Middlesex Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Middlesex vacation 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 ￥29,372
￥32,467 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥15,395
￥17,862 total
includes taxes & fees
Jan 18 - Jan 19
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 ￥24,358
￥61,257 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥16,945
￥23,723 total
includes taxes & fees
Jan 16 - Jan 17
Montego Bay Club Beach Resort
Reception
Negril Beachside

Negril Beachside

Negril Beachside
2.0 star property
Negril
The price is ￥24,476
￥28,650 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥26,830
￥33,694 total
includes taxes & fees
Jan 11 - Jan 12
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, (45 reviews)
"The room was well equipped, bed was comfortable and close to everything. We'll definitely be back. "
United States
niesha
The price is ￥21,181
￥30,008 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥22,437
￥35,373 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥67,706
￥87,433 total
includes taxes & fees
Jan 11 - Jan 12
Blue Seas Two Unity Hall
Terrace/patio
The Shallhome

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is ￥78,450
￥90,374 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥10,199
￥14,514 total
includes taxes & fees
Jan 11 - Jan 12
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 ￥12,595
￥27,707 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥71,777
￥101,529 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥23,852
￥39,798 total
includes taxes & fees
Jan 20 - Jan 21
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 ￥9,143
￥10,670 total
includes taxes & fees
Feb 1 - Feb 2
Oceanview 1-bed Apt w/ Pool, Bar & Beach Access
Comfort House | Private kitchen | Full-size fridge, oven, stovetop, cookware/dishes/utensils
Casia Villa

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is ￥50,993
￥66,644 total
includes taxes & fees
Jan 11 - Jan 12
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex Hotel Reviews

Grand Palladium Jamaica Resort & Spa All Inclusive

Grand Palladium Jamaica Resort & Spa All Inclusive

10/10 Excellent
"Great place, excellent service and lots of evening activities for all ages. "
Paulette 2-night trip
Posted 3 days ago
Grand Palladium Jamaica Resort & Spa 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
  • Use the map to find apartments and other holiday homes in the Middlesex neighbourhood you prefer
  • 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 vacation rentals in Middlesex?

Yes, we have vacation rentals near popular local attractions in Middlesex, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Middlesex has to offer?

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL: You might want to consider this vacation home rental near Middlesex, which 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 larger area.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Middlesex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.