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Middlesex Vacation Rentals

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Middlesex vacation rentals

Basic Loft | View from room

Claudeville Condo

Claudeville Condo
3.0 star property
Montego Bay
8.6 out of 10, Excellent, (24 reviews)
"Room was clean and staff was very welcoming with great communication. "
United States
Kenneth
$96 nightly
The price is $111
Jun 28 - Jun 29
Total with taxes and fees
Claudeville Condo
Restaurant

Sky Beach Rooms

Sky Beach Rooms
5.0 star property
Montego Bay
2.0 out of 10, (1 review)
"The room was very clean, however the rooms are located in a very local shopping mall with lots of loitering outside, very noisy, no windows so felt claustrophobic. The outside was dirty , crowded and noisy I did not feel safe enough to stay there so I left."
United States
chevone
$90 nightly
The price is $100
Jul 8 - Jul 9
Total with taxes and fees
Sky Beach Rooms
View from property

Montego Bay Club Beach Resort

Montego Bay Club Beach Resort
3.5 star property
Hip Strip
4.4 out of 10, (85 reviews)
"The view is amazing just imagine waking to a beautiful blue ocean. Walking distance to the beach and the best restaurants, I recommend this place any day and the price is right.."
United States
Natalie
$146 nightly
The price is $166
Jul 24 - Jul 25
Total with taxes and fees
Montego Bay Club Beach Resort
Exterior

La Costa Villa

La Costa Villa
3.0 star property
Montego Bay
$779 nightly
The price is $897
Jul 1 - Jul 2
Total with taxes and fees
La Costa Villa
House, 2 Bedrooms, Smoking, Balcony | Balcony

Modern Home 10minstobeach, Private Cliff, AC Wifi

Modern Home 10minstobeach, Private Cliff, AC Wifi
2.0 star property
Negril
9.0 out of 10, Wonderful, (2 reviews)
"Great atmosphere and awesome service. Clean and spacious apartment with a modern touch. Definitely looking forward to a future stay"
United States
Shantel
$112 nightly
The price is $130
Jul 5 - Jul 6
Total with taxes and fees
Modern Home 10minstobeach, Private Cliff, AC Wifi
Standard Studio Suite | Free WiFi

Grassroots Negril

Grassroots Negril
3.0 star property
West End
$77 nightly
The price is $89
Jul 1 - Jul 2
Total with taxes and fees
Grassroots Negril
Property grounds

Beach House Condos Negril

Beach House Condos Negril
3.5 star property
Negril
9.0 out of 10, Wonderful, (62 reviews)
"Second time staying here.. reasonably priced, low-key idyllic spot"
United States
Elizabeth
$132 nightly
The price is $151
Jul 8 - Jul 9
Total with taxes and fees
Beach House Condos Negril
Comfort House | Private kitchen | Full-size fridge, oven, stovetop, cookware/dishes/utensils

Casia Villa

Casia Villa
3.0 star property
Montego Bay
$441 nightly
The price is $508
Jun 30 - Jul 1
Total with taxes and fees
Casia Villa
Terrace/patio

The Shallhome

The Shallhome
3.0 star property
Montego Bay
$478 nightly
The price is $550
Jul 28 - Jul 29
Total with taxes and fees
The Shallhome
Premium Cottage, 1 Queen Bed, Pool View | Balcony view

Villas Sur Mer

Villas Sur Mer
4.0 star property
West End
8.8 out of 10, Excellent, (153 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
$171 nightly
The price is $189
Jul 24 - Jul 25
Total with taxes and fees
Villas Sur Mer
Family Townhome, 2 Bedrooms, Kitchen, Ocean View | In-room dining

Stunning Ocean View

Stunning Ocean View
4.0 star property
Negril
10.0 out of 10, Exceptional, (14 reviews)
"Clean and beautiful scenery! Needed assistance after hours and the manager responded quickly to my questions and concerns. Would book again"
United States
Willie
$646 nightly
The price is $726
Jul 5 - Jul 6
Total with taxes and fees
Stunning Ocean View
2 outdoor pools, free cabanas, pool umbrellas

Sunshine Seashore Escape Jamaica

Sunshine Seashore Escape Jamaica
3.5 star property
Lucea
$204 nightly
The price is $236
Jul 24 - Jul 25
Total with taxes and fees
Sunshine Seashore Escape Jamaica
Beach nearby, white sand, beach towels

Hospitality Expert CP

Hospitality Expert CP
2.5 star property
Hip Strip
$280 nightly
The price is $323
Jul 7 - Jul 8
Total with taxes and fees
Hospitality Expert CP
Sundeck

Little Waters on the Cliff

Little Waters on the Cliff
4.0 star property
West End
10.0 out of 10, Exceptional, (2 reviews)
"Spectacular views of the sunset, and a very comfortable, spacious place with everything you need for a upscale comfortable stay. The pool is perfect to cool down in after getting the sunny exposure the afternoons provide. The staff is fantastic Delkia and Rose are exceptional the meals were fantastic and Delkia is outstanding at arranging any tours or transportation you may need or want. On site security at night makes for great peace of mind as well. We really enjoyed the cliffs for our own...
Canada
Anonymous traveler
$1,167 nightly
The price is $1,343
Jul 26 - Jul 27
Total with taxes and fees
Little Waters on the Cliff
Exterior

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL

RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
4.0 star property
Negril
$97 nightly
The price is $113
Jun 28 - Jun 29
Total with taxes and fees
RUNTINGS HIDEAWAY STAY NOMPREL ROAD NEGRIL
Studio | Blackout drapes, iron/ironing board, free WiFi

Eleven30 Luxury Apartments

Eleven30 Luxury Apartments
3.0 star property
Negril
$123 nightly
The price is $142
Jun 28 - Jun 29
Total with taxes and fees
Eleven30 Luxury Apartments
Beach towels

Montego Bay Club Apartments

Montego Bay Club Apartments
3.0 star property
Hip Strip
7.4 out of 10, Good, (76 reviews)
"It was a nice stay."
United States
Leslyn
$168 nightly
The price is $195
Jun 30 - Jul 1
Total with taxes and fees
Montego Bay Club Apartments
Exterior

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
$112 nightly
The price is $130
Jun 28 - Jun 29
Total with taxes and fees
Unity Villa
Front of property

Unity Villa

Unity Villa
3.0 star property
Montego Bay
$81 nightly
The price is $91
Jul 1 - Jul 2
Total with taxes and fees
Unity Villa
House, 3 Bedrooms, Smoking, Patio | Exterior

Sunny-shore Hideaway

Sunny-shore Hideaway
2.0 star property
Lucea
$224 nightly
The price is $247
Jul 2 - Jul 3
Total with taxes and fees
Sunny-shore Hideaway
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

Deja Resort All Inclusive

Deja Resort All Inclusive

10/10 Excellent
"Great location. Loved the entertainment."
Charity 4-night trip
Posted less than an hour ago
Deja Resort All Inclusive

Find out more about Middlesex

Everything you need to know about Middlesex vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesex vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesex vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesex vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesex. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $100 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesex rentals

At Expedia, we put the best Middlesex vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesex vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Hope Botanical Garden and Zoo, 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.