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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Middlesex vacation rentals

2 outdoor pools, free cabanas, pool umbrellas

1. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is SAR 532
SAR 897 total
includes taxes & fees
1 Sep - 2 Sep
Sunshine Seashore Escape Jamaica
Beach nearby, beach towels

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

The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Lucea
8.0 out of 10, Very Good, (6 reviews)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
The price is SAR 482
SAR 758 total
includes taxes & fees
10 Aug - 11 Aug
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Beach nearby, beach towels

3. 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 SAR 455
SAR 830 total
includes taxes & fees
9 Aug - 10 Aug
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
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 SAR 375
SAR 451 total
includes taxes & fees
10 Aug - 11 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 SAR 188
SAR 263 total
includes taxes & fees
24 Aug - 25 Aug
VIVIENNE'S ROOMS #6
House, 3 Bedrooms, Smoking, Patio | Exterior

6. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is SAR 631
SAR 1,023 total
includes taxes & fees
23 Aug - 24 Aug
Sunny-shore Hideaway
Restaurant

7. 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 SAR 342
SAR 380 total
includes taxes & fees
13 Aug - 14 Aug
Sky Beach Rooms
Outdoor pool

8. 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 SAR 413
SAR 582 total
includes taxes & fees
8 Aug - 9 Aug
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Interior

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 SAR 939
SAR 1,996 total
includes taxes & fees
6 Sep - 7 Sep
FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!
On the beach, sun loungers, beach towels

10. 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 SAR 676
SAR 1,164 total
includes taxes & fees
10 Aug - 11 Aug
Brand New Luxurious Townhouse in Little Bay Country Club Negril
Outdoor dining

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

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Montego Bay
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful view from the hills of Mobay! We enjoyed swimming in the pool and listening to nature in the evening. Mel was a great host and drove us into town for lunch and shopping. Outdoor covered seating was nice for midday shade and bedroom air conditioning made for very comfortable sleeping. "
United States
Amber P.
The price is SAR 1,141
SAR 1,303 total
includes taxes & fees
11 Aug - 12 Aug
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

12. 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 SAR 2,005
SAR 2,760 total
includes taxes & fees
17 Aug - 18 Aug
Stunning Ocean View
Pool

13. Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.

Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
roundhill
9.8 out of 10, Exceptional, (20 reviews)
"I enjoyed my time here. It truly felt like it was my home. Mel made every effort to ensure that we were comfortable. I felt safe. The pool was refreshing."
United States
Yolande W.
The price is SAR 1,141
SAR 1,303 total
includes taxes & fees
10 Aug - 11 Aug
Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
Front of property

14. 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 SAR 244
SAR 347 total
includes taxes & fees
8 Aug - 9 Aug
Unity Villa
Terrace/patio

15. 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 SAR 668
SAR 931 total
includes taxes & fees
2 Sep - 3 Sep
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.
House, 2 Bedrooms, Smoking, Balcony | Balcony

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 SAR 378
SAR 438 total
includes taxes & fees
9 Aug - 10 Aug
Modern Home 10minstobeach, Private Cliff, AC Wifi
Property grounds

17. Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (63 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is SAR 451
SAR 567 total
includes taxes & fees
12 Aug - 13 Aug
Beach House Condos Negril
Outdoor pool, sun loungers

18. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is SAR 561
SAR 1,024 total
includes taxes & fees
11 Aug - 12 Aug
Turquoise Sea Villa
On the beach, sun loungers, beach towels

19. 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 SAR 357
SAR 657 total
includes taxes & fees
4 Sep - 5 Sep
Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi
Terrace/patio

20. Seaside Escape

Seaside Escape
Montego Bay
The price is SAR 389
SAR 501 total
includes taxes & fees
6 Sep - 7 Sep
Seaside Escape
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

Toby's Resort

Toby's Resort

10/10 Excellent
"The staff were always welcoming and very helpful.... I'd checked out and checked back in with ease. I was helped with my luggage and connecting to the WiFi. The receptionists are all nice, the handymen as well as thean who is always at the bar. I find that the food was a bit expensive."
Sophia 3-night trip
Posted 4 hours ago
Toby's Resort

Frequently asked questions

Can I find vacation rentals in Middlesex?

Yes, we have vacation rentals near popular local attractions in Middlesex, or you can choose a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals that Middlesex has to offer?

5 bed villa, gated community, private pool, fully staffed, private chauffeur: Visitors like this Middlesex vacation home rental. It is located next to a golf course and has an outdoor pool, a balcony, and a barbecue grill 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 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 larger area.

What are vacation rentals like in Middlesex?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Middlesex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.