Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

Turquoise Sea Villa

3.5 star property
Montego Bay
The price is AU$320
includes taxes & fees
18 Nov - 19 Nov
Turquoise Sea Villa

Firefly cottage with Ocean view

Cave District
10.0 out of 10, Exceptional, (27)
"Incredible views from the cottage. Tropical flowers perfume the mountain air. Great bird watching and snorkeling. Sean and Geneva are great hosts. We loved interacting with their boys and cooking meals in their traditional outdoor kitchen. Geneva is a great cook, we recommend trying it out. We are glad we rented a 4 wheel drive vehicle to get to the small community of Kentucky in the Jamaican Highlands. It is a 30 minute drive to the beach at Bluefields. We rented a double kayak from Luna Sea...
United States
Mike C.
The price is AU$123
includes taxes & fees
18 Nov - 19 Nov
Firefly cottage with Ocean view

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$110
includes taxes & fees
18 Nov - 19 Nov
The Artist cabin is a mountain cabin 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)
"Ein ganz tolles Erlebnis. Sehr nette Gastgeber Familie. Traumhaftes Grundstück, schöner Ausblick. Ein mega Abenteuer. Man kommt gut zurecht mit dem was man hat. Man kann unglaublich viele Tiere und Pflanzen/Blumen etc. sehen und beobachten. Ausstattung reicht aus. Wenn was fehlt hilft der Gastgeber immer weiter. 2 Wochen pure Erholung. Unser Sohn wurde von den Kindern toll mit integriert und hatte mega Spaß und viel zu entdecken. Unsere Gastgeberin hat sehr leckeres Essen gekocht. Würden wir...
Germany
Nicole B.
The price is AU$125
includes taxes & fees
18 Nov - 19 Nov
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

4.0 star property
Negril
The price is AU$177
includes taxes & fees
18 Dec - 19 Dec
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Dragon fly Cottage

Cave
10.0 out of 10, Exceptional, (7)
"Our absolute favorite part of being in Jamacia was staying in the Dragon Fly Cottage hosted by Geneva and her husband Shawn and their three sons. Everyday Geneva would cook a fantastic breakfast and dinner, served hot and after the meal would take the dirty dishes away. Right off our deck was avocados, jackfruit, all spice, papaya as well as a mango tree just down the path. The view was amazing. The rain on the tin roof, the treefrogs singing, the multiple hummingbirds and geckos made every day...
Canada
John H.
The price is AU$130
includes taxes & fees
18 Nov - 19 Nov
Dragon fly Cottage

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$125
includes taxes & fees
25 Nov - 26 Nov
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

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$269
includes taxes & fees
18 Nov - 19 Nov
Bak A Yaad Timberland Cottage

Monimo Ridge Suites

3.0 star property
Montego Bay
8.6 out of 10, Excellent, (20)
"The property is well kept, great hospitality. I felt safe and at peace while staying at the property. This is my second time staying there. I recommend staying at this property to anyone to wishes to have peace of mind. "
United States
Dianna
Monimo Ridge Suites

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Hopewell
10.0 out of 10, Exceptional, (3)
"Wanna forgo the resort and truly experience Jamaica instead? I have to suggest that you stay at Bonnie's. The place is perfect for someone like myself who loves to travel without a crowd. Imagine waking up to the sea view someplace that feels more like home. Imagine floating in the pool with a view of the stars without dozens of tourists around. Have you caught my drift? If you would like an authentic experience of Jamaican culture, you should try something different. Old Steamer Beach isn't far...
United States
ASpecial T.
The price is AU$210
includes taxes & fees
13 Dec - 14 Dec
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

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$246
includes taxes & fees
18 Nov - 19 Nov
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Wabi-Sabi Villa

5.0 star property
Lucea
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...
United States
Princess
Wabi-Sabi Villa

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

Negril
10.0 out of 10, Exceptional, (7)
"A nice property, close to town and the supermarket. Jean was very accommodating with a few of our requests. Wifi is spotty but could be found if needed."
United States
Lynn J.
The price is AU$176
includes taxes & fees
19 Nov - 20 Nov
Negril Beach Condo - Jamaica - Hotel Room, no kitchen, Unit 3

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

Lucea
8.0 out of 10, Very good, (4)
"Host was very nice and always there for support on the booking and assisting true the entree. Cleanness is a bit lacking. Overall it was a nice place."
Canada
Isabelle-Zaza D.
The price is AU$263
includes taxes & fees
1 Dec - 2 Dec
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.

Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi

Negril
10.0 out of 10, Exceptional, (11)
"close proximity for an early check in at hedo "
United States
Alicia C.
The price is AU$234
includes taxes & fees
18 Nov - 19 Nov
Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi

Quiet relaxing mountainous get away!

Montego Bay
9.2 out of 10, Wonderful, (5)
"Nice plave to stay, quite and clean. You will need a car cause location is not close to town and travel isn’t easy. Must have Netflix downloaded on your phone to be able to look at television in your room. Unit did have wifi, worked good. "
United States
Cail B.
The price is AU$130
includes taxes & fees
18 Nov - 19 Nov
Quiet relaxing mountainous get away!

Oceanpointe Villa, Brand new, Clean, Cottage with all the resort amenities.

Lucea
The price is AU$569
includes taxes & fees
19 Nov - 20 Nov
Oceanpointe Villa, Brand new, Clean, Cottage with all the resort amenities.

Brand New Luxurious Townhouse in Little Bay Country Club Negril

Negril
9.4 out of 10, Exceptional, (6)
"Everything about the 4 day stay at this rental property was great! I wanted to stay at a property that was close to a beach, close to Margaritaville, Rick's Cafe and the local Negril restaurants. This property checked all those boxes. (It actually has a private beach within the gated community). The home itself was high quality. It has new appliances in the kitchen, comfortable couches in the living room and comfortable mattresses in the bedrooms. The patio furniture was pretty comfortable...
United States
reggie p.
The price is AU$470
includes taxes & fees
18 Nov - 19 Nov
Brand New Luxurious Townhouse in Little Bay Country Club Negril

Tranquil Park

Orange Bay
The price is AU$143
includes taxes & fees
18 Nov - 19 Nov
Tranquil Park

Muris Light Sanctuary

Savanalamar
10.0 out of 10, Exceptional, (1)
"Host was attentive and super nice to deal with. Great stay. No air conditioning but was pleaaant regardless. "
Canada
Leeann D.
The price is AU$206
includes taxes & fees
18 Nov - 19 Nov
Muris Light Sanctuary
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$177 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.