Jamaica Winter Rental
Villa
10.0(120 Reviews)
5 Bedrooms
5 Baths
10 Guests
7500 ft²
Private Pool
Oceanfront
Fireplace/Heating
Pool
US $1,854/Night
7 Nights - US $12,978
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
Resort
10.0(2 Reviews)
1 Bath
- Hot Tub
Spa- Pool
- Balcony/Terrace
US $3,779/Night
7 Nights - US $26,453
Villa
10.0(94 Reviews)
3 Bedrooms
3 Baths
6 Guests
2800 ft²
- Private Pool
- Pool
Ocean View- Balcony/Terrace
US $788/Night
7 Nights - US $5,516
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
Condo
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Pool
- Balcony/Terrace
Kitchen- Parking
US $428/Night
7 Nights - US $2,998
House
10.0(2 Reviews)
9 Bedrooms
9 Baths
25 Guests
1533.86 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
US $208/Night
7 Nights - US $1,458
New
Villa
10.0(76 Reviews)
8 Bedrooms
8 Baths
20 Guests
10000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,191/Night
7 Nights - US $8,337
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(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $269/Night
7 Nights - US $1,880
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
4004.17 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $79/Night
7 Nights - US $554
Villa
10.0(52 Reviews)
5 Bedrooms
3 Baths
10 Guests
8000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,329/Night
7 Nights - US $9,300
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
Saint Andrew
Ocho Rios
Saint James
Ocho Rios
Saint Catherine
Frequently Asked Questions About Jamaica Winter Rentals
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:
- Luxury Oceanfront Villa @ Chukka Cove, St Ann, private deck, sleeps upto 6, cook
- Oceanfront Luxury Villa in Jamaica
- ZYANI Boutique Resort Breathtaking Seaside location Chef, Massage therapist,
- Beautiful VILLA SEAGULL in Silver Sands Beach Resort 3 bedroom 3.5 baths
- Jamaica Luxury, Pampered Living Where Dreams can be a Reality
- The Inn at 6 - Elegant & Pristine Home an Oasis in The City of Kingston
- The Sun Seeker Villa Ja. 7 bedroom villa with butler & chef, and housekeeping.
- Luxury 13-bedroom, 7-acre, oceanfront villa, with all-inclusive option.
- A beautiful villa with magnificent views of the Caribbean Sea in Negril, Jamaica
- The Sun Seeker Villa Ja. 5 Bedrooms in Montego Bay. Fully staffed.
2. How many Winter Rentals are available in Jamaica?
Currently, the total number of properties listed by RBO in 2026 is over 2001 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(2 Reviews)
4 Bedrooms
3 Baths
6 Guests
143.52 ft²
- Hot Tub
- Balcony/Terrace
- View
- Parking
US $55/Night
7 Nights - US $385
Apartment
10.0(51 Reviews)
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $471/Night
7 Nights - US $3,297
Villa
10.0(50 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $2,183/Night
7 Nights - US $15,279
Villa
10.0(48 Reviews)
8 Bedrooms
8 Baths
18 Guests
7000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $2,369/Night
7 Nights - US $16,585
Villa
10.0(39 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,705/Night
7 Nights - US $11,933
Villa
10.0(38 Reviews)
10 Bedrooms
10 Baths
20 Guests
13000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,067/Night
7 Nights - US $14,467
Villa
10.0(31 Reviews)
8 Bedrooms
9 Baths
17 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $2,915/Night
7 Nights - US $20,405
Villa
10.0(27 Reviews)
5 Bedrooms
4 Baths
8 Guests
5000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,827/Night
7 Nights - US $12,791
Cottage
10.0(27 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $340/Night
7 Nights - US $2,378
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
4500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $950/Night
7 Nights - US $6,649
House
10.0(25 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $1,587/Night
7 Nights - US $11,111
Villa
10.0(23 Reviews)
5 Bedrooms
5 Baths
10 Guests
6000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Breakfast
US $515/Night
7 Nights - US $3,605
