Middlesex holiday rentals

We found 196 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Middlesex to find one that's perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a pool. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find the perfect holiday rental for your Middlesex getaway

Learn about the unique charm of Middlesex with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Middlesex

Are you hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middlesex a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Negril Hills Golf Club (13.1 mi / 21.1 km)
  • Hope Botanical Garden and Zoo (14.8 mi / 23.8 km)

Exploring the natural features in Middlesex

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Middlesex is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Seven Mile Beach (13.7 mi / 22 km)
  • Half Moon Beach (7.8 mi / 12.5 km)
  • Bloody Bay Beach (11.3 mi / 18.2 km)
  • Bloody Bay (11.3 mi / 18.2 km)
  • Booby Cay (12.1 mi / 19.5 km)
  • Royal Palm Reserve (12.2 mi / 19.6 km)

Transport options to and around Middlesex

The nearest airport is in Montego Bay (MBJ-Sir Donald Sangster Intl.), located 18.3 mi (29.5 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middlesex when booking a holiday rental?
When considering a holiday rental in Middlesex, Hanover, Jamaica, the area of Montego Bay stands out as an excellent choice. This vibrant destination is renowned for its stunning beaches and lively option. Visitors can indulge in the beauty of Doctor's Cave Beach, famous for its crystal-clear waters and soft white sands, great for sunbathing or a refreshing swim. Additionally, the nearby Hip Strip offers a delightful mix of shops, restaurants, and nightlife, ensuring that there's always something to enjoy.Another appealing option is the charming town of Lucea, which provides a more laid-back vibe while still being close to the coast. Lucea boasts the picturesque Walter Fletcher Beach, where you can relax and soak up the sun. The town is also rich in history, with local attractions such as the historic Fort Charlotte, which offers stunning views of the surrounding area and an insight into Jamaica's past.In terms of holiday rentals, both Montego Bay and Lucea have a variety of properties available, ranging from luxury villas to cosy apartments, suiting different preferences and budgets.
What are the top attractions in Middlesex?
In Middlesex, Hanover, visitors can explore the stunning beaches along the north coast, particularly in areas like Negril, known for its famous Seven Mile Beach, offering crystal-clear waters and vibrant nightlife. The nearby town of Lucea features historical attractions like the Fort Charlotte, which provides insights into the area's historic past and spectacular views of the coastline.For nature enthusiasts, the Green Grotto Caves, located a short drive from the coast, offer a fascinating underground adventure with unique rock formations and rich history. Additionally, the picturesque village of Hopewell is a charming spot to experience local culture and cuisine, with opportunities for exploring local markets and enjoying authentic Jamaican dishes.In Hanover, the secluded beaches such as Half Moon Beach provide a more tranquil setting, ideal for relaxation and swimming. Visitors can also enjoy water sports and boat tours that showcase the scenic beauty of the region.
Are all fees included in the Middlesex holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Middlesex holiday homes with parking?
Stayz offers a wide selection of holiday homes in Middlesex with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Middlesex holiday homes?
You can find great discounts on holiday homes in Middlesex on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Middlesex holiday home booking on Stayz?
To find Middlesex holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middlesex?
A long-stay holiday home in Middlesex is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Middlesex holiday home?
Book your Middlesex holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middlesex?
Prices for holiday homes in Middlesex vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Middlesex to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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