Middlesex Holiday Rentals

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Holiday Rentals in Middlesex

Our top choices for Middlesex holiday rentals

Sand and Blue Seas

3.0 star property
8.2 out of 10, Very good, (127)
"They were so friendly and hospitable. "
Sand and Blue Seas

Villas Sur Mer

4.0 star property
8.8 out of 10, Excellent, (149)
"Amazing as always!!! "
Villas Sur Mer

Idle Awhile Cliffs

3.5 star property
9.0 out of 10, Wonderful, (119)
"We adored this “rustic” property with its early morning birdsong, simple clean (very clean!) rooms and lovely pool overlooking the ocean. Delicious breakfast poolside or on our terrace. Courteous and kind staff. Highly recommend!"
Idle Awhile Cliffs

Montego Bay Club Apartments

4.0 star property
7.2 out of 10, Good, (37)
"I enjoyed my stay, the location was great."
Montego Bay Club Apartments

Dalley's Cozy Apartments

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

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

10.0 out of 10, Exceptional, (63)
"Staying at Windfall villas was a fantastic experience. The property was impeccably clean and well maintained with a beautiful and well manicured lawn with an amazing ocean view, great for taking pictures. The location was ideal, in a safe and close to most things and places we needed to visit. The Villa was spacious and well-equipped with everything we needed for a comfortable stay, including a coffee maker, a blender, a well stocked kitchen, toiletries and most of the basic items that we...
The price is NZ$624
includes taxes & fees
6 Oct - 7 Oct
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.

9.2 out of 10, Wonderful, (17)
"We love everything about this place. "
The price is NZ$388
includes taxes & fees
23 Oct - 24 Oct
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.

Beach House Condos Negril

3.5 star property
9.0 out of 10, Wonderful, (56)
"Pro: separate AC in all rooms. Fully equipped kitchen. Clean. Approachable and helpful staff. Con: no toiletries. Tiny private beach with only four dry grass beach umbrellas. "
The price is NZ$257
includes taxes & fees
25 Sept - 26 Sept
Beach House Condos Negril

Unity Villa

3.0 star property
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 "
Unity Villa

Monimo Ridge Suites

3.0 star property
8.6 out of 10, Excellent, (19)
"Was comfortable and safe "
Monimo Ridge Suites

MoBay Life

2.5 star property
4.0 out of 10, (2)
"The property is in a great location to be able to walk into the town, harmony park beach, and the hip strip. That was the only plus "
MoBay Life

Waterfront Villa Private Pool Floating Breakfast Inc. Fully Staffed Chef Avaible

10.0 out of 10, Exceptional, (44)
"Mr Ralph was an amazing host! Our flight got canceled due to the Heathrow chaos and he was so patient and kind, making sure we could reschedule. The villa is absolutely stunning and the staff made our trip unforgettable.The chefs spoiled us with incredible Jamaican food, and they went all out for my mum’s birthday….decorations, a floating breakfast, the works! Couldn’t have asked for a better experience. Highly recommend!"
Waterfront Villa Private Pool Floating Breakfast Inc. Fully Staffed Chef Avaible

Unity Villa

3.0 star property
8.0 out of 10, Very good, (1)
"I like that the property was quiet. The place was clean. The neighbor I met was really nice. I like that. It was outside of the tourist area."
The price is NZ$158
includes taxes & fees
5 Oct - 6 Oct
Unity Villa

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

9.4 out of 10, Exceptional, (39)
"Troy was very helpful & professional! Neighborhood was nice & house was very nice "
The price is NZ$303
includes taxes & fees
6 Oct - 7 Oct
Come relax and unwind and enjoy a piece of Paradise in montego Bay Jamaica

Montego Bay Club Beach Resort

3.5 star property
4.4 out of 10, (40)
"Good location and Great view of the Caribbean Sea"
Montego Bay Club Beach Resort

Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica

10.0 out of 10, Exceptional, (32)
"Property was great. Staff was extremely helpful and nice. Great house, great location. Would highly recommend to anyone wanting to relax and enjoy"
Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica

Private Luxury Beachfront/Oceanfront Townhome in Beautiful Negril, Jamaica

10.0 out of 10, Exceptional, (57)
"This property was clean,had everything you need for a perfect vacation.The host Anna was excellent and able to be reached if needed.The beach and pool were very clean and easily accessible with a short walk. Thank you for a great vacation."
Private Luxury Beachfront/Oceanfront Townhome in Beautiful Negril, Jamaica

Ocean View Suit-Montego Bay Club Resort

3.5 star property
Ocean View Suit-Montego Bay Club Resort

Solet's Paradise Negril

2.5 star property
9.8 out of 10, Exceptional, (9)
"Great little gem in Negril.If you are looking for a nice relaxing place away from the hustle and bustle, this is the place. Rooms are beautiful and the staff was awesome. would absolutely stay again. Dave"
Solet's Paradise Negril

Stunning Ocean View

4.0 star property
10.0 out of 10, Exceptional, (11)
"The view and ambience was pure bliss!"
The price is NZ$1,103
includes taxes & fees
3 Oct - 4 Oct
Stunning Ocean View
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

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$158 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. Half Moon Beach and Tryall Golf Club 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.