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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
15 Oct - 16 Oct
Sky Beach Rooms
A coastal swimming area with boats and people.

2. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is ฿4,758
฿8,023 total
includes taxes & fees
15 Oct - 16 Oct
Sunshine Seashore Escape Jamaica
A beach with thatched umbrellas, a white building, and pink flowers.

3. 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
23 Oct - 24 Oct
Beach House Condos Negril
Exterior

4. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ฿5,080
฿8,433 total
includes taxes & fees
15 Oct - 16 Oct
Sunny-shore Hideaway
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 ฿3,172
฿4,353 total
includes taxes & fees
15 Oct - 16 Oct
Unity Villa
A dining area with a wooden table and chairs, a fruit bowl, and a view of the ocean through large glass doors.

6. 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
15 Oct - 16 Oct
Stunning Ocean View
A swimming pool with a hot tub, surrounded by palm trees and a white building.

7. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is ฿4,559
฿8,633 total
includes taxes & fees
15 Oct - 16 Oct
Turquoise Sea Villa
A staircase with stone steps and metal railings, leading upwards.

8. 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
19 Oct - 20 Oct
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
A lush garden with a swimming pool, surrounded by dense foliage and tropical plants.

9. 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 ฿7,343
฿8,111 total
includes taxes & fees
15 Oct - 16 Oct
Villas Sur Mer
Exterior

10. Grassroots Negril

Grassroots Negril
3.0 star property
West End
The price is ฿2,182
฿3,046 total
includes taxes & fees
24 Oct - 25 Oct
Grassroots Negril
A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

11. 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
15 Oct - 16 Oct
Claudeville Condo
A hanging chair on a balcony with a white railing and a view of trees.

12. 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 ฿4,330
฿5,013 total
includes taxes & fees
15 Oct - 16 Oct
Modern Home 10minstobeach, Private Cliff, AC Wifi
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

Princess Senses The Mangrove Resort - Adults Only

Princess Senses The Mangrove Resort - Adults Only

10/10 Excellent
"EVERYONE WAS EXCELLENT"
Chester 5-night trip
Posted 1 hour ago
Princess Senses The Mangrove Resort - Adults Only

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.