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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Middlesex vacation rentals

View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
The price is P5,846
P6,784 total
includes taxes & fees
Jun 25 - Jun 26
Claudeville Condo
Restaurant

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
The price is P6,602
P7,323 total
includes taxes & fees
Jun 26 - Jun 27
Sky Beach Rooms
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (85 reviews)
"The view is amazing just imagine waking to a beautiful blue ocean. Walking distance to the beach and the best restaurants, I recommend this place any day and the price is right.."
United States
Natalie
The price is P7,537
P10,318 total
includes taxes & fees
Jun 26 - Jun 27
Montego Bay Club Beach Resort
Exterior

La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is P46,016
P56,048 total
includes taxes & fees
Jun 25 - Jun 26
La Costa Villa
Balcony

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
9.0 out of 10, Wonderful, (2 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 P6,488
P7,522 total
includes taxes & fees
Jul 1 - Jul 2
Modern Home 10minstobeach, Private Cliff, AC Wifi
Free WiFi

Grassroots Negril

Grassroots Negril
3.0 star property
West End
The price is P3,973
P5,548 total
includes taxes & fees
Jul 2 - Jul 3
Grassroots Negril
Property grounds

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (62 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is P7,336
P9,231 total
includes taxes & fees
Jul 8 - Jul 9
Beach House Condos Negril
Private kitchen

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is P24,849
P31,705 total
includes taxes & fees
Jun 25 - Jun 26
Casia Villa
Terrace/patio

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is P30,565
P35,211 total
includes taxes & fees
Jun 30 - Jul 1
The Shallhome
Balcony view

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (153 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 P11,955
P13,211 total
includes taxes & fees
Jul 15 - Jul 16
Villas Sur Mer
In-room dining

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (14 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 P32,642
P44,935 total
includes taxes & fees
Jul 2 - Jul 3
Stunning Ocean View
2 outdoor pools, free cabanas, pool umbrellas

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is P8,665
P14,611 total
includes taxes & fees
Jul 1 - Jul 2
Sunshine Seashore Escape Jamaica
Beach nearby, white sand, beach towels

Hospitality Expert CP

Hospitality Expert CP
2.5 star property
Hip Strip
The price is P18,278
P24,748 total
includes taxes & fees
Jul 20 - Jul 21
Hospitality Expert CP
Sundeck

Little Waters on the Cliff

Little Waters on the Cliff
4.0 star property
West End
10.0 out of 10, Exceptional, (2 reviews)
"Spectacular views of the sunset, and a very comfortable, spacious place with everything you need for a upscale comfortable stay. The pool is perfect to cool down in after getting the sunny exposure the afternoons provide. The staff is fantastic Delkia and Rose are exceptional the meals were fantastic and Delkia is outstanding at arranging any tours or transportation you may need or want. On site security at night makes for great peace of mind as well. We really enjoyed the cliffs for our own...
Canada
Anonymous traveler
Little Waters on the Cliff
Exterior

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is P6,212
P7,205 total
includes taxes & fees
Jun 25 - Jun 26
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Blackout drapes, iron/ironing board, free WiFi

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is P7,455
P8,705 total
includes taxes & fees
Jun 25 - Jun 26
Eleven30 Luxury Apartments
Beach towels

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (76 reviews)
"It was a nice stay."
United States
Leslyn
The price is P8,528
P12,007 total
includes taxes & fees
Jun 27 - Jun 28
Montego Bay Club Apartments
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
The price is P5,777
P7,927 total
includes taxes & fees
Jun 30 - Jul 1
Unity Villa
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 P3,973
P5,655 total
includes taxes & fees
Jun 25 - Jun 26
Unity Villa
Exterior

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is P9,382
P15,523 total
includes taxes & fees
Jul 7 - Jul 8
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

Hotel 39 Jamaica

Hotel 39 Jamaica

10/10 Excellent
"It’s a good value for the location, but the towels, paint, shower transitions, and other everyday items and facilities need updating."
Iyun 10-night trip
Posted 10 hours ago
Hotel 39 Jamaica

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 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?

Deluxe appartment at Point village: Visitors like this Middlesex vacation home rental. It has air-conditioning and a plasma TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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.