Middlesex Vacation Rentals

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Our top choices for Middlesex vacation rentals

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Staff was very friendly and welcoming. "
United Kingdom
Sophia
The price is CA $133
CA $154 total
includes taxes & fees
Apr 4 - Apr 5
Claudeville Condo

Nianna Chatham

Nianna Chatham
2.5 star property
Hip Strip
The price is CA $293
CA $421 total
includes taxes & fees
May 1 - May 2
Nianna Chatham

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.2 out of 10, (58 reviews)
"The ocean view and street view from the 4th floor were great. Our morning coffee and breakfast were fantastic on the balcony."
Canada
Dean
The price is CA $168
CA $231 total
includes taxes & fees
Apr 27 - Apr 28
Montego Bay Club Beach Resort

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
The price is CA $169
CA $197 total
includes taxes & fees
Apr 4 - Apr 5
Eleven30 Luxury Apartments

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 CA $100
CA $117 total
includes taxes & fees
May 2 - May 3
Modern Home 10minstobeach, Private Cliff, AC Wifi

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (58 reviews)
"It was like staying in a 5 star hotel. Was comfortable like home. Rooms were spotless. Beautiful ambiance and clean grounds. Staff was professional and pleasant. "
United States
Tamar
The price is CA $195
CA $245 total
includes taxes & fees
May 1 - May 2
Beach House Condos Negril

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
3.5 star property
Montego Bay
The price is CA $214
CA $588 total
includes taxes & fees
Apr 16 - Apr 17
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

Negril Beachside

Negril Beachside
2.0 star property
Negril
8.0 out of 10, Very good, (1 review)
The price is CA $160
CA $192 total
includes taxes & fees
Apr 21 - Apr 22
Negril Beachside

Montego Bay Club Apartments

Montego Bay Club Apartments
4.0 star property
Hip Strip
7.4 out of 10, Good, (62 reviews)
"I enjoyed my stay although there was no room service "
United States
Nigeria
The price is CA $120
CA $189 total
includes taxes & fees
May 2 - May 3
Montego Bay Club Apartments

The Shallhome

The Shallhome
3.0 star property
Montego Bay
The price is CA $696
CA $801 total
includes taxes & fees
Apr 7 - Apr 8
The Shallhome

Idle Awhile Cliffs

Idle Awhile Cliffs
4.0 star property
West End
9.0 out of 10, Wonderful, (121 reviews)
"Staying at Idle awhile cliff is a great stay, however be aware of the very idle vibe. Things are extremely relaxed. Most people go out for dinner in the evenings, so staff is normally gone by 7pm on the dot. This property has so much potential but I am afraid it’s a tad bit neglected because it is the smaller of the 3 properties. The concept of the room is amazing. At night it’s extremely dark in this area and away from most of what’s happening on the west end. Upon arriving we notice a few...
United States
Annie-Kay
The price is CA $233
CA $293 total
includes taxes & fees
Apr 5 - Apr 6
Idle Awhile Cliffs

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 CA $131
CA $180 total
includes taxes & fees
Apr 2 - Apr 3
Unity Villa

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
The price is CA $219
CA $358 total
includes taxes & fees
Apr 3 - Apr 4
Sunshine Seashore Escape Jamaica

Casia Villa

Casia Villa
3.0 star property
Montego Bay
The price is CA $563
CA $719 total
includes taxes & fees
Apr 4 - Apr 5
Casia Villa

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
The price is CA $141
CA $163 total
includes taxes & fees
Apr 4 - Apr 5
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
The price is CA $214
CA $352 total
includes taxes & fees
Apr 2 - Apr 3
Sunny-shore Hideaway

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (12 reviews)
"The view and ambience was pure bliss!"
United States
Roxanne
The price is CA $743
CA $1,023 total
includes taxes & fees
Apr 7 - Apr 8
Stunning Ocean View

La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
The price is CA $981
CA $1,199 total
includes taxes & fees
Apr 8 - Apr 9
La Costa Villa

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is CA $111
CA $354 total
includes taxes & fees
Apr 18 - Apr 19
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (151 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 CA $247
CA $273 total
includes taxes & fees
May 2 - May 3
Villas Sur Mer
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

Find out more about Middlesex

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesex. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 cable 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.