Middlesex Holiday Rentals

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Our top choices for Middlesex holiday rentals

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is AU$166
includes taxes & fees
16 Feb - 17 Feb
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Montego Bay
10.0 out of 10, Exceptional, (63 reviews)
"Such a nice stay at windfall Villas, Mel was great and always able to get us to anywhere at almost anytime we needed. It was beautiful and peaceful at the property. Would highly recommend to anyone checking out Montego Bay. Think twice begore trying drive here. In my opinion this is one dangerous place to drive unless you’ve driven here before. Mel made this part of our trip completely safe. "
United States
Jeff B.
The price is AU$468
includes taxes & fees
19 Feb - 20 Feb
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is AU$114
includes taxes & fees
16 Feb - 17 Feb
Firefly cottage with Ocean view

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is AU$289
includes taxes & fees
16 Feb - 17 Feb
Nianna Chatham

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
Unity Villa

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
Wabi-Sabi Villa

Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc

Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
Lucea
10.0 out of 10, Exceptional, (1 review)
"We fully enjoyed our stay. On arrival we had a few issues mainly because we arrived early and had some missed communication with Nadia. She promptly helped us resolve a few minor issues and the rest of our stay was literally a breeze, as in wonderful sea breezes! The accommodations were just as described, it felt safe and comfortable."
United States
Noel B.
The price is AU$287
includes taxes & fees
22 Feb - 23 Feb
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc

Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR

Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR
Hanover, Parish
The price is AU$290
includes taxes & fees
19 Feb - 20 Feb
Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR

Tranquil Park

Tranquil Park
Orange Bay
The price is AU$132
includes taxes & fees
16 Feb - 17 Feb
Tranquil Park

Hospitality Expert Seawind - Pool, Beach, Chef

Hospitality Expert Seawind - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"Nice place and breakfast"
Spain
Xavier
The price is AU$357
includes taxes & fees
23 Feb - 24 Feb
Hospitality Expert Seawind - Pool, Beach, Chef

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
Eleven30 Luxury Apartments

Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.

Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
roundhill
9.8 out of 10, Exceptional, (20 reviews)
"This trip was planned for our daughter's 21st birthday, so we wanted to make sure it was memorable for her. Mel communicated and responded quickly to me prior to our trip which made everything so much easier. Mel met us at the airport, took us to the store to grab provisions before heading to the villa. He was friendly and made us feel welcome immediately. Once we arrived at the villa, we were in paradise, the pictures and description were spot on and didn't disappoint. The view was nothing...
United States
Sarah H.
The price is AU$468
includes taxes & fees
19 Feb - 20 Feb
Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.

1 Bedroom Ocean view Apartment, The Lagoons

1 Bedroom Ocean view Apartment, The Lagoons
Montego Bay
7.6 out of 10, Good, (7 reviews)
"Places is nice view is good"
United States
Thomas G.
The price is AU$263
includes taxes & fees
16 Feb - 17 Feb
1 Bedroom Ocean view Apartment, The Lagoons

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is AU$731
includes taxes & fees
16 Feb - 17 Feb
Casia Villa

Bak A Yaad Timberland Cottage

Bak A Yaad Timberland Cottage
West End
10.0 out of 10, Exceptional, (3 reviews)
"My family and I stayed for 2 days and it was unforgettable! The place was clean and tidy! Jordan (host) offered great recommendations for restaurants nearby- many within walking distance. Rick’s cafe across the street with amazing views! We had a great time and can’t wait to be back "
United States
Bridgette A.
The price is AU$241
includes taxes & fees
18 Feb - 19 Feb
Bak A Yaad Timberland Cottage

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is AU$814
includes taxes & fees
16 Feb - 17 Feb
The Shallhome

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
The price is AU$120
includes taxes & fees
16 Feb - 17 Feb
Dragon fly Cottage

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is AU$116
includes taxes & fees
16 Feb - 17 Feb
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
The price is AU$136
includes taxes & fees
24 Feb - 25 Feb
Modern Home 10minstobeach, Private Cliff, AC Wifi

Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica

Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica
Paradise Acres
9.4 out of 10, Exceptional, (39 reviews)
"Troy was very helpful & professional! Neighborhood was nice & house was very nice "
United States
Shemeka M.
The price is AU$233
includes taxes & fees
17 Mar - 18 Mar
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica
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 favourite 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 depend 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 AU$131 per night. Entering your travel dates in the search wizard might find you 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?

Stunning Ocean View: This holiday home rental outside of Middlesex is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a terrace and a private garden.

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.