Middlesex Holiday Rentals
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Holiday Rentals in Middlesex
Sand and Blue Seas
Sand and Blue Seas
3.0 star property
Negril
8.2 out of 10, Very good, (128)
8.2/10
Very good
(128)
"They were so friendly and hospitable. "
Villas Sur Mer
Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (149)
8.8/10
Excellent
(149)
"Amazing as always!!! "
The price is S$254
S$254
includes taxes & fees
13 Oct - 14 Oct
Idle Awhile Cliffs
Idle Awhile Cliffs
3.5 star property
West End
9.0 out of 10, Wonderful, (119)
9.0/10
Wonderful
(119)
"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!"
Montego Bay Club Apartments
Montego Bay Club Apartments
4.0 star property
Hip Strip
7.2 out of 10, Good, (38)
7.2/10
Good
(38)
"I enjoyed my stay, the location was great."
Beach House Condos Negril
Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (56)
9.0/10
Wonderful
(56)
"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. "
The price is S$194
S$194
includes taxes & fees
23 Oct - 24 Oct
Dalley's Cozy Apartments
Dalley's Cozy Apartments
3.0 star property
Hip Strip
8.8 out of 10, Excellent, (8)
8.8/10
Excellent
(8)
"The location was great walking distance to everything was easy "
Monimo Ridge Suites
Monimo Ridge Suites
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (20)
8.6/10
Excellent
(20)
"The property is well kept, great hospitality. I felt safe and at peace while staying at the property. This is my second time staying there. I recommend staying at this property to anyone to wishes to have peace of mind. "
Unity Villa
Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
8.0/10
Very good
(1)
"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 "
Unity Villa
Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
8.0/10
Very good
(1)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
The price is S$119
S$119
includes taxes & fees
6 Oct - 7 Oct
MoBay Life
MoBay Life
2.5 star property
Montego Bay
4.0 out of 10, (2)
4.0/10
(2)
"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 "
Solet's Paradise Negril
Solet's Paradise Negril
2.5 star property
Negril
9.8 out of 10, Exceptional, (9)
9.8/10
Exceptional
(9)
"Great little gem in Negril.If you are looking for a nice relaxing place away from the hustle and bustle, this is the place. Rooms are beautiful and the staff was awesome. would absolutely stay again.
Dave"
Stunning Ocean View
Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (11)
10/10
Exceptional
(11)
"The view and ambience was pure bliss!"
The price is S$833
S$833
includes taxes & fees
5 Oct - 6 Oct
Apartamento Vacacional en Bahía Montego
Apartamento Vacacional en Bahía Montego
3.0 star property
Montego Bay
Idle Awhile Villas
Idle Awhile Villas
4.0 star property
Negril
10.0 out of 10, Exceptional, (15)
10/10
Exceptional
(15)
"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!!"
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
The price is S$198
S$198
includes taxes & fees
10 Oct - 11 Oct
Ocean View Suit-Montego Bay Club Resort
Ocean View Suit-Montego Bay Club Resort
3.5 star property
Hip Strip
Seascape Apartment
Seascape Apartment
2.5 star property
Negril
7.6 out of 10, Good, (10)
7.6/10
Good
(10)
"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+"
Luxury villa in Montego Bay Jamaica
Luxury villa in Montego Bay Jamaica
3.0 star property
Montego Bay
Sunrise at Point Village
Sunrise at Point Village
2.5 star property
Negril
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
3.5 star property
Montego Bay
The price is S$433
S$433
includes taxes & fees
6 Oct - 7 Oct
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.
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.
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Top Middlesex Hotel Reviews
Secrets Wild Orchid Montego Bay - Luxury - Adults Only - All Inclusive
10/10 Excellent
"Resort was very quiet, clean and service perfect. People who work there were so friendly."
Secrets St. James Montego Bay - Luxury - Adults Only - All Inclusive
10/10 Excellent
"Loved it "
Princess Grand Jamaica Resort - All Inclusive
10/10 Excellent
"Rooms need to clean more detailed but overall a very good stay ,I’ll definitely be back."
Princess Senses The Mangrove Resort - Adults Only
10/10 Excellent
"Spa was amazing, room was amazing but it be nice if it had hot water. "
SeaGarden Beach Resort - All Inclusive
10/10 Excellent
"I loved this property. It was almost perfect as the staff was absolutely wonderful. They were so nice, especially in the restaurants. They should consider a few upgrades and have a cleaning checklist to make sure rooms are thoroughly cleaned, otherwise this was such a wonderful place."
Breathless Montego Bay - Adults Only - All Inclusive
10/10 Excellent
"A Truly Unforgettable Stay!
From start to finish, our stay was absolutely amazing! From the moment we arrived, we were treated like royalty. The resort is perfectly located, with stunning views and easy access to local attractions. The Jamaican food was out of this world — every bite was full of flavor and authenticity.
I want to give huge shoutout to Bellboy Stephen, who went above and beyond to make sure we were always having a great time. His positive energy and dance moves were the highlight of the night.
Bartender Keino at the Altitude Rooftop Bar, kept the good vibes flowing with perfectly mixed drinks and a welcoming attitude. We also had the pleasure of chatting with lifeguard Audley (Tony), whose stories about Jamaican culture and his younger days gave us a deeper appreciation for the island.
But most of all, I want to recognize Radalfi and Demar, part of the hotel management team, for truly going the extra mile. They consistently checked in to make sure everything was perfect and that we were having the best time of our lives. Their attentiveness, warmth, and genuine care made us feel like family, not just guests.
In fact, because of the incredible staff, we ended up extending our stay by an extra day — we simply didn’t want to leave!
We left with full hearts, big smiles, and unforgettable memories. Highly recommend this resort — we’ll definitely be back!"
Deja Resort All Inclusive
10/10 Excellent
"We loved everything. I took my husband there for his birthday and had them to set the room up, upon arrival we had rose petals, balloons, banner, champagne, cake, etc it was very romantic. We will be going back again and everyday the buffet had a variety of foods. It's also all inclusive"
CocoLaPalm Seaside Resort
10/10 Excellent
"The best hotel on the 7 mile beach."
Toby's Resort
10/10 Excellent
"Love the authentic feeling…property needs to be updated."
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?
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL: This holiday home rental outside of Middlesex has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, an oven and a microwave.
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. Tryall Golf Club 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.
