Middlesex Vacation Rentals

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Check prices for these dates

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Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
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Nov 21 - Nov 23
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Dec 19 - Dec 21

Vacation Rentals in Middlesex

Our top choices for Middlesex vacation rentals

Sand and Blue Seas
Outdoor dining

Sand and Blue Seas

3.0 star property
8.2 out of 10, Very Good, (127)
"They were so friendly and hospitable. "
Sand and Blue Seas
Villas Sur Mer
Balcony view

Villas Sur Mer

4.0 star property
8.8 out of 10, Excellent, (149)
"Amazing as always!!! "
Villas Sur Mer
Idle Awhile Cliffs
Outdoor pool, pool umbrellas, sun loungers

Idle Awhile Cliffs

3.5 star property
9.0 out of 10, Wonderful, (119)
"We adored this “rustic” property with its early morning birdsong, simple clean (very clean!) rooms and lovely pool overlooking the ocean. Delicious breakfast poolside or on our terrace. Courteous and kind staff. Highly recommend!"
Idle Awhile Cliffs
Montego Bay Club Apartments
Beach towels

Montego Bay Club Apartments

4.0 star property
7.2 out of 10, Good, (37)
"I enjoyed my stay, the location was great."
Montego Bay Club Apartments
Dalley's Cozy Apartments
Balcony view

Dalley's Cozy Apartments

3.0 star property
8.8 out of 10, Excellent, (8)
"The location was great walking distance to everything was easy "
Dalley's Cozy Apartments
Beach House Condos Negril
Restaurant

Beach House Condos Negril

3.5 star property
9.0 out of 10, Wonderful, (56)
"Pro: separate AC in all rooms. Fully equipped kitchen. Clean. Approachable and helpful staff. Con: no toiletries. Tiny private beach with only four dry grass beach umbrellas. "
Beach House Condos Negril
Unity Villa
Electric kettle, toaster

Unity Villa

3.0 star property
8.0 out of 10, Very Good, (1)
"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 "
Unity Villa
Monimo Ridge Suites
Property grounds

Monimo Ridge Suites

3.0 star property
8.6 out of 10, Excellent, (19)
"Was comfortable and safe "
Monimo Ridge Suites
MoBay Life
Bed sheets

MoBay Life

2.5 star property
4.0 out of 10, (2)
"The property is in a great location to be able to walk into the town, harmony park beach, and the hip strip. That was the only plus "
MoBay Life
Unity Villa
Front of property

Unity Villa

3.0 star property
8.0 out of 10, Very Good, (1)
"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."
The price is P3,724
P5,299 total
includes taxes & fees
Sep 26 - Sep 27
Unity Villa
Montego Bay Club Beach Resort
View from property

Montego Bay Club Beach Resort

3.5 star property
4.4 out of 10, (40)
"Good location and Great view of the Caribbean Sea"
Montego Bay Club Beach Resort
Ocean View Suit-Montego Bay Club Resort
Outdoor pool

Ocean View Suit-Montego Bay Club Resort

3.5 star property
Ocean View Suit-Montego Bay Club Resort
Solet's Paradise Negril
Beach/ocean view

Solet's Paradise Negril

2.5 star property
9.8 out of 10, Exceptional, (9)
"Great little gem in Negril.If you are looking for a nice relaxing place away from the hustle and bustle, this is the place. Rooms are beautiful and the staff was awesome. would absolutely stay again. Dave"
Solet's Paradise Negril
Stunning Ocean View
In-room dining

Stunning Ocean View

4.0 star property
10.0 out of 10, Exceptional, (11)
"The view and ambience was pure bliss!"
Stunning Ocean View
Apartamento Vacacional en Bahía Montego
Exterior

Apartamento Vacacional en Bahía Montego

3.0 star property
Apartamento Vacacional en Bahía Montego
Idle Awhile Villas
Outdoor pool

Idle Awhile Villas

4.0 star property
10.0 out of 10, Exceptional, (15)
"The property was beautiful and the service was phenomenal. We had an amazing chef Raquel and butler Ryan. They accommodated our every need and Ryan had a lot of great recommendations for restaurants and activities. Would love to come back!!"
Idle Awhile Villas
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
1 bedroom, iron/ironing board, free WiFi

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

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is P4,691
P9,502 total
includes taxes & fees
Sep 26 - Sep 27
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Terrace/patio

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

4.0 star property
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Sunrise at Point Village
On the beach

Sunrise at Point Village

2.5 star property
Sunrise at Point Village
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
Property grounds

YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning

3.5 star property
The price is P7,788
P19,271 total
includes taxes & fees
Oct 8 - Oct 9
YanceyLargo- 4BR Villa Jacuzzi & Mountain Views by RedAwning
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
"Enjoy our stay "
MARK 9-night trip
Posted 9 hours ago
Princess Grand Jamaica Resort - All Inclusive

Find out more about Middlesex

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:

  • View our selection of featured holiday rentals in Middlesex
  • Use the map to find apartments and other holiday homes in the Middlesex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex while they last

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. Half Moon Beach and Tryall Golf Club 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.