Jamaica Winter Rental
Villa
10.0(198 Reviews)
4 Bedrooms
4 Baths
8 Guests
5000 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
US $1,515/Night
7 Nights - US $10,605
House
10.0(22 Reviews)
5 Bedrooms
5 Baths
14 Guests
254.02 ft²
Oceanfront
Fireplace/Heating- Ocean View
- Balcony/Terrace
US $145/Night
7 Nights - US $1,015
House
10.0(12 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $633/Night
7 Nights - US $4,429
Villa
10.0(143 Reviews)
6 Bedrooms
5 Baths
17 Guests
9000 ft²
- Private Pool
- Oceanfront
Hot Tub- Pool
US $1,759/Night
7 Nights - US $12,311
House
10.0(14 Reviews)
4 Bedrooms
5 Baths
19 Guests
5995.5 ft²
- Hot Tub
- Balcony/Terrace
View
Breakfast
US $324/Night
7 Nights - US $2,270
Villa
10.0(140 Reviews)
4 Bedrooms
4 Baths
10 Guests
5000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,509/Night
7 Nights - US $10,564
Apartment
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Hot Tub
- Balcony/Terrace
Parking
Air Conditioner
US $86/Night
7 Nights - US $605
House
10.0(119 Reviews)
5 Bedrooms
5 Baths
10 Guests
7500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,620/Night
7 Nights - US $11,340
Villa
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1528.48 ft²
- Pool
- Balcony/Terrace
Kitchen- Parking
US $149/Night
7 Nights - US $1,043
House
10.0(96 Reviews)
5 Bedrooms
4 Baths
10 Guests
3000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $699/Night
7 Nights - US $4,893
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
2400.35 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $441/Night
7 Nights - US $3,087
Villa
10.0(93 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $690/Night
7 Nights - US $4,830
Why Choose Rent By Owner for your Jamaica 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 Jamaica
How to Book Your Jamaica 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 Jamaica
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 Jamaica
North Coast
Montego Bay
Middlesex County
Cornwall County
Surrey County
Kingston
Saint Ann
Ocho Rios
Saint Andrew
Saint James
Ocho Rios
Saint Catherine
Jamaica Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Jamaica?
There are a lot of options in Jamaica. If you plan on staying in the Jamaica area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Jamaica:
- Villa Paradiso, Mammee Bay, Ocho Rios, Jamaica
- The Most Beautiful 4-acre Villa Directly on The Beach with Pool and Chef
- LUXURY MODERN VILLA 180 VIEWS POOL, FREE BEACH/GOLF FIVE STAR RESORT MEMBERSHIP
- Villa FANTASY - ON PRIVATE BEACH IN A GATED COMMUNITY
- Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica
- Private Oasis in Negril: Beachfront Luxury!
- Siesta - Spacious Seaside villa, modern, spectacular location, pool, cook
- Serene, private retreat with magnificent views. 15-19 bedrooms, full staff
- Pattoo Castle: An Exquisite Jamaican experience: Weddings & Private Parties
- OCEAN VIEW,PRIVATE POOL,Montego Bay, Jamaica, Housekeeper daily. 5 Acres
2. How many Winter Rentals are available in Jamaica?
Currently, the total number of properties listed by RBO in 2026 is over 2039 in the Jamaica area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Jamaica.
More Rentals You May Like Near Jamaica
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
Skiing- Fireplace/Heating
- View
- Breakfast
US $181/Night
7 Nights - US $1,267
Villa
10.0(85 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $730/Night
7 Nights - US $5,110
Condo
10.0(84 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $375/Night
7 Nights - US $2,625
Villa
10.0(76 Reviews)
8 Bedrooms
8 Baths
20 Guests
10000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,118/Night
7 Nights - US $7,823
Condo
10.0(69 Reviews)
2 Bedrooms
3 Baths
4 Guests
1400 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $479/Night
7 Nights - US $3,353
Villa
10.0(68 Reviews)
3 Bedrooms
4 Baths
5 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $320/Night
7 Nights - US $2,240
House
10.0(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $239/Night
7 Nights - US $1,673
House
10.0(54 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $900/Night
7 Nights - US $6,300
Apartment
10.0(51 Reviews)
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $321/Night
7 Nights - US $2,245
Villa
10.0(50 Reviews)
5 Bedrooms
3 Baths
10 Guests
8000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,163/Night
7 Nights - US $8,141
Villa
10.0(49 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $2,231/Night
7 Nights - US $15,614
House
10.0(49 Reviews)
6 Bedrooms
7 Baths
12 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,746/Night
7 Nights - US $12,222
