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Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Middlesex vacation rentals

2 outdoor pools, free cabanas, pool umbrellas

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is ￥23,225
￥39,162 total
includes taxes & fees
Jul 31 - Aug 1
Sunshine Seashore Escape Jamaica
Beach nearby, beach towels

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 ￥20,942
￥33,042 total
includes taxes & fees
Jul 26 - Jul 27
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Beach nearby, beach towels

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 ￥19,636
￥35,781 total
includes taxes & fees
Aug 5 - Aug 6
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
Beach

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 ￥8,193
￥11,470 total
includes taxes & fees
Jul 26 - Jul 27
VIVIENNE'S ROOMS #6
Interior

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

Charming 2-bedroom house with WiFi, fitness room in Lucea
Lucea
The price is ￥16,385
￥19,662 total
includes taxes & fees
Jul 26 - Jul 27
Charming 2-bedroom house with WiFi, fitness room in Lucea
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

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 ￥87,480
￥120,426 total
includes taxes & fees
Jul 28 - Jul 29
Stunning Ocean View
House, 3 Bedrooms, Smoking, Patio | Exterior

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is ￥26,552
￥43,383 total
includes taxes & fees
Aug 24 - Aug 25
Sunny-shore Hideaway
Property grounds

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (62 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
The price is ￥19,662
￥24,741 total
includes taxes & fees
Jul 26 - Jul 27
Beach House Condos Negril
Terrace/patio

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 ￥30,968
￥44,240 total
includes taxes & fees
Aug 23 - Aug 24
Negril Bungalow Paradise overlooking cliffs with Private Snorkeling Entrance.
Interior

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 ￥40,958
￥84,783 total
includes taxes & fees
Aug 22 - Aug 23
FREE AIRPORT PICKUP AND DROP OFF FOR UP TO 6 PEOPLE!
Premium Cottage, 1 Queen Bed, Pool View | Balcony view

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.6 out of 10, Excellent, (155 reviews)
"We did not use the hot tub put the pool area including the hot tub looked very relaxing. Located in a beautiful garden area "
Canada
Faye
The price is ￥30,104
￥33,278 total
includes taxes & fees
Jul 30 - Jul 31
Villas Sur Mer
On the beach, sun loungers, beach towels

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 ￥29,493
￥50,466 total
includes taxes & fees
Jul 26 - Jul 27
Brand New Luxurious Townhouse in Little Bay Country Club Negril
Restaurant

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
The price is ￥16,103
￥17,878 total
includes taxes & fees
Aug 9 - Aug 10
Sky Beach Rooms
Outdoor pool

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, (5 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 ￥18,021
￥25,393 total
includes taxes & fees
Aug 22 - Aug 23
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Basic Loft | View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.8 out of 10, Excellent, (27 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
The price is ￥15,666
￥18,180 total
includes taxes & fees
Jul 29 - Jul 30
Claudeville Condo
Outdoor dining

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 ￥49,810
￥57,019 total
includes taxes & fees
Jul 27 - Jul 28
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (90 reviews)
"The view is amazing just imagine waking to a beautiful blue ocean. Walking distance to the beach and the best restaurants, I recommend this place any day and the price is right.."
United States
Natalie
The price is ￥20,201
￥27,654 total
includes taxes & fees
Jul 27 - Jul 28
Montego Bay Club Beach Resort
Outdoor pool, pool umbrellas, sun loungers

Idle Awhile Cliffs

Idle Awhile Cliffs
4.0 star property
West End
9.0 out of 10, Wonderful, (123 reviews)
"Beautiful property in the woods. Very quiet, friendly staff."
United States
Mazie Kaylia Horace
The price is ￥31,148
￥39,099 total
includes taxes & fees
Jul 31 - Aug 1
Idle Awhile Cliffs
Pool

Charming 2-bedroom ocean-front townhouse in Point Village Negril

Charming 2-bedroom ocean-front townhouse in Point Village Negril
Negril
10.0 out of 10, Exceptional, (3 reviews)
"The stay was wonderful. Checking process was good. It took a while for us to find our room because the property is huge, but that was no major issue. The hosts were awesome, the people on the property were great as well. I have no complaints."
United States
Martecia
The price is ￥32,442
￥46,205 total
includes taxes & fees
Jul 26 - Jul 27
Charming 2-bedroom ocean-front townhouse in Point Village Negril
House, 2 Bedrooms, Smoking, Balcony | Balcony

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 ￥18,652
￥21,612 total
includes taxes & fees
Aug 19 - Aug 20
Modern Home 10minstobeach, Private Cliff, AC Wifi
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 Jamaica Resort & Spa All Inclusive

Grand Palladium Jamaica Resort & Spa All Inclusive

10/10 Excellent
"Everything was good. Food great."
Desire' 5-night trip
Posted 2 hours ago
Grand Palladium Jamaica 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 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?

Modern Home 10minstobeach, Private Cliff, AC Wifi: You might want to consider this vacation home rental near Middlesex, which comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

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.