Villa
10.0(77 Reviews)
8 Bedrooms
8 Baths
20 Guests
10000 ft²
Private Pool
Hot Tub
Parking
Pool
AU $1,774/Night
7 Nights - AU $12,419
Middlesex County Winter Rental
10.0
House
10.0(14 Reviews)
4 Bedrooms
5 Baths
28 Guests
5995.5 ft²
- Hot Tub
Breakfast- Parking
Balcony/Terrace
AU $414/Night
7 Nights - AU $2,901
Villa
10.0(7 Reviews)
1 Bedroom
4 Baths
6 Guests
- Private Pool
- Breakfast
- Parking
- Pool
AU $1,098/Night
7 Nights - AU $7,688
Villa
10.0(34 Reviews)
5 Bedrooms
5 Baths
13 Guests
- Private Pool
Oceanfront- Parking
- Pool
AU $1,550/Night
7 Nights - AU $10,852
Villa
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1528.48 ft²
- Parking
- Pool
- Balcony/Terrace
View
AU $212/Night
7 Nights - AU $1,484
Villa
10.0(33 Reviews)
20 Bedrooms
17 Baths
55 Guests
20000 ft²
- Private Pool
- Breakfast
- Parking
- Pool
AU $5,110/Night
7 Nights - AU $35,768
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
1248.61 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
AU $183/Night
7 Nights - AU $1,282
Cottage
10.0(27 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Breakfast
- Parking
Ocean View
AU $439/Night
7 Nights - AU $3,073
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
2400.35 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $627/Night
7 Nights - AU $4,392
House
10.0(25 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
AU $2,276/Night
7 Nights - AU $15,929
Apartment
10.0(1 Review)
7 Bedrooms
5 Baths
13 Guests
669.51 ft²
Private Beach- Hot Tub
- Parking
- Pool
AU $155/Night
7 Nights - AU $1,084
Villa
10.0(23 Reviews)
3 Bedrooms
3 Baths
6 Guests
2500 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
AU $1,024/Night
7 Nights - AU $7,167
Why Choose Rent By Owner for your Middlesex County 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.
How to Book Your Middlesex County 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.
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 Middlesex County
Jamaica
North Coast
Saint Ann
Ocho Rios
Ocho Rios
Saint Catherine
Clarendon
Thompson Town
Morgans Pass
Saint Mary
Portmore
St. Ann's Bay
Frequently Asked Questions About Middlesex County Winter Rentals
1. What are the top Winter Rentals in Middlesex County?
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Middlesex County:
- Zade's Vacation Home with Private pool, Ocho Rios
- Private Rustic Cottage Tucked in a Tropical Garden | Pool + Beach Access
- *SPECIAL OFFERS* Luxury 5 bedroom Ocean Front Villa in Ocho Rios
- Reefside Villa- 8 Bedroom Luxury Seaside Property near Ocho Rios
- Sunshine Oasis @Pyramid Point
- Modern 3 Bedroom Beachfront Villa
- OCEANVIEW GRANDE 3BR: Walk To Town and Beach Max 6 Guests
- PLAN YOUR GETAWAY UNDER THE SUN Dazzle Key Suite
- Experience Luxury/PS5/Wifi/65`TV/Cozy Bed/5min twn
- Runaway Bay Gem!
2. How many Winter Rentals are available in Middlesex County?
Currently, the total number of properties listed by RBO in 2026 is over 834 in the Middlesex County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Middlesex County.
More Rentals You May Like Near Middlesex County
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $107/Night
7 Nights - AU $751
House
10.0(20 Reviews)
3 Bedrooms
3 Baths
6 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $437/Night
7 Nights - AU $3,059
Apartment
10.0(13 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
AU $231/Night
7 Nights - AU $1,621
Villa
10.0(12 Reviews)
13 Bedrooms
13 Baths
26 Guests
11000 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $4,987/Night
7 Nights - AU $34,909
House
10.0(9 Reviews)
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $3,633/Night
7 Nights - AU $25,431
Villa
10.0(8 Reviews)
4 Bedrooms
6 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,170/Night
7 Nights - AU $8,190
Apartment
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $256/Night
7 Nights - AU $1,793
House
10.0(6 Reviews)
8 Bedrooms
9 Baths
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,178/Night
7 Nights - AU $8,247
Villa
10.0(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
AU $691/Night
7 Nights - AU $4,836
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
8 Guests
1650 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $468/Night
7 Nights - AU $3,277
Condo
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $189/Night
7 Nights - AU $1,325
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Breakfast
- Parking
- Ocean View
- Balcony/Terrace
AU $310/Night
7 Nights - AU $2,171
