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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middlesex vacation rentals

An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

1. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.4 out of 10, 5, (5 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
The price is ￥13,819
￥15,355 total
includes taxes & fees
Sep 19 - Sep 20
Sky Beach Rooms

2. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ￥25,100
￥41,140 total
includes taxes & fees
Oct 15 - Oct 16
Sunny-shore Hideaway
A dining area with a wooden table and chairs, a fruit bowl, and a view of the ocean through large glass doors.

3. Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, 15, (15 reviews)
"Clean and beautiful scenery! Needed assistance after hours and the manager responded quickly to my questions and concerns. Would book again"
United States
Willie
The price is ￥82,023
￥112,914 total
includes taxes & fees
Sep 15 - Sep 16
Stunning Ocean View
A swimming pool with a hot tub, surrounded by palm trees and a white building.

4. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is ￥11,921
￥29,224 total
includes taxes & fees
Sep 15 - Sep 16
Turquoise Sea Villa
A large house with a swimming pool, surrounded by lush greenery and palm trees.

5. La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is ￥112,904
￥141,515 total
includes taxes & fees
Sep 28 - Sep 29
La Costa Villa
A beach with thatched umbrellas, a white building, and pink flowers.

6. Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, 64, (64 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is ￥18,433
￥23,195 total
includes taxes & fees
Sep 17 - Sep 18
Beach House Condos Negril
A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

7. Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, 27, (27 reviews)
"The property was very close to the airport. Bed is comfortable. Only thing is I would av appreciated a kitchen curtain. Apart from that it was great and I love the host she is sweet"
United States
Devine
The price is ￥14,689
￥17,047 total
includes taxes & fees
Sep 16 - Sep 17
Claudeville Condo
A two-story building with a balcony on the upper floor, featuring decorative railings and barred windows.

8. Unity Villa

Unity Villa
3.0 star property
Montego Bay
5.0 out of 10, 2, (2 reviews)
"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 ￥9,985
￥14,210 total
includes taxes & fees
Sep 15 - Sep 16
Unity Villa

9. Grassroots Negril

Grassroots Negril
3.0 star property
West End
The price is ￥9,985
￥13,941 total
includes taxes & fees
Sep 15 - Sep 16
Grassroots Negril
A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

10. Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, 1, (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
The price is ￥14,516
￥19,919 total
includes taxes & fees
Sep 15 - Sep 16
Unity Villa
A bedroom with a bed, a ceiling fan, an air conditioner, and a view of the outdoors.

11. Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is ￥18,663
￥21,794 total
includes taxes & fees
Sep 15 - Sep 16
Eleven30 Luxury Apartments
A hanging chair on a balcony with a white railing and a view of trees.

12. Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
7.6 out of 10, 4, (4 reviews)
"Great atmosphere and awesome service. Clean and spacious apartment with a modern touch. Definitely looking forward to a future stay"
United States
Shantel
The price is ￥17,474
￥20,248 total
includes taxes & fees
Sep 15 - Sep 16
Modern Home 10minstobeach, Private Cliff, AC Wifi
A staircase with stone steps and white metal railings, leading to a door with a decorative white wall.

13. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ￥14,931
￥17,325 total
includes taxes & fees
Sep 18 - Sep 19
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
A beach with clear turquoise water, a sandy shore, and lounge chairs.

14. Seawind E202

Seawind E202
2.0 star property
Montego Bay
The price is ￥17,205
￥37,605 total
includes taxes & fees
Oct 15 - Oct 16
Seawind E202
A balcony with a view of the ocean and a tropical landscape.

15. The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is ￥76,805
￥88,480 total
includes taxes & fees
Sep 15 - Sep 16
The Shallhome
A lush garden with a swimming pool, surrounded by dense foliage and tropical plants.

16. Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.6 out of 10, 155, (155 reviews)
"We did not use the hot tub put the pool area including the hot tub looked very relaxing. Located in a beautiful garden area "
Canada
Faye
The price is ￥30,914
￥34,159 total
includes taxes & fees
Sep 16 - Sep 17
Villas Sur Mer
A dining area with a round table set for four, surrounded by chairs. There is a sofa and a chair in the background, and a window with curtains.

17. Casia Villa

Casia Villa
3.0 star property
Montego Bay
2.0 out of 10, 1, (1 review)
"We waited forever in a shadycary office"
United States
Michael
The price is ￥62,212
￥79,379 total
includes taxes & fees
Sep 15 - Sep 16
Casia Villa
A beach with clear turquoise water, a sandy shore, and a view of the ocean.

18. Montego Bay Club Apartments

Montego Bay Club Apartments
3.5 star property
Hip Strip
7.2 out of 10, 94, (94 reviews)
"Love everything"
United States
Neema
The price is ￥18,843
￥27,199 total
includes taxes & fees
Sep 16 - Sep 17
Montego Bay Club Apartments
A person standing on a beach with arms raised, facing a calm sea and a small island in the distance.

19. Deluxe appartment at Point village

Deluxe appartment at Point village
3.0 star property
West End
9.0 out of 10, 14, (14 reviews)
"The apartment is nice, comfortable and accommodating."
United States
Nikki
The price is ￥17,168
￥19,897 total
includes taxes & fees
Sep 16 - Sep 17
Deluxe appartment at Point village
A resort with a swimming pool, multiple villas, and a beach area.

20. Idle Awhile Cliffs

Idle Awhile Cliffs
4.0 star property
West End
9.0 out of 10, 123, (123 reviews)
"Beautiful property in the woods. Very quiet, friendly staff."
United States
Mazie Kaylia Horace
Idle Awhile Cliffs
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

8/10 Good
"It’s not a five star hotel but the staff treats you like it is. Willingness to change my room to one of my liking and accommodated my early arrival by getting me a room earlier"
Winston 3-night trip
Posted 1 hour 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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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?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: Visitors like this Middlesex vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Hope Botanical Garden and Zoo, 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.