Jamaica Winter Rental
5000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
US $1,536/Night
For 7 Nights US $10,751
254.02 ft²
14 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $145/Night
For 7 Nights US $1,015
US $735/Night
For 7 Nights US $5,145
9000 ft²
17 Guests
6 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
US $1,744/Night
For 7 Nights US $12,205
5995.5 ft²
19 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- View
US $324/Night
For 7 Nights US $2,270
5000 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,509/Night
For 7 Nights US $10,564
172.22 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Bed & Breakfast
- Hot Tub
- Balcony/Terrace
- View
US $90/Night
For 7 Nights US $630
7500 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,400/Night
For 7 Nights US $9,800
1496.18 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Balcony/Terrace
- Parking
US $86/Night
For 7 Nights US $605
3000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $699/Night
For 7 Nights US $4,893
193.75 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Private Pool
- Hot Tub
- Pool
US $88/Night
For 7 Nights US $616
2800 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
US $697/Night
For 7 Nights US $4,879
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
Saint Ann
Kingston
Ocho Rios
Saint James
Saint Andrew
Ocho Rios
Clarendon
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:
- The Most Beautiful 4-acre Private Beachfront Villa with Pool and Chef
- LUXURY MODERN VILLA 180 VIEWS POOL, FREE BEACH/GOLF FIVE STAR RESORT MEMBERSHIP
- Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica
- Villa FANTASY - ON PRIVATE BEACH IN A GATED COMMUNITY
- Siesta - Spacious Seaside villa, modern, spectacular location, pool, cook
- Private Oasis in Negril: Beachfront Luxury!
- Serene, private retreat with magnificent views. 15-19 bedrooms, full staff
- Pattoo Castle: An Exquisite Jamaican experience: Weddings & Private Parties
- Villa on the Beach. Charming, Quaint 3 bedroom at Cannon Villas Ocho Rios
- 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 2009 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.
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- Private Pool
- Oceanfront
- Hot Tub
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8000 ft²
10 Guests
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- Private Pool
- Oceanfront
- Fireplace/Heating
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12 Guests
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- Private Pool
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- Hot Tub
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7000 ft²
12 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
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- Private Pool
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- Balcony/Terrace
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- Private Pool
- Hot Tub
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