Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
8.6 out of 10, Excellent, (7 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
The price is P6,804
P7,548 total
includes taxes & fees
Nov 7 - Nov 8
Sky Beach Rooms
A modern outdoor pool area with lounge chairs, a hot tub, and a fireplace.

2. 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
The price is P49,349
P63,169 total
includes taxes & fees
Nov 13 - Nov 14
Wabi-Sabi Villa
A row of colorful houses with a white staircase leading up to a porch.

3. Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (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 P33,641
P46,311 total
includes taxes & fees
Nov 7 - Nov 8
Stunning Ocean View
A coastal swimming area with boats and people.

4. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is P8,931
P15,058 total
includes taxes & fees
Nov 7 - Nov 8
Sunshine Seashore Escape Jamaica
A cliffside property with a swimming pool, outdoor seating, and a staircase leading to the water.

5. Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.6 out of 10, Excellent, (155 reviews)
"Carmen was very accommodating during my stay at the villa. The upgraded room was beautiful. The amenities and proximity to other restaurants in walking distance was a great."
United States
Nadine
The price is P11,057
P12,226 total
includes taxes & fees
Nov 18 - Nov 19
Villas Sur Mer
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, Wonderful, (65 reviews)
"Clean room. Beach view was excellent. Staff was very good."
United States
Patrick
The price is P11,970
P15,026 total
includes taxes & fees
Nov 7 - Nov 8
Beach House Condos Negril
A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

7. 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
The price is P5,954
P8,170 total
includes taxes & fees
Nov 25 - Nov 26
Unity Villa
A swimming pool with a hot tub, surrounded by palm trees and a white building.

8. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is P9,507
P17,296 total
includes taxes & fees
Nov 7 - Nov 8
Turquoise Sea Villa
A staircase with stone steps and metal railings, leading upwards.

9. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
A large house with a swimming pool, surrounded by lush greenery and palm trees.

10. La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is P47,252
P59,127 total
includes taxes & fees
Nov 7 - Nov 8
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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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:

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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 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.