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 with Pools in Montserrat

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €155 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    Travellers to Montserrat are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in MontserratView all 23 rentals
    Sort by:
    Default
    Crows Nest Villa - Montserrat1 / 10
    (13)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Vista De Redonda, Isles Bay, Montserrat1 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Ocean Front Villa with World Class Views1 / 17
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Oasis Villa1 / 18
    (2)Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Secure Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Patio
    • Terrace
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    The property is very nice, a lot of room and taken care of well. It is located close to beaches and not far from town. It is just off the main road and there is traffic noise...
    See all reviews
    About this property
    Oasis is a beautiful secluded caribbean villa, built in a lush green garden in woodlands, Montserrat. Its a two bedroom villa with two bathrooms. Master suite has an ensuite and kitchenette, laundry room, kitchen, dining room, living room, large porch overlooking the ocean, garden and a forty foot...
    View all property information
    Location Information
    Woodlands, Montserrat MSR01
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Gorgeous sea view villa with huge pool and terrace1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Grill
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2014
    We have been visiting the islands of the Caribbean for several years now and Montserrat was certainly different! The effects of the volcano on the southern half of the island...
    See all reviews
    About this property
    A beautiful sea-view villa set on a secluded wooded hillside overlooking the Caribbean Sea, the best beach on Montserrat, the Belham River Valley, Garibaldi Hill and all 3,500 feet of Mount Soufriere itself. It was built in the late nineties in traditional colonial style and has a huge (800 square...
    View all property information
    Location Information
    Old Town, Montserrat N A
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Woodlands Estate House1 / 100
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 December 2014
    Thanksgiving Adventure:I didn't know what to expect but was pleasantly surprised. We were there to enjoy the property and also to inspect the property. We were accompanied...
    Reviewed 13 December 2014
    Woodlands Estate is the luxury rental to stay at while vacationing on Montserrat! I recently spent Thanksgiving at the property with my wife and in-laws, and it was the...
    See all reviews
    About this property
    This outstanding three-bedroom home is set in six acres of mature landscaping, with several fruit trees, a pineapple plantation, and a rain forest ghut filled with birds and the sounds of the river. Pick mangos, bananas, and star fruit for breakfast. One of the most unusual homes on Montserrat,...
    View all property information
    Location Information
    Woodlands, Montserrat NONE
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Montserrat Villa for Rent  3 bedrooms 2 baths pool1 / 18
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2017
    We really enjoyed our stay in the villa it was very family friendly and had a was in a great location, I would definitely stay there again.
    Reviewed 30 August 2016
    Beautiful home perfectly decorated for total relaxation. Lovely garden where one can sit and enjoy the moonlight and embrace nature .
    See all reviews
    About this property
    If you are in search of a Caribbean Island that feels safe and friendly, look no further than Montserrat. Often times, you may be the only one on the beach. The restaurants are small, quaint and privately owned by many locals and ex-Pats. The tropical rain forests are a perfect back drop for hiking...
    View all property information
    Location Information
    Montserrat, Caribbean 00000
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Inis Elau Villa1 / 10
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    We visited Montserrat in March 2017 for St Patrick’s Day. Our stay at Inis Elau was wonderful. This two bedroom villa is set in a very good location, not far from the area...
    See all reviews
    About this property
    Inis Elau is a stunning secluded Villa. Located on a lovely lot approximately 0.7 of an acre in size at the end of Sweet Lime Lane Inis Ealu, (Irish Gaelic for Island Escape) is a custom villa designed and built in 2006. It features a blue steel roof, cherry cabinetry and granite counter tops in...
    View all property information
    Location Information
    Olveston, Montserrat NONE
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Enquiry
    Chez Mango Luxury Ocean View Villa1 / 24
    (11)Excellent
    12 Bedrooms, 11 Bathrooms, Sleeps 25 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Housekeeping Included
    • Patio
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    We stayed here in March 2017 during part of the St Patricks Day Festivities. Gary was kind enough to meet us at the ferry even though we had a ride and escorted us back to Chex...
    Reviewed 7 March 2017
    Chez Mango Villa is paradise! The view of the ocean from the balcony is absolutely breathtaking. I loved waking up in the morning with my cup of tea and just enjoying the ocean...
    See all reviews
    About this property
    Located on 1 acre on Logwood Drive in Montserrat, this villa is completely furnished and equipped with numerous luxury amenities. It has oversized bedroom Suites with private baths and even an outdoor shower. Several of the patios are also private and offer magnificent views. This Luxury Villa...
    View all property information
    Location Information
    Old Town, Montserrat 00000
    Holiday Rental House - 12 Bedrooms, 11 Bathrooms, Sleeps 25
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in Montserrat's rainforest-covered hills, with breathtaking sea views and a ten minute walk to an often deserted beach, this secluded hideaway is perfect for those seeking a restorative and utterly peaceful vacation. This is a elegant, recently renovated two storey villa with four...
    View all property information
    Location Information
    Woodlands, Montserrat NO ZIP
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Save time - get the best Montserrat rentals sent straight to your email!
    Get the List
    Montserrat Private Paradise; Min-y-Don1 / 14
    (18)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Housekeeping Included
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2018
    I cant imagine a better place to stay in Montserrat! 180 degree ocean view from my spacious private apartment - lush exotic palm trees, fabulous pool, full kitchen, immaculate...
    Reviewed 11 March 2018
    We set out to find a peaceful, out-of-the-way, comfortable place to spend a week. Boy did we get it right! Peter and Sian are delightful hosts - we so enjoyed them and their...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Caribbean Get Away- Pride Villa Montserrat1 / 7
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Patio
    • Private Garden
    • Grill
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2018
    These pictures do not do justice to the view, or the large pool area. There is a large lanai that runs the full length of the back of the house and you have a 180 view, it's...
    See all reviews
    About this property
    Ssshhh it's a secret. Experience the mystique of Montserrat. Never heard of it? Sure you have. Listen to The Beach Boys song Kokomo from the soundtrack of Cocktail. 'That Montserrat Mystique ' is embedded in the lyrics. The island is small, friendly and safe. There are no chain hotels, no chain...
    View all property information
    Location Information
    Old Town, Montserrat MSR1110
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2017
    Let's start this off with, this is a BEAUTIFUL piece of land! Over looking the ocean with gorgeous sunsets. More mangos then a group of four could eat. Iguanas sunning by the...
    See all reviews
    About this property
    This unique property consists of a large 3-bedroom plus home, with formal living room open to the extensive grounds through sliding doors, formal dining room, large kitchen, laundry area, 'maid's room', and den/office. With several covered and open deck spaces, one can choose to eat, read, or...
    View all property information
    Location Information
    Woodlands, Montserrat NONE
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 7
    Make Enquiry
    Garden Suite apartment, Cassava House1 / 11
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2018
    Before I say how wonderful my stay was at Cassava House, I would like it to be known that the owners/hosts Ray and Audrey are the cutest couple I have ever met. They were...
    See all reviews
    About this property
    Cassava House is one of Montserrat's prestigious homes. It has wonderful views both of the Caribbean Sea and lush Mountains. Garden Suite apartment offers comfort and privacy. The bedroom has two single beds,.Guests have use of the attractive swimming pool plus the use of the Sunset Lounge...
    View all property information
    Location Information
    Woodlands, Montserrat MSR1110
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Cable/satellite TV
    • Mountain Views
    • Ocean Views
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on an expansive 1 acre lot on Logwood Drive in beautiful Montserrat, this villa is completely adorned with contemporary furnishings and equipped with numerous luxury amenities. It is one of the largest villas on island with 12 beautiful bedroom Suites and 11 private baths and even an...
    View all property information
    Location Information
    Old Town, Montserrat NONE
    Condo/Apartment - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For your peaceful beach getaway in secluded Woodlands Bay, book this spacious 3-bedroom, 3-bathroom Caribbean villa. Comfortably sleeping 6 and boasting a private pool against a stunning backdrop, it's perfect for 1 to 3 couples, families, or groups of friends seeking out all that Montserrat has to...
    View all property information
    Location Information
    Woodlands, Montserrat MSR1350
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in