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Middlesex Holiday Rentals

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Our top choices for Middlesex holiday rentals

1. 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 NZ$372
includes taxes & fees
24 Aug - 25 Aug
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc

2. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.0 out of 10, Very good, (4 reviews)
"I recommend them and will book agin"
United States
Ainsley
The price is NZ$181
includes taxes & fees
24 Aug - 25 Aug
Sky Beach Rooms

3. VIVIENNE'S ROOMS #6

VIVIENNE'S ROOMS #6
Green Island
9.6 out of 10, Exceptional, (7 reviews)
"As Green Island starts to become more popular due to the Princess Hotel this remains the gem in the area. Tucked away, peaceful, serene. "
United States
Ixchel L.
The price is NZ$117
includes taxes & fees
24 Aug - 25 Aug
VIVIENNE'S ROOMS #6

4. Charming 2-bedroom house with WiFi, fitness room in Lucea

Charming 2-bedroom house with WiFi, fitness room in Lucea
Lucea
The price is NZ$201
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom house with WiFi, fitness room in Lucea

5. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is NZ$453
includes taxes & fees
6 Sept - 7 Sept
Sunny-shore Hideaway

6. Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
8.8 out of 10, Excellent, (6 reviews)
"Bonnie was amazing and goes over and beyond to make you feel at home. She is very friendly but gives you your space and privacy I really enjoyed her house with the amazing view and her pool. "
United States
Roberta M.
The price is NZ$259
includes taxes & fees
24 Aug - 25 Aug
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

7. Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (64 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is NZ$253
includes taxes & fees
25 Aug - 26 Aug
Beach House Condos Negril

8. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is NZ$171
includes taxes & fees
31 Aug - 1 Sept
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

9. FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!

FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!
Sandy Bay
The price is NZ$881
includes taxes & fees
24 Aug - 25 Aug
FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!

10. Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (15 reviews)
"Clean and beautiful scenery! Needed assistance after hours and the manager responded quickly to my questions and concerns. Would book again"
United States
Willie
The price is NZ$1,230
includes taxes & fees
25 Aug - 26 Aug
Stunning Ocean View

11. Brand New Luxurious Townhouse in Little Bay Country Club Negril

Brand New Luxurious Townhouse in Little Bay Country Club Negril
Negril
9.6 out of 10, Exceptional, (7 reviews)
"Andrea was vet accommodating and understanding. Our travel plans got delayed many times due to flights and she was always quick to respond to messages and offer assistance. "
Canada
andrea m.
The price is NZ$504
includes taxes & fees
26 Aug - 27 Aug
Brand New Luxurious Townhouse in Little Bay Country Club Negril

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

Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi
Negril
10.0 out of 10, Exceptional, (14 reviews)
"Everything was great at the place and the owner contacted back very soon after we messaged her."
United States
mark K.
The price is NZ$293
includes taxes & fees
24 Aug - 25 Aug
Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi

13. Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.

Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.
Hanover Parish
9.2 out of 10, Wonderful, (23 reviews)
"Location was fantastic! Short walk to the beach & pool. The condo was clean with great amenities. There were some issues at the condo, but they were taken care of by the host immediately. Would gladly stay again in the future. "
United States
Andrew J.
The price is NZ$395
includes taxes & fees
14 Sept - 15 Sept
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.

14. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is NZ$318
includes taxes & fees
24 Aug - 25 Aug
Turquoise Sea Villa

15. Idle Awhile Cliffs

Idle Awhile Cliffs
4.0 star property
West End
9.0 out of 10, Wonderful, (124 reviews)
"Beautiful property in the woods. Very quiet, friendly staff."
United States
Mazie Kaylia Horace
The price is NZ$399
includes taxes & fees
26 Aug - 27 Aug
Idle Awhile Cliffs

16. Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
8.0 out of 10, Very good, (3 reviews)
"Great atmosphere and awesome service. Clean and spacious apartment with a modern touch. Definitely looking forward to a future stay"
United States
Shantel
The price is NZ$228
includes taxes & fees
23 Sept - 24 Sept
Modern Home 10minstobeach, Private Cliff, AC Wifi

17. Beautiful 2-bedroom house with AC in peaceful Savanna la mar

Beautiful 2-bedroom house with AC in peaceful Savanna la mar
Savanna la mar
10.0 out of 10, Exceptional, (1 review)
"From the moment I arrived, the property felt very secure, which immediately gave me peace of mind. The space itself was warm, cozy, and inviting it really felt like a home away from home rather than just a place to sleep.The amenities were exactly as advertised and on point. Everything I needed for a comfortable stay was readily available, and the overall setup made it easy to settle in and relax.One of the standout parts of the stay was the communication with the host, Latoya She was excellent,...
United States
Chris R.
The price is NZ$375
includes taxes & fees
25 Aug - 26 Aug
Beautiful 2-bedroom house with AC in peaceful Savanna la mar

18. Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (27 reviews)
"The property was very close to the airport. Bed is comfortable. Only thing is I would av appreciated a kitchen curtain. Apart from that it was great and I love the host she is sweet"
United States
Devine
The price is NZ$186
includes taxes & fees
24 Aug - 25 Aug
Claudeville Condo

19. 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
The price is NZ$217
includes taxes & fees
24 Aug - 25 Aug
Unity Villa

20. Hospitality Expert SWF104 - Pool, Beach, Chef

Hospitality Expert SWF104 - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
The price is NZ$350
includes taxes & fees
20 Sept - 21 Sept
Hospitality Expert SWF104 - Pool, Beach, Chef
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlesex holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlesex. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middlesex. Seeing all the best attractions is bound to make you fall in love with Middlesex. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middlesex short-term rentals, that won’t be hard to do.

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?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: This holiday home rental outside of Middlesex is located next to a golf course, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Middlesex?

Explore the area and family-friendly sights such as Hope Botanical Garden and Zoo, 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.