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, (122)
8.2/10
Very good
(122)
"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!"
Montego Bay Club Apartments
Montego Bay Club Apartments
4.0 star property
Hip Strip
7.2 out of 10, Good, (31)
7.2/10
Good
(31)
"The exact location was a little tricky but Karl was a phone call away to assist. The building was safe and close to everything, but it’s in need of repairs and updating. The apartment itself met our expectations for the price paid. Loved the balcony to watch sunsets and the hip strip. My family loved the fact that the beach was across the street and dining out was walkable. I would definitely book this place again, only about 10mins to the airport. "
Dalley's Cozy Apartments
Dalley's Cozy Apartments
3.0 star property
Hip Strip
10.0 out of 10, Exceptional, (2)
10.0/10
Exceptional
(2)
"It was a great place, right spot clean big place i have everything i need to have a good time i do recommend this place"
Idle Awhile Villas
Idle Awhile Villas
4.0 star property
Negril
10.0 out of 10, Exceptional, (14)
10.0/10
Exceptional
(14)
"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!!"
Monimo Ridge Suites
Monimo Ridge Suites
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (15)
8.6/10
Excellent
(15)
"Was a clean and safe space to spend a night before my flight back home. Very close to Montego Bay airport."
Beach House Condos Negril
Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (53)
9.0/10
Wonderful
(53)
"Spacious condo and perfect location on the amazing 7 mile beach with a nice large private balcony. Bed was very comfortable. Would have been nice to have better water pressure in the shower and a curtain on the bathroom window. Staff is wonderful and ocean front restaurant was good. "
The price is S$194
S$194
includes taxes & fees
21 Jun - 22 Jun
Sunny-shore Hideaway
Sunny-shore Hideaway
2.0 star property
Lucea
Villas Sur Mer
Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (147)
8.8/10
Excellent
(147)
"Beautiful property. Daniela was warm and friendly and super helpful/accommodating. A wonderful spot for a quiet retreat "
The price is S$206
S$206
includes taxes & fees
4 Jul - 5 Jul
Montego Bay Club Beach Resort
Montego Bay Club Beach Resort
3.5 star property
Hip Strip
3.8 out of 10, (31)
3.8/10
(31)
"Room was not ready to after 4pm. Property is poorly maintained. Later check out was not granted. No amenities at all. "
The price is S$193
S$193
includes taxes & fees
23 Jun - 24 Jun
Sky Beach Rooms
Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1)
2.0/10
(1)
"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."
The price is S$154
S$154
includes taxes & fees
14 Jun - 15 Jun
Stunning Ocean View
Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (10)
10.0/10
Exceptional
(10)
"The view and ambience was pure bliss!"
The price is S$825
S$825
includes taxes & fees
24 Jun - 25 Jun
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!"
Turquoise Sea Villa
Turquoise Sea Villa
3.5 star property
Montego Bay
The price is S$257
S$257
includes taxes & fees
13 Jun - 14 Jun
Unity Villa
Unity Villa
3.0 star property
Montego Bay
Luxury villa in Montego Bay Jamaica
Luxury villa in Montego Bay Jamaica
3.0 star property
Montego Bay
King Suite at Oceanview Resort in Jamaica - Enjoy 7 Miles Of White Sand Beach! 1 Bedroom Villa by RedAwning
King Suite at Oceanview Resort in Jamaica - Enjoy 7 Miles Of White Sand Beach! 1 Bedroom Villa by RedAwning
3.0 star property
Negril
Sativa cottages
Sativa cottages
2.0 star property
Little London
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)
"Solet's Paradise is a litte 'safe haven', the place is safe and secure, the location is near to many shops, dinning and entertainment location. Ms Solets ensure that my friend and i were comfortable."
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$444
S$444
includes taxes & fees
15 Jun - 16 Jun
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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Recent reviews of Middlesex properties
Recent reviews of Middlesex properties
Hotel Riu Palace Tropical Bay - All Inclusive
5/5 Excellent
"Awesome"
A verified traveller stayed at Hotel Riu Palace Tropical Bay - All Inclusive
Posted 1 day ago
SeaGarden Beach Resort - All Inclusive
5/5 Excellent
"Best stay! Staff was very helpful and friendly!"
A verified traveller stayed at SeaGarden Beach Resort - All Inclusive
Posted 1 day ago
CocoLaPalm Seaside Resort
5/5 Excellent
"It very quite, not crowded and very relaxing "
A verified traveller stayed at CocoLaPalm Seaside Resort
Posted 1 day ago
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
5/5 Excellent
"My stay at S Hotel was nothing short of magical. From the moment I arrived, I felt like royalty. The staff were incredibly warm, welcoming, and attentive—every single person I encountered made me feel like I truly mattered.
The rooms were stunning—modern, clean, and designed with thoughtful touches that made all the difference. The view from the balcony was absolutely breathtaking—overlooking the crystal-clear waters of Doctor’s Cave Beach.
The food? Incredible. From the Jamaican breakfast to the gourmet dinners, every meal was fresh, flavorful, and beautifully plated. The poolside service was top-tier too—cocktails, coconut water, and snacks brought right to your lounger.
One of my favorite parts was the spa and wellness vibe throughout the hotel. It felt peaceful, relaxing, and luxurious—like a true escape from the world. Whether I was lounging by the rooftop pool or taking a sunset stroll along the beach, I felt completely at peace.
S Hotel has a perfect blend of authentic Jamaican culture and modern luxury. I can’t wait to return—it’s officially my go-to spot in Montego Bay. Highly, highly recommend!"
A verified traveller stayed at S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Posted 2 days ago
Deja Resort All Inclusive
5/5 Excellent
"It could be more updated but I always enjoy my time at Deja . I stayed here on 2 separate occasions and had a blast . The scenery outside of the hotel to take picture I loveeeeeee . The food was excellent the jerk chicken and fries omg I could eat it all day "
A verified traveller stayed at Deja Resort All Inclusive
Posted 2 days ago
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
5/5 Excellent
"The fact that it had lazy beds in pool where non-swimmers could still enjoy it."
A verified traveller stayed at Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Posted 3 days ago
Princess Senses The Mangrove Resort - Adults Only
5/5 Excellent
"We have to walk too mcuh"
A verified traveller stayed at Princess Senses The Mangrove Resort - Adults Only
Posted 3 days ago
Hotel 39 Jamaica
5/5 Excellent
"I love it. The service was great & friendly. The room was nice & clean. And the view from my balcony was breathtaking. Def highly recommend this hotel to many others who want to visit Montego Bay. "
A verified traveller stayed at Hotel 39 Jamaica
Posted 3 days ago
Secrets Wild Orchid Montego Bay - Luxury - Adults Only - All Inclusive
5/5 Excellent
"Best experience I’ve ever had. "
A verified traveller stayed at Secrets Wild Orchid Montego Bay - Luxury - Adults Only - All Inclusive
Posted 3 days ago
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 Bloody Bay 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.