Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Middlesex vacation rentals

Exterior

Vacation Home in Negril

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
The price is ￥14,562
￥16,901 total
includes taxes & fees
Mar 10 - Mar 11
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Front of property

Villa in Lucea

Wabi-Sabi Villa
5.0 star property
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
Wabi-Sabi Villa
Outdoor dining

Vacation Home in Cave District

Firefly cottage with Ocean view
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is ￥9,070
￥12,163 total
includes taxes & fees
Feb 25 - Feb 26
Firefly cottage with Ocean view
Beach nearby

Apartment in Montego Bay

Hospitality Expert Seawind - Pool, Beach, Chef
10.0 out of 10, Exceptional, (1 review)
"Nice place and breakfast"
Spain
Xavier
The price is ￥20,946
￥36,073 total
includes taxes & fees
Mar 2 - Mar 3
Hospitality Expert Seawind - Pool, Beach, Chef
Exterior

Apartment in Montego Bay

Unity Villa
3.0 star property
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
Unity Villa
Comfort House | Private kitchen | Full-size fridge, oven, stovetop, cookware/dishes/utensils

Vacation Home in Montego Bay

Casia Villa
3.0 star property
The price is ￥62,629
￥79,910 total
includes taxes & fees
Feb 25 - Feb 26
Casia Villa
Outdoor dining

Villa in Montego Bay

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
10.0 out of 10, Exceptional, (65 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 ￥47,011
￥50,722 total
includes taxes & fees
Mar 2 - Mar 3
Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
Pool

Villa in roundhill

Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
9.8 out of 10, Exceptional, (20 reviews)
"This trip was planned for our daughter's 21st birthday, so we wanted to make sure it was memorable for her. Mel communicated and responded quickly to me prior to our trip which made everything so much easier. Mel met us at the airport, took us to the store to grab provisions before heading to the villa. He was friendly and made us feel welcome immediately. Once we arrived at the villa, we were in paradise, the pictures and description were spot on and didn't disappoint. The view was nothing...
United States
Sarah H.
The price is ￥47,011
￥53,351 total
includes taxes & fees
Feb 26 - Feb 27
Free Transportation. Private Villa. Amazing Ocean View, Pool, And housekeeper.
Terrace/patio

Apartment in Montego Bay

The Shallhome
3.0 star property
The price is ￥77,320
￥89,073 total
includes taxes & fees
Feb 25 - Feb 26
The Shallhome
Property grounds

Vacation Home in Cave

Dragon fly Cottage
10.0 out of 10, Exceptional, (7 reviews)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
The price is ￥9,773
￥12,866 total
includes taxes & fees
Feb 25 - Feb 26
Dragon fly Cottage
Beach nearby, white sand, beach towels

Vacation Home in Hip Strip

Nianna Chatham
2.5 star property
The price is ￥21,332
￥33,965 total
includes taxes & fees
Mar 2 - Mar 3
Nianna Chatham
Beach nearby, beach towels

Vacation Home in Lucea

Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
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 ￥15,026
￥26,713 total
includes taxes & fees
Mar 4 - Mar 5
Cozy yet elegant Jamaican vacation home with access to pool, beach, gym etc
Interior

Vacation Home in Hanover, Parish

Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR
The price is ￥21,650
￥31,856 total
includes taxes & fees
Mar 7 - Mar 8
Cozy Home in Oceanpointe, Lucea, Hanover in Jamaica - 2BR 2WR
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | Building design

Vacation Home in Negril

Stunning Ocean View
4.0 star property
10.0 out of 10, Exceptional, (12 reviews)
"The view and ambience was pure bliss!"
United States
Roxanne
The price is ￥82,573
￥113,671 total
includes taxes & fees
Feb 27 - Feb 28
Stunning Ocean View
Daily cooked-to-order breakfast for a fee

Villa in West End

Idle Awhile Cliffs
3.5 star property
9.0 out of 10, Wonderful, (119 reviews)
"Friendly staff, excellent customer service. Enjoyed the ambience and accommodations. Clean and pleasant."
United States
Nayana
Idle Awhile Cliffs
1 bedroom, WiFi, bed sheets

Vacation Home in Cave

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
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 ￥9,278
￥12,371 total
includes taxes & fees
Feb 25 - Feb 26
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Studio | Blackout drapes, iron/ironing board, free WiFi

Apartment in Negril

Eleven30 Luxury Apartments
3.0 star property
Eleven30 Luxury Apartments
Basic Loft | View from room

Apartment in Montego Bay

Claudeville Condo
3.0 star property
8.6 out of 10, Excellent, (24 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
Claudeville Condo
Terrace/patio

Apartment in montego bay

1 Bedroom Ocean view Apartment, The Lagoons
7.6 out of 10, Good, (7 reviews)
"Places is nice view is good"
United States
Thomas G.
The price is ￥25,052
￥28,609 total
includes taxes & fees
Feb 25 - Feb 26
1 Bedroom Ocean view Apartment, The Lagoons
Property grounds

Vacation Home in Orange Bay

Tranquil Park
The price is ￥9,588
￥14,119 total
includes taxes & fees
Feb 25 - Feb 26
Tranquil Park
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
"The staff was excellent, they go out of their way to be friendly and accommodating. If you’re looking for a lot of action, stay somewhere else, this place has a very laid back vibe. Never had to wait for a lounge by the pool or on the beach. I was looking for a place to snorkel without going on an excursion, and this fit the bill. There are coral reefs right in front of the place."
Daniel 3-night trip
Posted 19 hours ago
S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

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 a plasma TV 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 Kool Runnings Water Park, 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.