Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

Montego Bay Club Apartments
4.0 star property
7.8 out of 10, Good, 18 reviews
"I enjoyed my stay at this appartment. The room was very clean and the view of the ocean from the balcony is breath taking. Shower had great flow and the wifi worked perfect. I only use the A/C twice durning my 7 day stay as the room stayed cool. The best part is the location to everything. Starbucks is just accross the street and resturants and grocery are just few min walk. I would definitley book another stay."
Montego Bay Club Apartments
Villas Sur Mer
4.0 star property
8.8 out of 10, Excellent, 131 reviews
"Will be back. Friendly staff and good location "
The price is NZ$311
per night
23 Jun - 24 Jun
Villas Sur Mer
Beach House Condos Negril
3.5 star property
8.8 out of 10, Excellent, 46 reviews
"Stayed with my family of 6. Staff was very friendly. We felt safe on the property. Upon check-we we’re given the wrong room. Staff apologized and quickly righted the situation. Stayed in the lower jungle unit. Plenty of space. Not much hot water. Kitchen pretty bare bones. Beach is beautiful. It is more towards the end of 7 mile beach. Can walk for miles on the Sandy beach. A wind storm unfortunately came through during our stay and made a mess of the beach. The staff did there best to clean...
The price is NZ$245
per night
23 Jun - 24 Jun
Beach House Condos Negril
Monimo Ridge Suites
3.0 star property
9.2 out of 10, Wonderful, 7 reviews
"The property was nice, hospitality of our agent Yollanda was great, away from the loud noise of the trucks that pass by on the highway my stay was great. I would stay at this cottage again"
The price is NZ$200
per night
10 Jul - 11 Jul
Monimo Ridge Suites
Montego Bay Club Resort
3.0 star property
4.0 out of 10, 32 reviews
"The property was nothing like the pictures. The receptionist was very friendly. The property itself was not very good. The sliding door to the balcony was broken, the tub didn’t drain and overall it just wasn’t as wxpected."
Montego Bay Club Resort
Idle Awhile Cliffs
3.5 star property
9.0 out of 10, Wonderful, 113 reviews
"Quiet property with rustic feel. It was away from night noise and traffic. Slept like a baby! Close to other good entertainment spots and easy to reach the beach! "
The price is NZ$379
per night
20 Jun - 21 Jun
Idle Awhile Cliffs
Luxury, beachfront private villa- fully staffed with a pool
10.0 out of 10, Exceptional, 21 reviews
"My fiancee visited this villa back in August 2023 with family. He raved about this villa and loved it so much he booked it for our honeymoon and invited family to join us as well later on in the week. This place was perfect, everyone loved it! The food, hospitality and over all experience was top notch. We were treated like royalty and family at the same time. Kudos to the chef Marie, house manager Krisanne, Ray and other staff for making our stay memorable. I highly recommend this villa and...
Luxury, beachfront private villa- fully staffed with a pool
Luxury Fully Staffed 5 Bedroom Ocean View Villa with Infinity Pool
10.0 out of 10, Exceptional, 55 reviews
"We had a great stay! The house is gorgeous, the views are breathtaking and the staff were so accommodating with the most phenomenal service! I would book a stay here again in a heartbeat!!"
Luxury Fully Staffed 5 Bedroom Ocean View Villa with Infinity Pool
Summers Dream.... your dreams become a reality.
9.8 out of 10, Exceptional, 45 reviews
"Very comfortable and equipped with everything. A short drive to the pool and beach. The pool and beach exceeded our expectations, quite beautiful and quiet. Loved the location of the property, but you really do need a car if you want to be able to get groceries, go to dinner, etc. We only did one or two excursions but we used the car every day."
Summers Dream.... your dreams become a reality.
Idle Awhile Villas
4.0 star property
10.0 out of 10, Exceptional, 11 reviews
"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!!"
Idle Awhile Villas
Deluxe appartment at Point village
3.0 star property
9.0 out of 10, Wonderful, 11 reviews
"Very nice complete with cooking are...easher abd dryer.....in a safe and secure gsted communiry...beautiful beach for swimming....."
Deluxe appartment at Point village
Rose Hall Great House & Golf Estate. Gated Community, 5 Bedroom, Fully Staffed.
10.0 out of 10, Exceptional, 87 reviews
"They staff are great Nikita, Shamar, Javon made the stay amazing. F.Y.I. When making your menu look up the prices of food you are asking the chef to prepare and also they only accept CASH for reimbursement. We had a great time and the view was amazing. Again the staff get ⭐️⭐️⭐️⭐️⭐️"
Rose Hall Great House & Golf Estate. Gated Community, 5 Bedroom, Fully Staffed.
Solet's Paradise Negril
2.5 star property
10.0 out of 10, Exceptional, 7 reviews
"Solet’s Paradise is very comfortable and a great value stay."
Solet's Paradise Negril
Tropical Breeze Villa - Beautiful 7 Bedroom Vacation Home Rental with Pool
9.0 out of 10, Wonderful, 26 reviews
"We stayed at this property for a funeral. It was very convenient as it was able to accommodate 12 adults and an infant to allow the whole family to stay one place. Karen was very accommodating from check in to check out. I will definitely stay again"
Tropical Breeze Villa - Beautiful 7 Bedroom Vacation Home Rental with Pool
WATERFRONT VILLA • BREAKFAST INCLUDED• CHEF AVBLE MASSAGES•YOGA•24hr SECURITY
10.0 out of 10, Exceptional, 33 reviews
"We had an absolutely wonderful stay at this beautiful house with stunning views and a gorgeous pool. From the moment we booked, Ralph, the host, was incredibly responsive and helpful, answering all our questions promptly. He ensured everything was perfect for our stay, both before and during our trip. Our driver, Sir Baker, was equally amazing. He was always on time, extremely courteous, and went out of his way to make our transportation smooth and stress-free. The chef, Miguel, prepared...
WATERFRONT VILLA • BREAKFAST INCLUDED• CHEF AVBLE MASSAGES•YOGA•24hr SECURITY
Estate Home - FREE AIRPORT PICK-UP
9.4 out of 10, Exceptional, 6 reviews
"Property is kept well host very nice I would stay there again very tranquil and quiet comfortable space "
Estate Home - FREE AIRPORT PICK-UP
Sand and Blue Seas
3.0 star property
8.2 out of 10, Very good, 98 reviews
"Love the updated rooms modern with nice bathrooms towels and washcloths looks new but the problem I had was I saw roaches this is not the first time I told management on a previous trip so housekeeping sprayed this time they came to my room and saw for themselves so in my opinion they need to exterminate "
Sand and Blue Seas
5 BDR LUX BEACHFRONT VILLA INFINITY POOL XMAS SPECIAL CHEF BUTLER
10.0 out of 10, Exceptional, 77 reviews
"The entire staff was very accommodating. Chef was fantastic and went above and beyond for our family. We will stay here on our next trip to Montego Bay!"
5 BDR LUX BEACHFRONT VILLA INFINITY POOL XMAS SPECIAL CHEF BUTLER
Coral Reef Beach Suite At Montego Bay Club Resort
2.5 star property
8.0 out of 10, Very good, 1 review
"Everything just needs up grading With better managers skill "
Coral Reef Beach Suite At Montego Bay Club Resort
Your own private hideaway with a bar on the beach! Middle of 7 mile beach!
9.8 out of 10, Exceptional, 19 reviews
"Went with our adult kids and a couple of grandkids. 7 in all.It's a little rustic which suited us perfectly. Spotless accomadations! Pauline makes sure of that. Awesome lady!!She cooked for us and it was excellent.Tony and Jullie at the bar were wonderful as well.Our favourite though would probably Wanda (Wander?).She's the household dog.We all fell in love with her!My favourite about her is she barks and chases the local police. Laughed my butt off!!! Was safe in the area. I wasn't out but my...
Your own private hideaway with a bar on the beach! Middle of 7 mile beach!
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See all available properties in Middlesex
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Middlesex you may be interested in

SeaGarden Beach Resort - All Inclusive
3.5 star property
7.4 out of 10, Good, 2,218 reviews
"Stay was awesome! Location is beautiful! Staff was so friendly and food was super good! They even have a bar and beach a rooms the road you walk to! Breakfast was so delicious and the lunch buffet was perfect. Love entertainment at night! Would definitely suggest going to!"
The price is NZ$418
per night
16 Jun - 17 Jun
SeaGarden Beach Resort - All Inclusive
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
4.0 star property
9.4 out of 10, Exceptional, 1,723 reviews
"My experience at the S hotel was amazing. The staff were very friendly and accommodating. The property was clean, my room was very spacious and the food was impeccable. The hotel was within walking distance to many local shops and dining facilities. I will always chose this location for lodging whenever I am in town "
The price is NZ$892
per night
30 Jun - 1 Jul
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
4.5 star property
7.6 out of 10, Good, 1,170 reviews
"Grand Palladium is so beautiful and clean. There were a lot of things to do at the resort. "
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlesex holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlesex. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middlesex. Seeing all the best attractions is bound to make you fall in love with Middlesex. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middlesex short-term rentals, that won’t be hard to do.

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 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. Bloody Bay 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.

Recent reviews of Middlesex properties
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