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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Middlesex vacation rentals

A beachside view with a wooden deck, a thatched umbrella, and a hammock.

1. Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
8.6 out of 10, Excellent, (7 reviews)
"Clean room and the staff were efficient and family friendly, the location was absolutely ideal."
United States
Clayton
The price is ￥15,154
￥16,827 total
includes taxes & fees
Nov 10 - Nov 11
Sky Beach Rooms
A dining area with a wooden table and chairs, a fruit bowl, and a view of the ocean through large glass doors.

2. 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 ￥84,186
￥115,891 total
includes taxes & fees
Nov 2 - Nov 3
Stunning Ocean View
A modern outdoor pool area with lounge chairs, a hot tub, and a fireplace.

3. Wabi-Sabi Villa

Wabi-Sabi Villa
5.0 star property
Lucea
10.0 out of 10, Exceptional, (2 reviews)
"This property had amazing staff and the place was beautiful. I absolutely loved them! "
United States
Andrea
The price is ￥122,455
￥156,747 total
includes taxes & fees
Nov 16 - Nov 17
Wabi-Sabi Villa
A modern hotel room with a large bed, a mirror, a wall-mounted air conditioner, and a ceiling light fixture.

4. 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
9.8 out of 10, Exceptional, (16 reviews)
"The staff was friendly, the room extremely clean, nice amenities. i will be back"
United States
Melinda
The price is ￥14,978
￥27,591 total
includes taxes & fees
Nov 18 - Nov 19
Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi
A lush garden with a swimming pool, surrounded by dense foliage and tropical plants.

5. Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.6 out of 10, Excellent, (155 reviews)
"Carmen was very accommodating during my stay at the villa. The upgraded room was beautiful. The amenities and proximity to other restaurants in walking distance was a great."
United States
Nadine
The price is ￥27,669
￥30,594 total
includes taxes & fees
Nov 15 - Nov 16
Villas Sur Mer
A spacious living area with a dining table, wicker chairs, a large potted plant, and a vase with flowers.

6. Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is ￥22,348
￥37,683 total
includes taxes & fees
Oct 31 - Nov 1
Sunshine Seashore Escape Jamaica
A beach with thatched umbrellas, a white building, and pink flowers.

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 ￥18,919
￥23,806 total
includes taxes & fees
Oct 31 - Nov 1
Beach House Condos Negril
A poolside area with lounge chairs, a pergola, and a sign indicating lifeguard on duty.

8. 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 ￥18,915
￥34,677 total
includes taxes & fees
Nov 4 - Nov 5
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
A residential street with palm trees and a well-maintained lawn.

9. VIVIENNE'S ROOMS #6

VIVIENNE'S ROOMS #6
Green Island
9.6 out of 10, Exceptional, (8 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 ￥7,883
￥11,036 total
includes taxes & fees
Nov 1 - Nov 2
VIVIENNE'S ROOMS #6
A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

10. 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 ￥14,899
￥20,444 total
includes taxes & fees
Nov 3 - Nov 4
Unity Villa
Two white chairs and a table under a green structure with a sign that reads "LIVE LAUGH LIVE".

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 ￥47,929
￥54,551 total
includes taxes & fees
Nov 2 - Nov 3
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
A wooden bench with a red cushion, a small table, and a stone wall overlooking the sea.

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, (25 reviews)
"Great location. Beautiful view from the backyard and the house was very nice. Will absolutely come back in the future."
United States
Nathanael
The price is ￥29,798
￥42,411 total
includes taxes & fees
Nov 7 - Nov 8
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.
A pool with a view of the ocean, surrounded by lounge chairs and umbrellas.

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 ￥47,929
￥54,551 total
includes taxes & fees
Nov 2 - Nov 3
Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
A swimming pool with a waterfall feature, surrounded by a brick patio and a white fence.

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

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
9.0 out of 10, Wonderful, (7 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 ￥18,919
￥26,014 total
includes taxes & fees
Nov 5 - Nov 6
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Dining room

15. Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ￥23,896
￥39,608 total
includes taxes & fees
Nov 6 - Nov 7
Sunny-shore Hideaway
A swimming pool with a hot tub, surrounded by palm trees and a white building.

16. Turquoise Sea Villa

Turquoise Sea Villa
3.5 star property
Montego Bay
The price is ￥23,790
￥43,283 total
includes taxes & fees
Oct 31 - Nov 1
Turquoise Sea Villa
A pool area with lounge chairs and an umbrella, surrounded by palm trees and a view of the ocean.

17. 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 ￥28,379
￥48,717 total
includes taxes & fees
Nov 3 - Nov 4
Brand New Luxurious Townhouse in Little Bay Country Club Negril
A resort with a white building featuring balconies, surrounded by lush greenery and palm trees.

18. Negril Beach Condo - Jamaica - Hotel Room, no Kitchen, Unit 2

Negril Beach Condo - Jamaica - Hotel Room, no Kitchen, Unit 2
Negril
8.0 out of 10, Very good, (4 reviews)
"My stay was excellent, very hospitable, friendly, and have no problem conversing. I will be back many times, I hope."
United States
Jeffrey M.
The price is ￥12,770
￥17,200 total
includes taxes & fees
Oct 31 - Nov 1
Negril Beach Condo - Jamaica - Hotel Room, no Kitchen, Unit 2
A staircase with stone steps and metal railings, leading upwards.

19. RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ￥14,367
￥16,680 total
includes taxes & fees
Nov 1 - Nov 2
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
A gated entrance with a number '81' on the wall, surrounded by greenery.

20. Serene 2-bedroom building in welcoming Hopewell neighborhood

Serene 2-bedroom building in welcoming Hopewell neighborhood
Hopewell
The price is ￥42,568
￥51,397 total
includes taxes & fees
Oct 31 - Nov 1
Serene 2-bedroom building in welcoming Hopewell neighborhood
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

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent
"Nice"
Rafiu 4-night trip
Posted 9 hours ago
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

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:

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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 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.