Compare Vacation Rentals & Rent By Owner Homes in Middlesex County, Jamaica
About Middlesex County Vacation Rentals
With more than 4533 Middlesex County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Middlesex County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Middlesex County, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Middlesex County. Places to stay near Middlesex County are 1196.55 ft² on average, with prices averaging AU $881 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Middlesex County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Middlesex County, JM
Frequently Asked Questions About Middlesex County?
What are the top vacation rentals in Middlesex County?
- 5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler
- Luxury Private Oasis w/Stunning Ocean Views, Private Pool & Chef Option
- Siesta - Spacious Seaside villa, modern, spectacular location, pool, cook
- Serene, private retreat with magnificent views. 15-19 bedrooms, full staff
- Chill on the Hill
- Bahia - charming seaside cottage, wooden loft and shutters, garden, staff
- Gated, Four Bedroom, Four Bath, BEACH FRONT, SEA VIEW, Staffed
- Luxury Oceanfront Villa @ Chukka Cove, St Ann, private deck, sleeps upto 6, cook
- Leah's Retreat! 3-bedroom, house located 5 minutes from Ocho Rios attractions.
- Komfort Getaway Villa at Countrymist
How many Rentbyowner vacation rentals are available in Middlesex County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 4533 in the Middlesex County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middlesex County.
Nearby Neighborhood (13)
| Neighborhood | Property Count |
|---|---|
| Caribbean Estates Vacation Rentals in Middlesex County, JM | 38 |
| Mammee Bay Estates Vacation Rentals in Middlesex County, JM | 512 |
| Bridgeport Vacation Rentals in Middlesex County, JM | 412 |
| River Oaks Vacation Rentals in Middlesex County, JM | 1317 |
| Spanish Town Zone Vacation Rentals in Middlesex County, JM | 138 |
| New Buckfield Vacation Rentals in Middlesex County, JM | 1151 |
| Great Pond Vacation Rentals in Middlesex County, JM | 1200 |
| Greenwich Estate Vacation Rentals in Middlesex County, JM | 525 |
| Caribbean Park Vacation Rentals in Middlesex County, JM | 484 |
| West Cumberland Vacation Rentals in Middlesex County, JM | 376 |
| Crystal Cove Vacation Rentals in Middlesex County, JM | 1258 |
| Horizon Park Vacation Rentals in Middlesex County, JM | 120 |
| Cave Hill Estate Vacation Rentals in Middlesex County, JM | 45 |



































































