Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Middlesex vacation rentals

Daily cooked-to-order breakfast for a fee

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
Beach towels

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (51 reviews)
"The room was well equipped, bed was comfortable and close to everything. We'll definitely be back. "
United States
niesha
The price is P7,382
P10,598 total
includes taxes & fees
Feb 9 - Feb 10
Montego Bay Club Apartments
View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (23 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
Claudeville Condo
Terrace/patio

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 P14,280
P15,767 total
includes taxes & fees
Feb 10 - Feb 11
Villas Sur Mer
Property grounds

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 P10,018
P12,581 total
includes taxes & fees
Feb 19 - Feb 20
Beach House Condos Negril
Reception

Negril Beachside

Negril Beachside
2.0 star property
Negril
8.0 out of 10, Very Good, (1 review)
The price is P9,139
P10,698 total
includes taxes & fees
Feb 9 - Feb 10
Negril Beachside
Exterior

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
2 bedrooms, desk, laptop workspace, iron/ironing board

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 reviews)
"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 P6,693
P19,386 total
includes taxes & fees
Feb 22 - Feb 23
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning
Balcony

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
The price is P4,845
P5,630 total
includes taxes & fees
Feb 9 - Feb 10
Modern Home 10minstobeach, Private Cliff, AC Wifi
Blackout drapes, iron/ironing board, free WiFi

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
Eleven30 Luxury Apartments
Beach

CPA3

CPA3
3.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is P7,675
P11,814 total
includes taxes & fees
Feb 11 - Feb 12
CPA3
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.2 out of 10, (48 reviews)
"The security guard was welcoming but that's about it. The place was unkept, challenging to find"
United States
Nicole
The price is P6,327
P8,858 total
includes taxes & fees
Feb 9 - Feb 10
Montego Bay Club Beach Resort
Front of property

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
Building design

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 P26,801
P37,910 total
includes taxes & fees
Feb 9 - Feb 10
Stunning Ocean View
Front of property

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 P3,808
P5,419 total
includes taxes & fees
Feb 18 - Feb 19
Unity Villa
Private kitchen

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is P23,727
P30,274 total
includes taxes & fees
Feb 9 - Feb 10
Casia Villa
Beach nearby, white sand, beach towels

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is P11,893
P17,250 total
includes taxes & fees
Feb 16 - Feb 17
Nianna Chatham
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 review)
The price is P4,919
P14,544 total
includes taxes & fees
Feb 9 - Feb 10
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Front of property

Blue Seas Two Unity Hall

Blue Seas Two Unity Hall
3.0 star property
Montego Bay
Blue Seas Two Unity Hall
Exterior

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is P10,036
P16,158 total
includes taxes & fees
Feb 24 - Feb 25
Sunny-shore Hideaway
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

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent
"Clean room, amazing staff, not one mosquito bite. Definitely staying here again. No complaints."
Deshawn 4-night trip
Posted 1 day ago
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

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?

Stunning Ocean View: You might want to consider this vacation home rental near Middlesex, which is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill 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 yard.

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.