Montserrat Winter Rental
House
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1 ft²
Private Pool
Hot Tub
Pool
Balcony/Terrace
CA $207/Night
7 Nights - CA $1,448
Apartment
9.7(12 Reviews)
1 Bedroom
1 Bath
2 Guests
1001.04 ft²
- Balcony/Terrace
View
Breakfast
Parking
CA $140/Night
7 Nights - CA $980
House
6.0(2 Reviews)
3 Bedrooms
2 Baths
4 Guests
Oceanfront- Hot Tub
Ocean View- Balcony/Terrace
CA $137/Night
7 Nights - CA $958
Villa
1 Bedroom
4 Baths
8 Guests
3003.13 ft²
- Oceanfront
- Hot Tub
Fireplace/Heating- Pool
CA $548/Night
7 Nights - CA $3,833
Villa
5.0(10 Reviews)
4 Bedrooms
5 Baths
8 Guests
5449 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $880/Night
7 Nights - CA $6,161
Apartment
4 Bedrooms
1 Bath
3 Guests
904.17 ft²
Private Beach- Oceanfront
Spa- Fireplace/Heating
CA $343/Night
7 Nights - CA $2,398
House
4.5(2 Reviews)
1 Bedroom
1 Bath
2 Guests
Kitchen
Internet
Child Friendly
Laundry
CA $68/Night
7 Nights - CA $479
CA $205/Night
7 Nights - CA $1,437
Villa
3 Bedrooms
1 Bath
8 Guests
3800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $142/Night
7 Nights - CA $997
Apartment
7 Bedrooms
2 Baths
13 Guests
1614.59 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $315/Night
7 Nights - CA $2,204
House
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
Air Conditioner
CA $56/Night
7 Nights - CA $393
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $560/Night
7 Nights - CA $3,918
People Visiting Montserrat Also Like
Why Choose Rent By Owner for your Montserrat Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Montserrat
How to Book Your Montserrat Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Montserrat
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Montserrat
Saint Peter Parish
Saint Anthony Parish
Woodlands
St. Peter's
Olveston
Cudjoe Head
Plymouth
Old Towne
St. John's
Garibaldi Hill
Little Bay
Frequently Asked Questions About Montserrat Winter Rentals
1. What are the top Winter Rentals in Montserrat?
There are a lot of options in Montserrat. If you plan on staying in the Montserrat area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Montserrat:
- Caribbean Villa with Spectacular Views
- Bananaquit at the beach!
- Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.
- Montserrat Mountain View Retreat
- Spacious 1 bedroom Apartment to rent in Montserrat West Indies.
- Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.
- Lucy's Sunshine Villa Palm Loop, Spacious 3 Bed 2 Bathroom,
- Modern North Side Hideaway with Aircon
- Paradise Villa Rooms
- Luxurious Penthouse with Breathtaking Views
2. How many Winter Rentals are available in Montserrat?
Currently, the total number of properties listed by RBO in 2026 is over 11 in the Montserrat area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Montserrat.
More Rentals You May Like Near Montserrat
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Internet
- Child Friendly
Security/Safety
CA $145/Night
7 Nights - CA $1,016
CA $148/Night
7 Nights - CA $1,035
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
1 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $287/Night
7 Nights - CA $2,009
Apartment
9.3(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
387.5 ft²
- Balcony/Terrace
- View
Pet Friendly- Parking
CA $126/Night
7 Nights - CA $882
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
CA $205/Night
7 Nights - CA $1,437
House
9.2(7 Reviews)
4 Bedrooms
4 Baths
10 Guests
166.84 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $83/Night
7 Nights - CA $582
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
2 Guests
35 ft²
- Internet
- Child Friendly
- Security/Safety
CA $82/Night
7 Nights - CA $572
Villa
9.0(5 Reviews)
4 Bedrooms
3 Baths
7 Guests
1614.59 ft²
- View
- Parking
- Air Conditioner
- Internet
CA $287/Night
7 Nights - CA $2,009
Villa
9.6(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
2400 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $721/Night
7 Nights - CA $5,050
Apartment
8.3(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- View
- Parking
- Internet
CA $133/Night
7 Nights - CA $929
House
9.6(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
CA $216/Night
7 Nights - CA $1,515
Apartment
1 Bedroom
1 Bath
2 Guests
10.76 ft²
- View
- Parking
- Air Conditioner
- Internet
CA $117/Night
7 Nights - CA $820
