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Check prices for these dates

Tonight
19 Nov - 20 Nov
Tomorrow
20 Nov - 21 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Top Holiday Rentals in Middlesex

Outdoor dining
Sand and Blue Seas

Sand and Blue Seas

3.0 star property
Negril
8.2 out of 10, Very good, (132)
"They were so friendly and hospitable. "
Canada
Jesslyn
Sand and Blue Seas
Beach towels
Montego Bay Club Apartments

Montego Bay Club Apartments

4.0 star property
Hip Strip
7.4 out of 10, Good, (41)
"I enjoyed my stay, the location was great."
United States
Michelle Iona
Montego Bay Club Apartments
Premium Cottage, 1 Queen Bed, Pool View | Balcony view
Villas Sur Mer

Villas Sur Mer

4.0 star property
West End
8.8 out of 10, Excellent, (149)
"Amazing as always!!! "
United States
ronesha
The price is ฿7,934
฿8,759 total
includes taxes & fees
20 Nov - 21 Nov
Villas Sur Mer
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
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)
"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!"
United States
Pamela
Idle Awhile Cliffs
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)
"Good location and Great view of the Caribbean Sea"
Canada
Owen
The price is ฿3,497
฿4,864 total
includes taxes & fees
20 Nov - 21 Nov
Montego Bay Club Beach Resort
Restaurant
Beach House Condos Negril

Beach House Condos Negril

3.5 star property
Negril
9.0 out of 10, Wonderful, (57)
"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 ฿6,153
฿7,723 total
includes taxes & fees
21 Nov - 22 Nov
Beach House Condos Negril
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
Exterior
Seascape Apartment

Seascape Apartment

2.5 star property
Negril
7.6 out of 10, Good, (10)
"Clean and family oriented. Owner were very accommodating. I wouldn’t mind staying there again."
United States
joselyn
Seascape Apartment
Luxury Villa, 5 Bedrooms | Outdoor pool | 4 outdoor pools
Idle Awhile Villas

Idle Awhile Villas

4.0 star property
Negril
10.0 out of 10, Exceptional, (15)
"Our villa was beyond our expectations for our family of 13!"
Canada
Mallory
Idle Awhile Villas
Balcony view
Dalley's Cozy Apartments

Dalley's Cozy Apartments

3.0 star property
Hip Strip
8.8 out of 10, Excellent, (8)
"The location was great walking distance to everything was easy "
United States
Nerval
Dalley's Cozy Apartments
Beach nearby, white sand, beach towels
Nianna Chatham

Nianna Chatham

2.5 star property
Hip Strip
The price is ฿5,796
฿8,641 total
includes taxes & fees
21 Nov - 22 Nov
Nianna Chatham
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

3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1)
The price is ฿2,668
฿5,445 total
includes taxes & fees
20 Nov - 21 Nov
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

4.0 star property
Negril
10.0 out of 10, Exceptional, (11)
"The view and ambience was pure bliss!"
United States
Roxanne
The price is ฿14,814
฿20,954 total
includes taxes & fees
1 Dec - 2 Dec
Stunning Ocean View
Outdoor pool
Ocean View Suit-Montego Bay Club Resort

Ocean View Suit-Montego Bay Club Resort

3.5 star property
Hip Strip
Ocean View Suit-Montego Bay Club Resort
Deluxe Double Room | Terrace/patio
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

4.0 star property
Negril
The price is ฿3,344
฿3,878 total
includes taxes & fees
3 Dec - 4 Dec
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Front of property
Turquoise Sea Villa

Turquoise Sea Villa

3.5 star property
Montego Bay
The price is ฿3,141
฿6,883 total
includes taxes & fees
20 Nov - 21 Nov
Turquoise Sea Villa
Beach/ocean view
Solet's Paradise Negril

Solet's Paradise Negril

2.5 star property
Negril
9.8 out of 10, Exceptional, (9)
"Solet’s Paradise is very comfortable and a great value stay."
United States
Noah
Solet's Paradise Negril
Basic Apartment | Terrace/patio
Luxury villa in Montego Bay Jamaica

Luxury villa in Montego Bay Jamaica

3.0 star property
Montego Bay
Luxury villa in Montego Bay Jamaica
Exterior
Apartamento Vacacional en Bahía Montego

Apartamento Vacacional en Bahía Montego

3.0 star property
Montego Bay
Apartamento Vacacional en Bahía Montego
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 Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

10/10 Excellent
"The staff were awesome well trained and we saw why because the head ( hotel manager) and other managers were immaculate and made our stay superb during hurricane Melissa."
Cagelia 1-night trip
Posted 2 days ago
Princess Grand Jamaica 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 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 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.