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Luxurious Villa with Panoramic Ocean Views

Bedrooms 5
Half Baths1
Space 6,000 sq. ft.
Property type villa
Minimum Stay 7 nights


About the property

5 Bedrooms, 5.5 Baths, (Sleeps 2-10) with privacy and spectacular ocean views

Montserrat Breezes is a beautifully appointed five bedroom, five and a half bath private Villa located high in the Woodlands section of Montserrat. Lovingly and carefully constructed by one of America's wealthiest families and updated by it's present owners, Montserrat Breezes boasts over 6000 square feet of indoor and outdoor living spaces, with breathtaking views (especially at Sunset) of the Caribbean Sea from virtually all living areas. Three king suites (all with king beds) feature spacious rooms with Plantation Shutters, en-suite baths and private verandas. Two lower suites include one king bedroom and an adjoining twin bedroom. Both of these bedrooms offer open ocean views, en-suite baths, and a shared covered veranda. The door between these bedrooms can be locked for privacy or opened for families with children.

This villa was designed to maximize the ocean views from all rooms with large 'disappearing' glass and screen panels in each room. In addition, the open air dining and family rooms feature large Plantation Shutters on the rear wall, which open to view the private courtyard and manicured garden. The grounds are tiered with stone walls and are extensively landscaped with multiple varieties of palms, flowering trees and bushes. The lower grounds have bananas, lemons,guava,coconuts and grapefruit (when in season).

Children will enjoy the variety of lizards, toads, and birds found on and around the property. Bring flashlights--the toads come out at night.

Montserrat Breezes will easily accommodate an extended family, two small families or up to five couples. The lower full kitchen is perfect for poolside dining or entertaining.

This villa is cooled by nearly constant trade winds and is situated across from an entrance to the famous Mountain Trails of Montserrat. It is ideal for hikers and nature enthusiasts.

***This villa is not suitable for toddlers or youths who cannot swim or would be inclined to push on the floor to ceiling screen panels. Renters assume full responsibility for pool safety.

Keywords: Villa

More Details

Property Manager
Property Manager
Member since: 2003
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
November 13, 2017

Why The Owner chose Olveston

My wife and I have travelled extensively in the Caribbean. Montserrat represents the 'Old Caribbean'...unspoiled by commercialism and the friendliest people on Earth. We feel as though we have moved back in time when we visit.

What makes this villa unique

Great privacy, incredible ocean and Sunset views. No crime...laid back lifestyle. Montserrat Breezes is one of the largest villas on island with multiple indoor, covered and open outdoor sitting and lounging spaces, making it perfect for larger groups but is incredible for just one or two couples as well. The disappearing glass panel doors bring the outdoors into all living spaces.

Guestbook comments from the manager

This Villa is the best value in the Caribbean for large groups. Clean, quiet, well maintained, amazing sunsets, watch the cruise ships pass by, view the volcano, enjoy the local people. All private bedrooms nicely decorated with a common living/dining area and 2 kitchens. It's not an all inclusive resort and that may be it's greatest feature. The owner is great to work with and has people on the island to assist with whatever you may need. Rent a car and explore the island, it's the friendliest place on earth. No traffic, no stress, nobody trying to sell you beads or a timeshare. Go once and you will go back.

This Villa is the best value in the Caribbean for large groups. Clean, quiet, well maintained, amazing sunsets, watch the cruise ships pass by, view the volcano, enjoy the local people. All private bedrooms nicely decorated with a common living/dining area and 2 kitchens. It's not an all inclusive resort and that may be it's greatest feature. The owner is great to work with and has people on the island to assist with whatever you may need. Rent a car and explore the island, it's the friendliest place on earth. No traffic, no stress, nobody trying to sell you beads or a timeshare. Go once and you will go back.
Apr 2012
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Olveston Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 6000 sq. ft.
House Rules:
  • Max. occupancy: 10
  • Minimum Age Limit for Renters
  • pets not allowed
  • non smoking only
Location Type:
  • Mountain View ...
  • Ocean View ...
  • Away From It All
  • Romantic
  • Broadband Access
  • Clothes Dryer
  • Covered Parking
  • Garage
  • Internet ...
  • Linens Provided
  • Parking Off Street
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wireless Internet ...
  • Cooking Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Refrigerator
  • Dining Room
  • 5 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
  • 5 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 king
    Bedroom 3 - 1 king
    Bedroom 4 - 1 king
    Bedroom 5 - 2 twin/ single
  • King size beds (1), Twin or Single Beds (1)
  • DVD Player
  • Ping Pong Table
  • Satellite / Cable
  • Stereo ...
  • Television
  • Video Library
  • Balcony ...
  • Deck / Patio
  • Lanai / Gazebo
  • Lawn / Garden ...
  • Outdoor Grill
Pool / Spa:
  • Private Pool ...
Leisure Activities:
  • bird watching
  • boating
  • eco tourism
  • scenic drives
  • sight seeing
  • walking
  • wildlife viewing
Sports & Adventure Activities:
  • fishing
  • hiking
  • mountain climbing
  • mountaineering
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
Second full kitchen on lower level near the pool.


Exceptional! 5/5 -
(9 traveler reviews)

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Luxurious Villa with Panoramic Ocean Views
average rating of 5.0 based on 10 reviews

Montserrat Breezes - Nice!

  • 5 of 5

The property was very nice, the pool well maintained and very refreshing, and the views from the villa and grounds were spectacular. Anita, the house keeper, was pleasant and did an amazing job with the cleaning. After booking, Mike the owner, shared helpful and useful information about the villa and about Montserrat. This villa is truly a bargain for the price!

  • Submitted: Jun 6, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Pedro, Thank you for your kind words. I am very happy that you enjoyed your stay at Montserrat Breezes. It is very important to me.
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Seclusion, Serenity and Sunshine

  • 5 of 5

My husband and I recently returned from a fabulous week at Breezes. This was our third trip to Montserrat, and this particular property met all our needs perfectly!! The location is convenient, the panoramic view is amazing - you cannot help but relax the minute you step foot on the property. Mike was responsive and more than helpful before and during the trip, providing us with all the critical travel info we would need, before we even asked for it.

The house is the last of three on a very secluded street, set up on a hill overlooking Woodlands. There is no way one can tire of the view. The ability to open the entire house to the outside makes the surroundings an extension of the living area. Each living space - bedrooms, kitchen and living/dining room have separate lockable entries off the open breezeway. Several dining areas are situated on the balcony/deck that overlooks the hillside, the ocean and the pool. We enjoyed most of our meals outside, except for the day it rained.

The kitchen is well equipped for cooking meals with up to date appliances and most cookware you can think of. Cocktail and wine glasses available as well. There were plenty of towels available for the bathroom which was right off the bedroom.

WiFi & Cable TV is available though I do admit, we didn't turn TV on once during our visit. The grocery store is only 5 minutes from the house and is relatively well stocked, so we were able to obtain what we needed easily. Do bring bug spray if you are a mosquito magnet like me. We were at the end of rainy season and I am told the mosquitos were particularly bad this season. I do not recall having an issue with them on previous trips, so they must be right.

The pool area, on the lower level is perfect - it is larger than the villa pools we have seen previously and the entry depth is probably around 4'. The seating is plentiful and comfy, you pick - sun or shade. It was very convenient to have access to a bathroom close by on that level. Plenty of beach towels are available.

The house is beautiful and is tastefully decorated. Landscaping is beautiful and quite honestly, there was not much more that could be done to top off our vacation. This house would be perfect for traveling couples or a family - each have their private space, but there is ample space for socializing as well.

Highly recommended - we thoroughly enjoyed doing absolutely nothing, taking a much needed break from reality! I have no doubt that we will return.

  • Submitted: Oct 28, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Sandy Hook, CT

Excellent stay

  • 5 of 5

My family of five stayed at Montserrat Breezes the week of April 9, 2017. It is a beautiful, spacious and comfortable home. The house is very private with sweeping views of the sea. It sits at the end of a short street in the Woodlands section. Woodlands Beach, Rams Grocery, The Olveston House and the Volcano Observatory are all very close to the home.

The home has 5 bedrooms, 4 of which have king size beds. The 5th has two twins. All have their own bath. There is also a half bath on the top floor.

The pool is a nice size and a great place to hang out.

The gardens on the property are very nice. I spent a lot of time just looking at all of the different flowers in the yard.

The hiking trails can be accessed by just taking a left out of the driveway and walking a short distance.

The home is well cared for by the various caretakers; Pickett the property manager, Anita the housekeeper, the pool guy whose name I did not catch. I never did see the gardener but he or she does a great job, and I'm sure that the gardener came by while we were out and about at some point.

I would highly recommend the home to anyone.

  • Submitted: Apr 19, 2017
  • Stayed: April 2017
  • Source: HomeAway
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This home is perfect in every way. It is beautifully maintained. The gardens are spectacular. The vi

  • 5 of 5

My wife and I have been to Monserrat three times in the last seven years. We have made many friends with whom we stay in contact. Monserrat breezes is an absolutely beautiful, tranquil property It is high on the mountain giving it beautiful views to the north and west. Tradewinds keep it very cool. There are no amenities missing. The property manager and others who maintain the property are very very helpful and friendly. Vacationing at Monserrat Breezes is relaxing and carefree. We can't wait to return

  • Submitted: Mar 17, 2017
  • Stayed: February 2017
  • Source: VRBO, from HomeAway
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Beautiful home perfect for large group

  • 5 of 5

This home is perfect for a family or group. The pool area, decks, outdoor eating area and large amount of patio furniture make the outside living a big part of the stay here. The bedrooms are beautiful and large. The bathrooms are grand. The sliding doors slide all the way into the walls making the rooms, including the great room, feel like the outdoors also. We walked to town and to one of the observatories. The beach is close and virtually private due to the lack of other people. Watch out for the waves-at times they are powerful. Mike was very responsive and helpful with many good suggestions. We hope to come back and stay again.

  • Submitted: Apr 14, 2016
  • Stayed: March 2016
  • Source: HomeAway
Owner's Response: Thanks Justin, We are sincerely happy that you enjoyed your stay at Montserrat Breezes. It is very important to us.
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Monkton, Maryland

Delightful Stay at Breezes

  • 5 of 5

My wife and I visited Montserrat twice before with the first only a few months before the first volcanic activity in 1995. This time we brought eight of our friends with us to enjoy and explore this beautiful island. Getting there is difficult with only small planes or a lousy and unreliable ferry.

Compared to other Caribbean islands Montserrat villas are less expensive and living expenses are modest. We've stayed in villas on other islands that had a full staff and found that in Montserrat we were far more likely to spend the days exploring the island, stopping at a simple roadside barbeque for jerk chicken and beer, returning for a swim in Breezes’ pool, then enjoying a cool drink on the porch before dinner.

One of the few properties in Montserrat that will accommodate 10 people, Breezes is also one of the most elegant. Each of the five bedrooms is comfortable and has views of the Caribbean. There are multiple places to congregate, whether at the pool, the covered porch on the upper floor (our favorite view of the sunset) or the living room. The upstairs kitchen has all the appliances you could ask for and there are plenty of dishes and silverware.

Pickett, the house manager, had pre-stocked the kitchen with our grocery list and ordered us dinner for the first night which he delivered, still warm, so we wouldn't have to shop. He had two cars waiting for us on arrival that we used for the week. While we arrived on separate flights, and two of us by boat, Pickett managed to get us all to the villa with a minimum of delay. He was always available for any assistance we needed. At the end of our week we simply left the cars at the airport with the keys in them.

Breezes is located only minutes from grocery shopping, a 15 minute walk to Woodlands beach, and the start to two of the many hiking trails are right behind the house. Tennis at the local school is less than a mile away. From Breezes you can drive anywhere on the island with a minimum of difficulty although road signs apparently aren't a priority for the Montserrat government. There are no traffic lights, no crowds, and the island is completely safe.

Our advice is to make the effort to get to this beautiful island, and then be as active as you wish or simply relax at this beautiful and comfortable villa. You won’t regret it.

  • Submitted: Feb 17, 2015
  • Stayed: February 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for the kind words. I am truly happy that everyone enjoyed their stay.
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Nearest Point of Interest
Runaway Ghaut

This Villa is located adjacent to an entrance to the famous hiking trails of Montserrat, yet has panoramic (Sunset)views of the Caribbean Sea.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500
Tax Rate 7.0%

Rates quoted are for the use of 1 bedroom for 1 week for up to 2 guests. Additional guest rates are based upon 2 guests per bedroom.

If paying by credit card, please add 2.5% convenience fee.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.

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