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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Middlesex holiday rentals

An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

1. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.4 out of 10, Very good, (6 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
The price is ฿3,263
฿3,623 total
includes taxes & fees
19 Oct - 20 Oct
Sky Beach Rooms
A modern outdoor pool area with lounge chairs, a hot tub, and a fireplace.

2. Wabi-Sabi Villa

Wabi-Sabi Villa
5.0 star property
Lucea
10.0 out of 10, Exceptional, (2 reviews)
"This property had amazing staff and the place was beautiful. I absolutely loved them! "
United States
Andrea
The price is ฿26,124
฿33,440 total
includes taxes & fees
13 Nov - 14 Nov
Wabi-Sabi Villa
A dining area with a wooden table and chairs, a fruit bowl, and a view of the ocean through large glass doors.

3. Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (15 reviews)
"Clean and beautiful scenery! Needed assistance after hours and the manager responded quickly to my questions and concerns. Would book again"
United States
Willie
The price is ฿16,869
฿23,461 total
includes taxes & fees
18 Oct - 19 Oct
Stunning Ocean View
A lush garden with a swimming pool, surrounded by dense foliage and tropical plants.

4. Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.6 out of 10, Excellent, (155 reviews)
"Carmen was very accommodating during my stay at the villa. The upgraded room was beautiful. The amenities and proximity to other restaurants in walking distance was a great."
United States
Nadine
The price is ฿6,559
฿7,248 total
includes taxes & fees
15 Nov - 16 Nov
Villas Sur Mer
A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

5. Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"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 "
United States
Susan
The price is ฿3,179
฿4,362 total
includes taxes & fees
16 Oct - 17 Oct
Unity Villa
A beach with thatched umbrellas, a white building, and pink flowers.

6. Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (64 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is ฿4,028
฿5,069 total
includes taxes & fees
29 Oct - 30 Oct
Beach House Condos Negril
A coastal swimming area with boats and people.

7. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is ฿4,758
฿8,023 total
includes taxes & fees
18 Oct - 19 Oct
Sunshine Seashore Escape Jamaica
Exterior

8. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ฿5,079
฿8,431 total
includes taxes & fees
15 Nov - 16 Nov
Sunny-shore Hideaway
A swimming pool with a hot tub, surrounded by palm trees and a white building.

9. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is ฿4,559
฿8,633 total
includes taxes & fees
25 Oct - 26 Oct
Turquoise Sea Villa
A two-story building with a balcony on the upper floor, featuring decorative railings and barred windows.

10. Unity Villa

Unity Villa
3.0 star property
Montego Bay
5.0 out of 10, (2 reviews)
"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."
United States
Fashira
The price is ฿2,186
฿3,111 total
includes taxes & fees
24 Oct - 25 Oct
Unity Villa
A staircase with stone steps and metal railings, leading upwards.

11. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ฿3,399
฿3,942 total
includes taxes & fees
16 Oct - 17 Oct
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
A beach view from a balcony with a clear ocean, a pier, and a few umbrellas on the sand.

12. Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.6 out of 10, (99 reviews)
"I liked the view and the location.I liked that it was clean and bright"
Canada
Gerald
The price is ฿4,078
฿5,596 total
includes taxes & fees
19 Oct - 20 Oct
Montego Bay Club Beach Resort
A large house with a swimming pool, surrounded by lush greenery and palm trees.

13. La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is ฿25,175
฿31,503 total
includes taxes & fees
25 Oct - 26 Oct
La Costa Villa
A person standing on a beach with arms raised, facing a calm sea and a small island in the distance.

14. Deluxe appartment at Point village

Deluxe appartment at Point village
3.0 star property
West End
9.0 out of 10, Wonderful, (14 reviews)
"I love the Location of the property it’s right on the beach"
United States
Schanna
The price is ฿3,759
฿4,357 total
includes taxes & fees
17 Oct - 18 Oct
Deluxe appartment at Point village
Exterior

15. Grassroots Negril

Grassroots Negril
3.0 star property
West End
The price is ฿2,182
฿3,046 total
includes taxes & fees
16 Oct - 17 Oct
Grassroots Negril
A beach with lounge chairs and a clear view of the ocean.

16. Seawind F104

Seawind F104
3.5 star property
Montego Bay
6.0 out of 10, (1 review)
"Let me start with the property was very nice including the apartment we stayed in. Very modern and tastefully decorated. Location of this property was perfect as we were visiting family and it was close by. To pay for the cleaning fee prior to check in was a little challenging; when traveling with a cell phone you are unable to pay using the link they provide. We were able to pay cash onsite which helped. I would like to focus on the false advertising of guest laundry, there is no guest laundry...
United States
Rachel
The price is ฿3,814
฿8,288 total
includes taxes & fees
16 Oct - 17 Oct
Seawind F104
A beach with clear turquoise water, a sandy shore, and a view of the ocean.

17. Montego Bay Club Apartments

Montego Bay Club Apartments
3.5 star property
Hip Strip
7.0 out of 10, Good, (103 reviews)
"We really enjoyed our stay. Karl was responsive and kind. Location was great, property clean, and everyone in the area kind and helpful. Definitely recommend and will book again."
United States
Heather
The price is ฿4,389
฿6,259 total
includes taxes & fees
16 Oct - 17 Oct
Montego Bay Club Apartments
A hanging chair on a balcony with a white railing and a view of trees.

18. Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
7.6 out of 10, Good, (4 reviews)
"Great atmosphere and awesome service. Clean and spacious apartment with a modern touch. Definitely looking forward to a future stay"
United States
Shantel
The price is ฿4,332
฿5,015 total
includes taxes & fees
28 Oct - 29 Oct
Modern Home 10minstobeach, Private Cliff, AC Wifi
A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

19. Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (29 reviews)
"Property was clean and host was accommodating. We had an additional request and host was able to assist."
United States
Sabrina
The price is ฿3,210
฿3,725 total
includes taxes & fees
20 Oct - 21 Oct
Claudeville Condo
A pool area with lounge chairs and a view of the ocean.

20. Little Waters on the Cliff

Little Waters on the Cliff
4.0 star property
West End
10.0 out of 10, Exceptional, (2 reviews)
"Spectacular views of the sunset, and a very comfortable, spacious place with everything you need for a upscale comfortable stay. The pool is perfect to cool down in after getting the sunny exposure the afternoons provide. The staff is fantastic Delkia and Rose are exceptional the meals were fantastic and Delkia is outstanding at arranging any tours or transportation you may need or want. On site security at night makes for great peace of mind as well. We really enjoyed the cliffs for our own...
Canada
Anonymous traveller
The price is ฿39,241
฿45,161 total
includes taxes & fees
26 Oct - 27 Oct
Little Waters on the Cliff
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

Hotel Grand A View

Hotel Grand A View

10/10 Excellent
"No matter how simple the problem was, someone was always there to help when you ask. The kitchen staff, the breakfast crew , house keeping and the bartenders were very friendly and kind. I had no complaints while I was there"
EVETTE 4-night trip
Posted 2 hours ago
Hotel Grand A View

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex
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Look no further and take a look at our great range of rental properties in Middlesex!

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 Hope Botanical Garden and Zoo, 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.