Middlesex Holiday Rentals

  • 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
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Middlesex holiday rentals

Beach nearby, white sand, beach towels

Hospitality Expert CP

Hospitality Expert CP
2.5 star property
Hip Strip
The price is S$346
includes taxes & fees
2 Jun - 3 Jun
Hospitality Expert CP
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 S$142
includes taxes & fees
1 Jun - 2 Jun
Claudeville Condo
Beach towels

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (69 reviews)
"Wonder place I would stay there again nice view and very clean"
United States
Germaine
The price is S$220
includes taxes & fees
28 Jun - 29 Jun
Montego Bay Club Apartments
Blackout curtains, iron/ironing board, free WiFi

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is S$181
includes taxes & fees
29 May - 30 May
Eleven30 Luxury Apartments
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)
"The property wasn’t as clean, especially the bathroom and the ac in one of the rooms isn’t working. Overall it’s good for the price"
United States
Brianna
The price is S$143
includes taxes & fees
15 Jun - 16 Jun
Modern Home 10minstobeach, Private Cliff, AC Wifi
Property grounds

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 S$540
includes taxes & fees
14 Jun - 15 Jun
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
Private beach, white sand

Deluxe appartment at Point village

Deluxe appartment at Point village
3.0 star property
West End
9.0 out of 10, Wonderful, (13 reviews)
"The apartment is nice, comfortable and accommodating."
United States
Nikki
The price is S$149
includes taxes & fees
29 May - 30 May
Deluxe appartment at Point village
Property grounds

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (61 reviews)
"Excellent property, with only 13 rooms there is no hustle and bustle. Very clean and everything you need to enjoy your stay. Would definitely become a repeat visitor."
Canada
Vincent
The price is S$193
includes taxes & fees
22 Jun - 23 Jun
Beach House Condos Negril
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (78 reviews)
"Amazing view great service super safe "
United States
Shavone
The price is S$216
includes taxes & fees
3 Jun - 4 Jun
Montego Bay Club Beach Resort
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 S$166
includes taxes & fees
2 Jun - 3 Jun
Unity Villa
Private kitchen

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is S$660
includes taxes & fees
9 Jun - 10 Jun
Casia Villa
Terrace/patio

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is S$736
includes taxes & fees
30 May - 31 May
The Shallhome
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 S$939
includes taxes & fees
9 Jun - 10 Jun
Stunning Ocean View
Outdoor pool, pool umbrellas, pool loungers

Idle Awhile Cliffs

Idle Awhile Cliffs
4.0 star property
West End
9.0 out of 10, Wonderful, (121 reviews)
"Staying at Idle awhile cliff is a great stay, however be aware of the very idle vibe. Things are extremely relaxed. Most people go out for dinner in the evenings, so staff is normally gone by 7pm on the dot. This property has so much potential but I am afraid it’s a tad bit neglected because it is the smaller of the 3 properties. The concept of the room is amazing. At night it’s extremely dark in this area and away from most of what’s happening on the west end. Upon arriving we notice a few...
United States
Annie-Kay
The price is S$305
includes taxes & fees
1 Jun - 2 Jun
Idle Awhile Cliffs
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 S$118
includes taxes & fees
21 Jun - 22 Jun
Unity Villa
Exterior

La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is S$1,167
includes taxes & fees
3 Jun - 4 Jun
La Costa Villa
Exterior

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is S$150
includes taxes & fees
4 Jun - 5 Jun
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
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)
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
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 S$276
includes taxes & fees
9 Jun - 10 Jun
Villas Sur Mer
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 S$139
includes taxes & fees
14 Jun - 15 Jun
Sky Beach Rooms
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

Toby's Resort

Toby's Resort

10/10 Excellent
"The staff are very professional and friendly also easy to talk to. Check in is very smooth and easy, sometimes you may have to wait a few minutes for your room. The food is real authentic Jamaican cuisine. My stay has always been superb and excellent."
Sandra Z 7-night trip
Posted 1 hour ago
Toby's Resort

Frequently asked questions

Can I find holiday rentals in Middlesex?

Yes, there are holiday rentals close to the most popular sights in Middlesex, or you can select a more secluded option if you're looking for a relaxing stay.

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

Modern Home 10minstobeach, Private Cliff, AC Wifi: This holiday home rental outside of Middlesex comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

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 wider area.

What are holiday rentals like in Middlesex?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middlesex. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.