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

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
Mar 1 - Mar 2
Firefly cottage with Ocean view
Property grounds

Vacation Home in Orange Bay

Tranquil Park
The price is ￥9,588
￥14,119 total
includes taxes & fees
Mar 5 - Mar 6
Tranquil Park
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 27 - Feb 28
Dragon fly Cottage
Exterior detail

Apartment in Montego Bay

Quiet relaxing mountainous get away!
9.2 out of 10, Wonderful, (5 reviews)
"The location was gorgeous, not far from the city. Easy/beautiful walk to cabs. Host was great and the bed/sheets felt great!!"
United States
Kintoria W.
The price is ￥9,742
￥12,835 total
includes taxes & fees
Feb 26 - Feb 27
Quiet relaxing mountainous get away!
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
Mar 5 - Mar 6
Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Interior

Apartment in Montego Bay

Charming & Comfortable 1-Bedroom Suite in Montego Bay
7.8 out of 10, Good, (9 reviews)
"It was a bit difficult to locate the property. Accommodation was comfortable, convenient and affordable. I will stay again when I need an affordable layover in Montego"
United States
Claudine
The price is ￥9,124
￥12,217 total
includes taxes & fees
Feb 26 - Feb 27
Charming & Comfortable 1-Bedroom Suite in Montego Bay
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
Living area

Vacation Home in Mount Salem

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
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 ￥7,732
￥12,371 total
includes taxes & fees
Mar 4 - Mar 5
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Front of property

Apartment in Montego Bay

Unity Villa
3.0 star property
8.0 out of 10, Very Good, (1 review)
"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 ￥10,134
￥14,422 total
includes taxes & fees
Mar 21 - Mar 22
Unity Villa
House, 2 Bedrooms, Smoking, Balcony | Balcony

Vacation Home in Negril

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
The price is ￥12,723
￥14,788 total
includes taxes & fees
Feb 26 - Feb 27
Modern Home 10minstobeach, Private Cliff, AC Wifi
Property grounds

Vacation Home in Cave

The Artist cabin is a mountain cabin overlooking the sea and coastline
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay in the mountains of Jamaica! The food was excellent, and we loved watching the sunset every evening. Terry was wonderful company — he even picked us up in Negril to bring us to the beautiful cabins in the woods. A truly magnificent stay!"
United States
Ana G.
The price is ￥7,732
￥10,825 total
includes taxes & fees
Mar 5 - Mar 6
The Artist cabin is a mountain cabin overlooking the sea and coastline
On the beach

Apartment in Hip Strip

Hip Strip Beach Apartment walkable to clubs, beaches and restaurants
8.6 out of 10, Excellent, (7 reviews)
"Such a great place great location!!"
United States
Matthew K.
The price is ￥9,742
￥12,835 total
includes taxes & fees
Mar 4 - Mar 5
Hip Strip Beach Apartment walkable to clubs, beaches and restaurants
Interior

Vacation Home in Montego Bay

The heart of Montego Bay
The price is ￥9,355
￥15,280 total
includes taxes & fees
Mar 1 - Mar 2
The heart of Montego Bay
Property grounds

Vacation Home in Savanalamar

Muris Light Sanctuary
10.0 out of 10, Exceptional, (1 review)
"Host was attentive and super nice to deal with. Great stay. No air conditioning but was pleaaant regardless. "
Canada
Leeann D.
The price is ￥5,412
￥20,567 total
includes taxes & fees
Mar 10 - Mar 11
Muris Light Sanctuary
Terrace/patio

Apartment in Montego Bay

Great panoramic views. Beach and shopping close by.
10.0 out of 10, Exceptional, (1 review)
"It was a beautiful home and convenient to the airport. The host was also very responsive and understanding . I appreciate her hospitality and kindness. I would def recommend this place and would stay again."
United States
Shannon S.
The price is ￥11,693
￥17,150 total
includes taxes & fees
Feb 26 - Feb 27
Great panoramic views. Beach and shopping close by.
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
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 9 - Mar 10
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Exterior

Vacation Home in Montego Bay

Bamboo Villa- Modern Home with relaxing backyard
The price is ￥13,144
￥20,876 total
includes taxes & fees
Mar 6 - Mar 7
Bamboo Villa- Modern Home with relaxing backyard
Villa, 1 Bedroom | 1 bedroom, iron/ironing board, free WiFi

Villa in Montego Bay

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,076
￥37,093 total
includes taxes & fees
Feb 26 - Feb 27
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
Property grounds

Vacation Home in Montego Bay

Heart of Montego Bay #3
The price is ￥13,918
￥20,799 total
includes taxes & fees
Mar 2 - Mar 3
Heart of Montego Bay #3
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 1 day 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?

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.