Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

Sand and Blue Seas

3.0 star property
Negril
8.2 out of 10, Very good, (132)
"Very close to the 7 miles beach silnet and a good location."
Canada
Zekiye
Sand and Blue Seas

Montego Bay Club Apartments

4.0 star property
Hip Strip
7.4 out of 10, Good, (41)
"I love everything about! My go to spot. In walking distance. "
United States
Monique
The price is NZ$338
includes taxes & fees
1 Dec - 2 Dec
Montego Bay Club Apartments

Villas Sur Mer

4.0 star property
West End
8.8 out of 10, Excellent, (149)
"Love this property. Great staff and the location was great for me. Only thing I would change is the couch in the room wasn't that great. Everything else was wonderful. "
United States
Chelsea
The price is NZ$430
includes taxes & fees
14 Nov - 15 Nov
Villas Sur Mer

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

Idle Awhile Cliffs

3.5 star property
West End
9.0 out of 10, Wonderful, (119)
"Very rustic and secluded loved the feeling of been surrounded by nature, had a peaceful stay. Great staff. Hopeton from the bar very friendly and gives excellent service. "
United States
Richard
Idle Awhile Cliffs

Seascape Apartment

2.5 star property
Negril
7.6 out of 10, Good, (10)
"I have never been so miserable in Negril. After a 13 hour flight, i arrived at the property to a locked gate. I called and called for the owner to let us in. She told us that Hotels.com had made no reservation for me to stay for 3 weeks. Eventually, she found the reservation, allocated us a room but said I'd have to transfer to another room in 4 days because the room was booked to a regular guest ! On day 3, she demanded that i moved to the second room and said that i had to cancel my plans for...
United Kingdom
Julia
Seascape Apartment

Unity Villa

3.0 star property
Montego Bay
8.0 out of 10, Very good, (1)
"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

Beach House Condos Negril

3.5 star property
Negril
9.0 out of 10, Wonderful, (57)
"The staff were very friendly. Excellent service with a smile. A great place for family reunion. "
Canada
Opal
The price is NZ$421
includes taxes & fees
8 Nov - 9 Nov
Beach House Condos Negril

Idle Awhile Villas

4.0 star property
Negril
10.0 out of 10, Exceptional, (15)
"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!!"
United States
Kaitlyn
Idle Awhile Villas

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

Paradise Acres
9.4 out of 10, Exceptional, (39)
"Excellent experience!!"
United States
MOHSIN
The price is NZ$323
includes taxes & fees
14 Nov - 15 Nov
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica

Dalley's Cozy Apartments

3.0 star property
Hip Strip
8.8 out of 10, Excellent, (8)
"The location was great walking distance to everything was easy "
United States
Nerval
Dalley's Cozy Apartments

Vivienne's Guest House #A5 2Bed+ AC+Hot Water+TV+Free Wifi

Green Island
9.6 out of 10, Exceptional, (7)
"Abbiamo trovato molta disorganizzazione. Sembrava avessero perso la nostra prenotazione. Non c'era la cucina ma solo una stanza con i letti e il bagno. Non c'era la prima colazione. Il personale e il proprietario hanno cercato in tutti i modi di rendere il nostro soggiorno piacevole ma per noi è stato tutto molto complicato."
Italy
Francesco
Vivienne's Guest House #A5 2Bed+ AC+Hot Water+TV+Free Wifi

Stunning Ocean View

4.0 star property
Negril
10.0 out of 10, Exceptional, (11)
"We had an amazing time with our family there. When we had any small issues, mr. Brown was very helpful and quick to react! Highly recommended host. The palapa and the ocean view were top notch! The walk to the private beach is short and no bother at all. "
Canada
Marie Eve
The price is NZ$1,142
includes taxes & fees
13 Nov - 14 Nov
Stunning Ocean View

Ocean View Suit-Montego Bay Club Resort

3.5 star property
Hip Strip
Ocean View Suit-Montego Bay Club Resort

Blue Seas Two Unity Hall

3.0 star property
Montego Bay
Blue Seas Two Unity Hall

Luxury villa in Montego Bay Jamaica

3.0 star property
Montego Bay
Luxury villa in Montego Bay Jamaica

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

3.5 star property
Montego Bay
The price is NZ$627
includes taxes & fees
10 Nov - 11 Nov
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

Solet's Paradise Negril

2.5 star property
Negril
9.8 out of 10, Exceptional, (9)
"Solet's Paradise is a litte 'safe haven', the place is safe and secure, the location is near to many shops, dinning and entertainment location. Ms Solets ensure that my friend and i were comfortable."
United States
anessa
Solet's Paradise Negril

Tropical Paradise. Modern 2 Bedroom with Spectacular views of the Caribbean Sea

Montego Bay
9.6 out of 10, Exceptional, (22)
"Loved the property, views, and very spacious home. Enjoyed my stay very much!"
Canada
Deshawna K.
Tropical Paradise. Modern 2 Bedroom with Spectacular views of the Caribbean Sea

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 NZ$285
includes taxes & fees
12 Nov - 13 Nov
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
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$285 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?

Stunning Ocean View: This holiday home rental outside 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. Tryall Golf Club 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.