Middlesex Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Middlesex

Outdoor pool, pool umbrellas, sun loungers
Idle Awhile Cliffs

Idle Awhile Cliffs

3.5 star property
West End
9.0 out of 10, Wonderful, (119)
"Very rustic and secluded loved the feeling of been surrounded by nature, had a peaceful stay. Great staff. Hopeton from the bar very friendly and gives excellent service. "
United States
Richard
Idle Awhile Cliffs
Front of property
Turquoise Sea Villa

Turquoise Sea Villa

3.5 star property
Montego Bay
The price is P5,726
P12,547 total
includes taxes & fees
Nov 10 - Nov 11
Turquoise Sea Villa
Balcony view
Villas Sur Mer

Villas Sur Mer

4.0 star property
West End
8.8 out of 10, Excellent, (149)
"Love this property. Great staff and the location was great for me. Only thing I would change is the couch in the room wasn't that great. Everything else was wonderful. "
United States
Chelsea
The price is P14,462
P15,967 total
includes taxes & fees
Nov 10 - Nov 11
Villas Sur Mer
Property grounds
Monimo Ridge Suites

Monimo Ridge Suites

3.0 star property
Montego Bay
8.6 out of 10, Excellent, (20)
"The property is well kept, great hospitality. I felt safe and at peace while staying at the property. This is my second time staying there. I recommend staying at this property to anyone to wishes to have peace of mind. "
United States
Dianna
Monimo Ridge Suites
Restaurant
Beach House Condos Negril

Beach House Condos Negril

3.5 star property
Negril
9.0 out of 10, Wonderful, (57)
"The staff were very friendly. Excellent service with a smile. A great place for family reunion. "
Canada
Opal
The price is P11,216
P14,078 total
includes taxes & fees
Nov 10 - Nov 11
Beach House Condos Negril
Property grounds
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 P8,709
P20,964 total
includes taxes & fees
Nov 10 - Nov 11
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
Beach towels
Montego Bay Club Apartments

Montego Bay Club Apartments

4.0 star property
Hip Strip
7.4 out of 10, Good, (41)
"I love everything about! My go to spot. In walking distance. "
United States
Monique
The price is P7,969
P11,289 total
includes taxes & fees
Dec 1 - Dec 2
Montego Bay Club Apartments
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
"Let me start off by saying this resort was so beautiful and the staff are all so friendly. It was very clean and so many things to do on this resort! Ingrid and Garth too great care of me and my husband during our stay. We were unfortunately stuck due to hurricane melissa and Ingrid and Garth kept us updated and informed immediately and was also open to any concerns or question we had. They also ensured that we were safe and indeed we were! This resort still had their buffet open to guest after a Catastrophic hurricane and bars were still open for us. They gave use 3+ free nights and were very understanding. I cannot expressed enough how much we appreciate you both Ingrid and Garth! Me and my husband will definitely be back soon as Jamaica recovers from this very devastating situation. This two definitely deserve a raise because you do not run across Amazon people like them very often in the customer service industry. Again, thank you guys for an Amazon stay at the Princess Grand Jamaica! "
Destiny 4-night trip
Posted 5 days ago
Princess Grand Jamaica Resort - 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:

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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?

Stunning Ocean View: You might want to consider this vacation home rental near Middlesex, which is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a terrace and a private yard.

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. Tryall Golf Club 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.