Middlesex Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middlesex

Villas Sur Mer
Outdoor pool, pool loungers

Villas Sur Mer

4.0 star property
8.6 out of 10, Excellent, (137)
"The time spend was quite relaxing, the accommodations allowed my girlfriend and I to take a much needed reset. I highly recommend Villa Sur Mer to those who seek accommodations outside of normal hotel stays on the west end. "
The price is S$305
includes taxes & fees
5 Dec - 6 Dec
Villas Sur Mer
Sand and Blue Seas
Dining

Sand and Blue Seas

3.0 star property
8.0 out of 10, Very good, (106)
"Good customer service! And very Very friendly "
Sand and Blue Seas
Montego Bay Club Apartments
Beach towels

Montego Bay Club Apartments

4.0 star property
7.0 out of 10, Good, (24)
"The building looks ruff but the inside of the apartment is very well kept and updated. The view is amazing and great location. I definitely recommend "
Montego Bay Club Apartments
Beach House Condos Negril
Terrace/patio

Beach House Condos Negril

3.5 star property
9.0 out of 10, Wonderful, (50)
"The property was great the tv program needed updating "
The price is S$321
includes taxes & fees
25 Nov - 26 Nov
Beach House Condos Negril
Solet's Paradise Negril
Beach/ocean view

Solet's Paradise Negril

2.5 star property
9.8 out of 10, Exceptional, (8)
"Solet’s Paradise is very comfortable and a great value stay."
Solet's Paradise Negril
Montego Bay Club Resort
View from property

Montego Bay Club Resort

3.0 star property
4.0 out of 10, (33)
"The property was nothing like the pictures. The receptionist was very friendly. The property itself was not very good. The sliding door to the balcony was broken, the tub didn’t drain and overall it just wasn’t as wxpected."
Montego Bay Club Resort
Monimo Ridge Suites
View from room

Monimo Ridge Suites

3.0 star property
9.2 out of 10, Wonderful, (9)
"The property was nice, hospitality of our agent Yollanda was great, away from the loud noise of the trucks that pass by on the highway my stay was great. I would stay at this cottage again"
The price is S$166
includes taxes & fees
25 Nov - 26 Nov
Monimo Ridge Suites
Idle Awhile Cliffs
View from property

Idle Awhile Cliffs

3.5 star property
9.0 out of 10, Wonderful, (115)
"Extremely beautiful "
The price is S$315
includes taxes & fees
27 Nov - 28 Nov
Idle Awhile Cliffs
Idle Awhile Villas
Outdoor pool

Idle Awhile Villas

4.0 star property
10.0 out of 10, Exceptional, (11)
"The property was beautiful and the service was phenomenal. We had an amazing chef Raquel and butler Ryan. They accommodated our every need and Ryan had a lot of great recommendations for restaurants and activities. Would love to come back!!"
Idle Awhile Villas
Coral Reef Beach Suite At Montego Bay Club Resort
View from property

Coral Reef Beach Suite At Montego Bay Club Resort

2.5 star property
8.0 out of 10, Very good, (1)
"Everything just needs up grading With better managers skill "
Coral Reef Beach Suite At Montego Bay Club Resort
Montego Bay Club Beach Resort
Balcony

Montego Bay Club Beach Resort

3.5 star property
4.0 out of 10, (23)
"Nice location, quiet, lots of shopping, restaurants. Some units need upgrade but if you are the party Type and just want somewhere to crash|sleep this is an ideal spot. Not your 7 star experience. "
The price is S$202
includes taxes & fees
8 Dec - 9 Dec
Montego Bay Club Beach Resort
The Polo Club at Racquet Club
Exterior

The Polo Club at Racquet Club

3.0 star property
The Polo Club at Racquet Club
Wabi-Sabi Villa
Exterior

Wabi-Sabi Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
"I recently had the pleasure of staying at Wabi Sabi Villa in Lucea, Jamaica, and it was truly an exceptional experience. This villa offers everything you could ask for in a private retreat, including a stunning private pool and jacuzzi for guests to enjoy. The all-inclusive package with a personal chef made our stay even more special, as we were treated to delicious meals in the comfort of our own villa. The rooms were beautifully appointed, and any issues we encountered were promptly addressed...
The price is S$1,473
includes taxes & fees
25 Nov - 26 Nov
Wabi-Sabi Villa
Deluxe appartment at Point village
Private beach, white sand

Deluxe appartment at Point village

3.0 star property
9.6 out of 10, Exceptional, (11)
"Very nice complete with cooking are...easher abd dryer.....in a safe and secure gsted communiry...beautiful beach for swimming....."
Deluxe appartment at Point village
Jamaican Loft at Sunshine Village
Exterior

Jamaican Loft at Sunshine Village

3.0 star property
6.4 out of 10, (5)
"It was fine for a place to sleep and had good air con. but the double bed was so small and the futon couch was extremely uncomfortable. I know it just opened up and they replaced the double with a queen the day after we left, so that’s good for future people who stay there. If you want luxury… this is not it!! We were not expecting luxury so it was adequate. The location however was perfect!! "
The price is S$189
includes taxes & fees
23 Dec - 24 Dec
Jamaican Loft at Sunshine Village
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning
Games room

YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning

3.5 star property
6.0 out of 10, (2)
"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...
The price is S$425
includes taxes & fees
25 Nov - 26 Nov
YanceyLargoEstate 2BR Villa w/Mountain Views by RedAwning
Stunning Ocean View
Gazebo

Stunning Ocean View

4.0 star property
10.0 out of 10, Exceptional, (7)
"The view and ambience was pure bliss!"
The price is S$833
includes taxes & fees
25 Nov - 26 Nov
Stunning Ocean View
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.
Don't see what you're looking for?
See all available properties in Middlesex
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Middlesex you may be interested in

SeaGarden Beach Resort - All Inclusive
Private beach nearby, white sand, beach massages, beach bar

SeaGarden Beach Resort - All Inclusive

3.5 star property
7.4 out of 10, Good, (2602)
"Great staff ,good selection of food on the buffets, beautiful private beach. Can walk too many shops and places nearby. Mattress was hard."
The price is S$297
includes taxes & fees
25 Nov - 26 Nov
SeaGarden Beach Resort - All Inclusive
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
On the beach, white sand, beach umbrellas, beach towels

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

4.0 star property
9.4 out of 10, Exceptional, (1765)
"Food experience"
The price is S$605
includes taxes & fees
25 Nov - 26 Nov
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
Aerial view

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

4.5 star property
7.8 out of 10, Good, (1348)
"The staff was exceptionally well. I really appreciate the housekeeping staff member chaundra. My room was 3013 please know she did a excellent service for my wife and I that needs to be recognized also the shuttle drivers to and from our room was awesome and helpful Sahsha was very hospitable to us. We loved her."
The price is S$462
includes taxes & fees
10 Dec - 11 Dec
Grand Palladium Lady Hamilton Resort & Spa All Inclusive
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 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. Tryall Golf Club and Bloody Bay 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.