocean Views
    • Patio
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Gorgeous oceanfront villa on the island of Montserrat, near Antigua and St. Kitts in the West Indies. The three-bedroom “Avalon” villa comfortably sleeps six, with king beds in each bedroom. For quiet and comfortable relaxation, there’s no better place! The villa has a pool, wifi and TV, as well as... View all property information
    Location Information
    Old Town, Montserrat 1350
    Olveston
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    €162
    / Night
    Payment Protection
    View Details
    View Details
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    With Private pool. Great views and sunsets! Court yard and 3 patio areas. View all property information
    Location Information
    Olveston, Montserrat 00000
    Olveston
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Owner online now
    From
    €128
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Housekeeping...
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Patio
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This home is very cozy with a large library of unique books to enjoy. The shuttered doors are designed in a colonial style which open out onto the large patio. The kitchen doors open unto the patio and outside dining area. This two bedroom is tucked away next to the Governor's residence overlooking... View all property information
    Location Information
    Olveston, Montserrat MSR110
    1 / 17
    5 of 5 stars (3) Excellent
    Olveston
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    €180
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Housekeeping...
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor...
    • Mountain Views
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Gorgeous villa sleeps up to eight guests, fabulous view of Caribbean Sea and the Centre Hills Mountains. Huge fenced yard, 30 ft swimming pool, it doesn't get better than this! Yard full of fruit trees such as mango, banana, guava, soursop, orange & grapefruit. Rates listed are for up to 4 guests,... View all property information
    Location Information
    Olveston, Montserrat 0000
    5 of 5 stars Reviewed 16 June 2015
    Tradewinds has the most amazing properties. The owner Susan is always available, great customer service, etc. The villas are completed with everything and upon arrival you are...
    5 of 5 stars Reviewed 13 February 2014
    From the moment we arrived we felt like we were home! We were met at the airport by Mr. Telesford, who took us to get our driver's license and then to the grocery store, all along...
    See all reviews
    Old Town
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Owner online now
    From
    €157
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Ocean Views
    • Grill
    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Patio
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fabulous Ocean & Mountain Views in Beautiful Montserrat Enjoy the Caribbean, the way it used to be, on the beautiful island of Montserrat. This spacious 3 bedroom and 3 bath home has some of the best ocean and beach views the island has to offer. The added bonus views of Souffriere Hills and the... View all property information
    Location Information
    Old Town, Montserrat NO ZIP CODE
    Old Town
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
    Enquire for rates
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Satellite TV
    • Balcony
    • DVD Player
    • Private Outdoor...
    • Washer
    • Secure Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spectacular panaramic view - Sea - Mountains - Isles Bay & Old Towne Bay Beaches Much sought after Comfortable, Well Located and Spacious Two Bedroom - both en suite - Villa set in an acre of well stocked gardens with beautiful shrubs and numerous fruit trees. Previous Tenants and Owners Guests... View all property information
    Location Information
    Old Town, Montserrat MONT