Middlesex Holiday Rentals from €103: Search Short-Term Rentals

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

Stunning Ocean View : This holiday home rental outside of Middlesex is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a terrace and a private garden.

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Holiday Rentals in Middlesex

"Beautiful clean property the chef cooks very good.. pool needs some paint .. otherwise this place is amazingly beautiful and on the beach just don’t expect anything fancy.. it’s simple and easy .. definitely a vibe I’ll be back!"

Premium Cottage, 1 Queen Bed, Pool View | Balcony view

"Amazing as always!!! "

includes taxes & fees

10 Aug - 11 Aug

"Pro: separate AC in all rooms. Fully equipped kitchen. Clean. Approachable and helpful staff. Con: no toiletries. Tiny private beach with only four dry grass beach umbrellas. "

includes taxes & fees

10 Aug - 11 Aug

"Nice spot. Check in could have been better but everything else was good. "

"Was a clean and safe space to spend a night before my flight back home. Very close to Montego Bay airport."

"The view is out of this world and the is kept clean. "

"Property was great. Staff was extremely helpful and nice. Great house, great location. Would highly recommend to anyone wanting to relax and enjoy"

"Great location "

"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "

"The owner daughter Ash was on the property handling it. She is beyond a sweetheart and very helpful!! ❤️This by far is the best Apartment style home where I felt safe and like as if I was surrounded by family! You will not make a bad choice by staying here for your vacation. It is in the center of everything car rental, grocery store and 7 mile beachfront is literally a walk across the street easy access!! I give this property a 10+"

Outdoor pool, pool umbrellas, pool loungers

"We adored this “rustic” property with its early morning birdsong, simple clean (very clean!) rooms and lovely pool overlooking the ocean. Delicious breakfast poolside or on our terrace. Courteous and kind staff. Highly recommend!"

"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."

includes taxes & fees

10 Aug - 11 Aug

"The property was beautiful and the service was phenomenal. We had an amazing chef Raquel and butler Ryan. They accommodated our every need and Ryan had a lot of great recommendations for restaurants and activities. Would love to come back!!"

Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

"The view and ambience was pure bliss!"

includes taxes & fees

9 Aug - 10 Aug

"The property is in a great location to be able to walk into the town, harmony park beach, and the hip strip. That was the only plus "

includes taxes & fees

9 Aug - 10 Aug

"We love everything about this place. "

includes taxes & fees

7 Sept - 8 Sept

"Staying at Windfall villas was a fantastic experience. The property was impeccably clean and well maintained with a beautiful and well manicured lawn with an amazing ocean view, great for taking pictures. The location was ideal, in a safe and close to most things and places we needed to visit. The Villa was spacious and well-equipped with everything we needed for a comfortable stay, including a coffee maker, a blender, a well stocked kitchen, toiletries and most of the basic items that we...

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

9 Aug - 10 Aug

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Top Middlesex Hotel Reviews

Royalton Negril, An Autograph Collection All-Inclusive Resort

10/10 Excellent

"Hospitality was good very friendly, staff are caring "

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

10/10 Excellent

"I loved everything about this resort. The staff were amazing and so accommodating with dealing with a young baby that naps and sleeps during the times everythig is open. He had a blast and especially loved and the wait staff at the MOBAY. when we come back to Jamaica we are staying here again, no doubt about it."

SeaGarden Beach Resort - All Inclusive

10/10 Excellent

"I did like the treatment of the staff to the guests l like how they were neatly dressed in their uniform. I also like the different types of food they prepared. The music in the restaurant was boring after listening to the same voice for every meal. I thought Jamaica had more recording artists. I grew up on more than one. "

Grand Palladium Jamaica Resort & Spa All Inclusive

10/10 Excellent

"We enjoyed our stay. The villas are clean and comfy but separate from main area so you have to walk or take golf carts. Food was delicious. Pool and beach are nice with plenty of shade. some peeling paint around the pool but wtvr. The food by the pool is rice and beans and chicken or pork every day. Would be nice to change it up. Drinks were great. My kids 10&12 loved spending time at the teen club- the kids club was too babyish for them. They made friends from across the world and still keep in touch with them. The staff at the teen club were great. They played video games with them and really kept them entertained. The shows at night were good but started a bit late for my liking. I think it’s bec they had a kids show earlier. Two issues: there was no entertainment by the pool. Most resorts have a schedule of activities/games, but it was just music all day. There was ONE single game when a staff member came and threw dominoes into the pool, and teams had to gather the most to win. It was fun and they should do more things like that! The biggest issue: Certain lifeguards making passes at me asking to exchange phone numbers (I said no). I was there as a single mom with my kids and it made me feel very vulnerable and uncomfortable. I’m sure some people on vacation might like that kind of thing but it was totally unsolicited and unprofessional and I felt like I had to avoid certain areas or making eye contact. I hope someone speaks to them about this unacceptable behavior. "

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 €103 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?

Stunning Ocean View: This holiday home rental outside of Middlesex is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a terrace and a private garden.

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 Tryall Golf Club 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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Holiday Rentals in Middlesex

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Holiday Rentals in Middlesex

Sand and Blue Seas

Villas Sur Mer

Beach House Condos Negril

Dalley's Cozy Apartments

Monimo Ridge Suites

Montego Bay Club Beach Resort

Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica

Montego Bay Club Apartments

Unity Villa

Seascape Apartment

Idle Awhile Cliffs

Sky Beach Rooms

Idle Awhile Villas

Stunning Ocean View

MoBay Life

Turquoise Sea Villa

Negril Beachside

Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Top Middlesex Hotel Reviews

Royalton Negril, An Autograph Collection All-Inclusive Resort

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Hotel Riu Palace Tropical Bay - All Inclusive

SeaGarden Beach Resort - All Inclusive

CocoLaPalm Seaside Resort

Princess Senses The Mangrove Resort - Adults Only

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

Deja Resort All Inclusive

Grand Palladium Jamaica Resort & Spa All Inclusive

Find out more about Middlesex

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