Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Middlesex vacation rentals

Exterior

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is ￥15,259
￥17,707 total
includes taxes & fees
Apr 22 - Apr 23
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Pool

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is ￥24,986
￥40,791 total
includes taxes & fees
Apr 27 - Apr 28
Sunshine Seashore Escape Jamaica
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
10.0 out of 10, Exceptional, (1 review)
"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 ￥11,676
￥13,587 total
includes taxes & fees
May 2 - May 3
Modern Home 10minstobeach, Private Cliff, AC Wifi
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, (4 reviews)
"We enjoyed ourselves. And our stay was very pleasant."
United States
Cynthia N.
The price is ￥15,759
￥27,230 total
includes taxes & fees
Apr 25 - Apr 26
The Chill Spot - Escape. Relax. Enjoy. Your perfect getaway.
Property grounds

Tranquil Park

Tranquil Park
Orange Bay
The price is ￥9,836
￥14,484 total
includes taxes & fees
May 18 - May 19
Tranquil Park
Private kitchen

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.

Cozy house in charming Montego Bay with AC, WiFi and all other amenities.
Montego Bay
The price is ￥14,278
￥21,258 total
includes taxes & fees
Apr 25 - Apr 26
Cozy house in charming Montego Bay with AC, WiFi and all other amenities.
Beach nearby, white sand, beach towels

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is ￥29,674
￥43,802 total
includes taxes & fees
May 18 - May 19
Nianna Chatham
Living area

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is ￥7,932
￥12,691 total
includes taxes & fees
May 8 - May 9
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
1 bedroom, WiFi, bed sheets

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is ￥9,518
￥12,691 total
includes taxes & fees
May 18 - May 19
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
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 ￥19,297
￥35,163 total
includes taxes & fees
Apr 29 - Apr 30
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
Interior

Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR

Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR
Hanover, Parish
The price is ￥22,210
￥32,204 total
includes taxes & fees
Apr 25 - Apr 26
Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR
Front of property

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 ￥135,501
￥171,849 total
includes taxes & fees
Apr 29 - Apr 30
Wabi-Sabi Villa
Exterior

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 ￥15,004
￥20,589 total
includes taxes & fees
Apr 22 - Apr 23
Unity Villa
1 bedroom, free WiFi

Bak A Yaad Cottage Lupine Cottage

Bak A Yaad Cottage Lupine Cottage
West End
The price is ￥16,578
￥22,238 total
includes taxes & fees
Apr 22 - Apr 23
Bak A Yaad Cottage Lupine Cottage
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, (68 reviews)
"Such a nice stay at windfall Villas, Mel was great and always able to get us to anywhere at almost anytime we needed. It was beautiful and peaceful at the property. Would highly recommend to anyone checking out Montego Bay. Think twice begore trying drive here. In my opinion this is one dangerous place to drive unless you’ve driven here before. Mel made this part of our trip completely safe. "
United States
Jeff B.
The price is ￥48,227
￥55,207 total
includes taxes & fees
May 18 - May 19
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Studio | Blackout drapes, iron/ironing board, free WiFi

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is ￥19,291
￥22,526 total
includes taxes & fees
Apr 22 - Apr 23
Eleven30 Luxury Apartments
Beach nearby

Hospitality Expert Seawind - Pool, Beach, Chef

Hospitality Expert Seawind - Pool, Beach, Chef
Montego Bay
10.0 out of 10, Exceptional, (2 reviews)
"Nice place and breakfast"
Spain
Xavier
The price is ￥21,488
￥37,958 total
includes taxes & fees
May 8 - May 9
Hospitality Expert Seawind - Pool, Beach, Chef
Outdoor pool

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Hopewell
10.0 out of 10, Exceptional, (4 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 ￥14,289
￥21,434 total
includes taxes & fees
May 2 - May 3
Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!
Outdoor pool

Bak A Yaad Timberland Cottage

Bak A Yaad Timberland Cottage
West End
10.0 out of 10, Exceptional, (3 reviews)
"My family and I stayed for 2 days and it was unforgettable! The place was clean and tidy! Jordan (host) offered great recommendations for restaurants nearby- many within walking distance. Rick’s cafe across the street with amazing views! We had a great time and can’t wait to be back "
United States
Bridgette A.
The price is ￥18,561
￥23,590 total
includes taxes & fees
May 18 - May 19
Bak A Yaad Timberland Cottage
Terrace/patio

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is ￥79,320
￥91,377 total
includes taxes & fees
Apr 25 - Apr 26
The Shallhome
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

Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

10/10 Excellent
"It’s a perfect spot for a family vacation beautiful view and amenity and a lot of activity for kids"
Eyobe 2-night trip
Posted 4 hours ago
Princess Grand Jamaica Resort - All Inclusive

Find out more about Middlesex

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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?

Deluxe appartment at Point village: Visitors like this Middlesex vacation home rental. It has air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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.