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Middlesex Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middlesex holiday rentals

2 outdoor pools, free pool cabanas, pool umbrellas

1. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
Sunshine Seashore Escape Jamaica
Beach nearby, beach towels

2. 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 HK$1,062
HK$1,891 total
includes taxes & fees
14 Sept - 15 Sept
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
Exterior

3. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is HK$1,335
HK$2,161 total
includes taxes & fees
17 Aug - 18 Aug
Sunny-shore Hideaway
Interior

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 HK$785
HK$942 total
includes taxes & fees
29 Aug - 30 Aug
Charming 2-bedroom house with WiFi, fitness room in Lucea
Beach

5. 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 HK$392
HK$549 total
includes taxes & fees
24 Aug - 25 Aug
VIVIENNE'S ROOMS #6
Restaurant

6. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"I recommend them and will book agin"
United States
Ainsley
The price is HK$763
HK$847 total
includes taxes & fees
17 Aug - 18 Aug
Sky Beach Rooms
Outdoor pool

7. 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 HK$863
HK$1,216 total
includes taxes & fees
17 Aug - 18 Aug
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Property grounds

8. 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 HK$942
HK$1,185 total
includes taxes & fees
17 Aug - 18 Aug
Beach House Condos Negril
In-room dining

9. Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (14 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 HK$4,190
HK$5,768 total
includes taxes & fees
14 Sept - 15 Sept
Stunning Ocean View
View from room

10. 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 HK$750
HK$871 total
includes taxes & fees
17 Aug - 18 Aug
Claudeville Condo
Interior

11. 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 HK$1,962
HK$4,171 total
includes taxes & fees
17 Aug - 18 Aug
FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!
Terrace/patio

12. 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 HK$1,279
HK$1,836 total
includes taxes & fees
14 Sept - 15 Sept
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.
On the beach, sun-loungers, beach towels

13. 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, (13 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 HK$745
HK$1,389 total
includes taxes & fees
17 Aug - 18 Aug
Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi
Outdoor pool, pool umbrellas, pool loungers

14. 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 HK$1,492
HK$1,873 total
includes taxes & fees
17 Aug - 18 Aug
Idle Awhile Cliffs
Exterior

15. 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 HK$742
HK$1,018 total
includes taxes & fees
17 Aug - 18 Aug
Unity Villa
Front of property

16. Unity Villa

Unity Villa
3.0 star property
Montego Bay
5.0 out of 10, (2 reviews)
"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."
United States
Fashira
The price is HK$510
HK$726 total
includes taxes & fees
17 Aug - 18 Aug
Unity Villa
Balcony

17. 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 HK$937
HK$1,086 total
includes taxes & fees
17 Aug - 18 Aug
Modern Home 10minstobeach, Private Cliff, AC Wifi
On the beach, sun-loungers, beach towels

18. 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 HK$1,412
HK$2,425 total
includes taxes & fees
19 Aug - 20 Aug
Brand New Luxurious Townhouse in Little Bay Country Club Negril
TV, books

19. 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 HK$777
HK$1,789 total
includes taxes & fees
17 Aug - 18 Aug
Beautiful 2-bedroom house with AC in peaceful Savanna la mar
Exterior

20. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is HK$795
HK$922 total
includes taxes & fees
17 Aug - 18 Aug
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
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

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Grand Palladium Lady Hamilton Resort & Spa All Inclusive

8/10 Good
"If you need a beautiful place to stay , Make this your place to go to beautiful beach.Beautiful pool lots of fun"
Samuel 4-night trip
Posted 2 hours ago
Grand Palladium Lady Hamilton Resort & Spa All Inclusive

Find out more about Middlesex

Search for holiday rentals in Middlesex on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex
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Look no further and take a look at our great range of rental properties in Middlesex!

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.