Middlesex Holiday Rentals

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Our top choices for Middlesex holiday rentals

Idle Awhile Cliffs

Idle Awhile Cliffs
3.5 star property
West End
9.0 out of 10, Wonderful, (119)
"Friendly staff, excellent customer service. Enjoyed the ambience and accommodations. Clean and pleasant."
United States
Nayana
Idle Awhile Cliffs

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)
"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$261
includes taxes & fees
3 Jan - 4 Jan
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc

Hospitality Expert CP: Private Pool/Beach/Chef

Hospitality Expert CP: Private Pool/Beach/Chef
Montego Bay
9.0 out of 10, Wonderful, (11)
"Lovely place"
United States
Thad A.
The price is AU$405
includes taxes & fees
12 Jan - 13 Jan
Hospitality Expert CP: Private Pool/Beach/Chef

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is AU$165
includes taxes & fees
17 Jan - 18 Jan
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27)
"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$120
includes taxes & fees
3 Jan - 4 Jan
Firefly cottage with Ocean view

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Lucea
8.0 out of 10, Very good, (4)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
The price is AU$263
includes taxes & fees
23 Jan - 24 Jan
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (22)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
Claudeville Condo

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)
The price is AU$258
includes taxes & fees
3 Jan - 4 Jan
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Great panoramic views. Beach and shopping close by.

Great panoramic views. Beach and shopping close by.
Montego Bay
10.0 out of 10, Exceptional, (1)
"It was a beautiful home and convenient to the airport. The host was also very responsive and understanding . I appreciate her hospitality and kindness. I would def recommend this place and would stay again."
United States
Shannon S.
The price is AU$167
includes taxes & fees
2 Jan - 3 Jan
Great panoramic views. Beach and shopping close by.

The Artist cabin is a mountain cabin overlooking the sea and coastline

The Artist cabin is a mountain cabin overlooking the sea and coastline
2.0 star property
Cave
10.0 out of 10, Exceptional, (1)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
The price is AU$108
includes taxes & fees
13 Jan - 14 Jan
The Artist cabin is a mountain cabin overlooking the sea and coastline

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

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
2.0 star property
Cave
9.0 out of 10, Wonderful, (2)
"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$122
includes taxes & fees
13 Jan - 14 Jan
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.

PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
Montego Bay
9.8 out of 10, Exceptional, (19)
"Everything was wonderful!! This was our second time staying there and we will definitely stay there whenever we visit Montego Bay!!!"
United States
Alicia W.
The price is AU$242
includes taxes & fees
10 Jan - 11 Jan
PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.

Bak A Yaad Timberland Cottage

Bak A Yaad Timberland Cottage
West End
10.0 out of 10, Exceptional, (3)
"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$263
includes taxes & fees
4 Jan - 5 Jan
Bak A Yaad Timberland Cottage

Sunset Arms 3: 2brm/2wsr, Airport-Beach-Hipstrip

Sunset Arms 3: 2brm/2wsr, Airport-Beach-Hipstrip
Montego Bay
10.0 out of 10, Exceptional, (1)
"My stay at Sunset Arms was amazing. The apartment was just the right amount of space that our family needed. It was clean, well lit and with modern decor. We enjoyed our time there immensely. Ana, our host, was super kind and helpful!"
United States
Nathalee
The price is AU$272
includes taxes & fees
13 Jan - 14 Jan
Sunset Arms 3: 2brm/2wsr, Airport-Beach-Hipstrip

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)
"Troy was very helpful & professional! Neighborhood was nice & house was very nice "
United States
Shemeka M.
The price is AU$269
includes taxes & fees
19 Jan - 20 Jan
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
10.0 out of 10, Exceptional, (3)
"We stayed here for 10 days and absolutely loved it. The bedroom is so perfect and our host (Bonnie) let us use the kitchen and whatever we needed anytime. The porch is lovely with a gorgeous ocean view. This was the perfect spot for our vacation!!! "
United States
Roger Y.
The price is AU$205
includes taxes & fees
11 Jan - 12 Jan
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7)
"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$127
includes taxes & fees
2 Jan - 3 Jan
Dragon fly Cottage

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is AU$122
includes taxes & fees
7 Jan - 8 Jan
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Negril Beach Condo - Jamaica - Hotel Room, no kitchen, Unit 3

Negril Beach Condo - Jamaica - Hotel Room, no kitchen, Unit 3
Negril
10.0 out of 10, Exceptional, (7)
"Jean was an awesome host."
Canada
Tammy
The price is AU$233
includes taxes & fees
3 Jan - 4 Jan
Negril Beach Condo - Jamaica - Hotel Room, no kitchen, Unit 3

Quiet relaxing mountainous get away!

Quiet relaxing mountainous get away!
Montego Bay
9.2 out of 10, Wonderful, (5)
"The location was gorgeous, not far from the city. Easy/beautiful walk to cabs. Host was great and the bed/sheets felt great!!"
United States
Kintoria W.
The price is AU$127
includes taxes & fees
3 Jan - 4 Jan
Quiet relaxing mountainous get away!
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$139 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?

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL: This holiday home rental outside of Middlesex has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, an oven and a microwave.

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.