Middlesex Holiday Rentals from €78: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Middlesex has to offer?

Deluxe appartment at Point village : This holiday home rental outside of Middlesex has air conditioning and a plasma TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

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Our top choices for Middlesex holiday rentals

Firefly cottage with Ocean view

Cave District

Rick B.

includes taxes & fees

28 Feb - 1 Mar

Tranquil Park

Orange Bay

includes taxes & fees

28 Feb - 1 Mar

Dragon fly Cottage

Cave

Kaili

includes taxes & fees

28 Feb - 1 Mar

Quiet relaxing mountainous get away!

Montego Bay

Kintoria W.

includes taxes & fees

12 Mar - 13 Mar

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Cave

David G.

includes taxes & fees

2 Mar - 3 Mar

Charming & Comfortable 1-Bedroom Suite in Montego Bay

Montego Bay

Claudine

includes taxes & fees

2 Mar - 3 Mar

Claudeville Condo

Montego Bay

Sophia

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Mount Salem

"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...

English C.

includes taxes & fees

12 Mar - 13 Mar

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Top Middlesex Hotel Reviews

Travellers Beach Resort

10/10 Excellent

"Brilliant hotel, great location and facilities. Family room was perfect. We will be back!"

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent

"The staff was excellent, they go out of their way to be friendly and accommodating. If you’re looking for a lot of action, stay somewhere else, this place has a very laid back vibe. Never had to wait for a lounge by the pool or on the beach. I was looking for a place to snorkel without going on an excursion, and this fit the bill. There are coral reefs right in front of the place."

Country Country

10/10 Excellent

"We stayed 5 nights in a cute single cottage. We’re a couple in our 30s, and most guests were a mix of friendly retirees and families, many of them regulars who come back every year and we understand why! We loved it — the cottage was colorful, comfortable, and had a nice patio. The property itself is beautiful, with plants everywhere, and the complimentary breakfast is just as delicious as other reviews mention. The place is small enough that it never feels crowded, and there are always enough lounge chairs and space for everyone. There’s also a grocery store conveniently located right across the street. We would definitely stay again!"

Hotel Riu Negril - All Inclusive

10/10 Excellent

"The Hotel Riu Negril was an amazing family vacation experience!! The hotel wasn't overcrowded, as some resorts can be. The food was phenomenal!! The pools and beach areas were clean. The entertainment staff worked long hours and earned for me high marks. Overall, I loved staying at the Hotel Riu Negril. I didn't know the distinction at the time until arriving in customs, but I was staying at the Hotel Riu Negril "Club". There is a separate "Palance" resort. However, I liked very much the Club resort, as it was recently renovated. Great experience!"

Find out more about Middlesex

Everything you need to know about Middlesex holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex holiday rentals we have selected for you start as low as €78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middlesex has to offer?

Deluxe appartment at Point village: This holiday home rental outside of Middlesex has air conditioning and a plasma TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Kool Runnings Water Park, or get out into nature at a spot like Seven Mile Beach. Half Moon Beach and Bloody Bay Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.

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