Middlesex Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Middlesex

Outdoor pool, pool umbrellas, pool loungers
Idle Awhile Cliffs

Idle Awhile Cliffs

3.5 star property
West End
9.0 out of 10, Wonderful, (119)
"Very rustic and secluded loved the feeling of been surrounded by nature, had a peaceful stay. Great staff. Hopeton from the bar very friendly and gives excellent service. "
United States
Richard
Idle Awhile Cliffs
Restaurant
Beach House Condos Negril

Beach House Condos Negril

3.5 star property
Negril
9.0 out of 10, Wonderful, (57)
"The staff were very friendly. Excellent service with a smile. A great place for family reunion. "
Canada
Opal
The price is HK$1,477
HK$1,854 total
includes taxes & fees
13 Nov - 14 Nov
Beach House Condos Negril
Beach towels
Montego Bay Club Apartments

Montego Bay Club Apartments

4.0 star property
Hip Strip
7.4 out of 10, Good, (41)
"I love everything about! My go to spot. In walking distance. "
United States
Monique
The price is HK$1,049
HK$1,486 total
includes taxes & fees
1 Dec - 2 Dec
Montego Bay Club Apartments
Property grounds
Monimo Ridge Suites

Monimo Ridge Suites

3.0 star property
Montego Bay
8.6 out of 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. "
United States
Dianna
Monimo Ridge Suites
Electric kettle, toaster
Unity Villa

Unity Villa

3.0 star property
Montego Bay
8.0 out of 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 "
United States
Susan
Unity Villa
Property grounds
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning

YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning

3.5 star property
Montego Bay
6.0 out of 10, (2)
"They was not any bed spread provided for one of the bed. The room -the the pressing iron for clothing was burn as shown in yhe picture. That's the first time ever wearing my nee suit smh. The flooring need cleaning The electronic not functional period. The bathroom shower dirty. The walls was stripping and needs of painting. The windows shows mold and grime No bathroom soap was provides The kitchen no soap was provides until later the following day smh. Things to wash pons and plates wasnt...
United States
Kenean
The price is HK$826
HK$2,332 total
includes taxes & fees
14 Nov - 15 Nov
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning
Front of property
Turquoise Sea Villa

Turquoise Sea Villa

3.5 star property
Montego Bay
The price is HK$731
HK$1,626 total
includes taxes & fees
13 Nov - 14 Nov
Turquoise Sea Villa
Beach
CPA3

CPA3

3.5 star property
Montego Bay
The price is HK$897
HK$1,428 total
includes taxes & fees
13 Nov - 14 Nov
CPA3
Balcony view
Villas Sur Mer

Villas Sur Mer

4.0 star property
West End
8.8 out of 10, Excellent, (149)
"Love this property. Great staff and the location was great for me. Only thing I would change is the couch in the room wasn't that great. Everything else was wonderful. "
United States
Chelsea
The price is HK$1,600
HK$1,767 total
includes taxes & fees
28 Nov - 29 Nov
Villas Sur Mer
Beach nearby, white sand, beach towels
Nianna Chatham

Nianna Chatham

2.5 star property
Hip Strip
The price is HK$1,078
HK$1,714 total
includes taxes & fees
13 Nov - 14 Nov
Nianna Chatham
Front of property
Unity Villa

Unity Villa

3.0 star property
Montego Bay
8.0 out of 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."
United States
Fashira
The price is HK$490
HK$702 total
includes taxes & fees
13 Nov - 14 Nov
Unity Villa
Pool
Sunny-shore Hideaway

Sunny-shore Hideaway

2.0 star property
Lucea
Sunny-shore Hideaway
Terrace/patio
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

4.0 star property
Negril
The price is HK$722
HK$839 total
includes taxes & fees
20 Nov - 21 Nov
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
View from property
Montego Bay Club Beach Resort

Montego Bay Club Beach Resort

3.5 star property
Hip Strip
4.4 out of 10, (42)
" "
United States
Edris
The price is HK$665
HK$967 total
includes taxes & fees
14 Nov - 15 Nov
Montego Bay Club Beach Resort
In-room dining
Stunning Ocean View

Stunning Ocean View

4.0 star property
Negril
10.0 out of 10, Exceptional, (11)
"We had an amazing time with our family there. When we had any small issues, mr. Brown was very helpful and quick to react! Highly recommended host. The palapa and the ocean view were top notch! The walk to the private beach is short and no bother at all. "
Canada
Marie Eve
The price is HK$3,449
HK$4,906 total
includes taxes & fees
13 Nov - 14 Nov
Stunning Ocean View
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

3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1)
The price is HK$596
HK$1,248 total
includes taxes & fees
14 Nov - 15 Nov
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Exterior
Wabi-Sabi Villa

Wabi-Sabi Villa

5.0 star property
Lucea
10.0 out of 10, Exceptional, (2)
"I recently had the pleasure of staying at Wabi Sabi Villa in Lucea, Jamaica, and it was truly an exceptional experience. This villa offers everything you could ask for in a private retreat, including a stunning private pool and jacuzzi for guests to enjoy. The all-inclusive package with a personal chef made our stay even more special, as we were treated to delicious meals in the comfort of our own villa. The rooms were beautifully appointed, and any issues we encountered were promptly addressed...
United States
Princess
Wabi-Sabi Villa
Private kitchen
Casia Villa

Casia Villa

3.0 star property
Montego Bay
The price is HK$3,053
HK$3,908 total
includes taxes & fees
13 Nov - 14 Nov
Casia Villa
Terrace/patio
The Shallhome

The Shallhome

3.0 star property
Montego Bay
The price is HK$3,769
HK$4,343 total
includes taxes & fees
13 Nov - 14 Nov
The Shallhome
Terrace/patio
La Costa Villa

La Costa Villa

3.0 star property
Montego Bay
The price is HK$5,421
HK$6,631 total
includes taxes & fees
16 Nov - 17 Nov
La Costa 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

Deja Resort All Inclusive

Deja Resort All Inclusive

10/10 Excellent
"The Staff Were Fantastic During The Recent Hurricane....They Were Courteous, Friendly, Understanding, Extremely Helpful, Cheerful And Professional...The Food Options Were Outstanding....The Property Was Very Safe And I Would Definitely Stay Here Again."
William 3-night trip
Posted 2 days ago
Deja Resort All Inclusive

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?

Stunning Ocean View: This holiday home rental outside 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. 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.