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Check prices for these dates

Tonight
12 Jan - 13 Jan
Tomorrow
13 Jan - 14 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Middlesex holiday rentals

Premium Cottage, 1 Queen Bed, Pool View | Balcony view
Villas Sur Mer

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (149 reviews)
"Amazing as always!!! "
United States
ronesha
The price is ฿6,118
฿6,761 total
includes taxes & fees
14 Jan - 15 Jan
Villas Sur Mer
Daily cooked-to-order breakfast for a fee
Idle Awhile Cliffs

Idle Awhile Cliffs

Idle Awhile Cliffs
3.5 star property
West End
9.0 out of 10, Wonderful, (119 reviews)
"Friendly staff, excellent customer service. Enjoyed the ambience and accommodations. Clean and pleasant."
United States
Nayana
Idle Awhile Cliffs
Basic Loft | View from room
Claudeville Condo

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (22 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
Claudeville Condo
Exterior
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ฿3,240
฿3,757 total
includes taxes & fees
13 Jan - 14 Jan
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Exterior
Unity Villa

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
Unity Villa
Villa, 4 Bedrooms | Property grounds
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

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 ฿5,043
฿12,462 total
includes taxes & fees
19 Jan - 20 Jan
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
View from property
Montego Bay Club Beach Resort

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.2 out of 10, (46 reviews)
"Room was neglected and unclean. Ceiling tile was missing. Sheets had fluids on them. Received a room that was not pictured in the booking "
United States
kayla
The price is ฿3,388
฿4,743 total
includes taxes & fees
16 Jan - 17 Jan
Montego Bay Club Beach Resort
Reception
Negril Beachside

Negril Beachside

Negril Beachside
2.0 star property
Negril
The price is ฿4,894
฿5,729 total
includes taxes & fees
13 Jan - 14 Jan
Negril Beachside
Front of property
Wabi-Sabi Villa

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
Wabi-Sabi Villa
Property grounds
Beach House Condos Negril

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (57 reviews)
"The unit was better than expected, very spacious, clean, and full of amenities. Furniture, beds, snd AC all great! I will be returning snd rentong beach view. Great prices too! Restaurant served one of the best ackee and saltfish breakfastvall trip! Security was also vey friendly abd generous!"
United States
Mark
The price is ฿5,365
฿6,737 total
includes taxes & fees
13 Jan - 14 Jan
Beach House Condos Negril
Beach towels
Montego Bay Club Apartments

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (46 reviews)
"The room was well equipped, bed was comfortable and close to everything. We'll definitely be back. "
United States
niesha
The price is ฿4,235
฿6,000 total
includes taxes & fees
13 Jan - 14 Jan
Montego Bay Club Apartments
Beach nearby, white sand, beach towels
Nianna Chatham

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is ฿5,616
฿8,372 total
includes taxes & fees
14 Jan - 15 Jan
Nianna Chatham
Front of property
Blue Seas Two Unity Hall

Blue Seas Two Unity Hall

Blue Seas Two Unity Hall
3.0 star property
Montego Bay
The price is ฿13,538
฿17,482 total
includes taxes & fees
13 Jan - 14 Jan
Blue Seas Two Unity Hall
Terrace/patio
The Shallhome

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is ฿15,686
฿18,070 total
includes taxes & fees
13 Jan - 14 Jan
The Shallhome
Front of property
Unity Villa

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"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 ฿2,039
฿2,902 total
includes taxes & fees
13 Jan - 14 Jan
Unity Villa
Villa, 1 Bedroom | 1 bedroom, iron/ironing board, free WiFi
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

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 review)
The price is ฿2,634
฿5,693 total
includes taxes & fees
13 Jan - 14 Jan
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining
Stunning Ocean View

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (11 reviews)
"The view and ambience was pure bliss!"
United States
Roxanne
The price is ฿14,352
฿20,301 total
includes taxes & fees
18 Jan - 19 Jan
Stunning Ocean View
House, 3 Bedrooms, Smoking, Patio | Exterior
Sunny-shore Hideaway

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ฿4,826
฿8,019 total
includes taxes & fees
19 Jan - 20 Jan
Sunny-shore Hideaway
Apartment | Exterior
Oceanview 1-bed Apt w/ Pool, Bar & Beach Access

Oceanview 1-bed Apt w/ Pool, Bar & Beach Access

Oceanview 1-bed Apt w/ Pool, Bar & Beach Access
3.0 star property
Montego Bay
6.0 out of 10, (2 reviews)
"The Oceanview was prefect. Allowed me to stay for an additional tonight with discount. Neighbors very friendly and helpful. The pool stays open 24 hours. Need a pass to get on the beach which locks at 6 pm. The Restaurant was great not over priced menu. There's a bar/gift shop on the premise. "
United States
Kinshasha
The price is ฿1,842
฿2,150 total
includes taxes & fees
1 Feb - 2 Feb
Oceanview 1-bed Apt w/ Pool, Bar & Beach Access
Comfort House | Private kitchen | Full-sized fridge, oven, stovetop, cookware/dishes/utensils
Casia Villa

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is ฿10,196
฿13,325 total
includes taxes & fees
13 Jan - 14 Jan
Casia Villa
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

Toby's Resort

Toby's Resort

10/10 Excellent
"Breakfast was delicious local cuisine. The staff very friendly. "
Donald 1-night trip
Posted 16 hours ago
Toby's Resort

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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  • Enter your travel dates to view the best deals on holiday rentals in Middlesex while they last

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 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. 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.