Middlesex Holiday Rentals

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Our top choices for Middlesex holiday rentals

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
The price is NZ$194
includes taxes & fees
12 Apr - 13 Apr
Claudeville Condo

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is NZ$518
includes taxes & fees
2 May - 3 May
Nianna Chatham

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (60 reviews)
"The ocean view and street view from the 4th floor were great. Our morning coffee and breakfast were fantastic on the balcony."
Canada
Dean
The price is NZ$295
includes taxes & fees
22 Apr - 23 Apr
Montego Bay Club Beach Resort

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is NZ$248
includes taxes & fees
7 Apr - 8 Apr
Eleven30 Luxury Apartments

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
10.0 out of 10, Exceptional, (1 review)
"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 NZ$147
includes taxes & fees
11 Apr - 12 Apr
Modern Home 10minstobeach, Private Cliff, AC Wifi

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (58 reviews)
"It was like staying in a 5 star hotel. Was comfortable like home. Rooms were spotless. Beautiful ambiance and clean grounds. Staff was professional and pleasant. "
United States
Tamar
The price is NZ$265
includes taxes & fees
4 May - 5 May
Beach House Condos Negril

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 NZ$740
includes taxes & fees
12 Apr - 13 Apr
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

Negril Beachside

Negril Beachside
2.0 star property
Negril
8.0 out of 10, Very good, (1 review)
The price is NZ$266
includes taxes & fees
22 Apr - 23 Apr
Negril Beachside

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (62 reviews)
"I enjoyed my stay although there was no room service "
United States
Nigeria
The price is NZ$250
includes taxes & fees
19 Apr - 20 Apr
Montego Bay Club Apartments

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is NZ$1,007
includes taxes & fees
7 Apr - 8 Apr
The Shallhome

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 NZ$370
includes taxes & fees
6 Apr - 7 Apr
Idle Awhile Cliffs

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 NZ$227
includes taxes & fees
11 Apr - 12 Apr
Unity Villa

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is NZ$452
includes taxes & fees
19 Apr - 20 Apr
Sunshine Seashore Escape Jamaica

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is NZ$904
includes taxes & fees
10 Apr - 11 Apr
Casia Villa

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is NZ$205
includes taxes & fees
19 Apr - 20 Apr
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is NZ$443
includes taxes & fees
11 Apr - 12 Apr
Sunny-shore Hideaway

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (12 reviews)
"The view and ambience was pure bliss!"
United States
Roxanne
The price is NZ$1,292
includes taxes & fees
7 Apr - 8 Apr
Stunning Ocean View

La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is NZ$1,507
includes taxes & fees
8 Apr - 9 Apr
La Costa Villa

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)
The price is NZ$445
includes taxes & fees
19 Apr - 20 Apr
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (151 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 NZ$344
includes taxes & fees
2 May - 3 May
Villas Sur Mer
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

Find out more about Middlesex

Everything you need to know about Middlesex holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesex holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesex holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesex holiday rentals we have selected for you start as low as NZ$163 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Deluxe appartment at Point village: This holiday home rental outside of Middlesex has air conditioning and free WiFi 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 Kool Runnings Water Park, 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.